# Chloroform

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CHCl3, historical anaesthetic and common solvent

For other uses, see [Chloroform (disambiguation)](/source/Chloroform_(disambiguation)).

You can help expand this article with text translated from the corresponding article in Turkish. (September 2024) Click [show] for important translation instructions. View a machine-translated version of the Turkish article. Machine translation, like DeepL or Google Translate, is a useful starting point for translations, but translators must follow the LLM translation guideline, revise errors as necessary and confirm that the translation is accurate, rather than simply copy-pasting machine-translated text into the English Wikipedia. Do not translate text that appears unreliable or low-quality. If possible, verify the text with references provided in the foreign-language article. You must provide copyright attribution in the edit summary accompanying your translation by providing an interlanguage link to the source of your translation. A model attribution edit summary is Content in this edit is translated from the existing Turkish Wikipedia article at [[:tr:Kloroform]]; see its history for attribution. You may also add the template {{Translated|tr|Kloroform}} to the talk page. For more guidance, see Wikipedia:Translation.

Chloroform Chloroform in its liquid state shown in a test tube Names Preferred IUPAC name Trichloromethane Other names Chloroformium Freon 20 Methane trichloride Methyl trichloride Methenyl trichloride Methenyl chloride Refrigerant-20 terchloride/perchloride of formyle[1][2] (archaic) Trichloretum Formylicum (Latin) Identifiers CAS Number 67-66-3 Y 3D model (JSmol) Interactive image Abbreviations R-20, TCM ChEBI CHEBI:35255 Y ChEMBL ChEMBL44618 Y ChemSpider 5977 Y ECHA InfoCard 100.000.603 EC Number 200-663-8 KEGG C13827 Y PubChem CID 6212 RTECS number FS9100000 UNII 7V31YC746X Y UN number 1888 CompTox Dashboard (EPA) DTXSID1020306 InChI InChI=1S/CHCl3/c2-1(3)4/h1H Y Key: HEDRZPFGACZZDS-UHFFFAOYSA-N Y InChI=1/CHCl3/c2-1(3)4/h1H Key: HEDRZPFGACZZDS-UHFFFAOYAG SMILES ClC(Cl)Cl Properties Chemical formula CHCl3 Molar mass 119.37 g·mol−1 Appearance Highly refractive colorless liquid Odor Sweet, minty, pleasant Density 1.564 g/cm3 (−20 °C) 1.489 g/cm3 (25 °C) 1.394 g/cm3 (60 °C) Melting point −63.5 °C (−82.3 °F; 209.7 K) Boiling point 61.15 °C (142.07 °F; 334.30 K) decomposes at 450 °C Solubility in water 10.62 g/L (0 °C) 8.09 g/L (20 °C) 7.32 g/L (60 °C) Solubility Soluble in benzene Miscible in diethyl ether, oils, ligroin, alcohol, CCl4, CS2 Solubility in acetone ≥ 100 g/L (19 °C) Solubility in dimethyl sulfoxide ≥ 100 g/L (19 °C) Vapor pressure 0.62 kPa (−40 °C) 7.89 kPa (0 °C) 25.9 kPa (25 °C) 313 kPa (100 °C) 2.26 MPa (200 °C) Henry's law constant (kH) 3.67 L·atm/mol (24 °C) Acidity (pKa) 15.7 (20 °C) UV-vis (λmax) 250 nm, 260 nm, 280 nm Magnetic susceptibility (χ) −59.30·10−6 cm3/mol Thermal conductivity 0.13 W/(m·K) (20 °C) Refractive index (nD) 1.4459 (20 °C) Viscosity 0.563 cP (20 °C) Structure Molecular shape Tetrahedral Dipole moment 1.15 D Thermochemistry Heat capacity (C) 114.25 J/(mol·K) Std molar entropy (S⦵298) 202.9 J/(mol·K) Std enthalpy of formation (ΔfH⦵298) −134.3 kJ/mol Gibbs free energy (ΔfG⦵) −71.1 kJ/mol Std enthalpy of combustion (ΔcH⦵298) 473.21 kJ/mol Pharmacology ATC code N01AB02 (WHO) Hazards[8] Occupational safety and health (OHS/OSH): Main hazards Decomposes into phosgene and hydrogen chloride in presence of heat – likely carcinogenic – reproductive toxicity – hepatotoxic[3][4] GHS labelling: Pictograms Signal word Danger Hazard statements H302, H315, H319, H331, H336, H351, H361d, H372 Precautionary statements P201, P202, P235, P260, P264, P270, P271, P280, P281, P301+P330+P331, P302+P352, P304+P340, P305+P351+P338, P308+P313, P310, P311, P314, P332+P313, P337+P313, P362, P403+P233, P405, P501 NFPA 704 (fire diamond) 2 0 0 Flash point Nonflammable Lethal dose or concentration (LD, LC): LD50 (median dose) 704 mg/kg (mouse, dermal)[5] LC50 (median concentration) 47,702 mg/m3 (rat, 4 hr)[6] LCLo (lowest published) 20,000 ppm (guinea pig, 2 hr) 7,056 ppm (cat, 4 hr) 25,000 ppm (human, 5 min) [7] NIOSH (US health exposure limits): PEL (Permissible) 50 ppm (240 mg/m3)[3] REL (Recommended) Ca ST 2 ppm (9.78 mg/m3) [60-minute][3] IDLH (Immediate danger) 500 ppm[3] Safety data sheet (SDS) [1] Related compounds Related compounds Deuterated chloroform CDCl3 Chloromethane CH3Cl Dichloromethane CH2Cl2 Tetrachloromethane CCl4 Fluoroform CHF3 Bromoform CHBr3 Iodoform CHI3 Chlorodifluoromethane CHF2Cl Dichlorofluoromethane CHFCl2 Bromodichloromethane CHCl2Br Dibromochloromethane CHClBr2 Bromodifluoromethane CHF2Br Dibromofluoromethane CHFBr2 Supplementary data page Chloroform (data page) Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Y verify (what is YN ?) Infobox references

Chemical compound

**Chloroform**,[9] or **trichloromethane** (often abbreviated as **TCM**), is an [organochloride](/source/Organochloride) with the [formula](/source/Chemical_formula) [C](/source/Carbon)[H](/source/Hydrogen)[Cl](/source/Chlorine)3 and a common [solvent](/source/Solvent). It is a [volatile](/source/Volatility_(chemistry)), colorless, sweet-smelling, dense liquid produced on a large scale as a precursor to [refrigerants](/source/Refrigerant) and [polytetrafluoroethylene (PTFE)](/source/Polytetrafluoroethylene).[10] Chloroform was once used as an [inhalational anesthetic](/source/Inhalational_anesthetic) between the 19th century and the first half of the 20th century.[11][12] It is miscible with many solvents but it is only very slightly soluble in water (only 8 g/L at 20°C).

## Structure and name

The molecule adopts a [tetrahedral molecular geometry](/source/Tetrahedral_molecular_geometry) with C3v [symmetry](/source/Symmetry_group).[13] The chloroform molecule can be viewed as a [methane](/source/Methane) molecule with three hydrogen atoms replaced with three chlorine atoms, leaving a single hydrogen atom.

The name "chloroform" is a [portmanteau](/source/Portmanteau) of *terchloride* (tertiary chloride, a trichloride) and *formyle*, an obsolete name for the [methylylidene](/source/Methylylidene) radical (CH) derived from [formic acid](/source/Formic_acid).[14]

## Natural occurrence

Many kinds of [seaweed](/source/Seaweed) produce chloroform, and [fungi](/source/Fungi) are believed to produce chloroform in soil.[15] Abiotic processes are also believed to contribute to natural chloroform productions in soils, although the mechanism is still unclear.[16]

## History

Chloroform was synthesized independently by several investigators c. 1831:

- Moldenhawer, a German pharmacist from [Frankfurt an der Oder](/source/Frankfurt_an_der_Oder), appears to have produced chloroform in 1830 by mixing [chlorinated lime](/source/Chlorinated_lime#Chlorine-based_bleaches) with [ethanol](/source/Ethanol); however, he mistook it for *Chloräther* (chloric ether, [1,2-dichloroethane](/source/1%2C2-dichloroethane)).[17][18]

- [Samuel Guthrie](/source/Samuel_Guthrie_(physician)), a U.S. physician from [Sackets Harbor, New York](/source/Sackets_Harbor%2C_New_York), also appears to have produced chloroform in 1831 by reacting chlorinated lime with ethanol, and noted its [anaesthetic](/source/Anesthetic) properties; however, he also believed that he had prepared chloric ether.[19][20][21]

- [Justus von Liebig](/source/Justus_von_Liebig) carried out the [alkaline cleavage](/source/Bond_cleavage) of [chloral](/source/Chloral). Liebig incorrectly states that the [empirical formula](/source/Empirical_formula) of chloroform was C2Cl5 and named it "*Chlorkohlenstoff*" ("carbon chloride").[22][23]

- [Eugène Soubeiran](/source/Eug%C3%A8ne_Soubeiran) obtained the compound by the action of [chlorine bleach](/source/Chlorine_bleach) on both [ethanol](/source/Ethanol) and [acetone](/source/Acetone).[24]

In 1834, French chemist [Jean-Baptiste Dumas](/source/Jean-Baptiste_Dumas) determined chloroform's empirical formula and named it:[25] "*Es scheint mir also erweisen, dass die von mir analysirte Substanz, … zur Formel hat: C2H2Cl6.*" (Thus it seems to me to show that the substance I analyzed … has as [its empirical] formula: C2H2Cl6.). [Note: The coefficients of his empirical formula should be halved.] ... "*Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen.*" (This had caused me to impose the name "chloroform" upon this substance [i.e., formyl chloride or chloride of formic acid].)

In 1835, Dumas prepared the substance by alkaline cleavage of [trichloroacetic acid](/source/Trichloroacetic_acid).

In 1842, [Robert Mortimer Glover](/source/Robert_Mortimer_Glover) in London discovered the anaesthetic qualities of chloroform on laboratory animals.[26]

In 1847, Scottish obstetrician [James Y. Simpson](/source/James_Y._Simpson) was the first to demonstrate the anaesthetic properties of chloroform (provided by local pharmacist [William Flockhart](/source/William_Flockhart) of Duncan, Flockhart and company,[27]) in humans, and helped to popularize the drug for use in medicine.[28]

The application of chloroform remained dangerous, and many deaths occurred through accidental [overdose](/source/Drug_overdose).[29][30] In 1848, English physician [John Snow](/source/John_Snow) developed an inhaler that regulated the dosage.[29]

By the 1850s, chloroform was being produced on a commercial basis.[30] An apparatus that could apply it safely and controllably was invented by English physician [Joseph Thomas Clover](/source/Joseph_Thomas_Clover) in 1862.[31][32]

In Britain, about 750,000 doses a week were being produced by 1895,[30] using the Liebig procedure, which retained its importance until the 1960s. Today, chloroform – along with [dichloromethane](/source/Dichloromethane) – is prepared exclusively and on a massive scale by the chlorination of methane and chloromethane.[10]

## Production

Industrially, chloroform is produced by heating a mixture of [chlorine](/source/Chlorine) and either [methyl chloride](/source/Methyl_chloride) (CH3Cl) or [methane](/source/Methane) (CH4).[10] At 400–500 °C, [free radical halogenation](/source/Free_radical_halogenation) occurs, converting these precursors to progressively more chlorinated compounds:

- CH4 + [Cl2](/source/Chlorine) → CH3Cl + [HCl](/source/Hydrogen_chloride)

- CH3Cl + Cl2 → [CH2Cl2](/source/Dichloromethane) + HCl

- CH2Cl2 + Cl2 → CHCl3 + HCl

Chloroform undergoes further chlorination to yield [carbon tetrachloride](/source/Carbon_tetrachloride) (CCl4):

