# Methylhexanamine

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Chemical compound

Pharmaceutical compound

Methylhexanamine Clinical data Other names Methylhexaneamine, methylhexamine, geranamine, geranium extract, geranium oil, 2-amino-4-methylhexane, dimethylamylamine, DMAA, 1,3-dimethylamylamine, 1,3-DMAA, 1,3-dimethylpentylamine, 4-methyl-2-hexanamine, 4-methyl-2-hexylamine Routes of administration Nasal spray, oral ATC code None Legal status Legal status AU: S10 (Dangerous substance)[5] BR: Class F2 (Prohibited psychotropics)[6] US: Unapproved drug; use in dietary supplements, food, or medicine is unlawful.[1][2][3][note 1] Pharmacokinetic data Elimination half-life ~8.5 hours Identifiers IUPAC name 4-Methylhexan-2-amine[7] CAS Number 105-41-9 Y PubChem CID 7753 ChemSpider 7467 N UNII X49C572YQO CompTox Dashboard (EPA) DTXSID60861715 ECHA InfoCard 100.002.997 Chemical and physical data Formula C7H17N Molar mass 115.220 g·mol−1 3D model (JSmol) Interactive image SMILES CCC(C)CC(C)N InChI InChI=1S/C7H17N/c1-4-6(2)5-7(3)8/h6-7H,4-5,8H2,1-3H3 N Key:YAHRDLICUYEDAU-UHFFFAOYSA-N N NY (what is this?)

**Methylhexanamine** (also known as **methylhexamine**, **1,3-dimethylamylamine**, **1,3-DMAA**, **dimethylamylamine**, and **DMAA**; trade names **Forthane** and **Geranamine**) is an indirect [sympathomimetic drug](/source/Sympathomimetic_drug) invented and developed by [Eli Lilly and Company](/source/Eli_Lilly_and_Company) and marketed as an inhaled [nasal decongestant](/source/Nasal_decongestant) from 1948 until it was voluntarily withdrawn from the market in the 1980s.[8][9]

Since 2006 methylhexanamine has been sold extensively under many names as a [stimulant](/source/Stimulant) or energy-boosting [dietary supplement](/source/Dietary_supplement) under the claim that it is similar to certain compounds found in [geraniums](/source/Geranium), but its safety has been questioned as a number of adverse events and at least five deaths have been associated with methylhexanamine-containing supplements.[10] It is banned by many sports authorities and governmental agencies. Despite multiple warning letters from the [FDA](/source/Food_and_Drug_Administration),[11] as of 2019,[\[update\]](https://en.wikipedia.org/w/index.php?title=Methylhexanamine&action=edit)[*[needs update](https://en.wikipedia.org/wiki/Wikipedia:Manual_of_Style/Dates_and_numbers#Chronological_items)*] the [stimulant](/source/Stimulant) remains available in sports and weight loss supplements in the [US](/source/United_States).[12]

## History

In April 1944, [Eli Lilly and Company](/source/Eli_Lilly_and_Company) introduced methylhexanamine under the brand name Forthane as an inhaled [nasal decongestant](/source/Nasal_decongestant); Lilly voluntarily withdrew methylhexanamine from the market in 1983.[13]: 12 The compound is an [aliphatic](/source/Aliphatic) [amine](/source/Amine); the pharmaceutical industry had a strong interest in compounds in this class as nasal decongestants in the early 20th century, which led to methylhexanamine and four other similar compounds being brought to market for that use: [tuaminoheptane](/source/Tuaminoheptane), [octin (isometheptene)](/source/Isometheptene), [oenethyl](/source/Oenethyl) (2-methylaminoheptane), and [propylhexedrine](/source/Propylhexedrine); octin and oenethyl were eventually approved for use in keeping blood pressure sufficiently high for patients under [anesthesia](/source/Anesthesia).[*[citation needed](https://en.wikipedia.org/wiki/Wikipedia:Citation_needed)*]: 95–96

## Marketing as dietary supplement

[Patrick Arnold](/source/Patrick_Arnold) reintroduced methylhexanamine in 2006 as a [dietary supplement](/source/Dietary_supplement),[14][15] after the final ban of [ephedrine](/source/Ephedrine) in the United States in 2005. Arnold introduced it under the trademarked name Geranamine, a name held by his company, Proviant Technologies. A large number of supplements focusing on fat loss and workout energy ([thermogenic](/source/Thermogenic) or general-purpose [stimulants](/source/Stimulant)) used the ingredient in concert with other substances such as [caffeine](/source/Caffeine), a combination similar to the combination of [ephedrine and caffeine](/source/ECA_stack).

