Methylhexanamine (sometimes spelled 'methylhexaneamine') is an aliphatic alkaloid
with sympathomimetic and stimulant
properties. It is also known as 1,3-dimethylamylamine (often abbreviated DMAA). Geranamine and Forthane are brand names. Methylhexanamine is a naturally occuring substance in Pelargonium graveolens
, a flowering plant in the Geraniaceae (Geranium) family.
[top]Ways of administration
Methylhexanamine may be used orally or insufflated. Smoking methylhexanamine salt has been reported to be ineffective. Insufflation
of methylhexanamine powder is painful. Dissolving the salt in water and insufflating with an atomizer has been reported to be pain-free. Suggested oral dose is 10-30 mg. Higher doses are associated with rapidly escalating side-effects.
[top]Effects of Methylhexanamine
- Euphoria is often reported. This may be more pronounced after taking methylhexanamine by insufflation, but is also reported after oral use. A few report no euphoria at all. If euphoria is experienced, it seems to vanish after the first few uses of the drug.
- Some reports state that methylhexanamine produces increased focus and productivity, while others report the opposite, and complain that the drug scatters the user's attention.
- Methylhexamine has been reported to elevate blood pressure, but not heart rate.
- Methylhexamine has been reported to suppress appetite] and not to suppress appetite.
Effects of methylhexanamine last 3-4 hours.
Nausea is often reported as a side-effect, even at moderate doses. Overdose can cause headache. After-effects are reported to include headache and depression, and drowsiness.
[top]Combinations with Methylhexanamine
[top]Combinations in Commercial Products
Methylhexanamine is a common ingredient in mixtures of non-prescription stimulants
marketed to bodybuilders, and in stimulants marketed as legal highs or 'herbal ecstasy
'. References to 'geranium', 'geranium oil' or 'Pelargonium graveolens' in the listed ingredients of legal highs are believed to mean methylhexanamine, although few of these products have been formally analzyed.
Note the many similar names. Products from the same manufacturer with identical ingredient lists may be maketed under different names in different countries. Products with the same name from the same manufacturer marketed in different countries may contain different ingredients. These products may also contain other, undisclosed, ingredients. Manufacturers may change ingredients at any time. This is a list for informational purposes only. It does not constitute an endorsement or recommendation of any of these products. There are experience reports about many of them on Drugs
-Forum, generally in the Herbal Ecstasy forum
Over-the-counter products that contain methylhexanamine:
(i) - Recently banned/ named illegal in the country or region specified. If you can still get a brand in a different country or region, please update the wiki or post in the page discussion section.
-- In Australia, the ban does not take effect until August 1, 2012
- (i) DynaPep (US) Mfg: Dynapep. Listed ingredients: caffeine, 2-amino-4-methylhexane, conjugated linoleic acid, B-12, chromium polynicotinate.
- (i) Ergolean Amp 2 (US) Mfg: ErgoPharm. Listed ingredients: caffeine, zingerone, raspberry ketone, coleus forskohlii extract, green coffee bean extract, dimethylpentylamine, fursultiamine, evodiamine, kaempferol.
- (i) IBE X-Force (US) Mfg: Innovative Body Enhancement. Listed ingredients: caffeine, methylhexaneamine, sulbutiamine.
- NitroX (Netherlands) Mfg: DNX. Listed ingredients: Geranium oil, vitamin B12, chromium(III)chloride, caffeine.
- (i) Jack3d Carnosine ATP Augmentor (US) Mfg: USP Labs. Listed ingredients: arginine, creatine, beta alanine, caffeine, 1,3-Dimethylamylamine, shizandrol A.
- Sunrise (Worldwide except NZ) Mfg: unknown. Listed ingredients: "99.9% pure DMAA"
- (i) Hummer (New Zealand, UK) Mfg: LightYears. Listed ingredients: Hamelia patens, Pelargonium graveolens, Polygonum multiflorum, Paulinia cupana, Citrus aurantium, "an amino acid blend"
- (i) Hummer (Australia) Mfg: LightYears. Listed ingredients: caffeine, Citrus aurantium extract, Pelargonium graveolens extract, Salvia sclarea extract, Piper nigrum extract, L-phenylalanine, vitamin c, "tableting aids"
- (i) Diablo Strong as Hell (Australia) Mfg: LightYears. Listed ingredients: caffeine, clary sage, Citrus aurantium, Pelargonium graveolens, Polygonum multiflorum, Theobroma cocao, "free form amino acids"
- (i) Storm (Australia) Mfg: LightYears. Listed ingredients: caffeine, Citrus aurantium extract, Pelargonium graveolens extract, Piper nigrum extract, Theobroma cocao extract, Hordeum vulgare extract, vitamin C, "tableting aids"
- (i) Hypnotic (Australia) Mfg: LightYears. Listed ingredients: guarana, geranium extract, poppy seed, calcium, magnesium and "tableting aids".
