# Trichloroethylene

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C2HCl3, widely used industrial solvent

"Trichlor" redirects here. For the reagent also known as "trichlor", see [trichloroisocyanuric acid](/source/Trichloroisocyanuric_acid). For Tri-clor, see [chloropicrin](/source/Chloropicrin).

Trichloroethylene Sample of trichloroethylene Names Pronunciation /trʌɪˌklɔːrəʊˈɛθɪliːn/ Preferred IUPAC name Trichloroethene Other names 1-Chloro-2,2-dichloroethylene; 1,1-Dichloro-2-chloroethylene; Acetylene Trichloride; Ethinyl Trichloride; Ethylene Trichloride Terchlorethylene;[1] Chloréthérise[2] Trade names: Algylen; Anamenth; Chlorylene; Gemalgene; Trethylene; Triclene; Trico; Trieline; Triklone; Trilene; Trimar Identifiers CAS Number 79-01-6 Y 3D model (JSmol) Interactive image Interactive image Interactive image Abbreviations TCE, HCO-1120, Tri, Trichlor ChEBI CHEBI:16602 N ChEMBL ChEMBL279816 Y ChemSpider 13837280 Y ECHA InfoCard 100.001.062 EC Number 201-167-4 KEGG C06790 Y PubChem CID 6575 RTECS number KX4550000 UNII 290YE8AR51 Y UN number 1710 CompTox Dashboard (EPA) DTXSID0021383 InChI InChI=1S/C2HCl3/c3-1-2(4)5/h1H Y Key: XSTXAVWGXDQKEL-UHFFFAOYSA-N Y InChI=1/C2HCl3/c3-1-2(4)5/h1H SMILES Cl\C=C(/Cl)Cl Cl\C=C(/Cl)Cl ClC=C(Cl)Cl Properties Chemical formula C2HCl3 Molar mass 131.38 g·mol−1 Appearance Colorless liquid Odor sweet, pleasant, chloroform-like Density 1.46 g/cm3 at 20 °C Melting point −84.8 °C (−120.6 °F; 188.3 K)[7] some sources also list –73 °C as the freezing point[8] Boiling point 86.7 °C (188.1 °F; 359.8 K)[3] Solubility in water 1.280 g/L[3] Solubility Ether, ethanol, chloroform log P 2.26[4] Vapor pressure 58 mmHg (0.076 atm) at 20 °C[5] Magnetic susceptibility (χ) −65.8·10−6 cm3/mol Refractive index (nD) 1.4777 at 19.8 °C Viscosity 0.532 mPa·s[6] Pharmacology ATC code N01AB05 (WHO) Hazards Occupational safety and health (OHS/OSH): Main hazards Acute exposure can cause dizziness, sedation, and loss of consciousness. Chronic high-concentration exposure may increase cancer risk. Unstable in presence of sunlight and caustic soda. GHS labelling: Pictograms NFPA 704 (fire diamond) 2 1 0 Autoignition temperature 420 °C (788 °F; 693 K) Explosive limits 8–10.5%[5] Lethal dose or concentration (LD, LC): LD50 (median dose) 7000 mg/kg (oral, human)[9] 4920 mg/kg (oral, rat), 29000 mg/kg (dermal, rabbit)[10] LC50 (median concentration) 8450 ppm (mouse, 4 hr) 26300 ppm (rat, 1 hr)[11] LCLo (lowest published) 2900 ppm (human) 37,200 ppm (guinea pig, 40 min) 5952 ppm (cat, 2 hr) 8000 ppm (rat, 4 hr) 11,000 ppm (rabbit)[11] NIOSH (US health exposure limits): PEL (Permissible) TWA 100 ppm C 200 ppm 300 ppm (5-minute maximum peak in any 2 hours)[5] REL (Recommended) Ca[5] IDLH (Immediate danger) Ca [1000 ppm][5] Safety data sheet (SDS) Carl Roth Legal status BR: Class B1 (Psychoactive drugs)[12] US: banned for medical use (1977), all use banned (2024) Related compounds Related vinyl halides Vinyl chloride Tetrachloroethylene Trifluoroethylene Related compounds Chloroform 1,1,1-Trichloroethane 1,1,2-Trichloroethane Chloral Supplementary data page Trichloroethylene (data page) Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N verify (what is YN ?) Infobox references

Chemical compound

**Trichloroethylene** (**TCE**, [IUPAC](/source/International_Union_of_Pure_and_Applied_Chemistry) name: **trichloroethene**) is an [organochloride](/source/Organochloride) with the formula C2HCl3, commonly used as an industrial degreaser. It is a clear, colourless, non-flammable, volatile liquid with a sweet [chloroform](/source/Chloroform)-like pleasant mild smell[5] and burning sweet taste.[13] Trichloroethylene has been sold under a variety of trade names for various purposes. Under the trade names **Trimar** and **Trilene**, it was used as a [volatile anesthetic](/source/Inhalational_anesthetic) and as an inhaled obstetrical [analgesic](/source/Analgesic) in millions of patients. Industrial abbreviations include **trichlor**, **Trike**, **Tricky** and **tri**. It should not be confused with the similar industrial solvent [1,1,1-trichloroethane](/source/1%2C1%2C1-trichloroethane), which was commonly known as *chlorothene*. Trichloroethylene is heavier than water and insoluble in water, therefore it sinks under water when spilt which causes it to migrate downward through soil and [aquifers](/source/Aquifer). It settles at the bottom of aquifers and forms persistent subsurface contamination that is difficult to detect and remediate.

