The Full Wiki

Methylhexanamine: Wikis

  
  

Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.

Encyclopedia

From Wikipedia, the free encyclopedia

Methylhexanamine
Systematic (IUPAC) name
4-methylhexan-2-amine
Identifiers
CAS number 105-41-9
ATC code  ?
PubChem 7753
Chemical data
Formula C 7H17N 
Mol. mass 115.22 g/mol
Synonyms 4-methyl-2-hexanamine;
4-methyl-2-hexylamine;
2-amino-4-methylhexane;
1,3-dimethylamylamine;
1,3-dimethylpentylamine
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status Uncontrolled
Routes Oral, Inhaled

Methylhexaneamine (Forthan, Forthane, Floradrene, Geranamine) or dimethylamylamine (DMAA) is a psychoactive drug and simple aliphatic amine used as a nasal decongestant, putatively via acting as a norepinephrine reuptake inhibitor (NRI) and/or norepinephrine releasing agent (NRA),[1 ] as well as treatment for hypertrophied or hyperplasic oral tissues[2], and as an active ingredient in party pills in New Zealand. Once trademarked under Forthane by Eli Lilly in 1971[3], 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.[4]

Contents

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. Geranamine itself has not been researched intensively, with its pharmacological profile not looked at since Eli Lilly filed its patent in 1944, stating that the stimulant effects on the CNS are less than that of amphetamine or ephedrine.[5]

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 geranamine is a dietary supplement as it is a component of the oil from Pelargonium graveolens which is approved for use in foods, geranamine comprises only 0.66% of geranium oil,[6] and pure synthetic geranamine is thus quite different from geranium oil.

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 [7], 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.[8] In November 2009 the New Zealand government indicated that DMAA would be scheduled as a restricted substance. [9]

Doping in sports

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,[10] 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.[11]

References

  1. ^ Rohrmann, Ewald; Shonle, H. A. (September 1944), "Aminoalkanes as Pressor Substances", J. Am. Chem. Soc. 66 (9): 1516–1520, doi:10.1021/ja01237a032  
  2. ^ Kosti, "PROCESS FOR THE TREATMENT OF HYPERTROPHIED GUMS", US 3574859, issued Apr 1971
  3. ^ US Trademark Serial Number: 72382454
  4. ^ US Trademark Serial Number: 78542697
  5. ^ Rohrmann, Ewald, "AMINOALKANES", US 2350318, issued May 30, 1944
  6. ^ Ping, Z.; Jun, Q. & Qing, L. (1996), "A Study on the Chemical Constituents of Geranium Oil", Journal of Guizhou Institute of Technology 25 (1): 82–85  
  7. ^ http://tvnz.co.nz/view/page/1316907/2174371
  8. ^ New party pills leave four seriously ill Stuff.co.nz. Monday, 12 January 2009
  9. ^ http://www.stuff.co.nz/the-press/news/3043395/Party-pill-inventor-backs-restriction
  10. ^ http://news.bbc.co.uk/sport2/hi/athletics/8194466.stm Jamaicans cleared over drug tests. news.bbc.co.uk Monday, 10 August 2009
  11. ^ IAAF wait for Jamaica drug ruling . BBC Sport (2009-08-11). Retrieved on 2009-08-13.







Got something to say? Make a comment.
Your name
Your email address
Message