- CHCl3 + Cl2 → CCl4 + HCl

The output of this process is a mixture of the four chloromethanes: [chloromethane](/source/Chloromethane), [methylene chloride](/source/Methylene_chloride) (dichloromethane), trichloromethane (chloroform), and [tetrachloromethane](/source/Carbon_tetrachloride) (carbon tetrachloride). These can then be separated by [distillation](/source/Distillation).[10]

Chloroform may also be produced on a small scale via the [haloform reaction](/source/Haloform_reaction) between [acetone](/source/Acetone) and [sodium hypochlorite](/source/Sodium_hypochlorite):

- 3 NaOCl + (CH3)2CO → CHCl3 + 2 [NaOH](/source/Sodium_hydroxide) + [CH3COONa](/source/Sodium_acetate)

### Deuterochloroform

Main article: [Deuterated chloroform](/source/Deuterated_chloroform)

[Deuterated chloroform](/source/Deuterated_chloroform) is an [isotopologue](/source/Isotopologue) of chloroform with a single [deuterium](/source/Deuterium) atom. CDCl3 is a common solvent used in [NMR spectroscopy](/source/NMR_spectroscopy). Deuterochloroform is produced by the reaction of [hexachloroacetone](/source/Hexachloroacetone) with [heavy water](/source/Heavy_water).[33] The haloform process is now obsolete for production of ordinary chloroform. Deuterochloroform can also be prepared by reacting [sodium deuteroxide](/source/Sodium_deuteroxide) with [chloral hydrate](/source/Chloral_hydrate).[34][35]

### Inadvertent formation of chloroform

The haloform reaction can also occur inadvertently in domestic settings. Sodium hypochlorite solution ([chlorine bleach](/source/Chlorine_bleach)) mixed with common household liquids such as [acetone](/source/Acetone), [methyl ethyl ketone](/source/Methyl_ethyl_ketone), [ethanol](/source/Ethanol), or [isopropyl alcohol](/source/Isopropyl_alcohol) can produce some chloroform, in addition to other compounds, such as [chloroacetone](/source/Chloroacetone) or [dichloroacetone](/source/Dichloroacetone).[36][37]

## Uses

In terms of scale, the most important reaction of chloroform is with [hydrogen fluoride](/source/Hydrogen_fluoride) to give [monochlorodifluoromethane](/source/Monochlorodifluoromethane) (HCFC-22), a precursor in the production of polytetrafluoroethylene ([Teflon](/source/Teflon)) and other fluoropolymers:[10]

- CHCl3 + 2 HF → CHClF2 + 2 HCl

The reaction is conducted in the presence of a [catalytic](/source/Catalysis) amount of [mixed antimony halides](/source/Antimony_trifluoride#Applications). Chlorodifluoromethane is then converted to [tetrafluoroethylene](/source/Tetrafluoroethylene), the main precursor of [Teflon](/source/Teflon).[38]

### Solvent

The [hydrogen](/source/Hydrogen) attached to [carbon](/source/Carbon) in chloroform participates in hydrogen bonding,[39][40] making it a good solvent for many materials.

Worldwide, chloroform is also used in pesticide formulations, as a [solvent](/source/Solvent) for [lipids](/source/Lipids), [rubber](/source/Rubber), [alkaloids](/source/Alkaloid), [waxes](/source/Wax), [gutta-percha](/source/Gutta-percha), and [resins](/source/Resin), as a cleaning agent, as a grain [fumigant](/source/Fumigant), in [fire extinguishers](/source/Fire_extinguishers), and in the rubber industry.[41][42] [CDCl3](/source/Deuterated_chloroform) is a common solvent used in [NMR spectroscopy](/source/NMR_spectroscopy).[43]

### Refrigerant

Chloroform is used as a precursor to make R-22 (chlorodifluoromethane). This is done by reacting it with [hydrofluoric acid](/source/Hydrofluoric_acid) (HF) which fluorinates the CHCl3 molecule and releases hydrochloric acid as a byproduct.[44] Before the [Montreal Protocol](/source/Montreal_Protocol) was enforced, most of the chloroform produced in the United States was used in the production of [chlorodifluoromethane](/source/Chlorodifluoromethane). However, its production remains high, as it is a key precursor of PTFE.[45]

Although chloroform has properties such as a low boiling point, and a low global warming potential of only 31 (compared to the 1760 of R-22), which are appealing properties for a refrigerant, there is little information to suggest that it has seen widespread use as a refrigerant in any consumer products.[46]

### Lewis acid

In solvents such as CCl4 and alkanes, chloroform hydrogen bonds to a variety of Lewis bases. HCCl3 is classified as a [hard acid](/source/HSAB), and the [ECW model](/source/ECW_model) lists its acid parameters as EA = 1.56 and CA = 0.44.

### Reagent

As a [reagent](/source/Reagent), chloroform serves as a source of the [dichlorocarbene](/source/Dichlorocarbene) intermediate CCl2.[47] It reacts with aqueous [sodium hydroxide](/source/Sodium_hydroxide), usually in the presence of a [phase transfer catalyst](/source/Phase_transfer_catalyst), to produce [dichlorocarbene](/source/Dichlorocarbene), CCl2.[48][49] This reagent effects ortho-formylation of activated [aromatic rings](/source/Aromatic_rings), such as [phenols](/source/Phenols), producing aryl [aldehydes](/source/Aldehyde) in a reaction known as the [Reimer–Tiemann reaction](/source/Reimer%E2%80%93Tiemann_reaction). Alternatively, the [carbene](/source/Carbene) can be trapped by an [alkene](/source/Alkene) to form a [cyclopropane](/source/Cyclopropane) derivative. In the [Kharasch addition](/source/Kharasch_addition), chloroform forms the •CHCl2 free radical which adds to alkenes.[50]

### Anaesthetic

Antique bottles of chloroform

Chloroform is a powerful [general anesthetic](/source/General_anesthetic), [euphoriant](/source/Euphoriant), [anxiolytic](/source/Anxiolytic), and [sedative](/source/Sedative) when inhaled or ingested. The [anaesthetic](/source/Anaesthetic) qualities of chloroform were first described in 1842 in a thesis by [Robert Mortimer Glover](/source/Robert_Mortimer_Glover), which won the Gold Medal of the [Harveian Society](/source/Harveian_Society) for that year.[51][52] Glover also undertook practical experiments on dogs to prove his theories, refined his theories, and presented them in his doctoral thesis at the [University of Edinburgh](/source/University_of_Edinburgh) in the summer of 1847, identifying anaesthetizing halogenous compounds as a "new order of poisonous substances".[51]

The Scottish [James Young Simpson](/source/James_Young_Simpson), an [obstetrician](/source/Obstetrics), was one of those examiners required to read the thesis, but later claimed to have never read it and to have come to his own conclusions independently.[51] Perkins-McVey, among others, have raised doubts about the credibility of Simpson's claim, noting that Simpson's publications on the subject in 1847 explicitly echo Glover's and, being one of the thesis examiners, Simpson was likely aware of the content of Glover's study, even if he skirted his duties as an examiner.[51] In 1847 and 1848, Glover would pen a series of heated letters accusing Simpson of stealing his discovery, which had already earned Simpson considerable notoriety.[51] Whatever the source of his inspiration, on 4 November 1847, Simpson argued that he had discovered the anaesthetic qualities of chloroform in humans. He and two colleagues entertained themselves by trying the effects of various substances, and thus revealed the potential for chloroform in medical procedures.[27]

An illustration depicting James Young Simpson and his friends found unconscious.

A few days later, during the course of a dental procedure in [Edinburgh](/source/Edinburgh), [Francis Brodie Imlach](/source/Francis_Brodie_Imlach) became the first person to use chloroform on a patient in a clinical context.[53]

In May 1848, [Robert Halliday Gunning](/source/Robert_Halliday_Gunning) made a presentation to the Medico-Chirurgical Society of Edinburgh following a series of laboratory [experiments on rabbits](/source/Domestic_rabbit#Experimentation) that confirmed Glover's findings and also refuted Simpson's claims of originality. The laboratory experiments that proved the dangers of chloroform were largely ignored.[54]

The use of chloroform during [surgery](/source/Surgery) expanded rapidly in Europe; in the 1850s chloroform was used by the physician [John Snow](/source/John_Snow) during the births of [Queen Victoria](/source/Queen_Victoria)'s last two children [Leopold](/source/Prince_Leopold%2C_Duke_of_Albany) and [Beatrice](/source/Princess_Beatrice_of_the_United_Kingdom).[55] In the United States, chloroform began to replace [ether](/source/Diethyl_ether) as an anesthetic at the beginning of the 20th century;[56] it was abandoned in favor of ether on discovery of its toxicity, especially its tendency to cause fatal [cardiac arrhythmias](/source/Cardiac_arrhythmia) analogous to what is now termed "[sudden sniffer's death](/source/Intoxicative_inhalant#Sudden_sniffing_death_syndrome)". Some people used chloroform as a recreational drug or to attempt suicide.[57] One possible mechanism of action of chloroform is that it increases the movement of [potassium](/source/Potassium) ions through certain types of [potassium channels](/source/Potassium_channel) in [nerve cells](/source/Nerve_cells).[58] Chloroform could also be mixed with other anesthetic agents such as ether to make C.E. mixture,[59] or ether and [alcohol](/source/Ethanol) to make [A.C.E. mixture](/source/A.C.E._mixture).[60][61]

In 1848, Hannah Greener, a 15-year-old girl who was having an infected toenail removed, died after being given the anaesthetic.[62] Her autopsy establishing the cause of death was undertaken by [John Fife](/source/John_Fife_(surgeon)) assisted by [Robert Mortimer Glover](/source/Robert_Mortimer_Glover).[26] A number of physically fit patients died after inhaling it. In 1848, however, John Snow developed an inhaler that regulated the dosage and so successfully reduced the number of deaths.[29] Joseph Thomas Clover improved on the design in 1862, further reducing the risk of accidental overdose.[31][32]

The opponents and supporters of chloroform disagreed on the question of whether the medical complications were due to respiratory disturbance or whether chloroform had a specific effect on the heart. Between 1864 and 1910, numerous commissions in Britain studied chloroform but failed to come to any clear conclusions. It was only in 1911 that Levy proved in experiments with animals that chloroform can cause [ventricular fibrillation](/source/Ventricular_fibrillation).[63] Despite this, between 1865 and 1920, chloroform was used in 80 to 95% of all narcoses performed in the UK and German-speaking countries. In Germany, comprehensive surveys of the fatality rate during anaesthesia were made by Gurlt between 1890 and 1897.[56] At the same time in the UK the medical journal *[The Lancet](/source/The_Lancet)* carried out a questionnaire survey[64] and compiled a report detailing numerous adverse reactions to anesthetics, including chloroform.[65] In 1934, Killian gathered all the statistics compiled until then and found that the chances of suffering fatal complications under ether were between 1:14,000 and 1:28,000, whereas with chloroform the chances were between 1:3,000 and 1:6,000.[56] The rise of gas anaesthesia using [nitrous oxide](/source/Nitrous_oxide), improved equipment for administering anesthetics, and the discovery of [hexobarbital](/source/Hexobarbital) in 1932 led to the gradual decline of chloroform narcosis.[66]

The latest reported anaesthetic use of chloroform in the Western world dates to 1987, when the last doctor who used it retired, about 140 years after its first use.[67]

### Recreational use

In the 1910s in England, a fast-living set called [The Coterie](/source/The_Coterie) used chloroform recreationally. [Margot Asquith](/source/Margot_Asquith), the wife of the Prime Minister, whose stepson [Raymond Asquith](/source/Raymond_Asquith) was a member, recorded that [Lady Diana Manners](/source/Lady_Diana_Cooper), who called it "jolly old chlorors", had said "I must be unconscious by midnight."

