Methylhexanamine

In April 1944, Eli Lilly and Company introduced methylhexanamine under the brand name Forthane as an inhaled nasal decongestant; Lilly voluntarily withdrew methylhexanamine from the market in 1983.{{cite report | vauthors = Lammie CJ, Lead SP | title = Report of the department of defense 1, 3 dimethylamylamine (DMAA) safety review panel. | work = The Pentagon | publisher = US Department of Defense. | date = June 2013 | url = http://home.fhpr.osd.mil/Libraries/pdf/Report_of_the_DoD_DMAA_Safety_Review_Panel_2013.sflb.ashx | archive-url = https://web.archive.org/web/20140119112259/http://home.fhpr.osd.mil/Libraries/pdf/Report_of_the_DoD_DMAA_Safety_Review_Panel_2013.sflb.ashx |archive-date=2014-01-19 }}{{rp|12}} The compound is an aliphatic 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, octin (isometheptene), oenethyl (2-methylaminoheptane), and propylhexedrine; octin and oenethyl were eventually approved for use in keeping blood pressure sufficiently high for patients under anesthesia.{{citation needed|date=November 2019}}{{rp|95–96}}

Patrick Arnold reintroduced methylhexanamine in 2006 as a dietary supplement,{{cite news|url=https://www.washingtonpost.com/wp-dyn/content/article/2006/05/07/AR2006050700913.html | newspaper=The Washington Post | vauthors = Shipley A | title=Chemist's New Product Contains Hidden Substance | date=May 8, 2006}}{{cite web | vauthors = Carroll W | date = 16 August 2010 | url = http://www.baseballprospectus.com/article.php?articleid=11761 | title = Under The Knife: 997 | work = Baseball Prospectus | access-date = 12 April 2012 }} after the final ban of 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 or general-purpose stimulants) used the ingredient in concert with other substances such as caffeine, a combination similar to the combination of ephedrine and caffeine.

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.{{cite journal | vauthors = Lisi A, Hasick N, Kazlauskas R, Goebel C | title = Studies of methylhexaneamine in supplements and geranium oil | journal = Drug Testing and Analysis | volume = 3 | issue = 11–12 | pages = 873–876 | year = 2011 | pmid = 22147493 | doi = 10.1002/dta.392 | s2cid = 21294033 }} 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.{{cite journal | vauthors = Fleming HL, Ranaivo PL, Simone PS | title = Analysis and Confirmation of 1,3-DMAA and 1,4-DMAA in Geranium Plants Using High Performance Liquid Chromatography with Tandem Mass Spectrometry at ng/g Concentrations | journal = Analytical Chemistry Insights | volume = 7 | issue = 7 | pages = 59–78 | year = 2012 | pmid = 23225994 | pmc = 3512447 | doi = 10.4137/ACI.S10445 }}{{cite journal | vauthors = Cohen PA | title = DMAA as a dietary ingredient-reply | journal = JAMA Internal Medicine | volume = 173 | issue = 7 | pages = 595 | date = April 2013 | pmid = 23568632 | doi = 10.1001/jamainternmed.2013.3776 }}

Methylhexanamine is synthesized by reacting 4-methylhexan-2-one with hydroxylamine, which converts the 4-methylhexan-2-one to 4-methylhexan-2-one oxime, which is reduced via catalytic hydrogenation; the resulting methylhexanamine can be purified by distillation.{{cite book | chapter = Methylhexaneamine Carbonate | vauthors = Sittig M | url = http://worldtracker.org/media/library/Reference/Encyclopedia's/Encyclopedia%20of%20Pharmaceutical%20Manufacturing.pdf | title = Pharmaceutical Manufacturing Encyclopedia | edition = Second | volume = 1 | date = 1988 | publisher = Noyes Publications | location = Westwood, New Jersey }}{{rp|995–996}}