## History

The earliest trichloroethylene synthesis was reported by [Auguste Laurent](/source/Auguste_Laurent) in 1836. Laurent obtained it from the action of [potassium hydroxide](/source/Potassium_hydroxide) on a mixture of [1,1,2,2-tetrachloroethane](/source/1%2C1%2C2%2C2-Tetrachloroethane) and [1,1,1,2-tetrachloroethane](/source/1%2C1%2C1%2C2-Tetrachloroethane) made from the chlorination of [ethylene dichloride](/source/1%2C2-Dichloroethane) and notated it as C4HCl3 (at the time, the atomic weight of carbon was thought to be half of what it really is[14]). He named trichloroethylene *chlorétherise* but did not investigate the compound further as his sample seemed unstable.[2][15]

E. Fischer obtained trichloroethylene in 1864 via the reduction of [hexachloroethane](/source/Hexachloroethane) with hydrogen. Fischer investigated the compound and noted its boiling point as between 87 and 90 degrees Celsius.[16][17][18]

First industrial plant for producing trichloroethylene was opened in [Jajce](/source/Jajce), [Austria-Hungary](/source/Austria-Hungary) (modern-day Bosnia) in 1908.[19]: 71 Commercial production of trichloroethylene began in Germany, in 1920 and in the United States in 1925.[20]

As early as 1920, trichloroethylene was reported to cause sickness and severe narcotic effects including sleepiness and fainting in exposed workers.[21]

The use of trichloroethylene in the food and pharmaceutical industries has been banned in some parts of the world since the 1970s[22] due to concerns about its toxicity.

### Anaesthesia

Trichloroethylene is a good analgesic at 0.35 to 0.5% concentrations.[23] Trichloroethylene has a blood/gas coefficient of 9, oil/gas coefficient of 714, and a [minimum alveolar concentration](/source/Minimum_alveolar_concentration) of 0.23% in humans.[24] It was mainly used as a general anaesthetic for small procedures and inhaled obsterical analgesic on millions of patients.[25]

Trichloroethylene was first used in the treatment of trigeminal neuralgia beginning in 1916[25] after the recommendation by the German neurologist [Hermann Oppenheim](/source/Hermann_Oppenheim) in 1915.[26] Trichloroethylene for use as an analgesic for neuralgia were sold under the trade names "Gemalgene", "Trethylene" and "Chlorylen" in the 1920s.

American pharmacologist Dennis Emerson Jackson used trichloroethylene on patients given by the inhaler he developed in 1933 and published the report in 1934. Jackson later published a larger report on applying trichloroethylene on 300 patients along with the researchers Cecil Striker, Samuel Goldblatt, Irwin S. Warm in 1935.[27] English anaesthetist Christopher Langton Hewer introduced trichloroethylene for anaesthetic use in Britain, in 1941.[28][29] Hewer found that [Imperial Chemical Industries](/source/Imperial_Chemical_Industries) (ICI) was already producing purified medical-grade trichloroethylene in Britain under the trade name *Trilene* (from *tri*chloroethy*lene*). *Trilene* was the purest TCE in the market at the time and other TCE formulations had impurities that could be unsafe for inhalation. Hewer noted that ICI sold *Trilene* for external wound cleaning. Hewer claimed that TCE would not pose cardiac danger based on a small group of patients, and mentions a death occurring during a TCE-[nitrous oxide](/source/Nitrous_oxide) anaesthesia.[30]

Pioneered by ICI in Britain, its development was hailed as an anesthetic revolution. It was also sold as "Trimar" in the United States. The *–mar* suffix indicated study and development at the [University of Maryland](/source/University_of_Maryland), e.g., "Fluoromar" for [fluroxene](/source/Fluroxene) and "Vinamar" for [ethyl vinyl ether](/source/Ethyl_vinyl_ether)".[31] From the 1940s through the 1980s, both in Europe and North America, trichloroethylene was used as a volatile anesthetic almost invariably administered with [nitrous oxide](/source/Nitrous_oxide). Marketed in the UK by [Imperial Chemical Industries](/source/Imperial_Chemical_Industries) under the trade name *Trilene* it was coloured blue with a dye called [waxoline blue](/source/Waxoline_blue) in 1:200,000 concentration[32] to avoid confusion with the similar-smelling chloroform. *Trilene* was stabilised with 0.01% [thymol](/source/Thymol).[32] "Anamenth" was an early German anaesthetic trichloroethylene formulation which contained [menthol](/source/Menthol) as the stabiliser.

Trichloroethylene was also used as an inhaled analgesic, mainly during childbirth, often self-applied by the patient. It was introduced for obstetrical anaesthesia in 1943, and used until the 1980s.[23] Self-admistration of trichloroethylene by the patient was common for obstetrical use with specialised devices that required little supervision by the medical staff. When used in analgesic doses, it did not affect the uterine muscles during labour. Other analgesic uses included dental operations, superficial plastic and orthopedic surgeries and other small procedures that did not require muscle relaxation.[29]

*Cyprane* handheld anaesthetic device for trichloroethylene, made in the UK, 1947. This device was designed for self-administration by the patient.

Triservice Anaesthetic Apparatus (TSAA) is a portable draw-over vapouriser originally designed for trichloroethylene and [halothane](/source/Halothane) using ambient air as the carrier gas for the anaesthetic vapour.[33] It was designed by Ivan Houghton for military/field use in 1981. It used trichloroethylene for its analgesic properties and halothane for main general anaesthesia.[34]

Originally thought to possess less [hepatotoxicity](/source/Hepatotoxicity) than [chloroform](/source/Chloroform), and without the unpleasant pungency and flammability of [ether](/source/Diethyl_ether), TCE replaced earlier anesthetics chloroform and ether in the 1940s. TCE use was nonetheless soon found to have several pitfalls. These included promotion of [cardiac arrhythmias](/source/Cardiac_arrhythmias), sensitivity to [catecholamines](/source/Catecholamine) in the heart, low volatility and high solubility preventing quick anesthetic induction, prolonged neurologic dysfunction from the reaction with [soda lime](/source/Soda_lime) used in carbon dioxide absorbing systems, and evidence of hepatotoxicity as had been found with chloroform, although the hepatotoxic effects (such as central necrosis and acute yellow atrophy) were reported to be temporary.[35] Alkali components of carbon dioxide absorbers reacted with trichloroethylene and released [dichloroacetylene](/source/Dichloroacetylene), a neurotoxin and a nephrotoxin. Most of the trichloroethylene toxicity cases were due to its breakdown into dichloroacetylene from the reaction with the soda lime, rather than trichloroethylene itself.[36] Dichloroacetylene poisoning was common and often fatal during trichloroethylene anaesthesia if [soda lime](/source/Soda_lime) was used. Patients exposed to dichloroacetylene showed symptoms such as nausea, vomiting, loss of apetite, headache, facial nervous and muscular issues, and formation of herpes-like lesions on the face.[37] Formation of dichloroacetylene lead to fatal encephalopathies and cranial nerve palsies.[29] The muscle relaxant effect of trichloroethylene was inefficient for surgery.[38]