### Criminal use

Chloroform has been used by criminals to knock out, daze, or murder victims. Joseph Harris was charged in 1894 with using chloroform to rob people.[68] [Serial killer](/source/Serial_killer) [H. H. Holmes](/source/H._H._Holmes) used chloroform overdoses to kill his female victims. In September 1900, chloroform was implicated in the murder of the U.S. businessman [William Marsh Rice](/source/William_Marsh_Rice). The serial killer [John Wayne Gacy](/source/John_Wayne_Gacy) chloroformed many of his victims. Chloroform was deemed a factor in the alleged murder of a woman in 1991, when she was asphyxiated while asleep.[69] In 2002, 13-year-old [Kacie Woody](/source/Murder_of_Kacie_Woody) was sedated with chloroform when she was abducted by David Fuller and during the time that he had her, before he shot and killed her.[70] In a 2007 plea bargain, a man confessed to using [stun guns](/source/Electroshock_weapon) and chloroform to sexually assault minors.[71]

The use of chloroform as an [incapacitating agent](/source/Incapacitating_agent) has become widely recognized, bordering on [cliché](/source/Clich%C3%A9), through the adoption by [crime fiction](/source/Crime_fiction) authors of plots involving criminals' use of chloroform-soaked rags to render victims unconscious. However, it is nearly impossible to incapacitate someone using chloroform in this way.[72] It takes at least five minutes of inhalation of chloroform to render a person unconscious. Most criminal cases involving chloroform involve co-administration of another drug, such as [alcohol](/source/Ethanol) or [diazepam](/source/Diazepam), or the victim being complicit in its administration. After a person has lost consciousness owing to chloroform inhalation, a continuous volume must be administered, and the chin must be supported to keep the tongue from obstructing the airway, a difficult procedure, typically requiring the skills of an [anesthesiologist](/source/Anesthesiologist). In 1865, as a direct result of the criminal reputation chloroform had gained, the medical journal *[The Lancet](/source/The_Lancet)* offered a "permanent scientific reputation" to anyone who could demonstrate "instantaneous insensibility", i.e. loss of consciousness, using chloroform.[73]

## Safety

### Exposure

Chloroform is formed as a by-product of [water chlorination](/source/Water_chlorination), along with a range of other [disinfection by-products](/source/Disinfection_by-product), and it is therefore often present in municipal tap water and swimming pools. Reported ranges vary considerably, but are generally below the current health standard for total [trihalomethanes](/source/Trihalomethanes) (THMs) of 100 μg/L.[74]

Historically, chloroform exposure may well have been higher, owing to its common use as an anesthetic, as an ingredient in cough syrups, and as a constituent of [tobacco smoke](/source/Tobacco_smoke), where [DDT](/source/DDT) had previously been used as a [fumigant](/source/Fumigant).[75]

### Pharmacology

Chloroform is well absorbed, metabolized, and eliminated rapidly by mammals after oral, inhalation, or dermal exposure. Accidental splashing into the eyes has caused irritation.[41] Prolonged dermal exposure can result in the development of sores as a result of [defatting](/source/Defatting_(medical)). Elimination is primarily through the lungs as chloroform and carbon dioxide; less than 1% is excreted in the urine.[42]

Chloroform is metabolized in the liver by the [cytochrome P-450](/source/Cytochrome_P-450) enzymes, by oxidation to trichloromethanol and by reduction to the dichloromethyl [free radical](/source/Free_radical). Other metabolites of chloroform include [hydrochloric acid](/source/Hydrochloric_acid) and diglutathionyl dithiocarbonate, with [carbon dioxide](/source/Carbon_dioxide) as the predominant end-product of metabolism.[76]

Like most other general anesthetics and sedative-hypnotic drugs, chloroform is a [positive allosteric modulator](/source/Allosteric_modulator) at [GABAA receptors](/source/GABAA_receptor).[77] Chloroform causes depression of the [central nervous system](/source/Central_nervous_system) (CNS), ultimately producing deep [coma](/source/Coma) and respiratory center depression.[76] When ingested, chloroform causes symptoms similar to those seen after inhalation. Serious illness has followed ingestion of 7.5 g (0.26 oz). The mean lethal oral dose in an adult is estimated at 45 g (1.6 oz).[41]

The anesthetic use of chloroform has been discontinued, because it caused deaths from respiratory failure and cardiac arrhythmias. Following chloroform-induced anesthesia, some patients suffered [nausea](/source/Nausea), [vomiting](/source/Vomiting), [hyperthermia](/source/Hyperthermia), [jaundice](/source/Jaundice), and coma owing to [hepatic dysfunction](/source/Hepatic_dysfunction). At autopsy, liver [necrosis](/source/Necrosis) and degeneration have been observed.[41] The hepatotoxicity and nephrotoxicity of chloroform is thought to be due largely to [phosgene](/source/Phosgene), one of its metabolites.[76]

### Conversion to phosgene

Chloroform converts slowly in the presence of UV light and air to the extremely poisonous gas [phosgene](/source/Phosgene) (COCl2), releasing [HCl](/source/HCl) in the process.[78]

- 2 CHCl3 + O2 → 2 COCl2 + 2 HCl

To prevent accidents, commercial chloroform is stabilized with [ethanol](/source/Ethanol) or [amylene](/source/Pentene), but samples that have been recovered or dried no longer contain any stabilizer. Amylene has been found to be ineffective, and the phosgene can affect analytes in samples, lipids, and nucleic acids dissolved in or extracted with chloroform.[79] When ethanol is used as a stabiliser for chloroform, it reacts with phosgene (which is soluble in chloroform) to form the relatively harmless [diethyl carbonate](/source/Diethyl_carbonate) ester:

- 2 CH3CH2OH + COCl2 → CO3(CH2CH3)2 + 2 HCl

Phosgene and HCl can be removed from chloroform by washing with saturated aqueous [carbonate](/source/Carbonate) solutions, such as [sodium bicarbonate](/source/Sodium_bicarbonate). This procedure is simple and results in harmless products. Phosgene reacts with water to form [carbon dioxide](/source/Carbon_dioxide) and HCl,[80] and the carbonate salt [neutralizes](/source/Neutralization_(chemistry)) the resulting acid.[81]

Suspected samples can be tested for phosgene using filter paper which when treated with 5% [diphenylamine](/source/Diphenylamine), 5% [dimethylaminobenzaldehyde](/source/Dimethylaminobenzaldehyde) in [ethanol](/source/Ethanol), and then dried, turns yellow in the presence of phosgene vapour.[82] There are several [colorimetric](/source/Colorimetry) and [fluorometric](/source/Fluorometry) reagents for phosgene, and it can also be quantified using [mass spectrometry](/source/Mass_spectrometry).[83]

### Regulation

Chloroform is suspected of causing [cancer](/source/Cancer) (i.e. it is possibly [carcinogenic](/source/Carcinogen), [IARC Group 2B](/source/IARC_Group_2B)) as per the [International Agency for Research on Cancer](/source/International_Agency_for_Research_on_Cancer) (IARC) Monograph. There is no convincing evidence that chloroform causes cancer in humans.[84]

It is classified as an [extremely hazardous substance](/source/List_of_extremely_hazardous_substances) in the United States, as defined in Section 302 of the US [Emergency Planning and Community Right-to-Know Act](/source/Emergency_Planning_and_Community_Right-to-Know_Act) (42 U.S.C. 11002), and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.[85]

## Bioremediation of chloroform

Some [anaerobic bacteria](/source/Anaerobic_organism) use chloroform for respiration, termed [organohalide respiration](/source/Halorespiration), converting it to [dichloromethane](/source/Dichloromethane).[86][87]

## Gallery

		- CHCl3 measured by the Advanced Global Atmospheric Gases Experiment ([AGAGE](http://agage.mit.edu/)) in the lower atmosphere ([troposphere](/source/Troposphere)) at stations around the world. Abundances are given as pollution free monthly mean mole fractions in [parts-per-trillion](/source/Parts-per_notation) (ppt).

## References

1. **[^](#cite_ref-1)** Gregory, William, A Handbook of Organic Chemistry (Third edition corrected and much extended), 1852, page 177

1. **[^](#cite_ref-2)** Daniel Pereira Gardner, Medicinal Chemistry for the Use of Students and the Profession: Being a Manual of the Science, with Its Applications to Toxicology, Physiology, Therapeutics, Hygiene, Etc (1848), page 271

1. ^ [***a***](#cite_ref-PGCH_3-0) [***b***](#cite_ref-PGCH_3-1) [***c***](#cite_ref-PGCH_3-2) [***d***](#cite_ref-PGCH_3-3) NIOSH Pocket Guide to Chemical Hazards. ["#0127"](https://www.cdc.gov/niosh/npg/npgd0127.html). [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health) (NIOSH).

1. **[^](#cite_ref-PubChem-2018_4-0)** Toxicity on [PubChem](https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity) [Archived](https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Toxicity) 17 August 2018 at the [Wayback Machine](/source/Wayback_Machine)

1. **[^](#cite_ref-5)** Lewis, Richard J. (2012). *Sax's Dangerous Properties of Industrial Materials* (12th ed.). Wiley. [ISBN](/source/ISBN_(identifier)) [978-0-470-62325-1](https://en.wikipedia.org/wiki/Special:BookSources/978-0-470-62325-1).

1. **[^](#cite_ref-6)** ["Chloroform"](https://www.epa.gov/sites/default/files/2016-09/documents/chloroform.pdf) (PDF). *Environmental Protection Agency*. September 2016. Retrieved 19 February 2024.

1. **[^](#cite_ref-IDLH_7-0)** ["Chloroform"](https://www.cdc.gov/niosh/idlh/67663.html). *Immediately Dangerous to Life or Health Concentrations*. [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health).

1. **[^](#cite_ref-PubChem_8-0)** ["PubChem: Safety and Hazards – GHS Classification"](https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards). National Center for Biotechnology Information, U.S. National Library of Medicine. [Archived](https://web.archive.org/web/20180817125017/https://pubchem.ncbi.nlm.nih.gov/compound/6212#section=Safety-and-Hazards) from the original on 17 August 2018. Retrieved 17 August 2018.

1. **[^](#cite_ref-iupac2013_9-0)** "Front Matter". *Nomenclature of Organic Chemistry: IUPAC Recommendations and Preferred Names 2013 (Blue Book)*. Cambridge: [The Royal Society of Chemistry](/source/Royal_Society_of_Chemistry). 2014. p. 661. [doi](/source/Doi_(identifier)):[10.1039/9781849733069-FP001](https://doi.org/10.1039%2F9781849733069-FP001). [ISBN](/source/ISBN_(identifier)) [978-0-85404-182-4](https://en.wikipedia.org/wiki/Special:BookSources/978-0-85404-182-4). The retained names 'bromoform' for HCBr3, 'chloroform' for HCCl3, and 'iodoform' for HCI3 are acceptable in general nomenclature. Preferred IUPAC names are substitutive names.

1. ^ [***a***](#cite_ref-Ullmann_10-0) [***b***](#cite_ref-Ullmann_10-1) [***c***](#cite_ref-Ullmann_10-2) [***d***](#cite_ref-Ullmann_10-3) [***e***](#cite_ref-Ullmann_10-4) Rossberg, M.; et al. "Chlorinated Hydrocarbons". *[Ullmann's Encyclopedia of Industrial Chemistry](/source/Ullmann's_Encyclopedia_of_Industrial_Chemistry)*. Weinheim: Wiley-VCH. [doi](/source/Doi_(identifier)):[10.1002/14356007.a06_233.pub2](https://doi.org/10.1002%2F14356007.a06_233.pub2). [ISBN](/source/ISBN_(identifier)) [978-3-527-30673-2](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-30673-2).