Methylhexanamine is an indirect sympathomimetic drug that constricts blood vessels and thus has effects on the heart, lungs, and reproductive organs. It also causes bronchodilation, inhibits peristalsis in the intestines, and has 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.{{rp|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)."{{rp|98}} Methylhexanamine has also been found to completely inhibit the function of 5-α-reductase in vitro, primarily preventing the peripheral conversion of testosterone to dihydrotestosterone (DHT).{{cite journal | vauthors = Liang T, Heiss CE | title = Inhibition of 5 alpha-reductase, receptor binding, and nuclear uptake of androgens in the prostate by a 4-methyl-4-aza-steroid | journal = The Journal of Biological Chemistry | volume = 256 | issue = 15 | pages = 7998–8005 | date = August 1981 | pmid = 7263637 | doi = 10.1016/S0021-9258(18)43378-9 | doi-access = free }}{{cite journal | vauthors = Leshin M, Wilson JD | title = Inhibition of steroid 5 alpha-reductase from human skin fibroblasts by 17 beta-N,N-diethylcarbamoyl-4-methyl-4-aza-5 alpha-androstan-3-one | journal = Journal of Steroid Biochemistry | volume = 17 | issue = 3 | pages = 245–250 | date = September 1982 | pmid = 6957692 | doi = 10.1016/0022-4731(82)90196-0 }} Reduction via 5-α-reductase was also reduced in 4-androstene-3,17-dione and cortisol as a result of the addition of methylhaxanamine. Additional studies have shown that methylhexanamine inhibits the function of the CYP2D6 enzyme, an enzyme that is found in the liver and is responsible for the metabolism of a quarter of all types of drugs, including antidepressants and antipsychotics.{{Cite journal | vauthors = Rodrigues AN, Dinis-Oliveira RJ |date=2023-07-03 |title=Pharmacokinetic and Toxicological Aspects of 1,3-Dimethylamylamine with Clinical and Forensic Relevance |journal=Psychoactives |language=en |volume=2 |issue=3 |pages=222–241 |doi=10.3390/psychoactives2030015 |doi-access=free |issn=2813-1851}}{{Cite journal |title=Fig. 1. Construction of DMAA, HVA and IMA angles. Note. DMAA — distal metatarsal articular angle, HVA — Hallux valgus angle, IMA — intermetatarsal angle. |url=https://doi.org/10.17816/vto569070-4207825 |access-date=2025-03-22 |website=doi.org|doi=10.17816/vto569070-4207825 |url-access=subscription }} Consumption of methylhexanamine in addition to any drug metabolized by CYP2D6 should be carefully monitored, as the resulting buildup caused by a defective enzyme could cause further, more devastating side effects.

In 2019 and 2023, methylhexanamine was found to show activity consistent with being a norepinephrine and dopamine releasing agent (NDRA).{{cite journal | vauthors = Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, Block ER | title = The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization | journal = The Journal of Pharmacology and Experimental Therapeutics | volume = 386 | issue = 2 | pages = 266–273 | date = August 2023 | pmid = 37348963 | pmc = 10353075 | doi = 10.1124/jpet.122.001573 }}{{cite journal | vauthors = Docherty JR, Alsufyani HA | title = Pharmacology of Drugs Used as Stimulants | journal = Journal of Clinical Pharmacology | volume = 61 | issue = Suppl 2 | pages = S53–S69 | date = August 2021 | pmid = 34396557 | doi = 10.1002/jcph.1918 | doi-access = free }}{{cite journal | vauthors = Alsufyani HA, Docherty JR | title = Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat | journal = European Journal of Pharmacology | volume = 843 | issue = | pages = 121–125 | date = January 2019 | pmid = 30395850 | doi = 10.1016/j.ejphar.2018.10.047 }}

