Methylhexaneamine (Forthan, Forthane, Floradrene, Geranamine), also known as dimethylamylamine (DMAA), is a drug and simple aliphatic amine used as a nasal decongestant, as well as treatment for hypertrophied or hyperplasic oral tissues, and as an active ingredient in party pills in New Zealand. Once trademarked under Forthane by Eli Lilly in 1971, the trademark has since expired, and so methylhexaneamine should not be confused with isoflurane, whose proprietary name in Australia is also Forthane. It is a vasoconstrictor, and can be administered by inhalation to the nasal mucosa to exert its effect. The trademark Geranamine is currently owned by Proviant Technologies. Methylhexaneamine is also a constituent of flower oil, sold as an integral component of nutritional supplements
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.
Methylhexaneamine is not FDA approved in its own right, although it is a component of geranium oil which is approved for use in foods, and so this has been used to justify claims that it should be classified as a dietary supplement rather than a pharmaceutical product. However while it may be technically correct to say that methylhexaneamine is a dietary supplement as it is a component of the oil from Pelargonium graveolens which is approved for use in foods, methylhexaneamine comprises only 0.66% of geranium oil, and pure synthetic methylhexaneamine is thus quite different from geranium oil.
Like all stimulants, methylhexaneamine carries a risk. Abusing any stimulant can have serious side effects and it is important to follow the proper dosing instructions and care must be taken to not abuse this substance past the recommended doses in products.
Use as a recreational drug
In New Zealand, methylhexanamine (under the name 1,3-dimethylamylamine or DMAA) is an emerging active ingredient of party pills, where it has replaced benzylpiperazine or BZP which has been illegal in that country since 2008. Serious adverse 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. Listing a drug as a restricted substance in New Zealand means it would be illegal to:
* Sell or supply methylhexanamine to anyone under 18
* Advertise methylhexanamine in the media
* Offer methylhexanamine as a gift or reward
* Sell or supply methylhexanamine from premises where alcohol is sold or from service stations
* Sell methylhexanamine from any premises where children or minors gather