1. **[^](#cite_ref-11)** ["Ether and Chloroform"](http://www.history.com/topics/ether-and-chloroform). 26 April 2010. [Archived](https://web.archive.org/web/20180324191303/https://www.history.com/topics/ether-and-chloroform) from the original on 24 March 2018. Retrieved 24 April 2018.

1. **[^](#cite_ref-12)** "Chloroform [MAK Value Documentation, 2000]". *The MAK-Collection for Occupational Health and Safety = 20–58*. 2012. pp. 20–58. [doi](/source/Doi_(identifier)):[10.1002/3527600418.mb6766e0014](https://doi.org/10.1002%2F3527600418.mb6766e0014). [ISBN](/source/ISBN_(identifier)) [978-3-527-60041-0](https://en.wikipedia.org/wiki/Special:BookSources/978-3-527-60041-0).

1. **[^](#cite_ref-13)** ["Illustrated Glossary of Organic Chemistry - Chloroform"](http://www.chem.ucla.edu/~harding/IGOC/C/chloroform.html). *www.chem.ucla.edu*. Retrieved 29 December 2022.

1. **[^](#cite_ref-14)** ["Chloroform - Etymology, Origin & Meaning"](https://www.etymonline.com/word/chloroform). *etymonline*. Retrieved 23 November 2025.

1. **[^](#cite_ref-15)** Cappelletti, M. (2012). "Microbial degradation of chloroform". *Applied Microbiology and Biotechnology*. **96** (6): 1395–409. [doi](/source/Doi_(identifier)):[10.1007/s00253-012-4494-1](https://doi.org/10.1007%2Fs00253-012-4494-1). [PMID](/source/PMID_(identifier)) [23093177](https://pubmed.ncbi.nlm.nih.gov/23093177). [S2CID](/source/S2CID_(identifier)) [12429523](https://api.semanticscholar.org/CorpusID:12429523).

1. **[^](#cite_ref-16)** Jiao, Yi; et al. (2018). "Halocarbon Emissions from a Degraded Forested Wetland in Coastal South Carolina Impacted by Sea Level Rise". *ACS Earth and Space Chemistry*. **2** (10): 955–967. [Bibcode](/source/Bibcode_(identifier)):[2018ESC.....2..955J](https://ui.adsabs.harvard.edu/abs/2018ESC.....2..955J). [doi](/source/Doi_(identifier)):[10.1021/acsearthspacechem.8b00044](https://doi.org/10.1021%2Facsearthspacechem.8b00044). [S2CID](/source/S2CID_(identifier)) [134649348](https://api.semanticscholar.org/CorpusID:134649348).

1. **[^](#cite_ref-17)** Moldenhawer (1830). ["Verfahren den Spiritus von dem Fuselöl auf leichte Weise zu befreien"](https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222) [Procedure for freeing ethanol of fusel oil in an easy way]. *Magazin für Pharmacie*. **8** (31): 222–227. [Archived](https://web.archive.org/web/20200729120000/https://books.google.com/books?id=a_E3AAAAMAAJ&pg=PA222) from the original on 29 July 2020. Retrieved 6 May 2016.

1. **[^](#cite_ref-18)** Defalque, Ray J.; Wright, A. J. (2000). ["Was chloroform produced before 1831?"](https://doi.org/10.1097%2F00000542-200001000-00060). *Anesthesiology*. **92** (1): 290–291. [doi](/source/Doi_(identifier)):[10.1097/00000542-200001000-00060](https://doi.org/10.1097%2F00000542-200001000-00060). [PMID](/source/PMID_(identifier)) [10638939](https://pubmed.ncbi.nlm.nih.gov/10638939).

1. **[^](#cite_ref-19)** Guthrie, Samuel (1832). ["New mode of preparing a spirituous solution of chloric ether"](https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64). *The American Journal of Science and Arts*. **21**: 64–65 and 405–408. [Archived](https://web.archive.org/web/20200729135541/https://books.google.com/books?id=iuzRAAAAMAAJ&pg=PA64) from the original on 29 July 2020. Retrieved 6 May 2016.

1. **[^](#cite_ref-20)** Guthrie, Ossian (1887). [*Memoirs of Dr. Samuel Guthrie, and the History of the Discovery of Chloroform*](https://archive.org/details/39002011125375.med.yale.edu). Chicago: George K. Hazlitt & Co. p. [1](https://archive.org/details/39002011125375.med.yale.edu/page/n43).

1. **[^](#cite_ref-21)** Stratmann, Linda (2003). ["Chapter 2"](https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30). *Chloroform: The Quest for Oblivion*. Stroud: Sutton Publishing. [ISBN](/source/ISBN_(identifier)) [978-0-7524-9931-4](https://en.wikipedia.org/wiki/Special:BookSources/978-0-7524-9931-4). [Archived](https://web.archive.org/web/20200729120316/https://books.google.com/books?id=VvA7AwAAQBAJ&pg=PT30) from the original on 29 July 2020. Retrieved 6 May 2016.

1. **[^](#cite_ref-22)** Liebig, Justus von (1831). ["Ueber die Zersetzung des Alkohols durch Chlor"](https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462) [On the decomposition of alcohol by chlorine]. *Annalen der Physik und Chemie*. **99** (11): 444. [Bibcode](/source/Bibcode_(identifier)):[1831AnP....99..444L](https://ui.adsabs.harvard.edu/abs/1831AnP....99..444L). [doi](/source/Doi_(identifier)):[10.1002/andp.18310991111](https://doi.org/10.1002%2Fandp.18310991111). [Archived](https://web.archive.org/web/20170510154137/https://babel.hathitrust.org/cgi/pt?id=uc1.a0002753747;view=1up;seq=462) from the original on 10 May 2017. Retrieved 6 May 2016.

1. **[^](#cite_ref-23)** Liebig, Justus von (1832). ["Ueber die Verbindungen, welche durch die Einwirkung des Chlors auf Alkohol, Aether, ölbildendes Gas und Essiggeist entstehen"](https://babel.hathitrust.org/cgi/pt?id=wu.89048351662&view=1up&seq=861) [On the compounds which arise by the reaction of chlorine with alcohol [ethanol], ether [diethyl ether], oil-forming gas [ethylene], and spirit of vinegar [acetone]]. *Annalen der Physik und Chemie*. **100** (2): 243–295. [Bibcode](/source/Bibcode_(identifier)):[1832AnP...100..243L](https://ui.adsabs.harvard.edu/abs/1832AnP...100..243L). [doi](/source/Doi_(identifier)):[10.1002/andp.18321000206](https://doi.org/10.1002%2Fandp.18321000206). On pages 259–265, Liebig describes *Chlorkohlenstoff* ("carbon chloride", chloroform), but on p. 264, Liebig incorrectly states that the [empirical formula](/source/Empirical_formula) of chloroform is C2Cl5.

1. **[^](#cite_ref-24)** Soubeiran, Eugène (1831). ["Recherches sur quelques combinaisons du chlore"](https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115) [Investigations into some compounds of chlorine]. *Annales de Chimie et de Physique*. Série 2. **48**: 113–157. [Archived](https://web.archive.org/web/20170510154147/https://babel.hathitrust.org/cgi/pt?id=ien.35556014127963;view=1up;seq=115) from the original on 10 May 2017. Retrieved 6 May 2016. - Reprinted in Soubeiran, Eugène (1831). ["Recherches sur quelques combinaisons du chlore"](https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657) [Investigations on some compounds of chlorine]. *Journal de Pharmacie et des Sciences Accessoires*. **17**: 657–672. [Archived](https://web.archive.org/web/20200729112744/https://books.google.com/books?id=QP1BAAAAcAAJ&pg=PA657) from the original on 29 July 2020. Retrieved 6 May 2016. - Reprinted in Soubeiran, Eugène (1832). ["Suite des recherches sur quelques combinaisons du chlore"](https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1) [Continuation of investigations on some compounds of chlorine]. *Journal de Pharmacie et des Sciences Accessoires*. **18**: 1–24. [Archived](https://web.archive.org/web/20200729121309/https://books.google.com/books?id=aBZJAQAAMAAJ&pg=PA1) from the original on 29 July 2020. Retrieved 6 May 2016.

1. **[^](#cite_ref-25)** Dumas, J.-B. (1834). "Récherches rélative à l'action du chlore sur l'alcool" [Experiments regarding the action of chlorine on alcohol]. *L'Institut, Journal Général des Sociétés et Travaux Scientifiques de la France et de l'Étranger*. **2**: 106–108 and 112–115. - Reprinted in Dumas, J.-B. (1834). ["Untersuchung über die Wirkung des Chlors auf den Alkohol"](https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668) [Investigation of the action of chlorine on alcohol]. *Annalen der Physik und Chemie*. **107** (42): 657–673. [Bibcode](/source/Bibcode_(identifier)):[1834AnP...107..657D](https://ui.adsabs.harvard.edu/abs/1834AnP...107..657D). [doi](/source/Doi_(identifier)):[10.1002/andp.18341074202](https://doi.org/10.1002%2Fandp.18341074202). [Archived](https://web.archive.org/web/20170510152609/https://babel.hathitrust.org/cgi/pt?id=umn.31951d00316736l;view=1up;seq=668) from the original on 10 May 2017. Retrieved 12 May 2016. On p. 653, Dumas states chloroform's empirical formula: 1. 1. *"Es scheint mir also erweisen, dass die von mir analysirte Substance, … zur Formel hat: C2H2Cl6."* (Thus it seems to me to show that the substance [that was] analyzed by me … has as [its empirical] formula: C2H2Cl6.) [Note: The coefficients of his empirical formula must be halved.] 1. Dumas then notes that chloroform's simple [empirical formula](/source/Empirical_formula) resembles that of [formic acid](/source/Formic_acid). Furthermore, if chloroform is boiled with [potassium hydroxide](/source/Potassium_hydroxide), one of the products is [potassium formate](/source/Potassium_formate). On p. 654, Dumas names chloroform: 1. *"Diess hat mich veranlasst diese Substanz mit dem Namen 'Chloroform' zu belegen."* (This caused me to bestow this substance with the name "chloroform" [i.e., formyl chloride or chloride of formic acid].) - Reprinted in Dumas, J.-B. (1835). ["Ueber die Wirkung des Chlors auf den Alkohol"](https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542) [On the action of chlorine on alcohol]. *Annalen der Pharmacie*. **16** (2): 164–171. [doi](/source/Doi_(identifier)):[10.1002/jlac.18350160213](https://doi.org/10.1002%2Fjlac.18350160213). [Archived](https://web.archive.org/web/20170510152601/https://babel.hathitrust.org/cgi/pt?id=uva.x002457902;view=1up;seq=542) from the original on 10 May 2017. Retrieved 12 May 2016.

1. ^ [***a***](#cite_ref-pdf1_26-0) [***b***](#cite_ref-pdf1_26-1) Defalque, R. J.; Wright, A. J. (2004). ["The short, tragic life of Robert M. Glover"](http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf) (PDF). *Anaesthesia*. **59** (4): 394–400. [doi](/source/Doi_(identifier)):[10.1111/j.1365-2044.2004.03671.x](https://doi.org/10.1111%2Fj.1365-2044.2004.03671.x). [PMID](/source/PMID_(identifier)) [15023112](https://pubmed.ncbi.nlm.nih.gov/15023112). [S2CID](/source/S2CID_(identifier)) [46428403](https://api.semanticscholar.org/CorpusID:46428403). [Archived](https://web.archive.org/web/20160309080158/http://www.ph.ucla.edu/epi/snow/anaesthesia59_394_400_2004.pdf) (PDF) from the original on 9 March 2016.