- (i) Exotic (Australia) Mfg: LightYears. Listed ingredients: caffeine, Citrus aurantium, Theobroma cocao, Pelargonium graveolens, Salvia sclarea, Hordeum vulgare, ascorbic acid, "tableting aids"
- (i) Giggle (Australia) Mfg: LightYears. Listed ingredients: guarana, Geranium extract, calcium, magnesium, "tableting aids"
- Clearshot 3X Concentrate Mfg: E-Pharm. Listed ingredients: L-citrulline malate, zingerone, caffeine, geranamine
- (i) Buzzz (Australia) Mfg: Legal Highs. Listed ingredients: L-citrulline malate, zingerone, caffeine, geranamine
- Vegas Nights (New Zealand) Mfg: Enjoi Products. Listed ingredients: Hamelia patens, Pelargonium graveolens, Polygonum multiflorum, Paulinia cupana, Citrus aurantium, "amino acids"
- (i) Diablo XXX (US) Mfg: AM-HI-CO. Listed ingredients: Vitamins B1, B5, B6, Hamelia patens, Pelargonium graveolens, kola nut extract, "amino acid blend", magnesium stearate
- (i) Exotix Super (Europe) Mfg: AM-HI-CO. Listed ingredients: Vitamins B1, B5, B6, Hamelia patens, Pelargonium graveolens, kola nut extract, "amino acid blend", magnesium stearate
- Charged (New Zealand) Mfg: A-Class. Listed ingredients: Citrus aurantium, Theobroma cocoa, Guarana, Pelagornium graveolens, caffeine
- Phat Freddy's Tripsta Mfg: Party Shnacks. (New Zealand) Listed ingredients: caffeine, green tea extract, geranium extract, yerba mate, guarana, capsaicin, kaia nut, ginseng, gelatin, stearic acid, magnesium stearate, titanium dioxide
- Groove (Worldwide) Mfg: London Underground. Listed ingredients: Synthetic equivalent of standardised Geranium oil extract, poppy seed, magnesium sterate, dicalcium phosphate
- Crank'd (New Zealand) Mfg: A-Class. Listed ingredients: caffeine, "free form amino acids", "antioxidants", guarana, green tea, cocoa, Citus aurantium, Pelargonium graveolens (synthetic equivalent)
- Redd Hearts (New Zealand) Mfg: A-Class. Listed ingredients: caffeine, Citrus aurantium, Griffonia simplicifolia, Hordeum vulgare, Pelargonium graveoleons (synthetic equivalent), Piper nigrum, Salix alba, Salvia sclarea, Theobroma cocao, "free form amino acids", vitamin C
- Red E (Worldwide) Mfg: Future Highs. Listed ingredients: unknown. There is an informal report that these contain caffeine and DMAA
- (i) Trance (UK) Mfg: Enjoi. Listed ingredients: Griffonia seed extract, caffeine, geranium extract, sodium chloride, magnesium aspartate, calcium ascorbate, "amino acid blend"
- (i) Envy (Europe) Mfg: unknown. Listed ingredients: Hamelia patens, Pelargonium graveollens, Polygonium multiflorium, Paulina cupana, Theobroma cacao, clary cage, Citrus aurantium, vitamins B and C, "amino acids", "tableting agents", "permitted colour coating"
- (i) Bliss Bomb (Europe) Mfg: Cosmic Party Productions. Listed ingredients: caffeine, "free form amino acids (l-tyrosine, l-phenylalanine)", griffonia seed extract, pelargonium extract (synthetic equivalent), Citrus aurantium extract, vitamin B6, "tableting aids"
- (i) Dr. Feelgood (Europe) Mfg: Cosmic Party Productions. Listed ingredients: caffeine, Theobroma cacao extract, pelargonium extract (synthetic equivalent), Hordeum vulgare extract, Citrus aurantium extract, clary sage extract, griffonia seed extract.