The introduction of [halothane](/source/Halothane) in 1956 greatly diminished the use of TCE as a general anesthetic in the 1960s, as halothane allowed much faster induction and recovery times and was considerably easier to administer. Trichloroethylene has also been used in the production of halothane.[39]

Bottle of trichloroethylene for anesthesia by ICI

Inhaler used for Trilene, 1961–1970

Pain Relief in Childbirth (1954) [1]

Anaesthetic use of trichloroethylene was banned in the United States in 1977 but the use in the United Kingdom remained until the late 1980s (especially for childbirth).[25] Concerns about the carcinogenic potential of TCE led to its abandonment in developed countries by the 1980s and ICI had ceased medical grade TCE production by 1984.[25] TCE was still in use as an anesthetic in some African countries as of 2000,[40] and in [Malawi](/source/Malawi) and [Nepal](/source/Nepal) as of 2005.[25]

## Production

Today, most trichloroethylene is produced from [ethylene](/source/Ethylene). First, ethylene is chlorinated over a [ferric chloride](/source/Iron(III)_chloride) catalyst to produce [1,2-dichloroethane](/source/1%2C2-Dichloroethane):[41]

- CH2=CH2 + Cl2 → ClCH2CH2Cl

When heated to around 400 °C with additional chlorine, 1,2-dichloroethane is converted to trichloroethylene:

- ClCH2CH2Cl + 2 Cl2 → ClCH=CCl2 + 3 HCl

This reaction can be catalyzed by a variety of substances. The most commonly used catalyst is a mixture of [potassium chloride](/source/Potassium_chloride) and [aluminum chloride](/source/Aluminium_chloride). However, various forms of porous [carbon](/source/Carbon) can also be used. This reaction produces [tetrachloroethylene](/source/Tetrachloroethylene) as a byproduct and depending on the amount of chlorine fed to the reaction, tetrachloroethylene can even be the major product. Typically, trichloroethylene and tetrachloroethylene are collected together and then separated by [distillation](/source/Distillation).[41]

Prior to the early 1970s, however, most trichloroethylene was produced in a two-step process from [acetylene](/source/Acetylene). First, acetylene was treated with chlorine using a [ferric chloride](/source/Iron(III)_chloride) [catalyst](/source/Catalyst) at 90 °C to produce [1,1,2,2-tetrachloroethane](/source/1%2C1%2C2%2C2-Tetrachloroethane) according to the [chemical equation](/source/Chemical_equation):[41]

- HC≡CH + 2 Cl2 → Cl2CHCHCl2

The 1,1,2,2-tetrachloroethane is then dehydrochlorinated to give trichloroethylene. This can be accomplished either with an aqueous solution of [calcium hydroxide](/source/Calcium_hydroxide):[41]

- 2 Cl2CHCHCl2 + Ca(OH)2 → 2 ClCH=CCl2 + CaCl2 + 2 H2O

or in the vapor phase by heating it to 300–500 °C on a [barium chloride](/source/Barium_chloride) or [calcium chloride](/source/Calcium_chloride) catalyst:

- Cl2CHCHCl2 → ClCH=CCl2 + HCl

Common impurities in reagent and technical grade TCE are [methyl chloroform](/source/Methyl_chloroform), [carbon tetrachloride](/source/Carbon_tetrachloride), [ethylene dichloride](/source/Ethylene_dichloride), [tetrachloroethanes](/source/Tetrachloroethane), [benzene](/source/Benzene) and [phenol](/source/Phenol). However, these compounds are present in very small amounts and do not possess any risk.[25]

## Uses

Trichloroethylene is an effective [solvent](/source/Solvent) for a variety of [organic](/source/Organic_chemistry) materials. It is mainly used for cleaning. Trichloroethylene is an active ingredient (solvent) in various [printing ink](/source/Printing_ink), [varnish](/source/Varnish) and industrial [paint](/source/Paint) formulations.[42][25] Other uses include [dyeing](/source/Dyeing) and finishing operations, adhesive formulations, [rubber](/source/Rubber) processing, adhesives, [lacquers](/source/Lacquers), and [paint strippers](/source/Paint_strippers). It is applied before [plating](/source/Plating), [anodizing](/source/Anodizing), and painting.[43]

When trichloroethylene was first widely produced in the 1920s, its major use was to extract [vegetable oils](/source/Vegetable_oil) from plant materials such as [soy](/source/Soy), [coconut](/source/Coconut), and [palm](/source/Palm_tree). Other uses in the food industry included [coffee](/source/Coffee) [decaffeination](/source/Decaffeination) (removal of [caffeine](/source/Caffeine)) and the preparation of flavoring extracts from [hops](/source/Hops) and [spices](/source/Spice).[25] TCE was used as a [freezing point](/source/Freezing_point) depressant in [carbon tetrachloride](/source/Carbon_tetrachloride) fire extinguishers.[25]

Trichloroethylene is also a [chain terminator](/source/Chain_termination) for [polyvinyl chloride](/source/Polyvinyl_chloride).[25] Chlorination gives [pentachloroethane](/source/Pentachloroethane).