1. ^ [***a***](#cite_ref-Gordon2002_27-0) [***b***](#cite_ref-Gordon2002_27-1) Gordon, H. Laing (November 2002). [*Sir James Young Simpson and Chloroform (1811–1870)*](https://books.google.com/books?id=pYer05UwKBYC&pg=PA106). Minerva Group. pp. 106–109. [ISBN](/source/ISBN_(identifier)) [978-1-4102-0291-8](https://en.wikipedia.org/wiki/Special:BookSources/978-1-4102-0291-8). [Archived](https://web.archive.org/web/20160506214333/https://books.google.com/books?id=pYer05UwKBYC&pg=PA106) from the original on 6 May 2016. Retrieved 5 January 2016.

1. **[^](#cite_ref-eb_28-0)** ["Sir James Young Simpson"](https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet). *Encyclopædia Britannica*. [Archived](https://web.archive.org/web/20130727130133/https://www.britannica.com/EBchecked/topic/545447/Sir-James-Young-Simpson-1st-Baronet) from the original on 27 July 2013. Retrieved 23 August 2013.

1. ^ [***a***](#cite_ref-Snow1858_29-0) [***b***](#cite_ref-Snow1858_29-1) [***c***](#cite_ref-Snow1858_29-2) Snow, John (1858). [*On Chloroform and Other Anaesthetics and Their Action and Administration*](https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler). London: John Churchill. pp. 82–85. [Archived](http://archive.wikiwix.com/cache/20151123021418/https://archive.org/stream/onchloroformothe1858snow#page/82/mode/2up/search/inhaler) from the original on 23 November 2015.

1. ^ [***a***](#cite_ref-Worling_30-0) [***b***](#cite_ref-Worling_30-1) [***c***](#cite_ref-Worling_30-2) Worling, P.M. (1998). "Duncan and Flockhart: the Story of Two Men and a Pharmacy". *Pharmaceutical Historian*. **28** (2): 28–33. [PMID](/source/PMID_(identifier)) [11620310](https://pubmed.ncbi.nlm.nih.gov/11620310).

1. ^ [***a***](#cite_ref-Sykes_31-0) [***b***](#cite_ref-Sykes_31-1) Sykes, W.S. (1960). *Essays on the First Hundred Years of Anaesthesia*. Vol. 2. Edinburgh: Churchill Livingstone. p. 30. [ISBN](/source/ISBN_(identifier)) [0-443-02866-4](https://en.wikipedia.org/wiki/Special:BookSources/0-443-02866-4). {{[cite book](https://en.wikipedia.org/wiki/Template:Cite_book)}}: ISBN / Date incompatibility ([help](https://en.wikipedia.org/wiki/Help:CS1_errors#invalid_isbn_date))

1. ^ [***a***](#cite_ref-Rushman_32-0) [***b***](#cite_ref-Rushman_32-1) Rushman, G.B.; Davies, N.J.H.; Atkinson, R.S. (1996). *A Short History of Anaesthesia: the First 150 Years*. Oxford: Butterworth Heinemann. p. 28. [ISBN](/source/ISBN_(identifier)) [0-7506-3066-3](https://en.wikipedia.org/wiki/Special:BookSources/0-7506-3066-3).

1. **[^](#cite_ref-33)** Paulsen, P. J.; Cooke, W. D. (1 September 1963). "Preparation of Deuterated Solvents for Nuclear Magnetic Resonance Spectrometry". *Analytical Chemistry*. **35** (10): 1560. [Bibcode](/source/Bibcode_(identifier)):[1963AnaCh..35.1560P](https://ui.adsabs.harvard.edu/abs/1963AnaCh..35.1560P). [doi](/source/Doi_(identifier)):[10.1021/ac60203a072](https://doi.org/10.1021%2Fac60203a072).

1. **[^](#cite_ref-34)** Breuer, F. W. (1935). "Chloroform-d (Deuteriochloroform)1". *Journal of the American Chemical Society*. **57** (11): 2236–2237. [Bibcode](/source/Bibcode_(identifier)):[1935JAChS..57.2236B](https://ui.adsabs.harvard.edu/abs/1935JAChS..57.2236B). [doi](/source/Doi_(identifier)):[10.1021/ja01314a058](https://doi.org/10.1021%2Fja01314a058).

1. **[^](#cite_ref-35)** Kluger, Ronald (1964). "A Convenient Preparation of Chloroform-d1". *The Journal of Organic Chemistry*. **29** (7): 2045–2046. [doi](/source/Doi_(identifier)):[10.1021/jo01030a526](https://doi.org/10.1021%2Fjo01030a526).

1. **[^](#cite_ref-36)** Helmenstine, Anne (17 March 2020). ["Bleach and Alcohol Make Chloroform - Why You Shouldn't Mix Disinfectants"](https://sciencenotes.org/bleach-and-alcohol-make-chloroform-why-you-shouldnt-mix-disinfectants/). *Science Notes and Projects*. Retrieved 23 November 2025.

1. **[^](#cite_ref-37)** Allen, Dale (22 May 2018). ["The Dangers of Mixing Bleach and Alcohol"](https://www.thechemicalsafetyassociation.org/post/dangers-of-mixing-bleach-alcohol). *IACS*. Retrieved 23 November 2025.

1. **[^](#cite_ref-38)** ["Chlorodifluoromethane | chemical compound"](https://www.britannica.com/science/chlorodifluoromethane). *Encyclopedia Britannica*. [Archived](https://web.archive.org/web/20210717174046/https://www.britannica.com/science/chlorodifluoromethane) from the original on 17 July 2021. Retrieved 8 September 2021.

1. **[^](#cite_ref-39)** Wiley, G. R.; Miller, S. I. (1972). "Thermodynamic parameters for hydrogen bonding of chloroform with Lewis bases in cyclohexane. Proton magnetic resonance study". *Journal of the American Chemical Society*. **94** (10): 3287–3293. [Bibcode](/source/Bibcode_(identifier)):[1972JAChS..94.3287W](https://ui.adsabs.harvard.edu/abs/1972JAChS..94.3287W). [doi](/source/Doi_(identifier)):[10.1021/ja00765a001](https://doi.org/10.1021%2Fja00765a001).

1. **[^](#cite_ref-40)** Kwak, K.; Rosenfeld, D. E.; Chung, J. K.; Fayer, M. D. (2008). ["Solute-solvent complex switching dynamics of chloroform between acetone and dimethylsulfoxide-two-dimensional IR chemical exchange spectroscopy"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2646412). *The Journal of Physical Chemistry B*. **112** (44): 13906–13915. [doi](/source/Doi_(identifier)):[10.1021/jp806035w](https://doi.org/10.1021%2Fjp806035w). [PMC](/source/PMC_(identifier)) [2646412](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2646412). [PMID](/source/PMID_(identifier)) [18855462](https://pubmed.ncbi.nlm.nih.gov/18855462).

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1. ^ [***a***](#cite_ref-pth_42-0) [***b***](#cite_ref-pth_42-1) Leikin, Jerrold B.; Paloucek, Frank P., eds. (2008). "Chloroform". *Poisoning and Toxicology Handbook* (4th ed.). Informa. p. 774.

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## External links

Wikimedia Commons has media related to [Chloroform](https://commons.wikimedia.org/wiki/Category:Chloroform).

- [Chloroform "The Molecular Lifesaver"](http://www.chm.bris.ac.uk/motm/chloroform/chloroformv.htm) – An article at Oxford University providing facts about chloroform.

- [Chloroform Administration](https://archive.org/details/0055-0000-7637-0000-0-0000-0000-0) – a short film of anaesthetic chloroform application, filmed in the 1930s

- [Concise International Chemical Assessment Document 58](http://www.inchem.org/documents/cicads/cicads/cicad58.htm)

- IARC Summaries & Evaluations: [Vol. 1 (1972)](http://www.inchem.org/documents/iarc/vol01/chloroform.html), [Vol. 20 (1979)](http://www.inchem.org/documents/iarc/vol20/chloroform.html), [Suppl. 7 (1987)](http://www.inchem.org/documents/iarc/suppl7/chloroform.html), [Vol. 73 (1999)](http://www.inchem.org/documents/iarc/vol73/73-05.html)

- [International Chemical Safety Card 0027](https://chemicalsafety.ilo.org/dyn/icsc/showcard.display?p_lang=en&p_card_id=0027&p_version=2)

- NIOSH Pocket Guide to Chemical Hazards. ["#0127"](https://www.cdc.gov/niosh/npg/npgd0127.html). [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health) (NIOSH).

- [NIST Standard Reference Database](http://webbook.nist.gov/cgi/cbook.cgi?ID=67-66-3&Units=SI&cTG=on&cTC=on&cTP=on)

v t e Halomethanes By substitution pattern Unsubstituted CH4 Monosubstituted CH3F CH3Cl CH3Br CH3I CH3At Disubstituted X,X CH2F2 CH2Cl2 CH2Br2 CH2I2 X,Y CH2ClF CH2BrF CH2FI CH2BrCl CH2ClI CH2BrI Trisubstituted X,X,X CHF3 CHCl3 CHBr3 CHI3 X,X,Y CHClF2 CHBrF2 CHF2I CHCl2F CHBr2F CHFI2 CHBrCl2 CHCl2I CHBr2Cl CHClI2 CHBr2I CHBrI2 X,Y,Z CHBrClF CHClFI CHBrFI CHBrClI Tetrasubstituted X,X,X,X CF4 CCl4 CBr4 CI4 X,X,X,Y CFI3 CClF3 CBrF3 CF3I CCl3F CBr3F CBrCl3 CCl3I CBr3Cl CClI3 CBr3I CBrI3 X,X,Y,Y CCl2F2 CBr2F2 CF2I2 CBr2Cl2 CCl2I2 CBr2I2 X,X,Y,Z CBrClF2 CClF2I CBrF2I CBrCl2F CCl2FI CBr2ClF CClFI2 CBr2FI CBrFI2 CBrCl2I CBr2ClI CBrClI2 X,Y,Z,W CBrClFI Special types Chiral CHBrClF CHClFI CHBrFI CHBrClI CBrClFI Isotopologues C2H2Cl2 (CD2Cl2) C2HCl3 (CDCl3) C2H3I (CD3I)

v t e General anesthetics (N01A) Inhalational Chloroform‡ Cyclopropane‡ Desflurane Diethyl ether‡ Enflurane Ethylene‡ Fluroxene‡ Halothane Isoflurane# Methoxyflurane Methoxypropane‡ Nitrous oxide# Sevoflurane# Trichloroethylene‡ Thiomethoxyflurane§ Vinyl ether‡ Xenon Injection Phenols Cipepofol (ciprofol)† Fospropofol Propofol# Barbiturates Amobarbital Hexobarbital Methohexital Narcobarbital Thiamylal Thiopental# Thiotetrabarbital Benzodiazepines Midazolam# Diazepam# Lorazepam# Remimazolam Opioids Morphine# Oxycodone Anileridine‡ Embutramide‡ Fentanyl# Alfentanil Phenoperidine Remifentanil÷ Sufentanil Arylcyclohexylamines Esketamine Ketamine# Phencyclidine‡ Tiletamine Neuroactive steroids Alfadolone Alfaxalone Hydroxydione Others Etomidate Propoxate Metomidate Propanidid‡ #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