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.{{cite journal | vauthors = Gee P, Tallon C, Long N, Moore G, Boet R, Jackson S | title = Use of recreational drug 1,3 Dimethylamylamine (DMAA) [corrected] associated with cerebral hemorrhage | journal = Annals of Emergency Medicine | volume = 60 | issue = 4 | pages = 431–434 | date = October 2012 | pmid = 22575212 | doi = 10.1016/j.annemergmed.2012.04.008 }}{{cite book | vauthors = Baselt RC | title = Disposition of toxic drugs and chemicals in man | edition = 10th | year = 2014 | publisher = Biomedical Publications | location = Seal Beach, Ca. | isbn = 978-0-9626523-9-4 | page = 1329 }}

The {{LD50}} for methylhexanamine is 39 mg/kg in mice and 72.5 mg/kg in rats, when administered intravenously.{{rp|95}}{{cite journal | vauthors = Miya TS, Edwards LD | title = A pharmacological study of certain alkoxyalkylamines | journal = Journal of the American Pharmaceutical Association. American Pharmaceutical Association | volume = 42 | issue = 2 | pages = 107–110 | date = February 1953 | pmid = 13034643 | doi = 10.1002/jps.3030420216 }}{{rp|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".{{cite web|url=https://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm302133.htm|archive-url=https://web.archive.org/web/20120429164527/http://www.fda.gov/NewsEvents/Newsroom/PressAnnouncements/ucm302133.htm|url-status=dead|archive-date=April 29, 2012|title=FDA challenges marketing of methylhexanamine products for lack of safety evidence: Agency cites ten companies in warning letters|publisher=United States Food and Drug Administration|access-date=March 17, 2013|date=April 27, 2012|quote=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.}} Numerous adverse events and at least five deaths have been reported in association with methylhexanamine-containing dietary supplements.{{cite news | work = New York Times | date = April 16, 2013 | access-date = April 16, 2013 | title = F.D.A. Issues Warning on Workout Supplement |url=https://www.nytimes.com/2013/04/13/business/fda-issues-warning-on-workout-booster.html | vauthors = Singer N, Lattman P }} There have also been reports of secondary open-angle glaucoma related to methylhexanamine supplementation.{{cite journal | vauthors = Balas M, Mathew DJ | title = Secondary open-angle glaucoma in a young male related to dimethylamylamine supplementation | language = English | journal = Canadian Journal of Ophthalmology. Journal Canadien d'Ophtalmologie | volume = 58 | issue = 4 | pages = e171–e175 | date = August 2023 | pmid = 36965509 | doi = 10.1016/j.jcjo.2023.02.011 | s2cid = 257710303 | doi-access = free }}

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."{{rp|10}}

In 2010, a 21-year-old man in New Zealand presented with a cerebral hemorrhage after ingesting 556 mg of methylhexanamine, caffeine, and alcohol.{{cite journal | vauthors = Gee P, Jackson S, Easton J | title = Another bitter pill: a case of toxicity from DMAA party pills | journal = The New Zealand Medical Journal | volume = 123 | issue = 1327 | pages = 124–127 | date = December 2010 | pmid = 21358791 | url = http://journal.nzma.org.nz/journal/123-1327/4480/ | access-date = 2012-02-01 | url-status = dead | archive-url = https://web.archive.org/web/20120120154827/http://journal.nzma.org.nz/journal/123-1327/4480/ | archive-date = 2012-01-20 }} Health authorities in Hawaii linked cases of liver failure and one death to OxyElite Pro, a weight loss and bodybuilding dietary supplement.{{cite journal | vauthors = Kuehn BM | title = Dietary supplement linked to cases of acute hepatitis | journal = JAMA | volume = 310 | issue = 17 | pages = 1784 | date = November 2013 | pmid = 24193065 | doi = 10.1001/jama.2013.281868 }}