### Cleaning solvent

Perhaps the greatest use of TCE is as a degreaser for metal parts. It has been widely used in degreasing and cleaning since the 1910s because of its low cost, low flammability, low toxicity, and high effectiveness as a solvent. The demand for TCE as a degreaser began to decline in the 1950s in favor of the less toxic [1,1,1-trichloroethane](/source/1%2C1%2C1-Trichloroethane). However, 1,1,1-trichloroethane production has been phased out in most of the world under the terms of the [Montreal Protocol](/source/Montreal_Protocol) due to its contribution to the [ozone depletion](/source/Ozone_depletion). As a result, trichloroethylene has experienced some resurgence in use as a degreaser.[25]

Trichloroethylene has been used as a [dry cleaning](/source/Dry_cleaning) solvent, although mostly replaced by tetrachloroethylene, except for spot cleaning – for grease and oil stains – where it is still often used under various tradenames. It was found unfavourable for dry cleaning because it tended to dissolve acetate dyes, which tetrachloroethylene did not. Trichloroethylene is used to remove grease and [lanolin](/source/Lanolin) from [wool](/source/Wool) before [weaving](/source/Weaving).[25]

TCE has also been used in the United States to clean kerosene-fueled rocket engines (TCE was not used to clean hydrogen-fueled engines such as the [Space Shuttle Main Engine](/source/Space_Shuttle_Main_Engine)). During static firing, the [RP-1](/source/RP-1) fuel would leave hydrocarbon deposits and vapors in the engine. These deposits had to be flushed from the engine to avoid the possibility of explosion during engine handling and future firing. TCE was used to flush the engine's fuel system immediately before and after each test firing. The flushing procedure involved pumping TCE through the engine's fuel system and letting the solvent overflow for a period ranging from several seconds to 30–35 minutes, depending upon the engine. For some engines, the engine's gas generator and [liquid oxygen](/source/Liquid_oxygen) (LOX) dome were also flushed with TCE before test firing.[44][45] The [F-1 rocket engine](/source/F-1_rocket_engine) had its LOX dome, gas generator, and thrust chamber fuel jacket flushed with TCE during launch preparations.[45]

### Refrigerants

TCE is also used in the manufacture of a range of fluorocarbon refrigerants[46] such as [1,1,1,2-tetrafluoroethane](/source/1%2C1%2C1%2C2-tetrafluoroethane) more commonly known as HFC-134a.[47]

- CHCl=CCl2 + 4 HF → CF3CH2F + 3 HCl

TCE was also used in industrial refrigeration applications due to its high heat transfer capabilities and its low-temperature specification.[*[citation needed](https://en.wikipedia.org/wiki/Wikipedia:Citation_needed)*]

## Reactions

Trichloroethylene reacts with alkalis to give [dichloroacetylene](/source/Dichloroacetylene) via [dehydrochlorination](/source/Dehydrochlorination).

1,1,2,2-tetrachloroethylsulfenyl chloride, used in the production of [captafol](/source/Captafol), is obtained from trichloroethylene and [sulfur dichloride](/source/Sulfur_dichloride):

- C2HCl3 + SCl2 → C2HCl4SCl

The reaction of trichloroethylene with chloroform can yield different compounds depending on the catalyst used. If sodium hydroxide is used, chloroform is dehydrochlorinated to [dichlorocarbene](/source/Dichlorocarbene) which adds to trichloroethylene, and [pentachlorocyclopropane](/source/Pentachlorocyclopropane) is obtained:

- C2HCl3 + :CCl2 → C3HCl5

The reaction of trichloroethylene with chloroform under the catalyst aluminum chloride gives [1,1,1,2,3,3-Hexachloropropane](https://en.wikipedia.org/w/index.php?title=1,1,1,2,3,3-Hexachloropropane&action=edit&redlink=1):

- CHCl3 + C2HCl3 → CHCl2CHClCCl3

The reaction of trichloroethylene with [carbon tetrachloride](/source/Carbon_tetrachloride) under similar conditions gives 1,1,1,2,3,3,3-heptachloropropane:[48]

- C2HCl3 + CCl4 → C3HCl7

## Safety

### Chemical instability

Despite its widespread use as a metal [degreaser](/source/Degreaser), trichloroethylene itself is unstable in the presence of metal over prolonged exposure. As early as 1961 this phenomenon was recognized by the manufacturing industry when stabilizing additives were added to the commercial formulation. Since the reactive instability is accentuated by higher temperatures, the search for stabilizing additives was conducted by heating trichloroethylene to its boiling point under a [reflux condenser](/source/Reflux_condenser) and observing decomposition. Definitive documentation of [1,4-dioxane](/source/1%2C4-dioxane) as a stabilizing agent for TCE is scant due to the lack of specificity in early patent literature describing TCE formulations.[49][50] [Epichlorohydrin](/source/Epichlorohydrin), [butylene oxide](/source/Butylene_oxide), *N*-methyl[pyrrole](/source/Pyrrole) and [ethyl acetate](/source/Ethyl_acetate) are common stabilisers for TCE, with epichlorohydrin being the most persistent and effective.[41] Other chemical stabilizers include [ketones](/source/Ketone) such as [methyl ethyl ketone](/source/Methyl_ethyl_ketone).

Two advertisements for trichloroethylene in two different uses, metal degreasing (1947) and anaesthesia (1952)

### Physiological effects

#### Neurological

When inhaled, trichloroethylene produces [central nervous system](/source/Central_nervous_system) depression resulting in [general anesthesia](/source/General_anesthesia). These effects may be mediated by trichloroethylene acting as a [positive allosteric modulator](/source/Positive_allosteric_modulator) of inhibitory [GABAA](/source/GABAA_receptor) and [glycine receptors](/source/Glycine_receptor).[51][52] Its high blood solubility results in a less desirable slower induction of anesthesia. At low concentrations, it is relatively non-irritating to the respiratory tract. Higher concentrations result in [tachypnea](/source/Tachypnea). Many types of cardiac [arrhythmias](/source/Arrhythmias) can occur and are exacerbated by [epinephrine](/source/Epinephrine) (adrenaline).