- Space Trips Mfg: unknown. Listed ingredients: galangal, geranamine, Citrus aurantium, caffeine, piperine
- Fast Lane Mfg: unknown. Listed ingredients: DMAA, Camellia sinensis, piperine, epimedium, passion flower
- (i) Colours (UK) Mfg: unknown Listed ingredients: 1,3-dimethylamylamine, methylmesembrine
- (i) Cosmic (UK) Mfg: Enjoi. Listed ingredients: geranium, Citus aranthium, choline bitartrate, caffeine, "mineral blend", "amino blend", synephrine, vitamin C, "absorbers", "tableting aids"
- (i) Mythic (UK) Mfg: Enjoi. Listed ingredients: geranium, Glacine, Citus aranthium, caffeine, "mineral blend", "amino blend", synephrine, vitamin C, "absorbers", "tableting aids"
- (i) Supasonic (UK) Mfg: Enjoi. Listed ingredients: geranium, caffeine, "mineral blend", "amino blend", vitamin C, "absorbers", "tableting aids"
- (i) Angelic (UK) Mfg: Enjoi. Listed ingredients: geranium, caffeine, "mineral blend", "amino blend", vitamin C, "absorbers", "tableting aids"
- (i) Move (UK) Mfg: London Underground. Listed ingredients: "Synthetic equivalent of standardized geranium oil extract", caffeine, magnesium stearate, dicalcium phosphate
- (i) Revive (UK) Mfg: Enjoi. Listed ingredients:: geranium, caffeine, "mineral blend", "amino blend", vitamin C, "absorbers", "tableting aids"
- Pure Go-E Party Pills (Netherlands) Mfg. Cosmic Party Products. Listed ingredients: caffeine, Theobroma cacao extract, Hordeum graveolens extract, Perlagonium graveolens extract, Citrus aurantium extract, clary sage extract, vitamin C
- Pure Bliss Party Pills (Netherlands) Mfg. Cosmic Party Products. Listed ingredients: caffeine, Guarana, Citrus aurantium, Perlagonium graveolens, "free form amino acids", vitamin B6
- Pure XS Party Pills (Netherlands) Mfg. Cosmic Party Products. Listed ingredients: caffeine, "free form amino acids (l-tyrosine, l-phenalanine)", Perlagonium graveolens extract, Theobroma cocoa extract, Hordeum vulgare extract, Salvia sclarea extract, Citrus aurantium, vitamin C, "tableting aids"
[top]Combinations Suggested by Individuals
- Methylhexanamine, 4-AcO-DMT, marijuana.
- Methylhexanamine and alcohol. (This combination is reported to be enjoyable, but to produce a severe hangover the following day.)
[top]Different Uses for Methylhexanamine
Methylhexanamine was originally marketed by Eli Lilly and Company as a nasal decongestant. It has also been used for treatment of hypertrophied oral tissue.
In its present day status as a research chemical
, these uses have been reported or recommended:
- As a mild mental stimulant, combined with caffeine or instead of caffeine.
- As a study and test-taking aid.
- For weight loss.
- To counteract daytime drowsiness.
- To aid in an athletic workout.
- As a substitute for propylhexedrine, methylphenidate or amphetamine.
It is notable that several individuals in the experience thread who initially thought methylhexanamine seemed promising later changed their minds and concluded it was not useful in any way. This may be on account of the rapid development of tolerance to the drug.
[top]Chemistry of Methylhexanamine
|Systematic (IUPAC) name:||4-methylhexan-2-amine|
|Synonyms:||Dimethylhexylamine, Pentylamine, 1,3-Dimethylamylamine, 1,3-Dimethylpentanamine, 1,3-Dimethylpentylamine, 2-Amino-4-methylhexane, 4-Methyl-2-hexylamine, NSC 1106, Forthane|
|Molar mass:||115.22 g/mol |
|CAS Registry Number:||105-41-9|
|Melting Point:|| |
|Boiling Point:||130-135°C @ 760 mmHg|
|Flash Point:||no data|
|Solubility:||Freely soluble in alcohol, chloroform, ether, dilute acids; very slightly soluble in water|
|Additionnal data:||density 0.7620-0.7655 g/cm3|
|Notes:||aspect : liquid, amine odor|
[top]Pharmacology of Methylhexanamine
Methylhexanamine is known to have sympathomimentic properties. It is believed to increase levels of norepinephrine in the synaptic cleft. However, there are no publicly available data on its specific mechanism of action, absorption, pharmacokinetics, metabolism, or excretion.
[top]The dangers of Methylhexanamine
in the mouse is 39 mg/kg intravenously and 185 mg/kg intraperitoneally. Oral LD50 is unknown.
Side-effects present at moderate doses can become overwhelming at higher doses. A dose of 200 mg is described as causing "12-14 hours of what feels EXACTLY like Xanax
withdrawal." An individual who combined 4 teaspoons of methylhexanamine (weight unknown, but a very large dose), 20 grams of kratom
, and alcohol reported "10 minutes of fantastic pleasure followed by 48 hours of vomiting." The combination of alcohol with methylhexanamine may be especially prone to cause severe nausea. Anxiety, rapid heart rate, and heavy sweating are also reported in overdose. Visual symptoms, "cant focus really good on the screen its going from left to right," reported with an 80 mg oral dose.