Pharmacodynamics v t e GABAA receptor positive modulators Alcohols Brometone Butanol Chloralodol Chlorobutanol (cloretone) Ethanol (alcohol) (alcoholic drink) Ethchlorvynol Isobutanol Isopropanol Menthol Methanol Methylpentynol Pentanol Petrichloral Propanol tert-Butanol (2M2P) tert-Pentanol (2M2B) Tribromoethanol Trichloroethanol Triclofos Trifluoroethanol Barbiturates (-)-DMBB Allobarbital Alphenal Amobarbital Aprobarbital Barbexaclone Barbital Benzobarbital Benzylbutylbarbiturate Brallobarbital Brophebarbital Butabarbital/Secbutabarbital Butalbital Buthalital Butobarbital Butallylonal Carbubarb Crotylbarbital Cyclobarbital Cyclopentobarbital Difebarbamate Enallylpropymal Ethallobarbital Eterobarb Febarbamate Heptabarb Heptobarbital Hexethal Hexobarbital Methallatal Metharbital Methitural Methohexital Methylphenobarbital Narcobarbital Nealbarbital Pentobarbital Phenallymal Phenobarbital Phetharbital Primidone Probarbital Propallylonal Propylbarbital Proxibarbital Reposal Secobarbital Sigmodal Spirobarbital Talbutal Tetrabamate Tetrabarbital Thialbarbital Thiamylal Thiobarbital Thiobutabarbital Thiopental Thiotetrabarbital Valofane Vinbarbital Vinylbital Benzodiazepines 2-Oxoquazepam 3-Hydroxyphenazepam Adinazolam Alprazolam Arfendazam Avizafone Bentazepam Bretazenil Bromazepam Bromazolam Brotizolam Camazepam Carburazepam Chlordiazepoxide Ciclotizolam Cinazepam Cinolazepam Clazolam Climazolam Clobazam Clonazepam Clonazolam Cloniprazepam Clorazepate Clotiazepam Cloxazolam CP-1414S Cyprazepam Delorazepam Demoxepam Diazepam Diclazepam Dimdazenil Doxefazepam Elfazepam Estazolam Ethyl carfluzepate Ethyl dirazepate Ethyl loflazepate Etizolam FG-8205 Fletazepam Flubromazepam Flubromazolam Fludiazepam Flunitrazepam Flunitrazolam Flurazepam Flutazolam Flutemazepam Flutoprazepam Fosazepam Gidazepam Halazepam Haloxazolam Iclazepam Imidazenil Irazepine Ketazolam Lofendazam Lopirazepam Loprazolam Lorazepam Lormetazepam Meclonazepam Medazepam Menitrazepam Metaclazepam Mexazolam Midazolam Motrazepam N-Desalkylflurazepam Nifoxipam Nimetazepam Nitrazepam Nitrazepate Nitrazolam Nordazepam Nortetrazepam Oxazepam Oxazolam Phenazepam Pinazepam Pivoxazepam Prazepam Premazepam Proflazepam Pyrazolam QH-II-66 Quazepam Reclazepam Remimazolam Rilmazafone Ripazepam Ro48-6791 Ro48-8684 SH-053-R-CH3-2′F Sulazepam Temazepam Tetrazepam Tolufazepam Triazolam Triflubazam Triflunordazepam (Ro5-2904) Tuclazepam Uldazepam Zapizolam Zolazepam Zomebazam Carbamates Carisbamate Carisoprodol Clocental Cyclarbamate Difebarbamate Emylcamate Ethinamate Febarbamate Felbamate Hexapropymate Hydroxyphenamate Lorbamate Mebutamate Meprobamate Nisobamate Pentabamate Phenprobamate Procymate Styramate Tetrabamate Tybamate Flavonoids 6-Methylapigenin Ampelopsin (dihydromyricetin) Apigenin Baicalein Baicalin Catechin EGC EGCG Hispidulin Linarin Luteolin Rc-OMe Skullcap constituents (e.g., baicalin) Wogonin Imidazoles Etomidate Metomidate Methoxyetomidate Propoxate Isopropoxate Butomidate Iso-butomidate Sec-butomidate CF2-Etomidate CF3-Etomidate CF3-Propoxate Flutomidate 2,6-Dichloro-3-fluoroetomidate Kava constituents 10-Methoxyyangonin 11-Methoxyyangonin 11-Hydroxyyangonin Desmethoxyyangonin 11-Methoxy-12-hydroxydehydrokavain 7,8-Dihydroyangonin Kavain 5-Hydroxykavain 5,6-Dihydroyangonin 7,8-Dihydrokavain 5,6,7,8-Tetrahydroyangonin 5,6-Dehydromethysticin Methysticin 7,8-Dihydromethysticin Yangonin Monoureides Acecarbromal Apronal (apronalide) Bromisoval Carbromal Capuride Ectylurea Neurosteroids Acebrochol Allopregnanolone (brexanolone) Alfadolone Alfaxalone 3α-Androstanediol Androstenol Androsterone Certain anabolic-androgenic steroids Cholesterol Cortisol (hydrocortisone) DHDOC 3α-DHP 5α-DHP 5β-DHP DHT Etiocholanolone ETX-155 Ganaxolone Hydroxydione LPCN-1154 Minaxolone NORA-520 ORG-20599 ORG-21465 P1-185 Posovolone PRAX-114 Pregnanolone (eltanolone) Progesterone Renanolone SAGE-105 SAGE-324 SAGE-516 SAGE-689 SAGE-872 Testosterone THDOC Zuranolone Nonbenzodiazepines Cyclopyrrolones: Eszopiclone Pagoclone Pazinaclone Suproclone Suriclone Zopiclone Imidazopyridines: Alpidem DS-1 Necopidem Saripidem Zolpidem Pyrazolopyrimidines: Divaplon Fasiplon Indiplon Lorediplon Ocinaplon Panadiplon Taniplon Zaleplon Others: Adipiplon AXS-17 (BAER-101, AZD-7325) CGS-8216 CGS-9896 CGS-13767 CGS-20625 CL-218,872 CP-615,003 CTP-354 ELB-139 GBLD-345 Imepitoin JM-1232 L-838,417 Lirequinil (Ro41-3696) Miltirone (rosmariquinone) NS-2664 NS-2710 NS-11394 NS-11821 Pipequaline ROD-188 RWJ-51204 SB-205,384 SX-3228 TGSC01AA TP-003 TPA-023 TP-13 U-89843A U-90042 Viqualine Y-23684 Phenols Cipepofol Fospropofol Propofol Propofol hemisuccinate Thymol Piperidinediones Glutethimide Methyprylon Piperidione Pyrithyldione Pyrazolopyridines Cartazolate Etazolate ICI-190,622 Tracazolate Quinazolinones Afloqualone Cloroqualone Diproqualone Etaqualone Mebroqualone Mecloqualone Methaqualone Methylmethaqualone Nitromethaqualone SL-164 Volatiles/gases Acetone Acetophenone Acetylglycinamide chloral hydrate Aliflurane Benzene Butane Butylene Centalun Chloral Chloral betaine Chloral hydrate Chloroform Cryofluorane Desflurane Dichloralphenazone Dichloromethane Diethyl ether Enflurane Ethyl chloride Ethylene Fluroxene Gasoline Halopropane Halothane Isoflurane Kerosine Methoxyflurane Methoxypropane Nitric oxide Nitrogen Nitrous oxide Norflurane Paraldehyde Propane Propylene Roflurane Sevoflurane Synthane Teflurane Toluene Trichloroethane (methyl chloroform) Trichloroethylene Vinyl ether Others/unsorted 3-Hydroxybutanal α-EMTBL AA-29504 Alogabat Avermectins (e.g., ivermectin) Bromide compounds (e.g., lithium bromide, potassium bromide, sodium bromide) Carbamazepine Chloralose Chlormezanone Clomethiazole Darigabat DEABL Deuterated etifoxine Dihydroergolines (e.g., dihydroergocryptine, dihydroergosine, dihydroergotamine, ergoloid (dihydroergotoxine)) DS2 Efavirenz Etazepine Etifoxine Fenamates (e.g., flufenamic acid, mefenamic acid, niflumic acid, tolfenamic acid) Fluoxetine Flupirtine Hopantenic acid KRM-II-81 Lanthanum Lavender oil Lignans (e.g., 4-O-methylhonokiol, honokiol, magnolol, obovatol) Loreclezole Menthyl isovalerate (validolum) Monastrol Nezavist (DCUK-Oet) Nicotinic acid Nicotinamide NTX-1955 (RO-7308480) Org 25,435 Phenytoin Propanidid Retigabine (ezogabine) Safranal Seproxetine Stiripentol Sulfonylalkanes (e.g., sulfonmethane (sulfonal), tetronal, trional) Terpenoids (e.g., borneol) Topiramate Valerian constituents (e.g., isovaleric acid, isovaleramide, valerenic acid, valerenol) Unsorted benzodiazepine site positive modulators: α-Pinene MRK-409 (MK-0343) TCS-1105 TCS-1205 See also: Receptor/signaling modulators • GABA receptor modulators • GABA metabolism/transport modulators v t e Ionotropic glutamate receptor modulators AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor Agonists: Main site agonists: 5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Pesampator (BIIB-104, PF-04958242) Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists: ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate RAP-219 Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline KARTooltip Kainate receptor Agonists: Main site agonists: 5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol (alcohol) Evans blue NS-3763 Pregnenolone sulfate NMDARTooltip N-Methyl-D-aspartate receptor Agonists: Main site agonists: AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687,414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEATooltip Dehydroepiandrosterone (prasterone) DHEA sulfate (prasterone sulfate) Epipregnanolone sulfate Plazinemdor Pregnenolone sulfate SAGE-201 SAGE-301 SAGE-718 Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel (d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel (NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel (ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel (GLYX-13) ZD-9379; Polyamine site antagonists: Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine; Uncompetitive pore blockers (mostly dizocilpine site): 2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine (SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine CNS-5161 Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine F-17475 Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol; Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine (nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz (CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil (CP-101606); NR2A-selective antagonists: MPX-004 MPX-007 TCN-201 TCN-213; Cations: Hydrogen Magnesium Zinc; Alcohols/volatile anesthetics/related: Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol (alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene; Unknown/unsorted antagonists: ARR-15896 BQ-869 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin (saffron) Unsorted: Allosteric modulators: AGN-241751 See also: Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism/transport modulators v t e Glycine receptor modulators Receptor (ligands) GlyRTooltip Glycine receptor Agonists: β-Alanine β-ABA (BABA) β-AIBA Caesium D-Alanine D-Serine GABA Glycine Hypotaurine Ivermectin L-Alanine L-Proline L-Serine L-Threonine MDL-27531 Milacemide Picolinic acid Propofol Quisqualamine Sarcosine Taurine Positive modulators: Alcohols (e.g., brometone, chlorobutanol (chloretone), ethanol (alcohol), tert-butanol (2M2P), tribromoethanol, trichloroethanol, trifluoroethanol) Alkylbenzene sulfonate Anandamide Barbiturates (e.g., pentobarbital, sodium thiopental) Chlormethiazole D12-116 Dihydropyridines (e.g., nicardipine) Etomidate Ginseng constituents (e.g., ginsenosides (e.g., ginsenoside-Rf)) Glutamic acid (glutamate) Ivermectin Ketamine Neuroactive steroids (e.g., alfaxolone, pregnenolone (eltanolone), pregnenolone acetate, minaxolone, ORG-20599) Nitrous oxide Penicillin G Propofol Tamoxifen Tetrahydrocannabinol Triclofos Tropeines (e.g., atropine, bemesetron, cocaine, LY-278584, tropisetron, zatosetron) Volatiles/gases (e.g., chloral hydrate, chloroform, desflurane, diethyl ether (ether), enflurane, halothane, isoflurane, methoxyflurane, sevoflurane, toluene, trichloroethane (methyl chloroform), trichloroethylene) Xenon Zinc Antagonists: 2-Aminostrychnine 2-Nitrostrychnine 4-Phenyl-4-formyl-N-methylpiperidine αEMBTL Bicuculline Brucine Cacotheline Caffeine Colchicine Colubrine Cyanotriphenylborate Dendrobine Diaboline Endocannabinoids (e.g., 2-AG, anandamide (AEA)) Gaboxadol (THIP) Gelsemine iso-THAZ Isobutyric acid Isonipecotic acid Isostrychnine Laudanosine N-Methylbicuculline N-Methylstrychnine N,N-Dimethylmuscimol Nipecotic acid Pitrazepin Pseudostrychnine Quinolines (e.g., 4-hydroxyquinoline, 4-hydroxyquinoline-3-carboxylic acid, 5,7-CIQA, 7-CIQ, 7-TFQ, 7-TFQA) RU-5135 Sinomenine Strychnine THAZ Thiocolchicoside Tutin Negative modulators: Amiloride Benzodiazepines (e.g., bromazepam, clonazepam, diazepam, flunitrazepam, flurazepam) Corymine Cyanotriphenylborate Daidzein Dihydropyridines (e.g., nicardipine, nifedipine, nitrendipine) Furosemide Genistein Ginkgo constituents (e.g., bilobalide, ginkgolides (e.g., ginkgolide A, ginkgolide B, ginkgolide C, ginkgolide J, ginkgolide M)) Imipramine NBQX Neuroactive steroids (e.g., 3α-androsterone sulfate, 3β-androsterone sulfate, deoxycorticosterone, DHEA sulfate, pregnenolone sulfate, progesterone) Opioids (e.g., codeine, dextromethorphan, dextrorphan, levomethadone, levorphanol, morphine, oripavine, pethidine, thebaine) Picrotoxin (i.e., picrotin and picrotoxinin) PMBA Riluzole Tropeines (e.g., bemesetron, LY-278584, tropisetron, zatosetron) Verapamil Zinc NMDARTooltip N-Methyl-D-aspartate receptor See here instead. Transporter (blockers) GlyT1Tooltip Sodium- and chloride-dependent glycine transporter 1 ACPPB ALX-5407 (NFPS) ASP2535 Bitopertin (RG1678/RO4917838) CP-802079 Ethanol (alcohol) Glycyldodecylamide GSK1018921 Iclepertin LY-2365109 Mardepodect ORG-24598 ORG-25935 (SCH-900435) Pesampator (BIIB-104, PF-04958242) PF-03463275 Sarcosine SNG-12 (Synapsinae) SSR-103,800 SSR-504,734 Tilapertin GlyT2Tooltip Glycine transporter 2 ALX-1393 Amoxapine Ethanol (alcohol) NAGly Opiranserin (VVZ-149) ORG-25543 VVZ-368 See also Receptor/signaling modulators GABA receptor modulators GABAA receptor positive modulators Ionotropic glutamate receptor modulators v t e Serotonin receptor modulators 5-HT1 5-HT1A Agonists: 4-F-5-MeO-pyr-T 5-MeO-pip-T 5-MeO-pyr-T 8-OH-DPAT Adatanserin Amphetamine Antidepressants (e.g., etoperidone, hydroxynefazodone, nefazodone, trazodone, triazoledione, vilazodone, vortioxetine) Atypical antipsychotics (e.g., aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, lurasidone, quetiapine, ziprasidone) Azapirones (e.g., buspirone, eptapirone (F-11440), gepirone, perospirone, tandospirone) Bay R 1531 Befiradol (NLX-112; F-13640) BMY-14802 Cannabidiol Dimemebfe Dopamine Ebalzotan Eltoprazine Enciprazine Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, lisuride, LSD, methylergometrine (methylergonovine), methysergide, pergolide) F-11461 F-12826 F-13714 F-14679 F-15063 F-15599 (NLX-101) F-17464 Flesinoxan Flibanserin Flumexadol GR-46611 Hypidone Lesopitron LY-293284 LY-301317 LY-315712 mCPP Naluzotan NBUMP NLX-204 NLX-266 Osemozotan (MKC-242) Oxaflozane Pardoprunox Piclozotan Rauwolscine Repinotan Roxindole RU-24969 S-14506 S-14671 S-15535 Sarizotan Serotonin (5-HT) SSR-181507 Sunepitron Tryptamines (e.g., 5-CT, 5-MeO-DMT, 5-MT, bufotenin, DMT, indorenate, N-Me-5-HT, psilocin, psilocybin) TGBA01AD TMU4142 U-92016-A Urapidil Vilazodone Xaliproden Yohimbine Positive allosteric modulators: Cannabicyclol (CBL) Oleamide Antagonists: Atypical antipsychotics (e.g., iloperidone, risperidone, sertindole) AV965 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, cyanopindolol, iodocyanopindolol, isamoltane, oxprenolol, penbutolol, pindobind, pindolol, propranolol, tertatolol) BMY-7378 CSP-2503 Dotarizine