It was noted in the 1940s that TCE reacted with carbon dioxide (CO2) absorbing systems ([soda lime](/source/Soda_lime)) to produce [dichloroacetylene](/source/Dichloroacetylene) by [dehydrochlorination](/source/Dehydrochlorination) and [phosgene](/source/Phosgene).[53] [Cranial nerve](/source/Cranial_nerve) dysfunction (especially the fifth cranial nerve) was common when TCE anesthesia was given using CO2 absorbing systems. Muscle relaxation with TCE anesthesia sufficient for surgery was poor. For these reasons as well as problems with [hepatotoxicity](/source/Hepatotoxicity), TCE lost popularity in North America and Europe to more potent anesthetics such as [halothane](/source/Halothane) by the 1960s.[54]

The symptoms of acute non-medical exposure are similar to those of [alcohol intoxication](/source/Alcohol_intoxication), beginning with sleepiness, dizziness, and confusion and progressing with increasing exposure to unconsciousness.[55] Much of what is known about the chronic human health effects of trichloroethylene is based on occupational exposures. Besides its effects on the central nervous system, industrial exposure to trichloroethylene is correlated with toxic effects in the liver and kidney.[55]

Long-term industrial[56] or ambient environmental[57] exposure to trichloroethylene is suspected to elevate the risk of developing [Parkinson's disease](/source/Parkinson's_disease).

### Carcinogenicity

Trichloroethylene has been classified as "[Group 1](/source/IARC_group_1): Carcinogenic to Humans" by the [International Agency for Research on Cancer](/source/International_Agency_for_Research_on_Cancer) (IARC) due to sufficient evidence in humans and experimental animals for cancer of the kidney and a positive association between exposures to trichloroethylene and development of non-Hodgkin lymphoma and liver cancer in humans, and limited evidence in humans and experimental animals for increased incidence of leukemia, lymphoma, reproductive cancers, and respiratory cancers.[58]

Epidemiologic research on exposed populations showed mixed results. For example, a research conducted on a group of 803 workers exposed to TCE in Denmark showed no overall increase in cancer incidence meanwhile another research on kidney cancer incidence in another group of exposed workers showed an increase. TCE was not found to be teratogenic in humans.[38]

One review of the epidemiology of kidney cancer rated cigarette smoking and obesity as more important risk factors for kidney cancer than exposure to solvents such as trichloroethylene.[59] In contrast, one overall assessment of human health risks associated with trichloroethylene states, "there is concordance between animal and human studies, which supports the conclusion that trichloroethylene is a potential kidney carcinogen".[60] The evidence appears to be less certain in this study regarding the relationship between humans and liver cancer observed in mice, with the [US NAS](/source/National_Academy_of_Sciences) suggesting that low-level exposure might not represent a significant liver cancer risk in the general population.

### Metabolism

Trichloroethylene is metabolised to trichloroepoxyethane (TCE oxide) which rapidly isomerises to [trichloroacetaldehyde](/source/Trichloroacetaldehyde) (chloral).[61] Chloral hydrates to [chloral hydrate](/source/Chloral_hydrate) in the body. Chloral hydrate is either reduced to [2,2,2-trichloroethanol](/source/2%2C2%2C2-trichloroethanol) or oxidised to [trichloroacetic acid](/source/Trichloroacetic_acid). [Monochloroacetic acid](/source/Monochloroacetic_acid),[62] [dichloroacetic acid](/source/Dichloroacetic_acid)[63] and [trichloromethane](/source/Trichloromethane)[62][64][65] were also detected as minor metabolites of TCE.

### Exposure and regulations

Main article: [List of trichloroethylene-related incidents](/source/List_of_trichloroethylene-related_incidents)

With a [specific gravity](/source/Specific_gravity) greater than 1 (denser than water), trichloroethylene can be present as a [dense non-aqueous phase liquid](/source/Dense_non-aqueous_phase_liquid) (DNAPL) if sufficient quantities are spilt in the environment.

The first known report of TCE in groundwater was given in 1949 by two English public chemists who described two separate instances of well contamination by industrial releases of TCE.[66] Based on available federal and state surveys, between 9% and 34% of the drinking water supply sources tested in the US may have some TCE contamination, though EPA has reported that most water supplies comply with the maximum contaminant level (MCL) of 5 ppb.[67]

Generally, atmospheric levels of TCE are highest in areas of concentrated industry and population. Atmospheric levels tend to be lowest in rural and remote regions. Average TCE concentrations measured in air across the United States are generally between 0.01 ppb and 0.3 ppb, although mean levels as high as 3.4 ppb have been reported.[68] TCE levels in the low parts per billion range have been measured in food; however, levels as high as 140 ppb were measured in a few samples of food.[68] TCE levels above background[*[how?](https://en.wikipedia.org/wiki/Wikipedia:Please_clarify)*] have been found in homes undergoing [renovation](/source/Renovation).[69]

#### Existing regulations

State, federal, and international agencies classify trichloroethylene as a known or probable carcinogen for humans. In 2014, the [International Agency for Research on Cancer](/source/International_Agency_for_Research_on_Cancer) updated its classification of trichloroethylene to [Group 1](/source/IARC_group_1_Carcinogens), indicating that sufficient evidence exists that it can cause cancer of the kidney in humans as well as some evidence of cancer of the liver and [non-Hodgkin's lymphoma](/source/Non-Hodgkin's_lymphoma).[70]

In the [European Union](/source/European_Union), the [Scientific Committee on Occupational Exposure Limit Values](/source/Scientific_Committee_on_Occupational_Exposure_Limit_Values) (SCOEL) recommends an exposure limit for workers exposed to trichloroethylene of 10 ppm (54.7 mg/m3) for 8-hour [TWA](/source/Permissible_exposure_limit) and of 30 ppm (164.1 mg/m3) for [STEL](/source/Permissible_exposure_limit) (15 minutes).[71]

Existing EU legislation aimed at protection of workers against risks to their health (including Chemical Agents Directive 98/24/EC[72] and Carcinogens Directive 2004/37/EC[73]) currently do not impose binding minimum requirements for controlling risks to workers' health during the use phase or throughout the life cycle of trichloroethylene.

