Methylhexanamine

Methylhexanamine

Systematic (IUPAC) name
4-methylhexan-2-amine
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	Oral, Inhaled
Identifiers
CAS number	105-41-9 Y
ATC code	?
PubChem	CID 7753
Synonyms	4-methyl-2-hexanamine; 4-methyl-2-hexylamine; 2-amino-4-methylhexane; 1,3-dimethylamylamine; 1,3-dimethylpentylamine 2-Hexanamine, 4-methyl- (9CI)
Chemical data
Formula	C7H17N
Mol. mass	115.22 g/mol
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Methylhexanamine (Forthan, Forthane, Floradrene, methylhexanenamine, dimethylamylamine), marketed under the name Geranamine or DMAA, is a dietary supplement and simple aliphatic amine used as a nasal decongestant, as well as treatment for hypertrophied or hyperplasic oral tissues. It is a vasoconstrictor, and can be administered by inhalation to the nasal mucosa to exert its effect.

History

In April 1944, Eli Lilly and Company trademarked methylhexanamine under Forthane for potential use as a nasal decongestant. Forthane was also used as a nasal decongestant and as treatment for hypertrophied or hyperplasic oral tissues The trademark for Forthane has since expired, and so methylhexanamine should not be confused with isoflurane, a general inhalation anaesthetic, which has the proprietary name in Australia of Forthane.

Patrick Arnold reintroduced methylhexanamine into the market in 2006 as a dietary supplement, after the final ban of ephedrine as a dietary supplement in the United States in 2005. Arnold introduced it under the trademarked name Geranamine, a name held by his company, Proviant Technologies.

Chemistry

Methylhexaneamine may be synthesized by reacting 4-methylhexan-2-one with hydroxylammonium chloride to give the oxime, followed by reduction via sodium in ethanol.

Uses

Although intended by Eli Lilly to be used as a nasal decongestant, methylhexaneamine has been marketed by certain companies as a dietary supplement in combination with caffeine and other ingredients, under trade names such as Geranamine and Floradrene, to be used as an OTC thermogenic or general purpose stimulant. Methylhexaneamine itself has not been studied intensively and its pharmacological profile has not been evaluated since Eli Lilly filed its patent in 1944, stating that the stimulant effects on the CNS are less than that of the related compounds amphetamine and ephedrine. Despite not being a catecholamine, methylhexanamine exhibits structural similarity to other monoamines such as phenethylamine and amphetamine, which may account for its similar mode of action to these compounds. The only structural difference between methylhexanamine and amphetamine is that methylhexanamine lacks the phenyl or benzene ring which is present in all phenethylamine derivatives, including all amphetamines, containing only 4 of the 6 carbons of the phenyl ring. The difference between geranamine and propylhexedrine is that is lacks two carbons that create a cyclohexyl ring in propylhexedrine and a methyl group on the amine group. Despite these differences, it has a similar mode of action, being a stimulant and having norepinephrinergic effects.

In New Zealand, methylhexanamine (under the name 1,3-dimethylamylamine or DMAA) is an emerging active ingredient of party pills. Side-effects including headache, nausea, and stroke have been reported in recreational users of these products. In November 2009, the New Zealand government indicated that methylhexanamine would be scheduled as a restricted substance. The New Zealand government has not banned methylhexanamine, however, its Ministry of Health has banned bulk powder purchases^{[citation needed]}, but its sale in the form of capsules and tablets is permitted.

Safety profile

Dimethylamylamine's (DMAA) safety and toxicological profile has not been established in humans. A 21 year old healthy male in New Zealand presented with a cerebral haemorrhage after taking "2 tablets" with 278 mg of 1,3 dimethylamylamine per capsule.