Two cases of stroke have been reported in users of methylhexanamine.
- In 2009, it was reported that a 45-year-old New Zealand man who took methylhexanamine suffered a stroke. Other details are not known.
- In 2010 the New Zealand Medical Journal published details of a case in which a 21-year-old New Zealand man suffered a hemorrhagic stroke after taking two pills labeled "99.9 percent-pure DMAA," beer, and a caffeine tablet. Symptoms developed 30 minutes later. CT scan showed a 'large' left-sided cerebral hemorrrhage. The man spent 20 days hospitalized, and was discharged with persistent neurologic deficits, including "severe impairments to his memory and abstract reasoning and mild impairments to his speech and right-hand co-ordination."
Hemorrhagic stroke (rupture of a cerebral blood vessel, causing bleeding into, or around, the brain) is usually related to hypertension
. Sympathomimetic stimulants such as methylhexanamine often cause hypertension during their duration of activity. Both hemorrahagic and ischemic (caused by the cut-off of blood flow) stroke are known complications of amphetamine use.
[top]Forms of Methylhexanamine
Methylhexanamine is commonly found as a white crystalline powder.
[top]Images of Methylhexanamine
Packaged methylhexanamine as distributed by a US vendor
[top]Legal status of Methylhexanamine
Methylhexanamine is not scheduled in the 1971 United Nations Convention on Psychotropic
Methylhexanamine (DMAA) is not an FDA approved drug product. It is not legal to market methylhexanamine in the US as a drug. Methyhexanamine was claimed by manufacturers to be a component of geranium oil, which is an approved food product, however this has been called into question by the FDA-- studies have shown that the levels of DMAA in the products is not compatible with extraction from geraniums. It is no longer legal to sell DMAA as a dietary supplement.
In May 2012 the FDA imposed a ban on DMAA. This would cease the sale of products containing DMAA, as well as DMAA powder in shops across the country; this would ban all sales of DMAA for human comsumption.
DMAA is not scheduled by the DEA, so possession and purchase/sale is not illegal so long as it is not intended for human consumption. Its chemical structure and pharmacologic effects do not closely resemble any Schedule I or II substances, and it is not likely to fall under the Controlled Substance Analog Enforcement Act of 1986. [21 U.S.C. 802(32), 21 U.S.C. § 813]
Methylhexanamine is not licensed by the European Medicines Agency. Methylhexanamine is not controlled at the EU level.
While it is currently unscheduled, the EU is currently targeting DMAA, removing it from store shelves. To be a "Dietary Supplement" it needs EU Novel Foods approval, and to be a drug, it needs Traditional Herbal Medicinal Product Directive (THMPD) approval and DMAA has neither. Since it is being target, it is on the very dangerous end of the 'grey' area. Be warned.
Dietary products / any product for human consumption containing DMAA is illegal.
Listed DMAA Products banned:
4. Marrow Matters
8. Lipo-6 Black
9. This list should not be viewed as including every potential product containing DMAA.
Methylhexanamine is scheduled as a restricted substance, but not banned outright. Methylhexanamine may be sold to adults age 18 or older, but may not be advertised, sold at gas stations, places where alcohol is sold, or in places frequented by minors, and may not be given as a gift or reward.
Banned in Australia effect August 1, 2012.
Methylhexanamine is on the World Anti-Doping Agency's list of prohibited substances. Athletes have been sanctioned for using it.
[top]History of Methylhexanamine
1944: Methylhexanamine is patented by Eli Lilly.
2005: Proviant, parent company to Ergopharm, registers for trademark protection of the brand name 'geranamine', and markets Ergolean AMP, a nutritional supplement which contains methylhexanamine.
2006: First mention of methylhexanamine on Drugs-Forum.
2008: Following a ban on BZP, methylhexanamine appears in party pills and is sold in bulk in New Zealand.
2009: The World Anti-Doping Agency adds methylhexanamine to its list of prohibited substances for athletes. After one New Zealand man who used methylhexanamine suffered a stroke, and several other users were hospitalized, methylhexanamine is scheduled as a restricted substance in New Zealand.
2010: Several international athletes, from Nigeria, Portugal, and Australia fail tests for methylhexanamine. Some are sanctioned. A second New Zealand man is reported to have suffered a stroke shortly after using methylhexanamine.
Popularity of Methylhexanamine over time:
[top]Methylhexanamine on Drugs-Forum
[top]Posts about methylhexanamine appear in the general Research Chemical forum. Here are the latest posts.
 Merck Index
, fifteenth edition (2013)
 Calculated from Atomic Weights of the Elements
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