In 2023, the United States [United States Environmental Protection Agency](/source/United_States_Environmental_Protection_Agency) (EPA) determined that trichloroethylene presents a risk of injury to human health in various uses, including during manufacturing, processing, mixing, [recycling](/source/Recycling), vapor degreasing, as a lubricant, adhesive, [sealant](/source/Sealant), cleaning product, and spray. EPA states that TCE is "dangerous from both inhalation and [dermal](/source/Dermal) exposure and was most strongly associated with [immunosuppressive](/source/Immunosuppression) effects for acute exposure, as well as [autoimmune](/source/Autoimmunity) effects for chronic exposures."[74] Chronic exposure to trichloroethylene has also been linked to an increased risk of [Parkinson's disease](/source/Parkinson's_disease) by some researchers.[75][76] As of June 1, 2023, two US states ([Minnesota](/source/Minnesota) and [New York](/source/New_York_(state))) have acted on the EPA's findings and banned trichloroethylene in all cases but research and development.[77][78]

According to the US EPA, in October 2023 it "proposed to ban the manufacture (including import), processing, and distribution in commerce of TCE for all uses, with longer compliance time frames and workplace controls (including an exposure limit) for some processing and industrial and commercial uses until the prohibitions come into effect" to "protect everyone including bystanders from the harmful health effects of TCE".[79] Following the EPA's recommendation the [Biden Administration](/source/Biden_Administration) announced a proposal to ban trichloroethylene later that month.[80]

In December 2024 the EPA issued a final ruling on the regulation of trichloroethylene, with the rule taking effect on January 16, 2025.[81] The rule bans the manufacture (including import), processing, and distribution in commerce of trichloroethylene for all uses, with longer compliance timeframes and stringent worker protections for some processing and industrial and commercial uses until the prohibitions come into effect.[82] The EPA is prohibiting most uses of trichloroethylene within one year of the rule taking effect including manufacture and processing for most commercial and all consumer products, with only a limited number of commercial uses being allowed after January 16, 2026.[83] These uses will eventually be phased out as well, though an exact timeframe hasn't been determined yet, but until they have been phased out more stringent worker protections will be required with a lower [inhalation](/source/Inhalation) [exposure limit](/source/Occupational_exposure_limit) for [airborne](/source/Particulates) trichloroethylene being put in place.[82]

Many of the trichloroethylene uses that are continuing for longer than one year occur in highly [industrialized](/source/Industrialized) settings with critical uses such as the cleaning of parts used in [medical devices](/source/Medical_devices), aircraft & other transportation, [security](/source/Security_alarm) and [defense systems](/source/U.S._critical_infrastructure_protection) and the manufacture of [battery](/source/Lead%E2%80%93acid_battery) [separators](/source/Separator_(electricity)) and [refrigerants](/source/Refrigerants).[82] These uses will ultimately be prohibited as well but are temporarily being allowed to continue in order to avoid negative impacts to [national security](/source/National_security) or [critical infrastructure](/source/Critical_infrastructure), and to allow time to transition to alternative chemicals and methods.[82]

## Remediation

Research has focused on the in-place remediation of trichloroethylene in soil and groundwater using [potassium permanganate](/source/Potassium_permanganate) instead of removal for off-site treatment and disposal. Naturally occurring [bacteria](/source/Bacteria) have been identified with the ability to degrade TCE. *[Dehalococcoides](/source/Dehalococcoides)* sp. degrade trichloroethylene by reductive dechlorination under anaerobic conditions. Under aerobic conditions, *[Pseudomonas fluorescens](/source/Pseudomonas_fluorescens)* can co-metabolize TCE. Soil and groundwater contamination by TCE has also been successfully remediated by chemical treatment and extraction. The bacteria *[Nitrosomonas europaea](/source/Nitrosomonas_europaea)* can degrade a variety of halogenated compounds including trichloroethylene.[84] [Toluene dioxygenase](/source/Toluene_dioxygenase) has been reported to be involved in TCE degradation by *[Pseudomonas putida](/source/Pseudomonas_putida)*.[85] In some cases, *[Xanthobacter autotrophicus](/source/Xanthobacter_autotrophicus)* can convert up to 51% of TCE to CO and CO2.[85]

## Society and culture

Trichloroethylene has been used as a [recreational drug](/source/Recreational_drug).[86] Reported methods of TCE abuse include inhalation and drinking.[87] It was abused for its euphoriant and slight hallucinogenic effect by mostly young people and workers who used the chemical.[87] Some industrial workers had become addicted to TCE.[88]

[Groundwater](/source/Groundwater_pollution) and [drinking water](/source/Drinking_water_pollution) contamination from industrial discharge including trichloroethylene is a major concern for human health and has precipitated numerous incidents and lawsuits in the United States. One notable example is that of Woburn, Massachusetts, (*[Anderson v. Cryovac](/source/Anderson_v._Cryovac)*) where improper disposal of industrial solvents including trichloroethylene by local companies led to the contamination of two municipal wells.[89] Families blamed the supposed local increase in leukemia cases on trichloroethylene pollution,[90] although trichloroethylene does not cause leukemia in humans. The incident gained national attention in the 1980s and was the subject of extensive litigation, culminating in a settlement between the companies and affected families[91] It later served as the basis for the book *[A Civil Action](/source/A_Civil_Action)* by Jonathan Harr, which was [adapted to cinema in 1998](/source/A_Civil_Action_(film)).

## See also

- [TaClo](/source/TaClo)

## References

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1. **[^](#cite_ref-66)** Lyne FA, McLachlan T (1949). "Contamination of water by trichloroethylene" p. 513 in Lilliman, B.; Houlihan, J. E.; Lyne, F. A.; McLachlan, T. (1949). "Notes". *The Analyst*. **74** (882): 510–513. [Bibcode](/source/Bibcode_(identifier)):[1949Ana....74..510L](https://ui.adsabs.harvard.edu/abs/1949Ana....74..510L). [doi](/source/Doi_(identifier)):[10.1039/AN9497400510](https://doi.org/10.1039%2FAN9497400510).