The death of Claire Squires, a runner who collapsed near the finish-line of the April 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{{citation|url=https://www.telegraph.co.uk/sport/othersports/athletics/london-marathon/9237808/Claire-Squires-runner-who-died-during-London-Marathon-suffered-from-heart-condition.html |archive-url=https://ghostarchive.org/archive/20220112/https://www.telegraph.co.uk/sport/othersports/athletics/london-marathon/9237808/Claire-Squires-runner-who-died-during-London-Marathon-suffered-from-heart-condition.html |archive-date=2022-01-12 |url-access=subscription |url-status=live|title=Claire Squires: runner who died during London Marathon 'suffered from heart condition'|date=May 2012| vauthors = Wardrop M }}{{cbignore}} 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.{{cite news|url=https://www.bbc.co.uk/news/uk-england-london-21262717|title=Claire Squires inquest: DMAA was factor in marathon runner's death|publisher=BBC News|date=30 January 2013|access-date=30 January 2013}}

File:Amphetamine vs methylhexaneamine.pngs of amphetamine and methylhexanamine compared.]]

Methylhexanamine, also known as 1,3-dimethylamylamine (1,3-DMAA), is an alkylamine.{{cite journal | vauthors = Rasmussen N, Keizers PH | title = History full circle: 'Novel' sympathomimetics in supplements | journal = Drug Testing and Analysis | volume = 8 | issue = 3–4 | pages = 283–286 | date = 2016 | pmid = 27072841 | doi = 10.1002/dta.1852 }}

It is closely structurally related to other alkylamines, including 1,3-dimethylbutylamine (1,3-DMBA), 1,4-dimethylamylamine (1,4-DMAA), heptaminol (2-methyl-6-amino-2-heptanol), iproheptine (N-isopropyl-1,5-dimethylhexylamine), isometheptene (2-methyl-6-methylamino-2-heptene), octodrine (2-amino-6-methylheptane or 1,5-dimethylhexylamine), and tuaminoheptane (tuamine; 2-aminoheptane or 1-methylhexylamine).

Methylhexanamine and other related alkylamines are similar in chemical structure to phenethylamines and amphetamines, but lack a closed ring.

The predicted log P (XLogP3) of methylhexanamine is 1.9.{{cite web | title=1,3-Dimethylpentylamine | website=PubChem | url=https://pubchem.ncbi.nlm.nih.gov/compound/7753 | access-date=8 December 2024}}

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.

Many professional and amateur sports bodies, such as the World Anti Doping Agency, have banned methylhexanamine as a performance-enhancing substance and suspended athletes that have used it.{{cite web | url = http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/WADA_Prohibited_List_2010_EN.pdf | title = WADA 2010 Prohibited List | archive-url = https://web.archive.org/web/20130911050811/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/WADA_Prohibited_List_2010_EN.pdf | archive-date=2013-09-11 | publisher = World Anti-Doping Agency | date = 19 September 2009 }}{{cite news |url=http://news.bbc.co.uk/sport1/hi/athletics/8194466.stm |title=IAAF wait for Jamaica drug ruling |date=August 11, 2009 |work= BBC Sport |publisher= BBC}}{{cite web |url=https://www.cyclingnews.com/news/rui-costa-and-his-brother-test-positive |title=Rui Costa and his brother test positive |date=October 18, 2010 |work= CyclingNews}}{{cite web |url=https://www.cyclingnews.com/news/belgian-amateur-champion-receives-one-year-ban |title=Belgian amateur champion receives one-year ban |date = December 9, 2010 |work=News|publisher= CyclingNews}}{{cite news |url=http://stlouis.cardinals.mlb.com/news/article.jsp?ymd=20111101&content_id=25861792¬ebook_id=25864342&vkey=notebook_stl&c_id=stl#25864344 |archive-url=https://web.archive.org/web/20111104002917/http://stlouis.cardinals.mlb.com/news/article.jsp?ymd=20111101&content_id=25861792¬ebook_id=25864342&vkey=notebook_stl&c_id=stl#25864344 |url-status=dead |archive-date=November 4, 2011 | title=Minor Leaguer suspended 50 games| date=2011-11-01 | access-date=2011-11-01 | work=MLB.com}}{{cite news | publisher=DNF-is-no-option.com |url=http://www.dnf-is-no-option.com/2012/02/doping-sperren-fur-schweizer-aquathlet.html | title=Doping: Sperren für Schweizer Aquathlet und Duathleten aus Portugal| date=2012-02-16 | access-date=2012-01-12 | work=DNF-is-no-option.com}}