Methylhexanamine-containing supplements sometimes list "geranium oil" or "geranium extract" as a source of methylhexanamine. However, geranium oils do not contain methylhexanamine, and the methylhexanamine in these supplements is added in the form of synthetic material.[16] A variety of studies have explored the possibility that DMAA is found in some types of geraniums, but at present, high quality evidence of DMAA's presence in plants is lacking.[17][18]

Methylhexanamine is [synthesized](/source/Chemical_synthesis) by [reacting](/source/Chemical_reaction) 4-methylhexan-2-one with hydroxylamine, which converts the 4-methylhexan-2-one to 4-methylhexan-2-one oxime, which is [reduced](/source/Organic_redox_reaction#Organic_reductions) via [catalytic hydrogenation](/source/Catalytic_hydrogenation); the resulting methylhexanamine can be purified by distillation.[19]: 995–996

## Pharmacology

Methylhexanamine is an indirect [sympathomimetic drug](/source/Sympathomimetic_drug) that [constricts blood vessels](/source/Vasoconstriction) and thus has effects on the heart, lungs, and reproductive organs. It also causes [bronchodilation](/source/Bronchodilation), inhibits [peristalsis](/source/Peristalsis) in the intestines, and has [diuretic](/source/Diuretic) effects.

Most studies have been done on pharmacological effects when the drug is inhaled; the understanding of what methylhexanamine does when taken orally are mostly based on extrapolating from the activities of similar compounds.: 97 A 2013 review concluded that: "Pharmacological effects after oral intake can be expected on the lungs (bronchodilation) and the nasal mucosa following a single oral dose of about 4–15 mg. Pharmacological effects on the heart can be expected following a single oral dose of about 50–75 mg. Pharmacological effects on the blood pressure can be expected after a single oral dose of about 100 mg. Because of the long half-life, there is a risk that repeated doses within 24–36 hours could lead to steadily stronger pharmacological effects (build-up).": 98

In 2019 and 2023, methylhexanamine was found to show activity consistent with being a [norepinephrine and dopamine releasing agent](/source/Norepinephrine%E2%80%93dopamine_releasing_agent) (NDRA).[20][21][22]

### Detection in body fluids

Methylhexanamine may be quantified in blood, plasma, or urine by gas or liquid chromatography-mass spectrometry to confirm a diagnosis of poisoning in hospitalized patients or to provide evidence in a medicolegal death investigation. Blood or plasma methylhexanamine concentrations are expected to be in a range of 10–100 μg/L in persons using the drug recreationally, >100 μg/L in intoxicated patients, and >300 μg/L in victims of acute overdosage.[23][24]

## Safety

The [LD50](/source/Median_lethal_dose) for methylhexanamine is 39 mg/kg in mice and 72.5 mg/kg in rats, when administered intravenously.: 95[25]: 110

The FDA has stated that methylhexanamine "is known to narrow the blood vessels and arteries, which can elevate blood pressure and may lead to cardiovascular events ranging from shortness of breath and tightening in the chest to heart attack".[26] Numerous adverse events and at least five deaths have been reported in association with methylhexanamine-containing dietary supplements.[10] There have also been reports of secondary open-angle [glaucoma](/source/Glaucoma) related to methylhexanamine supplementation.[27]

A 2012 review by a panel convened by the U.S. Department of Defense to study whether the military should ban methylhexanamine supplements from stores on its bases concluded that: "The existing evidence does not conclusively establish that DMAA-containing substances are causally-associated with adverse medical events. However, a consistent theme among the studies is that DMAA use potentially affects cardiovascular function, just as other sympathomimetic stimulants. Without further rigorous study designs developed to evaluate the safety of DMAA, especially in patients with concomitant use of other substances, co-morbid conditions and high frequency use, the magnitude of the association of DMAA with adverse medical events is uncertain. Widespread use of DMAA-containing products by tens of thousands of Service members – often in combination with other substances – increases the likelihood of observing serious adverse events, even if the overall risk of a DMAA-related event is low, resulting in consequential impact to some Service members and other beneficiaries. DMAA should be further studied to evaluate its safety. Data from the case control study suggest that the frequency and amount of DMAA use and risk of specific [acquired medical events], particularly heat injuries and rhabdomyolysis, need to be examined in greater detail. ... The Safety Review Panel recommended ... to continue the prohibition of sales of DMAA-containing products in Exchanges and concessions. The Panel judged that the evidence supports sufficient risk, even if very low, of another death or catastrophic illness of a Service member who has used DMAA-containing products, without any offsetting benefit of these products."[13]: 10

### Deaths and injuries

In 2010, a 21-year-old man in New Zealand presented with a [cerebral hemorrhage](/source/Cerebral_hemorrhage) after ingesting 556 mg of methylhexanamine, caffeine, and alcohol.[28] Health authorities in Hawaii linked cases of liver failure and one death to OxyElite Pro, a weight loss and bodybuilding dietary supplement.[29]

The death of Claire Squires, a runner who collapsed near the finish-line of the April [2012 London Marathon](/source/2012_London_Marathon), has been linked to methylhexanamine. The coroner stated that methylhexanamine was "probably an important factor" during the inquest. Despite, according to a friend, having been diagnosed with an irregular heartbeat[30] and advised not to consume methylhexanamine, it is believed that she consumed the substance through drinking an energy drink, which was subsequently reformulated to exclude methylhexanamine.[31]

## Chemistry

[Chemical structures](/source/Chemical_structure) of [amphetamine](/source/Amphetamine) and methylhexanamine compared.