Research

In September of 2011, research published by University of Memphis' Department of Health and Sport Sciences showed that Methylhexanamine's effects could not be explained by circulating NE and EPI. ; regarding heart rate and BP the study stated (at 75 mg DMAA, peak changes seen at one hour) "acute ingestion of 1,3-dimethylamylamine alone and in combination with caffeine results in an increase in SBP, DBP, and RPP without an increase in HR". "

Controversy

In 2009, the World Anti-Doping Agency added methylhexanamine to the 2010 prohibited list.

Methylhexanamine was implicated as a stimulant used by five Jamaican athletes in 2009. JADCO, the Jamaican anti-doping panel, was initially unable to determine whether it was prohibited by the rules, but subsequently decided to impose sanctions on some of the affected athletes on the grounds that the drug was similar in structure to the banned substance tuaminoheptane.

During the 2010 Commonwealth Games, Nigerian athlete Damola Osayemi was stripped of her gold medal in the 100m after methylhexanamine was detected during drug testing. Subsequently, another Nigerian athlete, Samuel Okon, who finished sixth in the 110m hurdles, also tested positive for the drug.

In October 2010, two Portuguese cyclists—Rui Costa and his brother Mario—tested positive for the substance. The samples were taken during the Portuguese National Championships at the end of June.

In October 2010, nine Australian athletes have been found by Australian Sports Anti-doping Authority to have tested positive for the substance. These players may include NRL and AFL players.

In November 2010 two South African rugby union players, Chiliboy Ralepelle and Bjorn Basson, were found to have tested positive for the substance on their annual tour of the Northern Hemisphere, and were immediately sent home from the tour by the South African Rugby Union, although it is possible that the players may have ingested the substance inadvertently in the form of medication for flu symptoms.

In 2010 Belgian National Amateur Masters Champion Rudy Taelman was suspended for one year for a positive test for methylhexanamine. He successfully defended himself from accusations of willful doping by proving that a supplement called "Crack" had caused the non-negative test. It should be noted that he was an active anti-doping advocate, and ironically the one to call for the doping controls to which he was submitted.

In January 2011, the Greek basketball team Iraklis indefinitely suspended Matt Bouldin after he tested positive for methylhexanamine.

In May 2011, English Rugby League player Martin Gleeson was charged by UK Anti-Doping in June 2011 with committing an anti-doping rule violation after he tested positive for the banned stimulant methylhexaneamine

American pro tennis player Robert Kendrick was disqualified from the 2011 French Open, and banned from tennis for 12 months by the International Tennis Federation (ITF) after testing positive for Methylhexaneamine at the event. The ban is currently being appealed by Kendrick, as he claims he took a pill to cope with jetlag without knowing it contained the substance, and the ITF wrote in their summary that it did not believe that Kendrick took the substance as a performance enhancer. However, it is the long stated practice of the Tennis Anti-Doping Program that the players are responsible for ensuring that no prohibited substances enter their body, unless they hold a valid exemption for therapeutic use, which Kendrick did not.^{[citation needed]}

In August 2011, American sprinter Mike Rodgers tested positive for methylhexanamine, claiming he drank vodka with an energy drink at a club two days before a meeting in Lignano, Italy, which supposedly caused the positive test.

In October 2011, Canadian wakeboarder Aaron Rathy was stripped of his silver medal at the Pan American Games in Guadalajara, Mexico, for testing positive for methylhexaneamine. In a statement, he blamed the use of the supplement OxyElite Pro, which he did not know contained the banned substance, for testing positive.

Also in October 2011, Saint Louis Cardinals Minor League outfielder Reggie Williams was suspended for 50 games for testing positive for methylhexaneamine.

In December 2011, Triathlete Dmitriy Smurov was suspended for 2 years for testing positive for methylhexaneamine.

In February 2012, the deaths of two U.S. soldiers who collapsed during physical training in the last few months have prompted a military investigation of the popular body-building supplement that was found in their systems.

In February 2012, Duathlete Sergio Silva was suspended for 6 months for testing positive for methylhexaneamine.

See also

• Heptaminol
• Isometheptene
• Pelargonium
• Tuaminoheptane