• March, 2012, a minor league baseball player, Cody Stanley, was suspended 50 games for testing positive after using a dietary supplement.{{cite web|url=https://www.news-leader.com/story/sports/baseball/2014/06/21/long-road-back-catcher-cody-stanley/11228725/|title=A long road back for catcher Cody Stanley|website=news-leader.com|access-date=27 March 2018}}
• In July 2012, Welsh boxer Enzo Maccarinelli was banned for six months after testing positive for methylhexanamine.{{cite news |url=https://www.bbc.co.uk/sport/0/wales/18887909|title=Enzo Maccarinelli handed six month drugs ban|access-date=2012-07-18|work=BBC Sport|date=2012-07-18}}
• VFL player Matthew Clark was suspended for two years after the banned substance was detected in his system after a game in 2011.{{cite web|url=https://www.watoday.com.au/afl/afl-news/st-kildas-ahmed-saad-faces-twoyear-drugs-ban-20130730-2qxha.html|title=St Kilda's Ahmed Saad faces two-year drugs ban| vauthors = Wilson C |date=31 July 2013|access-date=27 March 2018|via=WA Today}}
• August, 2012, then minor league baseball player Marcus Stroman was suspended 50 games for testing positive for methylhexanamine.{{cite web|url=http://sports.nationalpost.com/2012/08/28/jays-prospect-marcus-stroman-suspended-50-games-for-use-of-banned-substance/|archive-url=https://archive.today/20130411110033/http://sports.nationalpost.com/2012/08/28/jays-prospect-marcus-stroman-suspended-50-games-for-use-of-banned-substance/|url-status=dead|archive-date=April 11, 2013|title=Jays prospect Marcus Stroman suspended 50 games for use of banned substance| vauthors = Lott J |publisher=The National Post|date=August 28, 2012|access-date=February 10, 2013}}
• 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.{{cite web | title = US Weightlifting Athlete, Wilhelm, Accepts Sanction For Anti-Doping Rule Violation | url = http://www.usada.org/media/sanction-wilhelm8813 | archive-url = https://web.archive.org/web/20140201204827/http://www.usada.org/media/sanction-wilhelm8813 | archive-date = 1 February 2014 | date = 8 August 2013 | work = U.S. Anti-Doping Agency (USADA) }}
• MotoGP rider Anthony West 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).{{cite web | vauthors = McLaren P | date = 28 November 2013 | title = Anthony West loses results after Anti-Doping appeal | work = Crash Media Group | url = http://www.crash.net/motogp/news/198653/1/moto2_anthony_west_erased_from_results.html }}
• In December 2013, boxer Brandon Rios, after losing a unanimous decision to Manny Pacquiao, was suspended by the China Professional Boxing Association after testing positive for the drug.{{cite web |url=http://www.boxingscene.com/brandon-rios-suspended-by-cpbo-april-24th--72801 |title=Brandon Rios is Suspended By CPBO Until April 24th |date=December 16, 2013 |access-date=2013-12-16 | vauthors = Nathanielsz R | publisher=BoxingScene.com}}
• During the 2014 Winter Olympics in Sochi, three athletes tested positive for the drug: Italian bobsleigh brakeman and former decathlete William Frullani, German biathlete Evi Sachenbacher-Stehle and Latvian ice hockey forward Vitalijs Pavlovs.{{cite news|url=https://www.bbc.co.uk/sport/0/winter-olympics/26289156|title=Evi Sachenbacher-Stehle and William Frullani sent home|date=21 February 2014|work=BBC News|publisher=BBC|access-date=23 February 2014}}{{cite news|url=https://www.espn.com/olympics/winter/2014/story/_/id/10502822/2014-sochi-olympics-vitalijs-pavlovs-marina-lisogor-expelled-doping|title=Two athletes expelled for doping|date=22 February 2014|publisher=ESPN|access-date=23 February 2014}}
• During the 2015 Asian Cup, Iraqi player Alaa Abdul-Zahra was subject to an investigation relating to illegal usage of the drug.{{cite web|url=https://www.persianfootball.com/news/2015/01/23/iran-issue-protest-over-ineligible-iraq-player-in-asian-cup-quarter-final/|title=Iran issue protest over ineligible Iraq player in Asian Cup quarter-final|website=www.persianfootball.com|access-date=27 March 2018}}
