In April 1944, Eli Lilly and Company trademarked methylhexanamine under Forthane for potential use as a nasal decongestant. Forthane was also patented as a nasal decongestant and a treatment for hypertrophied or hyperplasic oral tissues[5] Aside from patent applications, there is no known reference to Methylhexanamine use in historical medical literature, and there is no recognized medical use of Methylhexanamine today. The trademark for Forthane has since expired, and so methylhexanamine should not be confused with isoflurane, a general inhalation anaesthetic,[6] which has the proprietary name in Australia of Forthane.
Patrick Arnold reintroduced methylhexanamine in 2006 as a dietary supplement,[7][8] 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. A large number of supplements focusing on fat loss and workout energy now use the ingredient in concert with other substances such as caffeine, a combination similar to the combination of Ephedrine and Caffeine, of which the former ingredient is now banned in a number of countries.
Chemistry
The structure of methylhexanamine has been described as similar to that of amphetamine.[9]
Methylhexaneamine is synthesized by converting 4-methylhexan-2-one into the oxime, followed by reduction via sodium in ethanol, conditions similar to the Bouveault–Blanc reduction. Methylhexaneamine is a releasing agent of the catecholamine neurotransmitter norepinephrine (noradrenaline) similar to related substances such as cyclopentamine and tuaminoheptane[10].
Uses
Although intended by Eli Lilly to be used as a nasal decongestant, methylhexaneamine has been marketed 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.[11]
In New Zealand, methylhexanamine (under the name 1,3-dimethylamylamine or DMAA) is an emerging active ingredient of party pills.[12] Side-effects including headache, nausea, and stroke have been reported in recreational users of these products.[13] In November 2009, the New Zealand government indicated that methylhexanamine would be scheduled as a restricted substance.[14] 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. The NZ Ministry of Health has now published a Temporary Class Drug Notice. The effect of this notice is to make illegal the sale of DMAA products after the 7 April 2012.