Methylhexanamine, also known as 1,3-dimethylamylamine (1,3-DMAA), is an [alkylamine](/source/Psychotropic_alkylamines).[32][33]

It is closely [structurally related](/source/Structural_analog) to other alkylamines, including [1,3-dimethylbutylamine](/source/1%2C3-dimethylbutylamine) (1,3-DMBA), [1,4-dimethylamylamine](/source/1%2C4-dimethylamylamine) (1,4-DMAA), [heptaminol](/source/Heptaminol) (2-methyl-6-amino-2-heptanol), [iproheptine](/source/Iproheptine) (*N*-isopropyl-1,5-dimethylhexylamine), [isometheptene](/source/Isometheptene) (2-methyl-6-methylamino-2-heptene), [octodrine](/source/Octodrine) (2-amino-6-methylheptane or 1,5-dimethylhexylamine), and [tuaminoheptane](/source/Tuaminoheptane) (tuamine; 2-aminoheptane or 1-methylhexylamine).[32][33]

Methylhexanamine and other related alkylamines are similar in [chemical structure](/source/Chemical_structure) to [phenethylamines](/source/Substituted_phenethylamine) and [amphetamines](/source/Substituted_amphetamine), but lack a closed [ring](/source/Ring_(chemistry)).[32][33]

The predicted [log P](/source/Partition_coefficient) ([XLogP3](/source/XLogP3)) of methylhexanamine is 1.9.[32]

## Regulation

A number of sporting authorities and countries have banned or heavily restricted the use of methylhexanamine as a dietary supplement, due to serious concerns about its safety. These countries include Australia, Brazil, Canada, Finland, New Zealand, Sweden, Switzerland, the United Kingdom, and the United States.

### Sports authorities

Many professional and amateur sports bodies, such as the [World Anti Doping Agency](/source/World_Anti_Doping_Agency), have banned methylhexanamine as a performance-enhancing substance and suspended athletes that have used it.[34][35][36][37][38][39]

- March, 2012, a minor league baseball player, Cody Stanley, was suspended 50 games for testing positive after using a dietary supplement.[40]

- In July 2012, Welsh boxer [Enzo Maccarinelli](/source/Enzo_Maccarinelli) was banned for six months after testing positive for methylhexanamine.[41]

- [VFL](/source/VFL) player Matthew Clark was suspended for two years after the banned substance was detected in his system after a game in 2011.[42]

- August, 2012, then minor league baseball player [Marcus Stroman](/source/Marcus_Stroman) was suspended 50 games for testing positive for methylhexanamine.[43]

- On 8 August 2013, US Weightlifter Brian Wilhelm accepted a nine-month suspension after testing positive for the drug in a urine sample from December 2012 at the American Open.[44]

- [MotoGP](/source/MotoGP) rider [Anthony West](/source/Anthony_West_(motorcycle_racer)) was suspended for one month by the FIM International Disciplinary Court (CDI) on 29 October 2012 after testing positive for the drug on 20 May 2012 at the French Grand Prix. This was increased retroactively to an 18-month suspension, starting from 20 May 2012, on 28 November 2013 after an appeal by the World Anti-Doping Agency (WADA).[45]

- In December 2013, boxer [Brandon Rios](/source/Brandon_Rios), after losing a unanimous decision to [Manny Pacquiao](/source/Manny_Pacquiao), was suspended by the China Professional Boxing Association after testing positive for the drug.[46]

- During the [2014 Winter Olympics](/source/2014_Winter_Olympics) in [Sochi](/source/Sochi), three athletes tested positive for the drug: Italian bobsleigh brakeman and former [decathlete](/source/Decathlon) [William Frullani](/source/William_Frullani), German [biathlete](/source/Biathlon) [Evi Sachenbacher-Stehle](/source/Evi_Sachenbacher-Stehle) and Latvian ice hockey forward [Vitalijs Pavlovs](/source/Vitalijs_Pavlovs).[47][48]

- During the [2015 Asian Cup](/source/2015_Asian_Cup), Iraqi player [Alaa Abdul-Zahra](/source/Alaa_Abdul-Zahra) was subject to an investigation relating to illegal usage of the drug.[49]

- In January 2016, [Algerian](/source/Algeria) [footballer](/source/Association_football) [Kheiredine Merzougi](/source/Kheiredine_Merzougi) was banned for two years by the [Confederation of African Football](/source/Confederation_of_African_Football) after testing positive for the drug.[50] However, in March 2016, the international body [FIFA](/source/FIFA) confirmed they were giving an extended four-year ban to apply worldwide through January 2020.[51]

- In November 2016, heavyweight boxer [Bermane Stiverne](/source/Bermane_Stiverne) was fined US$75,000 after testing positive for methylhexanamine by the [World Boxing Council](/source/World_Boxing_Council).[52] The WBC, however, still allowed this fight to happen.

