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| Summary sheet: Methylhexanamine |
| Methylhexanamine | |||||||||||||||||||||||||||||||
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| Chemical Nomenclature | |||||||||||||||||||||||||||||||
| Common names | 1,3-DMAA, 2-amino-4-methylhexane | ||||||||||||||||||||||||||||||
| Substitutive name | 1,3-dimethylamylamine | ||||||||||||||||||||||||||||||
| Systematic name | 4-methylhexan-2-amine | ||||||||||||||||||||||||||||||
| Class Membership | |||||||||||||||||||||||||||||||
| Psychoactive class | Stimulant | ||||||||||||||||||||||||||||||
| Chemical class | Amine | ||||||||||||||||||||||||||||||
| Routes of Administration | |||||||||||||||||||||||||||||||
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Methylhexanamine (also known as 1,3-dimethylamylamine, 1,3-DMAA, and 2-amino-4-methylhexane) is a lesser-known novel stimulant substance of the amine class. It has structural similarities to amphetamine and is most notably used in dietary supplements related to resistance training.
History and culture
Methylhexanamine was developed by Eli Lilly & Co. and marketed starting in 1948 as an inhaled nasal decongestant. The company voluntarily withdrew it by the 1970s.[1] For a molecule to be legally used in a dietary supplement in the United States, it must be naturally occurring and have a documented history of use prior to 1994. In 1996, a study found methylhexanamine to be contained in trace amounts in geranium oil.[2] These findings were subsequently not reproduced in multiple peer-reviewed publications.[3]
Starting in 2006, methylhexanamine was used in several marketed sport supplements, most famously Jack3d by USPlabs. In April 2013, the FDA warned about methylhexanamine after 86 reports of heart problems, nervous system disorders, or death, and motioned manufacturers to stop using the substance.[4] The US Department of Defense published an investigation into methylhexanamine following the death of four soldiers which were linked with the substance in recreational doses.[5]
Chemistry
Methylhexanamine is synthesized by reacting 4-methylhexan-2-one with hydroxylamine, which converts the 4-methylhexan-2-one to 4-methylhexan-2-one oxime, which is reduced with hydrogen by means of a catalyst; the resulting methylhexanamine can be purified by distillation.
Pharmacology
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This pharmacology section is incomplete. You can help by adding to it. |
Subjective effects
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This subjective effects section is a stub. As such, it is still in progress and may contain incomplete or wrong information. You can help by expanding or correcting it. |
Disclaimer: The effects listed below cite the Subjective Effect Index (SEI), an open research literature based on anecdotal user reports and the personal analyses of PsychonautWiki contributors. As a result, they should be viewed with a healthy degree of skepticism.
It is also worth noting that these effects will not necessarily occur in a predictable or reliable manner, although higher doses are more liable to induce the full spectrum of effects. Likewise, adverse effects become increasingly likely with higher doses and may include addiction, severe injury, or death ☠.
Physical effects 
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- Stimulation - In terms of its effects on the physical energy levels of the user, methylhexanamine is usually considered to be extremely energetic and stimulating in a fashion that is extremely similar to that of amphetamine or methamphetamine, and stronger than that of modafinil, caffeine, and methylphenidate. It is similar to the stimulation experienced on racemic or the levorotorary form of amphetamine or the racemic methamphetamine, encouraging physical activities such as dancing, socializing, running, or cleaning. The particular style of stimulation which methylhexanamine presents can be described as forced or pressing and is noticeably more adrenergic and tense on the body. This means that at higher dosages, it becomes difficult or impossible to keep still as jaw clenching, involuntarily bodily shakes and vibrations become present, resulting in extreme shaking of the entire body, unsteadiness of the hands, and a general lack of motor control.
- Abnormal heartbeat
- Increased blood pressure
- Increased heart rate
- Pupil dilation
- Appetite suppression
- Bronchodilation
- Dehydration
- Frequent urination
- Increased bodily temperature
- Increased perspiration
- Stamina enhancement
- Teeth grinding
- Temporary erectile dysfunction
- Vasoconstriction
Cognitive effects 
After effects 
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The effects which occur during the offset of a stimulant experience generally feel negative and uncomfortable in comparison to the effects which occurred during its peak. This is often referred to as a "comedown" and occurs because of neurotransmitter depletion. Its effects commonly include:
- Anxiety
- Appetite suppression
- Cognitive fatigue
- Depression
- Irritability
- Motivation suppression
- Thought deceleration
- Wakefulness - According to anecdotal reports, residual feelings of wakefulness can persist for up to 6 hours after the initial high wears off.
Experience reports
There are currently 0 experience reports which describe the effects of this substance in our experience index.
Additional experience reports can be found here:
Toxicity and harm potential
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This toxicity and harm potential section is a stub. As a result, it may contain incomplete or even dangerously wrong information! You can help by expanding upon or correcting it. |
It is strongly recommended that one use harm reduction practices when using this substance. Health authorities in Hawaii linked cases of liver failure and one death to OxyElite Pro, a weight loss and bodybuilding dietary supplement containing methylhexanamine.
Lethal dosage
The LD50 for methylhexanamine is 39 mg/kg in mice and 72.5 mg/kg in rats, when administered intravenously. In 2010, a 21-year-old male in New Zealand presented with a cerebral hemorrhage after ingesting 556 mg of methylhexanamine, caffeine, and alcohol.
Tolerance and addiction potential
Dangerous interactions
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This dangerous interactions section is a stub. As such, it may contain incomplete or invalid information. You can help by expanding upon or correcting it. |
Warning: Many psychoactive substances that are reasonably safe to use on their own can suddenly become dangerous and even life-threatening when combined with certain other substances. The following list provides some known dangerous interactions (although it is not guaranteed to include all of them).
Always conduct independent research (e.g. Google, DuckDuckGo, PubMed) to ensure that a combination of two or more substances is safe to consume. Some of the listed interactions have been sourced from TripSit.
Legal status
As of 2013, Methylhexanamine has been banned for legal sale in Canada, Sweden, Brazil, Australia, the United Kingdom, New Zealand, and the United States, and may be regulated to one degree or another in other countries. Possession of the drug itself is not criminal in most jurisdictions.
See also
External links
Literature
- APA formatted reference
Please see the citation formatting guide if you need assistance properly formatting citations.
References
- ↑ https://jamanetwork.com/journals/jamainternalmedicine/fullarticle/1157413
- ↑ Ping, Z., Jun, Q., & Qing, L. (1996). A study on the chemical constituents of geranium oil. Journal of Guizhou Institute of Technology, 25(1), 82-5.
- ↑ https://scribd.com/document/82744576/DMAA-Health-Canada-2011
- ↑ https://www.fda.gov/consumers/consumer-updates/stimulant-potentially-dangerous-health-fda-warns?source=govdelivery
- ↑ Lammie, C. J., & Lead, S. P. (2013). Report of the Department of Defense 1, 3 Dimethylamylamine (DMAA) Safety Review Panel. The Pentagon: US Department of Defense, 97-98.