• In January 2016, Algerian footballer Kheiredine Merzougi was banned for two years by the Confederation of African Football after testing positive for the drug.{{Cite web|url=https://www.alaraby.co.uk/english/indepth/2016/2/3/doping-on-algerias-football-pitches|title=Doping on Algeria's football pitches| vauthors = Fodil H |website=alaraby|date=3 February 2016|language=en|access-date=2016-03-22}} However, in March 2016, the international body FIFA confirmed they were giving an extended four-year ban to apply worldwide through January 2020.{{Cite web|url=https://www.espnfc.com/algeria/story/2834737/fifa-extends-three-algerian-players-bans-worldwide|title=FIFA extends three Algerian players' bans worldwide for four years|website=ESPNFC.com|date=21 March 2016|access-date=2016-03-22}}
• In November 2016, heavyweight boxer Bermane Stiverne was fined US$75,000 after testing positive for methylhexanamine by the World Boxing Council.{{cite web |url=https://www.espn.com/boxing/story/_/id/18050121/bermane-stiverne-tests-positive-banned-substance-fight-alexander-povetkin-held|title=Bermane Stiverne tests positive for banned substance, fight Alexander Povetkin held|access-date=2016-12-15|date=2016-11-14}} The WBC, however, still allowed this fight to happen.
• In 2017, the International Olympic Committee disqualified Jamaica's 2008 gold-winning 4x100 men's relay in Beijing due to Nesta Carter's positive testing for methylhexanamine. This cost Usain Bolt a medal.{{Cite web|url=https://apple.news/AwrE2onaqQ86nSt9je3tTOg|title=Usain Bolt: Sprinter loses one Olympic gold over teammate's failed dope test - CNN|access-date=2017-01-25}}
• 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 on 10 February 2018.{{cite web|url=https://www.fim-live.com/en/article/rider-broc-tickle-provisionally-suspended/|title=Rider Broc Tickle provisionally suspended|website=www.fim-live.com}}
• On May 22, 2018, Filipino basketball player Kiefer Ravena was handed 18 months suspension by FIBA to compete in international competition. He was found testing positive for methylhexanamine and 1,3-dimethlybutylamine by WADA. Urine samples were taken after the Philippines vs Japan game at Manila during the 2019 FIBA Basketball World Cup Qualification. Ravena explained that he consumes a pre-workout drink called C4, which can be bought from retailers around 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.{{Cite web| url=http://www.foxsports.ph/basketball/gilas-pilipinas/862143/fiba-slaps-18-month-ban-ravena-doping-violation| title=FIBA slaps 18-month ban on Ravena for doping violation| date=2018-05-28| access-date=2018-05-28| archive-date=2018-05-29| archive-url=https://web.archive.org/web/20180529203014/http://www.foxsports.ph/basketball/gilas-pilipinas/862143/fiba-slaps-18-month-ban-ravena-doping-violation/| url-status=dead}}
• On August 26, 2019, NASCAR crew chief 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."{{Cite web | url=https://racer.com/2019/08/26/dillon-crew-chief-borland-suspended-after-failed-drug-test-cites-diet-coffee-as-possible-cause/ |title = Dillon crew chief Borland suspended after failed drug test; cites diet coffee as possible cause|date = 2019-08-26}} The suspension was lifted on September 24 after completing NASCAR's mandatory "Road to Recovery Program".{{Cite web | url=https://sports.yahoo.com/crew-chief-matt-borland-reinstated-123010573.html | title=Crew chief Matt Borland reinstated after completing Road to Recovery Program | access-date=2019-10-06 | archive-date=2019-10-06 | archive-url=https://web.archive.org/web/20191006053511/https://sports.yahoo.com/crew-chief-matt-borland-reinstated-123010573.html | url-status=dead }}