- In 2017, the International Olympic Committee disqualified Jamaica's 2008 gold-winning 4 ×‍100 men's relay in [Beijing](/source/2008_Summer_Olympics) due to [Nesta Carter](/source/Nesta_Carter)'s positive testing for methylhexanamine. This cost [Usain Bolt](/source/Usain_Bolt) a medal.[53]

- [AMA Supercross Championship](/source/AMA_Supercross_Championship) rider Broc Tickle was provisionally suspended by the FIM International Disciplinary Court (CDI) on 13 April 2018 after testing positive for the drug following a drug test after the supercross round held in [San Diego](/source/San_Diego) on 10 February 2018.[54]

- On May 22, 2018, [Filipino](/source/Filipinos) basketball player [Kiefer Ravena](/source/Kiefer_Ravena) was handed 18 months suspension by [FIBA](/source/FIBA) to compete in international competition. He was found testing positive for methylhexanamine and 1,3-dimethlybutylamine by [WADA](/source/World_Anti-Doping_Agency). Urine samples were taken after the Philippines vs Japan game at Manila during the [2019 FIBA Basketball World Cup Qualification](/source/2019_FIBA_Basketball_World_Cup_qualification_(Asia)). Ravena explained that he consumes a pre-workout drink called C4, which can be bought from retailers around [Metro Manila](/source/Metro_Manila). He ran out of supplies shortly before a training camp in Australia and took Blackstone Labs DUST, a supplement which is mixed with water and is supposedly similar to C4.[55]

- On August 26, 2019, [NASCAR](/source/NASCAR) [crew chief](/source/Crew_chief_(auto_racing)) [Matt Borland](/source/Matt_Borland) was indefinitely suspended under the sanctioning body's substance abuse policy after testing positive for DMAA. In a statement, Borland said that the positive test was most likely caused by a diet coffee he had felt comfortable drinking "after doing my due diligence." Team owner Bob Germain Jr. also said that he did not believe Borland “had reason to know that the coffee contained a banned substance. However, we also understand and respect NASCAR’s decisions to strictly uphold their policies for each and every owner, driver and crew member in the garage."[56] The suspension was lifted on September 24 after completing NASCAR's mandatory "Road to Recovery Program".[57]

### Governmental agencies

In 2010, the US military issued a recall of all methylhexanamine-containing products from all military exchange stores worldwide.[58][59]

In July 2011, [Health Canada](/source/Health_Canada) decided methylhexanamine was not a dietary substance, but was a drug requiring further approval. Consequently, Health Canada banned all sales of methylhexanamine.[60]

In June 2012, the National Food Agency of Sweden issued a general warning regarding use of methylhexanamine products, resulting in a sales ban in parts of the country.[61]

In July 2012, the National Health Surveillance Agency of Brazil issued a warning to the general public on the hazards of products that contain methylhexanamine.[62] It also updated the list of prohibited substances to insert methylhexanamine, which translates into the banishment of products containing such ingredient from the Brazilian market.[63]

In 2012, Australia banned methylhexanamine. In New South Wales, methylhexanamine was classed as a "highly dangerous substance" on the poisons list.[64]

In August 2012, the UK Medicines and Healthcare products Regulatory Agency (MHRA) has ruled that the popular DMAA containing sports supplement Jack3D is an unlicensed medicinal product and that it and all other methylhexanamine containing products need to be removed from the UK market amid concerns of potential risks to public safety.[65]

In 2012 the New Zealand Ministry of Health banned the sale of methylhexanamine products,[66] due in part to its growing recreational use as [party pills](/source/Party_pills).[67][68]

In April 2013, the [US Food and Drug Administration](/source/US_Food_and_Drug_Administration) determined that methylhexanamine was potentially dangerous and did not qualify as a legal [dietary supplement](/source/Dietary_supplement); it warned supplement makers that it was illegal to market methylhexanamine and warned consumers of potentially serious health risks associated with methylhexanamine-containing products.[10][69] The FDA has issued warning letters to manufacturers and distributors who continued to market products containing methylhexanamine.[70]

## See also

- [1,3-Dimethylbutylamine](/source/1%2C3-Dimethylbutylamine)

- [Benzedrine](/source/Benzedrine)

- [Cyclopentamine](/source/Cyclopentamine)

- [Deterenol](/source/Deterenol)

- [Heptaminol](/source/Heptaminol)

- [Iproheptine](/source/Iproheptine)

- [Isometheptene](/source/Isometheptene)

- [Levomethamphetamine](/source/Levomethamphetamine)

- [Octodrine](/source/Octodrine)

- [Propylhexedrine](/source/Propylhexedrine)

- [Pseudoephedrine](/source/Pseudoephedrine)

- [Tuaminoheptane](/source/Tuaminoheptane)

## Notes

1. **[^](#cite_ref-5)** The N.D.A (New Drug Application) for methylhexanamine was withdrawn in 1983. Consequently, any product containing methylhexanamine cannot be marketed in the [United States](/source/United_States) until a new application is approved.[4]

## References

1. **[^](#cite_ref-1)** ["DMAA: A prohibited stimulant"](https://www.opss.org/article/dmaa-prohibited-stimulant). *United States Department of Defense: Operation Supplement Safety*. [U.S. Department of Defense](/source/DoD). October 12, 2022. Retrieved August 28, 2023.