1. **[^](#cite_ref-67)** ["Consumer Factsheet on: Trichloroethylene"](https://web.archive.org/web/20090515172629/http://www.epa.gov/safewater/pdfs/factsheets/voc/trichlor.pdf) (PDF). Epa.gov. Archived from [the original](http://www.epa.gov/safewater/pdfs/factsheets/voc/trichlor.pdf) (PDF) on May 15, 2009. Retrieved 22 February 2015.

1. ^ [***a***](#cite_ref-:0a_68-0) [***b***](#cite_ref-:0a_68-1) ["Trichloroethylene Toxicity: Where is Trichloroethylene Found? | Environmental Medicine | ATSDR"](https://www.atsdr.cdc.gov/csem/trichloroethylene/where_found.html). *www.atsdr.cdc.gov*. 2022-09-09. Retrieved 2023-03-02. This article incorporates text from this source, which is in the [public domain](/source/Public_domain).

1. **[^](#cite_ref-69)** ["Trichloroethylene (tce) TEACH Chemical Summary - epa nepis"](https://nepis.epa.gov/Exe/ZyPURL.cgi?Dockey=P100BNS7.TXT).

1. **[^](#cite_ref-70)** [*Trichloroethylene (IARC Summary & Evaluation, Volume 106, 2014)*](https://monographs.iarc.fr/ENG/Monographs/vol106/mono106-001.pdf) (PDF). iarc.fr. Retrieved 2016-03-08.

1. **[^](#cite_ref-71)** ["Recommendation from the Scientific Committee on Occupational Exposure Limits for Trichloroethylene (SCOEL/SUM/142)"](http://ec.europa.eu/social/BlobServlet?docId=6405&langId=en) (PDF). April 2009.

1. **[^](#cite_ref-72)** [Council Directive 98/24/EC of 7 April 1998 on the protection of the health and safety of workers from the risks related to chemical agents at work (fourteenth individual Directive within the meaning of Article 16(1) of Directive 89/391/EEC)](https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:31998L0024)

1. **[^](#cite_ref-73)** [Directive 2004/37/EC of the European Parliament and of the Council of 29 April 2004 on the protection of workers from the risks related to exposure to carcinogens, mutagens or reprotoxic substances at work (Sixth individual Directive within the meaning of Article 16(1) of Council Directive 89/391/EEC) (codified version)](https://eur-lex.europa.eu/legal-content/EN/TXT/?uri=CELEX:02004L0037-20240408)

1. **[^](#cite_ref-74)** US EPA, OCSPP (2020-02-12). ["Final Risk Evaluation for Trichloroethylene"](https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/final-risk-evaluation-trichloroethylene) (PDF). *[United States Environmental Protection Agency](/source/United_States_Environmental_Protection_Agency)*. Retrieved 2023-06-03.

1. **[^](#cite_ref-Link_to_Parkinson's_75-0)** Dorsey, E. R.; Zafar, M.; Lettenberger, S. E.; Pawlik, M. E.; Kinel, D.; Frissen, M.; Schneider, R. B.; Kieburtz, K.; Tanner, C. M.; De Miranda, B. R.; Goldman, S. M.; Bloem, B. R. (14 March 2023). ["Trichloroethylene: An Invisible Cause of Parkinson's Disease?"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10041423). *Journal of Parkinson's Disease*. **13** (2). National Library of Medicine: 203–218. [doi](/source/Doi_(identifier)):[10.3233/JPD-225047](https://doi.org/10.3233%2FJPD-225047). [PMC](/source/PMC_(identifier)) [10041423](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10041423). [PMID](/source/PMID_(identifier)) [36938742](https://pubmed.ncbi.nlm.nih.gov/36938742).

1. **[^](#cite_ref-76)** Wexler, MS, Marisa (17 March 2023). ["Ban sought for TCE, common chemical likely linked to Parkinson's"](https://parkinsonsnewstoday.com/news/ban-sought-tce-common-chemical-likely-linked-parkinsons/). *Parkinson's News Today*. BioNews. Retrieved 30 January 2025.

1. **[^](#cite_ref-77)** ["How Minnesota passed the country's first ban on trichloroethylene"](https://www.pca.state.mn.us/news-and-stories/tce-ban-in-effect). *www.pca.state.mn.us/news-and-stories*. Minnesota Pollution Control Agency. 28 August 2023. [Archived](https://web.archive.org/web/20230906174016/https://www.pca.state.mn.us/news-and-stories/tce-ban-in-effect) from the original on 6 September 2023. Retrieved 6 September 2023.

1. **[^](#cite_ref-78)** [Minnesota Statutes](https://www.revisor.mn.gov/statutes/2022/cite/116.385) (act 116.38 (also known as "White Bear Area Neighborhood Concerned Citizens Group Ban TCE Act"), Environmental Protection, Chapter 116, Section 116.385). Minnesota Legislature. 2022. [Archived](https://web.archive.org/web/20230906174558/https://www.revisor.mn.gov/statutes/2022/cite/116.385) from the original on 6 September 2023.

1. **[^](#cite_ref-US_EPA_h041_79-0)** ["Risk Management for Trichloroethylene (TCE)"](https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-trichloroethylene-tce). *US EPA*. 21 Nov 2023. Retrieved 23 Nov 2023.

1. **[^](#cite_ref-80)** ["Biden-Harris Administration Proposes Ban on Trichloroethylene to Protect Public from Toxic Chemical Known to Cause Serious Health Risks"](https://www.epa.gov/newsreleases/biden-harris-administration-proposes-ban-trichloroethylene-protect-public-toxic). *EPA Press Office*. United States Environmental Protection Agency. 23 October 2023. Retrieved 30 January 2025.