In 2010, the US military issued a recall of all methylhexanamine-containing products from all military exchange stores worldwide.{{cite web |url=http://www.armytimes.com/offduty/health/offduty-dmma-products-pulled-from-shelves-122911/ |title=DMAA products pulled from base shelves |access-date=24 January 2013}}{{cite web | url = http://www.armytimes.com/offduty/health/offduty-dmma-products-pulled-from-shelves-122911/ | title = DMAA products pulled from base shelves – Military Off Duty, Army Health, military fitness, army physical fitness | work = Army Times | access-date = 2012-04-12 }}

In July 2011, Health Canada decided methylhexanamine was not a dietary substance, but was a drug requiring further approval. Consequently, Health Canada banned all sales of methylhexanamine.{{cite news|vauthors=Rovell D|title=DMAA Brands Start To Reformulate Products Without the Ingredient|url=https://www.cnbc.com/2012/05/02/dmaa-brands-start-to-reformulate-products-without-the-ingredient.html|archive-url=https://archive.today/20130119094919/http://www.cnbc.com/id/47266147/DMAA_Brands_Start_To_Reformulate_Products_Without_the_Ingredient|url-status=live|archive-date=January 19, 2013|access-date=1 August 2012|newspaper=CNBC|date=2 May 2012}}

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.{{cite web|title=Varning för kosttillskott som innehåller DMAA|url=http://www.slv.se/sv/grupp3/Pressrum/Nyheter/Pressmeddelanden/Varning-for-kosttillskott-som-innehaller-DMAA/|access-date=2012-08-13|archive-url=https://web.archive.org/web/20120804062245/http://www.slv.se/sv/grupp3/Pressrum/Nyheter/Pressmeddelanden/Varning-for-kosttillskott-som-innehaller-DMAA/|archive-date=2012-08-04|url-status=dead}}

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.{{cite web|title=Anvisa alerta para risco de consumo de suplemento alimentar, July 2012|url=http://portal.anvisa.gov.br/wps/content/anvisa+portal/anvisa/sala+de+imprensa/assunto+de+interesse/noticias/anvisa+alerta+para+risco+de+consumo+de+suplemento+alimentar|publisher=Brazilian Government: National Health Surveillance Agency (ANVISA)|access-date=22 January 2013|archive-url=https://web.archive.org/web/20130202110354/http://portal.anvisa.gov.br/wps/content/anvisa+portal/anvisa/sala+de+imprensa/assunto+de+interesse/noticias/anvisa+alerta+para+risco+de+consumo+de+suplemento+alimentar|archive-date=2 February 2013|url-status=dead}} 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.{{cite web|title=Resolução de Diretoria Colegiada (RDC) no. 37, July 2012|url=http://www.anvisa.gov.br/sngpc/Documentos2012/Resolu%C3%A7%C3%A3o%20RDC%20n%C2%BA%2037%20%202012.pdf|publisher=Brazilian Government: National Health Surveillance Agency (ANVISA)|access-date=22 January 2013}}

In 2012, Australia banned methylhexanamine. In New South Wales, methylhexanamine was classed as a "highly dangerous substance" on the poisons list.{{cite news| vauthors = McNeilage A |title=Drug in workout drinks to be illegal|url=http://www.smh.com.au/national/health/drug-in-workout-drinks-to-be-illegal-20120801-23f3i.html|access-date=1 August 2012|newspaper=The Sydney Morning Herald|date=1 August 2012}}