1. **[^](#cite_ref-2)** ["DMAA in Products Marketed as Dietary Supplements"](https://www.fda.gov/food/information-select-dietary-supplement-ingredients-and-other-substances/dmaa-products-marketed-dietary-supplements?ref=smartchoicelist.com). *[United States Food and Drug Administration](/source/Food_and_Drug_Administration)*. February 22, 2023. Retrieved August 28, 2023. [Methylhexanamine] is not a dietary ingredient, and [Methylhexanamine]-containing products marketed as dietary supplements are illegal and their marketing violates the law.

1. **[^](#cite_ref-3)** ["United States v. Hi-Tech Pharmaceuticals, Inc., No. 17-13376 (11th Cir. 2019)"](https://law.justia.com/cases/federal/appellate-courts/ca11/17-13376/17-13376-2019-08-30.html). *Justia Law*. August 30, 2019. Retrieved 2023-08-29. DMAA is not an 'herb or other botanical.' It is not a 'constituent' of an herb or other botanical. And it is not generally recognized by qualified experts, as adequately shown through scientific procedures, to be safe under the conditions of its intended use.

1. **[^](#cite_ref-4)** Meyer H (November 9, 1983). ["E. R. Squibb & Sons, inc. et al.; Withdrawal of Approval of New Drug Applications"](https://www.govinfo.gov/content/pkg/FR-1983-11-09/pdf/FR-1983-11-09.pdf) (PDF). *[Federal Register](/source/Federal_Register)*. [U.S. Food and Drug Administration](/source/Food_and_Drug_Administration) through the [United States Government Publishing Office](/source/United_States_Government_Publishing_Office).

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1. **[^](#cite_ref-7)** [Anvisa](/source/Brazilian_Health_Regulatory_Agency) (2023-07-24). ["RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"](https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451) [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). [Diário Oficial da União](/source/Di%C3%A1rio_Oficial_da_Uni%C3%A3o) (published 2023-07-25). [Archived](https://web.archive.org/web/20230827163149/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451) from the original on 2023-08-27. Retrieved 2023-08-27.

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1. **[^](#cite_ref-12)** ["Products & Ingredients - DMAA in Products Marketed as Dietary Supplements"](https://web.archive.org/web/20160117210608/http://www.fda.gov/Food/DietarySupplements/ProductsIngredients/ucm346576.htm). *Center for Food Safety and Applied Nutrition (CFSAN)*. U.S Food and Drug Administratio. May 2019. Archived from [the original](https://www.fda.gov/food/dietarysupplements/productsingredients/ucm346576.htm) on January 17, 2016.

1. **[^](#cite_ref-13)** Cohen PA, Wen A, Gerona R (December 2018). ["Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration"](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6583602). *JAMA Internal Medicine*. **178** (12): 1721–1723. [doi](/source/Doi_(identifier)):[10.1001/jamainternmed.2018.4846](https://doi.org/10.1001%2Fjamainternmed.2018.4846). [PMC](/source/PMC_(identifier)) [6583602](https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6583602). [PMID](/source/PMID_(identifier)) [30422217](https://pubmed.ncbi.nlm.nih.gov/30422217).

1. ^ [***a***](#cite_ref-DODTox_14-0) [***b***](#cite_ref-DODTox_14-1) Lammie CJ, Lead SP (June 2013). [Report of the department of defense 1, 3 dimethylamylamine (DMAA) safety review panel](https://web.archive.org/web/20140119112259/http://home.fhpr.osd.mil/Libraries/pdf/Report_of_the_DoD_DMAA_Safety_Review_Panel_2013.sflb.ashx). *The Pentagon* (Report). US Department of Defense. Archived from [the original](http://home.fhpr.osd.mil/Libraries/pdf/Report_of_the_DoD_DMAA_Safety_Review_Panel_2013.sflb.ashx) on 2014-01-19.

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## External links

- ["Stimulant Potentially Dangerous to Health, FDA Warns"](https://web.archive.org/web/20130413233832/http://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm). [U.S. Food and Drug Administration](/source/U.S._Food_and_Drug_Administration). April 11, 2013. Archived from [the original](https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm) on April 13, 2013.

