Educate Thy Self: (sounds like some stupid "energy" product)
http://en.wikipedia.org/wiki/Methylhexaneamine
Methylhexanamine, commonly known as 1,3-dimethylamylamine or DMAA, 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] but its safety has been questioned. 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.
Contents [hide]
1 History
2 Chemistry
3 Uses
4 Safety
5 Controversy
6 Regulations
7 See also
8 References
[edit]History
In April 1944, Eli Lilly and Company trademarked methylhexanamine, as 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, methylhexanamine use is not mentioned in historical medical literature, and no medical use of methylhexanamine is recognized today. The trademark for Forthane has since expired. 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; the former ingredient is now banned in a number of countries.
A 2012 Dutch literature study on the regulatory status of methylhexamine concluded that food supplements with > 4 mg methylhexamine are pharmacologically effective and therefore require licensing as a medicine. The authors deduce that oral methylhexamine acts as a bronchodilator (above 4 mg), increases heart rate (above 50–75 mg), and increases blood pressure (above 100 mg). Serious adverse effects are expected for oral dosages above 200 mg.[9]
[edit]Chemistry
The structure of methylhexanamine has been described as similar to that of amphetamine.[10]
Methylhexanamine 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. Methylhexanamine is a releasing agent of the catecholamine neurotransmitter norepinephrine (noradrenaline) similar to related substances such as cyclopentamine and tuaminoheptane.[11]
[edit]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 over-the-counter thermogenic or general-purpose stimulant. Methylhexaneamine 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.[12]
In New Zealand, methylhexanamine (under the name 1,3-dimethylamylamine or DMAA) is an emerging active ingredient of party pills.[13] In November 2009, the New Zealand government indicated methylhexanamine would be scheduled as a restricted substance.[14] The New Zealand government has not banned methylhexanamine, but its Ministry of Health has banned bulk powder purchases,[citation needed] and 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 7 April 2012.
[edit]Safety
The LD50 for methylhexanamine is 39 mg/kg for intravenous and 185 mg/kg for intraperitoneal administration (mouse).[15][16]
Anecdotal reports indicate 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 556 mg 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 (Pelargonium 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, "geranium oils do not contain methylhexaneamine" and "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 acute ingestion of 1,3-dimethylamylamine (75 mg) alone and in combination with caffeine results in increased blood pressure without an increase in heart rate.[20]
A study of 25 healthy men taking a methylhexanamine-containing preworkout sports supplement found 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] "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," said DoD spokesman Peter Graves. "DoD has asked that the products be pulled from the shelves as a precautionary measure."[24]
The death of Claire Squires, a runner who collapsed near the finish line of the April 2012 London marathon, has been linked to DMAA. The Coroner stated that DMAA was "probably an important factor" during the inquest. It is believed that she consumed the substance through drinking an energy drink, which was subsequently adjusted to exclude DMAA.[25]
[edit]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.[26][27][28][29][30][31]
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.[32] This prompted the Department of Defense to pull products containing methylhexaneamine from on-base store shelves pending an investigation.[33] 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.”[33] 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]
On 19 June 2012, the South African Institute for Drug-Free Sport (SAIDS) confirmed the 2012 Comrades Marathon winner, Ludwick Mamabolo, tested positive for the banned stimulant. Mamabolo could face a two-year ban and be stripped of his title if found guilty by an independent tribunal.
[edit]Regulations
In July 2011, Health Canada decided DMAA was not a dietary substance, but was a drug requiring further approval. Consequently, Health Canada banned all sales of DMAA.[34]
In March 2012, New Zealand issued a notice to declare DMAA a temporary class drug.[35] In April 2012, New Zealand formally banned DMAA, citing its use in "party pills".[36]
In April 2012, the United States' FDA issued warning letters to manufacturers of DMAA products. The FDA has challenged the manufacturers' marketing of DMAA products for lack of safety evidence.[37]
In June 2012, the National Food Agency of Sweden issued a general warning regarding use of DMAA products, resulting in a sales ban in parts of the country.[38]
In July 2012, Australia issued a notice on DMAA.[39] On 1 August 2012, Australia decided to ban DMAA. In New South Wales, DMAA was classed as a "highly dangerous substance" on the poisons list.[40]
In July 2012, the National Health Surveillance Agency (ANVISA) of Brazil issued an update to the general public, stating the hazards of use of products that contain DMAA.[41] It also update the list of prohibited substances to insert DMAA, which translates into the banishment of products containing such ingredient from the Brazilian market.[42]
In August 2012, The Medicines and Healthcare products Regulatory Agency (MHRA) has ruled that the popular DMAA containing sports supplement Jack3D is an unlicensed medicinal product and that it and all other DMAA containing products need to be removed from the UK market amid concerns of potential risks to public safety.[43]
In January 2013, a coroner ruled that DMAA was a contributory factor in the death of a 30-year old woman who collapsed and died during the final stretch of the 2012 London Marathon.[44]
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