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.{{cite web|title=Press release: MHRA to remove popular sports supplement used by international athletes from the market|url=http://www.mhra.gov.uk/NewsCentre/Pressreleases/CON180711|access-date=2013-01-30|archive-url=https://web.archive.org/web/20130106165636/http://www.mhra.gov.uk/NewsCentre/Pressreleases/CON180711|archive-date=2013-01-06|url-status=dead}}

In 2012 the New Zealand Ministry of Health banned the sale of methylhexanamine products,{{cite web | work = New Zealand Ministry of Health | url = http://www.beehive.govt.nz/release/dunne-announces-temporary-class-drug-notice | title = Dunne announces Temporary Class Drug Notice | date = 8 March 2012 }} due in part to its growing recreational use as party pills.{{cite news |url=http://tvnz.co.nz/view/page/1316907/2174371 |title=New pill ingredient worries ministry |date=October 4, 2008 |work=Television New Zealand |access-date=October 23, 2011}}{{cite news |url=http://www.stuff.co.nz/the-press/news/3043395/Party-pill-inventor-backs-restriction |title=Party pill inventor backs restriction | vauthors = Steward I |date=November 9, 2009 |work=The Press |access-date=October 23, 2011}}

In April 2013, the US Food and Drug Administration determined that methylhexanamine was potentially dangerous and did not qualify as a legal 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.{{cite web | publisher = U.S. Food and Drug Administration | title = Stimulant Potentially Dangerous to Health, FDA Warns |url=https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm |archive-url=https://web.archive.org/web/20130413233832/http://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm |url-status=dead |archive-date=April 13, 2013 | date = April 11, 2013 | access-date = April 16, 2013}} The FDA has issued warning letters to manufacturers and distributors who continued to market products containing methylhexanamine.FDA Press Release. {{cite web | url = https://www.fda.gov/Safety/MedWatch/SafetyInformation/SafetyAlertsforHumanMedicalProducts/ucm374398.htm?source=govdelivery | title = OxyElite Pro Dietary Supplements by USP Labs: Recall - Products Linked to Liver Illnesses | date = 10 November 2013 | work = U.S. Food and Drug Administration }}{{dead link|date=May 2025|bot=medic}}{{cbignore|bot=medic}}

{{div col|colwidth=20em}}

• 1,3-Dimethylbutylamine
• Benzedrine
• Cyclopentamine
• Deterenol
• Heptaminol
• Iproheptine
• Isometheptene
• Levomethamphetamine
• Octodrine
• Propylhexedrine
• Pseudoephedrine
• Tuaminoheptane

{{div col end}}

{{reflist|group=note}}

{{Reflist|2}}

• {{cite web|publisher=U.S. Food and Drug Administration|title=Stimulant Potentially Dangerous to Health, FDA Warns|url=https://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm|archive-url=https://web.archive.org/web/20130413233832/http://www.fda.gov/ForConsumers/ConsumerUpdates/ucm347270.htm|url-status=dead|archive-date=April 13, 2013|date=April 11, 2013}}
• {{cite web|url=http://www.sciencebasedmedicine.org/index.php/dmaa-efficacious-but-is-it-safe/|title=DMAA: Efficacious but is it Safe?| vauthors = Bussel II, Pavlov Jr AA |publisher=Science Based Medicine Blog|date=June 7, 2013}}

{{Stimulants}}

{{Nasal preparations}}

{{Monoamine releasing agents}}

Category:Alkylamines

Category:Bodybuilding supplements

Category:Decongestants

Category:Drugs developed by Eli Lilly and Company

Category:Hepatotoxins

Category:Norepinephrine-dopamine releasing agents

Category:Stimulants

Category:Sympathomimetics

Category:Withdrawn drugs