- Bussel II, Pavlov Jr AA (June 7, 2013). ["DMAA: Efficacious but is it Safe?"](http://www.sciencebasedmedicine.org/index.php/dmaa-efficacious-but-is-it-safe/). Science Based Medicine Blog.

v t e Stimulants Adamantanes Adapromine Amantadine Bromantane Memantine Rimantadine Adenosine antagonists 8-Chlorotheophylline 8-Cyclopentyltheophylline 8-Phenyltheophylline Aminophylline Caffeine CGS-15943 Dimethazan Istradefylline Paraxanthine SCH-58261 Theobromine Theophylline Alkylamines Cyclopentamine Cypenamine Cyprodenate Heptaminol Isometheptene Methylhexaneamine Octodrine Propylhexedrine Tuaminoheptane Ampakines CX-516 CX-546 CX-614 CX-691 CX-717 IDRA-21 LY-404,187 LY-503,430 Nooglutyl Org 26576 PEPA S-18986 Sunifiram Unifiram Arylcyclohexylamines Benocyclidine Dieticyclidine Esketamine Eticyclidine Gacyclidine Ketamine Phencyclamine Phencyclidine Rolicyclidine Tenocyclidine Tiletamine Benzazepines 6-Br-APB SKF-77434 SKF-81297 SKF-82958 Cathinones 3-FMC 3-MMC 3,4-DMMC 4-BMC 4-CMC 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-Methylpentedrone Amfepramone Benzedrone Buphedrone Bupropion Butylone Cathinone Dimethylcathinone Ethcathinone Ethylone Flephedrone Hexedrone Isoethcathinone Mephedrone Methcathinone Methedrone Methylenedioxycathinone Methylone Mexedrone N-Ethylbuphedrone N-Ethylhexedrone Pentedrone Pentylone Phthalimidopropiophenone Cholinergics A-84,543 A-366,833 ABT-202 ABT-418 AR-R17779 Altinicline Anabasine Arecoline Bradanicline Cotinine Cytisine Dianicline Epibatidine Epiboxidine GTS-21 Ispronicline Nicotine PHA-543,613 PNU-120,596 PNU-282,987 Pozanicline Rivanicline Sazetidine A SIB-1553A SSR-180,711 TC-1698 TC-1827 TC-2216 Tebanicline UB-165 Varenicline WAY-317,538 Convulsants Anatoxin-a Bicuculline DMCM Flurothyl Gabazine Pentetrazol Picrotoxin Strychnine Thujone Eugeroics Adrafinil Armodafinil CRL-40,940 CRL-40,941 Fluorenol Modafinil Oxazolines 4-Methylaminorex Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines 1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fluoroamphetamine 2-Fluoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fluoroamphetamine 3-Fluoroethamphetamine 3-Methoxyamphetamine 3-Methylamphetamine 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-ME 4-MMA 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine, Levoamphetamine) Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Camfetamine Cathine Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D-Deprenyl Denopamine Dimethoxyamphetamine Dimethylamphetamine Dobutamine DOPA (Dextrodopa, Levodopa) Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethylnorepinephrine Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine, Levofenfluramine) Fenproporex Feprosidnine FDE Fludorex 4-Fluorodeprenyl Formetorex Furfenorex Gepefrine Hexapradol HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoprenaline L-Deprenyl (Selegiline) Lefetamine Lisdexamfetamine Lomardexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine, Levomethamphetamine) Methoxamine Methoxyphenamine MMA Methoxyphenamine MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L-Norpseudoephedrine Octopamine Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Prenylamine Propylamphetamine Pseudoephedrine Pyr-AI Ropinirole Salbutamol (Levosalbutamol) Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines 3-Fluorophenmetrazine Fenbutrazate Fenmetramide G-130 Manifaxine Morazone Morforex Oxaflozane PD-128,907 Phendimetrazine Phenmetrazine 2-Phenyl-3,6-dimethylmorpholine Pseudophenmetrazine Radafaxine Piperazines 2C-B-BZP 3C-PEP BZP CM156 DBL-583 GBR-12783 GBR-12935 GBR-13069 GBR-13098 GBR-13119 JJC8-088 MeOPP MBZP oMPP Vanoxerine Piperidines 1-Benzyl-4-(2-(diphenylmethoxy)ethyl)piperidine 2-Benzylpiperidine 2-Methyl-3-phenylpiperidine 3,4-Dichloromethylphenidate 4-Benzylpiperidine 4-Fluoromethylphenidate 4-Methylmethylphenidate Desoxypipradrol Difemetorex Diphenylpyraline Ethylnaphthidate Ethylphenidate Methylnaphthidate Isopropylphenidate JZ-IV-10 Methylphenidate (Dexmethylphenidate) Nocaine Phacetoperane Pipradrol Propylphenidate Serdexmethylphenidate SCH-5472 Phenethylpyrrolidines 2-Diphenylmethylpyrrolidine 4-Cl-PVP 5-DBFPV α-PPP α-PBP α-PCYP α-PHiP α-PHP α-PHPP α-PVP α-PVT Diphenylprolinol DMPVP FPOP FPVP MDPPP MDPBP MPBP MPEP MPHP MPPP MOPVP MOPPP Indapyrophenidone MDPV Naphyrone PEP Picilorex Prolintane Pyrovalerone Racetams Oxiracetam Phenylpiracetam Phenylpiracetam hydrazide Psychedelics 2,5-DMA (DOH) 2C-B 2C-D 2C-G-N 5-MeO-DiPT 5-MeO-MiPT Ariadne (4C-DOM; BL-3912; Dimoxamine) ASR-2001 (2CB-5PrO) DOET DOM DON DOPR LSD MTFEM Tropanes 4-fluorotropacocaine 4'-Fluorococaine Altropane (IACFT) Brasofensine CFT (WIN 35,428) β-CIT (RTI-55) Cocaethylene Cocaine Dichloropane (RTI-111) Difluoropine FE-β-CPPIT FP-β-CPPIT Ioflupane (123I) Norcocaine PIT PTT RTI-31 RTI-32 RTI-51 RTI-112 RTI-113 RTI-120 RTI-121 (IPCIT) RTI-126 RTI-150 RTI-177 RTI-229 RTI-336 RTI-354 RTI-371 RTI-386 Salicylmethylecgonine Tesofensine Troparil (β-CPT, WIN 35,065-2) Tropoxane WF-23 WF-33 Tryptamines 4-HO-αMT 4-Methyl-αET 4-Methyl-αMT 5-Chloro-αMT 5-Fluoro-αMT 5-MeO-αET 5-MeO-αMT 5-MeO-DIPT 6-Fluoro-αMT 7-Methyl-αET αET αMT Others 2-MDP 3,3-Diphenylcyclobutanamine Amfonelic acid Amineptine Amiphenazole Atipamezole Atomoxetine Bemegride Benzydamine BTQ BTS 74,398 Centanafadine Ciclazindol Clofenciclan Cropropamide Crotetamide D-161 Desipramine Diclofensine Dimethocaine Efaroxan Etamivan Fenisorex Fenpentadiol Gamfexine Gilutensin GSK1360707F GYKI-52895 Hexacyclonate Idazoxan Indanorex Indatraline JNJ-7925476 Lazabemide Leptacline Lomevactone LR-5182 Mazindol Meclofenoxate Medifoxamine Mefexamide Methamnetamine Methastyridone Methiopropamine Naphthylaminopropane Nefopam Nikethamide Nomifensine O-2172 Oxaprotiline PNU-99,194 PRC200-SS Rasagiline Rauwolscine Rubidium chloride Setazindol Tametraline Tandamine Thiopropamine Thiothinone Trazium UH-232 Yohimbine ATC code: N06B