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1. ^ [***a***](#cite_ref-EPA_trichloroethylene_ban_82-0) [***b***](#cite_ref-EPA_trichloroethylene_ban_82-1) [***c***](#cite_ref-EPA_trichloroethylene_ban_82-2) [***d***](#cite_ref-EPA_trichloroethylene_ban_82-3) ["Risk Management for Trichloroethylene (TCE)"](https://www.epa.gov/assessing-and-managing-chemicals-under-tsca/risk-management-trichloroethylene-tce). *Assessing and Managing Chemicals under TSCA*. United States Environmental Protection Agency. December 2024. Retrieved 30 January 2025.

1. **[^](#cite_ref-EPA_phasing_out_commercial_trichloroethylene_use_83-0)** ["Trichloroethylene (TCE); Regulation Under the Toxic Substances Control Act (TSCA)"](https://www.federalregister.gov/documents/2024/12/17/2024-29274/trichloroethylene-tce-regulation-under-the-toxic-substances-control-act-tsca). *National Archives Federal Register*. United States Government. 17 December 2024. Retrieved 30 January 2025.

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1. ^ [***a***](#cite_ref-Irvine_85-0) [***b***](#cite_ref-Irvine_85-1) Robert L. Irvine; Subhas K. Sikdar (1998). [*Bioremediation Technologies: Principles and Practice*](https://books.google.com/books?id=oLNtgk_VKXsC&q=Bioremediation+of+gypsum&pg=PA81). CRC Press. pp. 142, 144. [ISBN](/source/ISBN_(identifier)) [978-1-56676-561-9](https://en.wikipedia.org/wiki/Special:BookSources/978-1-56676-561-9). Retrieved 21 February 2015.

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## Further reading

- Agency for Toxic Substances and Disease Registry (ATSDR). 1997. [Toxicological Profile for Trichloroethylene.](https://web.archive.org/web/20110605235058/http://www.atsdr.cdc.gov/toxprofiles/tp19.html)

- Doherty, Richard E. (2000). "A History of the Production and Use of Carbon Tetrachloride, Tetrachloroethylene, Trichloroethylene and 1,1,1-Trichloroethane in the United States: Part 2 – Trichloroethylene and 1,1,1-Trichloroethane". *Environmental Forensics*. **1** (2): 83–93. [Bibcode](/source/Bibcode_(identifier)):[2000EnvFo...1...83D](https://ui.adsabs.harvard.edu/abs/2000EnvFo...1...83D). [doi](/source/Doi_(identifier)):[10.1006/enfo.2000.0011](https://doi.org/10.1006%2Fenfo.2000.0011). [S2CID](/source/S2CID_(identifier)) [97370778](https://api.semanticscholar.org/CorpusID:97370778).

- Lipworth, Loren; Tarone, Robert E.; McLaughlin, Joseph K. (2006). "The Epidemiology of Renal Cell Carcinoma". *The Journal of Urology*. **176** (6): 2353–2358. [doi](/source/Doi_(identifier)):[10.1016/j.juro.2006.07.130](https://doi.org/10.1016%2Fj.juro.2006.07.130). [PMID](/source/PMID_(identifier)) [17085101](https://pubmed.ncbi.nlm.nih.gov/17085101).

- Matei, Adrienne (7 Apr 2021). ["Rates of Parkinson's disease are exploding. A common chemical may be to blame"](https://www.theguardian.com/commentisfree/2021/apr/07/rates-of-parkinsons-disease-are-exploding-a-common-chemical-may-be-to-blame). *The Guardian*.

- US Environmental Protection Agency (USEPA). 2011. [Toxicological Review for Trichloroethylene](https://web.archive.org/web/20111001035730/http://www.epa.gov/IRIS/supdocs/0199index.html)

- US National Academy of Sciences (NAS). 2006. [Assessing Human Health Risks of Trichloroethylene – Key Scientific Issues.](http://www.nap.edu/catalog/11707.html) Committee on Human Health Risks of Trichloroethylene, National Research Council.

- US National Toxicology Program (NTP). 2021. [Trichloroethylene, in the 15th Annual Report of Carcinogens.](https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/trichloroethylene.pdf)

## External links

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

- [US EPA: Trichloroethylene – TCE information website](https://web.archive.org/web/20050917135330/http://cfpub.epa.gov/ncea/cfm/recordisplay.cfm?deid=119268) – US [Environmental Protection Agency](/source/United_States_Environmental_Protection_Agency) (EPA)

- [Case Studies in Environmental Medicine: Trichloroethylene Toxicity](https://www.atsdr.cdc.gov/csem/csem.html) [Archived](https://web.archive.org/web/20160204174821/https://www.atsdr.cdc.gov/csem/csem.html) 2016-02-04 at the [Wayback Machine](/source/Wayback_Machine) – [Agency for Toxic Substances and Disease Registry](/source/Agency_for_Toxic_Substances_and_Disease_Registry) (ATSDR), of the US [Department of Health and Human Services](/source/Department_of_Health_and_Human_Services) (public domain)

- [Assessing Human Health Risks of Trichloroethylene – Key Scientific Issues](https://nap.nationalacademies.org/catalog/11707/assessing-the-human-health-risks-of-trichloroethylene-key-scientific-issues) – US [National Academy of Sciences](/source/National_Academy_of_Sciences) (NAS)

- [US NIH: Fifteenth Report on Carcinogens: Trichloroethylene Monograph](https://ntp.niehs.nih.gov/sites/default/files/ntp/roc/content/profiles/trichloroethylene.pdf) – US [National Institutes of Health](/source/National_Institutes_of_Health) (NIH)

- [Workplace Safety and Health Topics: Trichloroethylene – TCE](https://www.cdc.gov/niosh/topics/trichloroethylene/) – US [National Institute for Occupational Safety and Health](/source/National_Institute_for_Occupational_Safety_and_Health) (NIOSH)

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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 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 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 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

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