Ergolines (e.g., metergoline) Flopropione Lecozotan LY-206130 LY-297996 ((–)-LY206130) LY-426965 Mefway Metitepine (methiothepin) MIN-117 (WF-516) MPPF NAN-190 Robalzotan S-15535 SB-272183 SB-649915 SDZ 216-525 Spiperone Spiramide Spiroxatrine UH-301 WAY-100135 WAY-100635 Xylamidine Unknown/unsorted: Acetryptine Carvedilol Ergolines (e.g., ergometrine (ergonovine)) 5-HT1B Agonists: Alniditan Anpirtoline AZ10419369 Benzofurans (e.g., 5-MAPB, 6-MAPB, BK-5-MAPB, BK-6-MAPB) Benzothiophenes (e.g., 5-MAPBT, 6-MAPBT, BK-5-MAPBT) CGS-12066 (CGS-12066A, CGS-12066B) CP-93129 CP-94253 CP-122288 CP-135807 Eltoprazine Ergolines (e.g., bromocriptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) GR-46611 mCPP Methylenedioxyphenethylamines (e.g., MDMA, methylone) PGI-7043 PZKKN-94 RU-24969 Serotonin (5-HT) Triptans (e.g., avitriptan, donitriptan, eletriptan, IS-159, sumatriptan, zolmitriptan) TFMPP Tryptamines (e.g., 5-BT, 5-CT, 5-MT, DMT) Vortioxetine Antagonists: AOP-208 (LB-208) AR-A000002 AZD-3676 Beta blockers (e.g., alprenolol, carteolol, isamoltane, oxprenolol, penbutolol, propranolol, tertatolol) Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 LY-393558 Metitepine (methiothepin) SB-216641 SB-224289 SB-236057 SB-272183 SB-616234 Trelanserin Yohimbine Negative allosteric modulators: 5-HT-moduline Miscellaneous: HG1 (5-HT-moduline antagonist) Unknown/unsorted: Ergolines (e.g., cabergoline, ergometrine (ergonovine), lisuride) 5-HT1D Agonists: Alniditan CGS-12066 (CGS-12066A, CGS-12066B) CP-122288 CP-135807 CP-286601 Ergolines (e.g., bromocriptine, cabergoline, dihydroergotamine, ergotamine, LSD, methysergide) GR-46611 L-694247 L-772405 mCPP PNU-109291 PNU-142633 Serotonin (5-HT) TGBA01AD Triptans (e.g., almotriptan, avitriptan, donitriptan, eletriptan, frovatriptan, IS-159, naratriptan, rizatriptan, sumatriptan, zolmitriptan) Tryptamines (e.g., 5-BT, 5-CT, 5-Et-DMT, 5-MT, 5-(nonyloxy)tryptamine, DMT) Antagonists: BRL-15572 Elzasonan Ergolines (e.g., metergoline) F-12682 F-14258 GR-127935 Ketanserin LY-310762 LY-367642 LY-393558 LY-456219 LY-456220 Metitepine (methiothepin) Mianserin Ritanserin SB-272183 Yohimbine Ziprasidone Negative allosteric modulators: 5-HT-moduline Unknown/unsorted: Acetryptine Ergolines (e.g., lisuride, lysergol, pergolide) 5-HT1E Agonists: BRL-54443 Ergolines (e.g., methysergide) Serotonin (5-HT) Triptans (e.g., eletriptan) Tryptamines (e.g., tryptamine) Antagonists: Metitepine (methiothepin) Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine), lysergol, methylergometrine (methylergonovine) 5-HT1F Agonists: BRL-54443 CP-122288 Ergolines (e.g., bromocriptine, lysergol, methylergometrine (methylergonovine) methysergide) Lasmiditan LY-334370 LY-344864 Serotonin (5-HT) Triptans (e.g., eletriptan, naratriptan, sumatriptan) Tryptamines (e.g., 5-MT) Antagonists: Metitepine (methiothepin) Mianserin Unknown/unsorted: LY-53857 LY-86057 5-HT2 5-HT2A Agonists: 25H/NB series (e.g., 25I-NBF, 25I-NBMD, 25I-NBOH, 25I-NBOMe, 25B-NBOMe, 25C-NBOMe, 25TFM-NBOMe, 2CBCB-NBOMe, 25CN-NBOH, 2CBFly-NBOMe, BMB-202) 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 2C-B-FLY 2CB-Ind 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) AL-34662 AL-37350A Aporphines and noraporphines (e.g., (S)-glaucine, 11-methoxyasimilobine, 2-hydroxy-11-(2-methylallyl)oxynoraporphine) BMB-201 Bromo-DragonFLY Dimemebfe DMBMPP DOx (e.g., DOB, DOC, DOI, DOM) Efavirenz Ergolines (e.g., 1P-LSD, ALD-52, bromocriptine, cabergoline, ergine (LSA), ergometrine (ergonovine), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, methylergometrine (methylergonovine), pergolide) Flumexadol IHCH-7113 Jimscaline Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) O-4310 Oxaflozane PHA-57378 PNU-22394 PNU-181731 RH-34 SCHEMBL5334361 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., BZP, quipazine, TFMPP, VCU-1012) Serotonin (5-HT) TCB-2 TFMFly Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Positive allosteric modulators: AB0124 CTW0404 CTW0419 JPC0323 (R)-Glaucine Oleamide Antagonists: 5-I-R91150 5-MeO-NBpBrT AC-90179 Adatanserin Altanserin Antihistamines (e.g., cyproheptadine, hydroxyzine, ketotifen, perlapine) AMDA Atypical antipsychotics (e.g., amperozide, aripiprazole, asenapine, blonanserin, brexpiprazole, carpipramine, clocapramine, clorotepine, clozapine, fluperlapine, gevotroline, iloperidone, lurasidone, melperone, mosapramine, ocaperidone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, zicronapine, ziprasidone, zotepine) Barettin Butanserin Chlorprothixene Cinanserin CSP-2503 Deramciclane DLX-2270 Dotarizine DSP-6745 Eplivanserin Ergolines (e.g., amesergide, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Fananserin FCE-24379 Flibanserin Glemanserin Irindalone KB-128 Ketanserin KML-010 Landipirdine LY03017 LY-393558 mCPP Medifoxamine Metitepine (methiothepin) Metrenperone MIN-117 (WF-516) MT-1207 Naftidrofuryl Nantenine Nelotanserin NH130 Opiranserin (VVZ-149) Pelanserin Phenoxybenzamine Pimavanserin Pirenperone Pizotifen Pruvanserin R-96544 R-102444 Rauwolscine Ritanserin Roluperidone S-14671 SpAMDA Sarpogrelate Seganserin Serotonin antagonists and reuptake inhibitors (e.g., etoperidone, hydroxynefazodone, lubazodone, mepiprazole, nefazodone, triazoledione, trazodone) Temanogrel Teniloxazine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TGBA01AD Trelanserin Tricyclic antidepressants (e.g., amitriptyline) Typical antipsychotics (e.g., chlorpromazine, fluphenazine, haloperidol, loxapine, perphenazine, pimozide, pipamperone, prochlorperazine, setoperone, spiperone, spiramide, thioridazine, thiothixene, trifluoperazine) Volinanserin Xylamidine Yohimbine Unknown/unsorted: Ergolines (e.g., dihydroergotamine, nicergoline) 5-HT2B Agonists: 4-Methylaminorex Aminorex Amphetamines (e.g., chlorphentermine, cloforex, dexfenfluramine, fenfluramine, levofenfluramine, norfenfluramine) BW-723C86 DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., cabergoline, dihydroergocryptine, dihydroergotamine, ergotamine, methylergometrine (methylergonovine), methysergide, pergolide) Lorcaserin MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) Piperazines (e.g., TFMPP) PNU-22394 Ro60-0175 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, 5-MT, α-Me-5-HT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine) Antagonists: 1-Methylmedmain Agomelatine Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, cariprazine, clozapine, N-desalkylquetiapine (norquetiapine), N-desmethylclozapine (norclozapine), olanzapine, pipamperone, quetiapine, risperidone, ziprasidone) Cyproheptadine EGIS-7625 Ergolines (e.g., amesergide, bromocriptine, lisuride, LY-53857, LY-272015, mesulergine) KB-128 Ketanserin LY-393558 mCPP Medmain Metadoxine Metitepine (methiothepin) Minaprine MW073 Pirenperone Pizotifen Propranolol PRX-08066 Rauwolscine Ritanserin RS-127445 Sarpogrelate SB-200646 SB-204741 SB-206553 SB-215505 SB-221284 SB-228357 SDZ SER-082 Tegaserod Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Trazodone Typical antipsychotics (e.g., chlorpromazine) TIK-301 Yohimbine Unknown/unsorted: Ergolines (e.g., ergometrine (ergonovine)) 5-HT2C Agonists: 2Cs (e.g., 2C-B, 2C-E, 2C-I, 2C-T-2, 2C-T-7, 2C-T-21) 5-Methoxytryptamines (5-MeO-DET, 5-MeO-DiPT, 5-MeO-DMT, 5-MeO-DPT, 5-MT) α-Alkyltryptamines (e.g., 5-Cl-αMT, 5-Fl-αMT, 5-MeO-αET, 5-MeO-αMT, α-Me-5-HT, αET, αMT) A-372159 AL-38022A Alstonine Aporphines and noraporphines (e.g., MQ02-439, (S)-glaucine, nornuciferine, asimilobine, 11-chloroasimilobine, 11-methoxyasimilobine) ATHX-105 Bexicaserin BMB-101 BMB-105 BMB-201 Centhaquine CP-809101 Dimemebfe DLX-2270 DOx (e.g., DOB, DOC, DOI, DOM) Ergolines (e.g., ALD-52, cabergoline, dihydroergotamine, ergine (LSA), ergotamine, lisuride, LA-SS-Az, LSB, LSD, LSD-Pip, LSH, LSP, pergolide) Flumexadol KB-128 Lorcaserin Lumocaserin LY03020 MDxx (e.g., MDA (tenamfetamine), MDMA (midomafetamine), MDOH, MMDA) MK-212 ORG-12962 ORG-37684 Oxaflozane PHA-57378 Phenethylamines (e.g., lophophine, mescaline) Piperazines (e.g., aripiprazole, BZP, mCPP, quipazine, TFMPP) PNU-22394 PNU-181731 PRX-00933 (BVT-933; GW-876167) Ro60-0175 Ro60-0213 Serotonin (5-HT) Tryptamines (e.g., 5-BT, 5-CT, bufotenin, DET, DiPT, DMT, DPT, psilocin, psilocybin, tryptamine, CPI-CG-8) Vabicaserin VR-1065 WAY-629 WAY-161503 YM-348 Positive allosteric modulators: CTW0415 CYD-1-79 JPC0323 Oleamide PNU-69176E VA012 VA240 Antagonists: Adatanserin Agomelatine Atypical antipsychotics (e.g., asenapine, clorotepine, clozapine, fluperlapine, iloperidone, melperone, olanzapine, paliperidone, quetiapine, risperidone, sertindole, ziprasidone, zotepine) Captodiame CEPC Cinanserin Cyproheptadine Deramciclane Desmetramadol Dotarizine DSP-6745 Eltoprazine Ergolines (e.g., amesergide, bromocriptine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) Etoperidone Fluoxetine FR260010 Irindalone Ketanserin Ketotifen Latrepirdine (dimebolin) LY03017 Medifoxamine Metitepine (methiothepin) Nefazodone Pirenperone Pizotifen Propranolol Ritanserin RS-102221 S-14671 SB-200646 SB-206553 SB-221284 SB-228357 SB-242084 SB-243213 SB-247853 SDZ SER-082 Seganserin Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, aptazapine, esmirtazapine, maprotiline, mianserin, mirtazapine) TIK-301 Tramadol Trazodone Tricyclic antidepressants (e.g., amitriptyline, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine, pimozide, pipamperone, thioridazine) Xylamidine Unknown/unsorted: Efavirenz Ergolines (e.g., ergometrine (ergonovine), methylergometrine (methylergonovine)) 5-HT3–7 5-HT3 Agonists: Alcohols (e.g., butanol, ethanol (alcohol), trichloroethanol) m-CPBG Phenylbiguanide Piperazines (e.g., BZP, mCPP, quipazine) RS-56812 Serotonin (5-HT) SR-57227 SR-57227A Tryptamines (e.g., 2-Me-5-HT, 5-CT, bufotenidine (5-HTQ)) Volatiles/gases (e.g., halothane, isoflurane, toluene, trichloroethane) YM-31636 Positive allosteric modulators: 5-Aminoindole 5-Chloroindole 5-Hydroxyindole Catechol Chloroform meta-Chlorophenylbiguanide (mCPBG) Colchicine Ethanol (alcohol) Halothane Indole Isoflurane TMPPAA Antagonists: Alosetron Anpirtoline Arazasetron AS-8112 Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine) Azasetron Batanopride Bemesetron (MDL-72222) Cilansetron CSP-2503 Dazopride Dolasetron Galanolactone Granisetron Itasetron Lerisetron Memantine Ondansetron Palonosetron Ramosetron Renzapride Ricasetron Tedatioxetine Tetracyclic antidepressants (e.g., amoxapine, mianserin, mirtazapine) Thujone Tropanserin Tropisetron Typical antipsychotics (e.g., loxapine) Volatiles/gases (e.g., nitrous oxide, sevoflurane, xenon) Vortioxetine Zacopride Zatosetron Negative allosteric modulators: Bupropion Colchicine Hydroxybupropion Unknown/unsorted: Piperazines (e.g., naphthylpiperazine) 5-HT4 Agonists: 5-MT BIMU8 Capeserod Cinitapride Cisapride CJ-033466 Dazopride Metoclopramide Minesapride Mosapride Prucalopride PRX-03140 Renzapride RS-67333 RS-67506 Serotonin (5-HT) Tegaserod Usmarapride Velusetrag Zacopride Antagonists: GR-113808 GR-125487 L-Lysine Piboserod RS-39604 RS-67532 SB-203186 SB-204070 5-HT5A Agonists: Ergolines (e.g., 2-Br-LSD (BOL-148), ergotamine, LSD) Serotonin (5-HT) Tryptamines (e.g., 5-CT) UCSF648 Valerenic acid Antagonists: Asenapine Latrepirdine (dimebolin) Metitepine (methiothepin) Ritanserin SB-699551 Unknown/unsorted: Ergolines (e.g., metergoline, methysergide) Piperazines (e.g., naphthylpiperazine) 5-HT6 Agonists: Ergolines (e.g., dihydroergocryptine, dihydroergotamine, ergotamine, lisuride, LSD, mesulergine, metergoline, methysergide) Hypidone Serotonin (5-HT) Tryptamines (e.g., 2-Me-5-HT, 5-BT, 5-CT, 5-MT, Bufotenin, E-6801, E-6837, EMD-386088, EMDT, LY-586713, N-Me-5-HT, ST-1936, tryptamine) WAY-181187 WAY-208466 Antagonists: ABT-354 Atypical antipsychotics (e.g., aripiprazole, asenapine, clorotepine, clozapine, fluperlapine, iloperidone, olanzapine, tiospirone) AVN-101 AVN-211 AVN-322 AVN-397 BGC20-760 BVT-5182 BVT-74316 Cerlapirdine EGIS-12233 GW-742457 Idalopirdine Ketanserin Landipirdine Latrepirdine (dimebolin) Masupirdine Metitepine (methiothepin) MS-245 PRX-07034 PZKKN-94 Ritanserin Ro 04-6790 Ro 63-0563 SB-258585 SB-271046 SB-357134 SB-399885 SB-742457 Tetracyclic antidepressants (e.g., amoxapine, mianserin) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, nortriptyline) Typical antipsychotics (e.g., chlorpromazine, loxapine) Unknown/unsorted: Ergolines (e.g., 2-Br-LSD (BOL-148), bromocriptine, lergotrile, pergolide) Piperazines (e.g., naphthylpiperazine) 5-HT7 Agonists: 8-OH-DPAT AS-19 Bifeprunox E-55888 Ergolines (e.g., LSD) LP-12 LP-44 LP-211 RU-24969 Sarizotan Serotonin (5-HT) Triptans (e.g., frovatriptan) Tryptamines (e.g., 5-CT, 5-MT, bufotenin, N-Me-5-HT) Antagonists: Atypical antipsychotics (e.g., amisulpride, aripiprazole, asenapine, brexpiprazole, clorotepine, clozapine, fluperlapine, olanzapine, risperidone, sertindole, tiospirone, ziprasidone, zotepine) Butaclamol DR-4485 DSP-6745 EGIS-12233 Ergolines (e.g., 2-Br-LSD (BOL-148), amesergide, bromocriptine, cabergoline, dihydroergotamine, ergotamine, LY-53857, LY-215840, mesulergine, metergoline, methysergide, sergolexole) JNJ-18038683 Ketanserin LY-215840 Metitepine (methiothepin) Ritanserin SB-258719 SB-258741 SB-269970 SB-656104 SB-656104A SB-691673 SLV-313 SLV-314 Spiperone SSR-181507 Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin, mirtazapine) Tricyclic antidepressants (e.g., amitriptyline, clomipramine, imipramine) Typical antipsychotics (e.g., acetophenazine, chlorpromazine, chlorprothixene, fluphenazine, loxapine, pimozide) Vortioxetine Negative allosteric modulators: Oleamide Unknown/unsorted: Ergolines (e.g., lisuride, pergolide) Piperazines (e.g., naphthylpiperazine) See also: Receptor/signaling modulators Adrenergics Dopaminergics Melatonergics Monoamine reuptake inhibitors and releasing agents Monoamine metabolism modulators Monoamine neurotoxins