v t e Decongestants and other nasal preparations (R01) Topical Sympathomimetics, plain Amidephrine Cyclopentamine Ephedrine Epinephrine Fenoxazoline Iproheptine Levmetamfetamine Methylephedrine Metizoline Naphazoline Oxymetazoline Phenylephrine Propylhexedrine Tetryzoline Tramazoline Tuaminoheptane Tymazoline Xylometazoline Antiallergic agents, excluding corticosteroids Spaglumic acid histamine antagonists (Levocabastine Antazoline Thonzylamine) mast cell stabilizer (some are also antihistamines) (Cromoglicic acid Nedocromil Azelastine Olopatadine Lodoxamide) Corticosteroids Beclometasone dipropionate Betamethasone# Budesonide Ciclesonide Dexamethasone Flunisolide Fluticasone (Fluticasone furoate, Fluticasone propionate) Mometasone furoate Prednisolone# Tixocortol Triamcinolone Triamcinolone acetonide Other nasal preparations Cafaminol Calcium hexamine thiocyanate Eucalyptus oil Framycetin Hexamidine Hyaluronan Ipratropium bromide Mupirocin Retinol Ritiometan Saline water Combination products Olopatadine/mometasone Systemic use: Sympathomimetics Ephedrine Phenylephrine Phenylpropanolamine‡ Pseudoephedrine (+azatadine, +carbinoxamine, +cetirizine, +dexbrompheniramine, +fexofenadine, +loratadine, +naproxen) #WHO-EM ‡Withdrawn from market Clinical trials: †Phase III §Never to phase III

