Methylhexanamine

Methylhexanamine
IUPAC name 4-Methylhexan-2-amine[1]
Other names 2-Amino-4-methylhexane[citation needed] Dimethylamylamine[citation needed] 1,3-Dimethylamylamine[citation needed] 1,3-Dimethylpentylamine[citation needed] Floradrene[citation needed] Forthan[citation needed] Forthane[citation needed] Geranamine[citation needed] 4-Methyl-2-hexanamine[citation needed] 4-Methyl-2-hexylamine[citation needed]
Identifiers
Abbreviations	DMAA[citation needed]
CAS number	105-41-9 Y
PubChem	7753, 55289161 (4S)-4-methyl, 642321 (2R,4R)-4-methyl, -2-amine, 36688719 (2R,4S)-4-methyl, -2-amine, 36688723 (2S,4S)-4-methyl, -2-amine, 36688721 (2S,4R)-4-methyl, -2-amine
ChemSpider	7464 Y, 557529 (2R,4R)-4-methyl, -2-amine Y
EC number	203-296-1
Jmol-3D images	Image 1
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 Y Key: YAHRDLICUYEDAU-UHFFFAOYSA-N Y
Properties
Molecular formula	C7H17N
Molar mass	115.22 g mol−1
Pharmacology
Routes of administration	Inhalation Oral
Related compounds
Related alkanamines	Pentylamine Cadaverine Hexamethylenediamine Tuaminoheptane
Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

Methylhexanamine is an organic compound with the formula CH₃CH₂CH(CH₃)CH₂CH(CH₃)NH₂. It is marketed under many names as a dietary supplement.^[2][3][4] It is also a simple aliphatic amine used as a nasal decongestant, as well as treatment for hypertrophied or hyperplasic oral tissues.^[5] 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 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.

Safety

The LD50 for methylhexanamine is 39 mg/kg for intravenous and 185 mg/kg for intraperitoneal administration (mouse).^[15][16]

Anecdotal reports indicate that extremely high doses of methylhexanamine combined with caffeine and alcohol may be harmful. A 21 year-old male in New Zealand presented with a cerebral hemorrhage after ingesting 556mg of methylhexanamine, caffeine, and alcohol.^[17] The man's hydration status, food intake, illicit drug use, and body weight were not reported. A spokesman for the manufacturer said, "DMAA is, in fact, a constituent of geranium (Pelagonium graveolens) and its derived oil and has been consumed as part of the human diet for more than 100 years."^[18]

However a study published in December 2011 by A. Lisi, N. Hasick, R. Kazlauskas, and C. Goebel contradicts the claim by methylhexaneamine manufacturers and reports that "geranium oils do not contain methylhexaneamine" and that "products labelled as containing geranium oil but which contain methylhexaneamine can only arise from the addition of synthetic material."^[19]

A September 2011 study reported that acute ingestion of 1,3-dimethylamylamine (75mg) alone and in combination with caffeine results in increased blood pressure without an increase in heart rate.^[20]

A study of twenty five healthy men taking a methylhexanamine-containing pre-workout sports supplement found that methylhexanamine does not change resting heart rate, blood pressure, or affect liver and kidney function when used at recommended dosage levels.^[21] According to an additional four studies, DMAA did not seem to cause any negative effects to the blood, blood pressure or heart rate when taken by test subjects for a short period.^[22]

The US military issued a massive recall of all methylhexanamine-containing products from all military exchange stores worldwide, after two soldiers suffered fatal heart attacks during training in 2010. Methylhexanamine was found in their blood.^[23]

Controversy

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.^{[24][25][26][27][28][29]}

In February 2012, the deaths of two US soldiers who collapsed during physical training in preceding months prompted a military investigation of the popular bodybuilding supplement that was found in their systems.^[30] This prompted the Department of Defense to pull products containing methylhexaneamine from on-base store shelves pending an investigation.^[31] A Pentagon spokesman, however, stressed, “These products are legal substances and, as yet, no link between DMAA and the medical conditions reported by military medical providers has been validated scientifically by us. DoD has asked that the products be pulled from the shelves as a precautionary measure.”^[31] DoD findings on the matter were expected in late March 2012. The Surgeon General of the US Army said, “I want to emphasize that no link between DMAA and the medical conditions reported by military medical providers has been validated scientifically by us. While the DOD leadership and the USAPHC take these reports very seriously, all of these medical conditions have multiple causes. It is too soon to tell if there is a relationship with DMAA.”^[18]

See also

• Heptaminol
• Isometheptene
• Pelargonium
• Tuaminoheptane

References

External links

Latest Party Pills Banned Ingredient DMAA in New Zealand