v t e Chloroform committees and commissions 1847 (Chloroform first used) Antique bottles of chloroform 1864 Chloroform Committee Royal Medico-Chirurgical Society See also: Clover bag 1877 The Glasgow Committee on Anæsthetics British Medical Association 1888 First Hyderabad Commissions Surgeon-Major Lawrie of the Bengal Medical Service appointed by the Nizam: Mahbub Ali Khan, Asaf Jah VI See also: Lawrie's Apparatus 1889 Second Hyderabad Commission (Surgeon-Major Lawrie with T. Lauder Brunton FRS of St. Bartholomew's Hospital) 1891 British Medical Association Anæsthetics Committee British Medical Association 1893 The Lancet commissioned Dudley Buxton to implement a questionnaire to report deaths, the method of induction and the clinical stance of chloroform. 1901 The Special Chloroform Committee of the British Medical Association British Medical Association 1912 American Medical Association Committee on Anæsthesia (American Medical Association) - ban chloroform The list shown in this table is referenced.to view its references see: Template:Chloroform committees and commissions.

Authority control databases International GND National United States France BnF data Czech Republic Israel Other Yale LUX

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Adapted from the Wikipedia article [Chloroform](https://en.wikipedia.org/wiki/Chloroform) by Wikipedia contributors ([contributor history](https://en.wikipedia.org/wiki/Chloroform?action=history)). Available under [Creative Commons Attribution-ShareAlike 4.0 International](https://creativecommons.org/licenses/by-sa/4.0/). Changes may have been made.