v t e Monoamine releasing agents DRAsTooltip Dopamine releasing agents Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA 5-APB 5-APBT 5-MAPB 6-APB 6-APBT 6-MAPB Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine (Dextroamphetamine Levoamphetamine) Amphetaminil β-Me-PEA BDB BOH Benzphetamine Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine D-Deprenyl DMA DMMA Dimethylamphetamine Ephedrine Ethcathinone EBDB Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine Lophophine Mefenorex Mephedrone Metamfepramone Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone MMDA MMDMA MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) MDMPEA MDOH MDPEA Methylone Morforex Ortetamine pBA pCA pIA Pholedrine Phenethylamine Pholedrine Phenpromethamine Prenylamine Propylamphetamine Pseudoephedrine SDA (3T-MDA) SDMA (3T-MDMA) Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines: 2C-B-BZP BZP MBZP MDBZP MeOPP oMPP Others: 2-ADN 2-AI 2-AT 4-BP 5-APDI 5-IAI Amineptine Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Naphthylaminopropane Octodrine Phthalimidopropiophenone Phenylbiguanide Propylhexedrine NRAsTooltip Norepinephrine releasing agents Morpholines: Fenbutrazate Fenmetramide Morazone Morforex Phendimetrazine Phenmetrazine Pseudophenmetrazine Oxazolines: 4-MAR Aminorex Clominorex Cyclazodone Fenozolone Fluminorex Pemoline Thozalinone Phenethylamines: 2-OH-PEA 4-CAB 4-FA 4-FMA 4-MA 4-MMA 4-ME 5-APB 5-APBT 5-MAPB 6-APB 6-APBT 6-MAPB Alfetamine Amfecloral Amfepentorex Amfepramone Amphetamine Dextroamphetamine Levoamphetamine Amphetaminil β-Me-PEA BDB Benzphetamine BOH Buphedrone Butylone Cathine Cathinone Clobenzorex Clortermine Deprenyl Dimethylamphetamine DMA DMMA EBDB Ephedrine Ethcathinone Ethylone Etilamfetamine Famprofazone Fenethylline Fenproporex Flephedrone Fludorex 4-Fluorodeprenyl Furfenorex Hordenine 4-Hydroxyamphetamine 5-APDI (IAP) Iofetamine (123I) Lisdexamfetamine Lomardexamfetamine Lophophine MBDB MDA (tenamfetamine) MDEA MDMA (midomafetamine) Metamfepramone MDMPEA MDOH MDPEA Mefenorex Mephedrone Mephentermine Methamphetamine Dextromethamphetamine Levomethamphetamine Methcathinone Methedrone Methylone Morforex Naphthylaminopropane Ortetamine pBA pCA Pentorex Phenethylamine Pholedrine Phenpromethamine Phentermine Phenylpropanolamine pIA Prenylamine Propylamphetamine Pseudoephedrine SDA (3T-MDA) SDMA (3T-MDMA) Selegiline (also D-Deprenyl) Tiflorex Tyramine Xylopropamine Zylofuramine Piperazines: 2C-B-BZP BZP MBZP mCPP MDBZP MeOPP oMPP pFPP Others: 2-ADN 2-AI 2-AT 2-BP 4-BP 5-IAI Clofenciclan Cyclopentamine Cypenamine Cyprodenate Feprosidnine Gilutensin Heptaminol Hexacyclonate Indanorex Isometheptene Methylhexanamine Octodrine Phthalimidopropiophenone Propylhexedrine Tuaminoheptane SRAsTooltip Serotonin releasing agents Aminoindanes: 5-IAI AMMI ETAI MDAI MDMAI MMAI TAI Aminotetralins: 6-CAT 8-OH-DPAT MDAT MDMAT Oxazolines: 4-Methylaminorex Aminorex Clominorex Fluminorex Phenethylamines: 2-Methyl-MDA pCPE 4-CAB 4-FA 4-FMA 4-HA 4-MTA 4-ME 5-APB 5-APBT 5-APDB 5-MAPB 5-Methyl-MDA 6-APB 6-APBT 6-APDB 6-MAPB 6-Methyl-MDA AEMMA Amiflamine BDB BOH Brephedrone Butylone Chlorphentermine Cloforex Amfepramone Metamfepramone DCA Dexfenfluramine DFMDA DMA DMMA EBDB EDMA Ethylone Etolorex Fenfluramine Flephedrone Flucetorex IAP Iofetamine Levofenfluramine Lophophine MBDB MDA (tenamfetamine) MDEA MDHMA MDMA (midomafetamine) MDMPEA MDOH MDPEA Mephedrone Methedrone Methylone MMA MMDA MMDA-3b MMDMA MMMA NAP Norfenfluramine 4-TFMA pBA pCA pIA PMA PMEA PMMA SDA (3T-MDA) SDMA (3T-MDMA) TAP Piperazines: 2C-B-BZP 3-MeOPP BZP DCPP MBZP mCPP MDBZP MeOPP Mepiprazole oMPP pCPP pFPP pTFMPP TFMPP Tryptamines: 4-Methyl-αET 4-Methyl-αMT 5-CT 5-MeO-αET 5-MeO-αMT 5-MT αET αMT DMT Tryptamine Others/unsorted: Indeloxazine PAL-335 Viqualine Others DAT modulators: Agonist-like: SoRI-9804 SoRI-20040; Antagonist-like: SoRI-20041 Adrenergic release blockers: Bethanidine Bretylium Guanadrel Guanazodine Guanethidine Guanoxan See also: Receptor/signaling modulators • Monoamine reuptake inhibitors • Adrenergics • Dopaminergics • Serotonergics • Monoamine metabolism modulators • Monoamine neurotoxins

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