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{{SummarySheet}}
{{SummarySheet}}
{{SubstanceBox/Amphetamine}}
{{SubstanceBox/Methylhexanamine}}
'''Methylhexanamine''' (also known as '''1,3-dimethylamylamine''', '''1,3-DMAA''', and '''2-amino-4-methylhexane''') is a lesser-known novel [[psychoactive class::stimulant]] substance of the [[chemical class::amine]] class. It has structural similarities to [[Amphetamine|amphetamine]] and is most notably used in dietary supplements related to resistance training. It is thought to produce its effects by increasing levels of the [[neurotransmitters]] [[epinephrine]], [[norepinephrine]], and to a lesser extent, [[dopamine]] in the brain.


==History and culture==
==History and culture==
{{historyStub}}
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.<ref>https://jamanetwork.com/journals/jamainternalmedicine/fullarticle/1157413</ref>
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.<ref>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.</ref>
These findings were subsequently not reproduced in multiple peer-reviewed publications.<ref>https://scribd.com/document/82744576/DMAA-Health-Canada-2011</ref>
 
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.<ref>https://www.fda.gov/consumers/consumer-updates/stimulant-potentially-dangerous-health-fda-warns?source=govdelivery</ref>
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.<ref>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.</ref>


==Chemistry==
==Chemistry==
{{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==
==Pharmacology==
{{pharmacology}}
{{pharmacology}}
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|{{effects/physical|
|{{effects/physical|


*'''[[Effect::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 [[adrenaline|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.  
*'''[[Effect::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]]. Although It is similar to the stimulation experienced on racemic or the levorotorary form of [[amphetamine]] or the racemic [[methamphetamine]], the stimulation that methylhexanamine presents can be also described as more physically stimulating rather than mentally, this is due to it being mainly focused on the [[neurotransmitters]] [[norepinephrine]] and [[epinephrine]], 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 [[adrenaline|adrenergic]] and tense on the body as mentioned before. 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.  
*'''[[Effect::Abnormal heartbeat]]'''
*'''[[Effect::Abnormal heartbeat]]'''
*'''[[Effect::Increased blood pressure]]'''
*'''[[Effect::Increased blood pressure]]'''
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*'''[[Effect::Increased bodily temperature]]'''
*'''[[Effect::Increased bodily temperature]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Increased perspiration]]'''
*'''[[Effect::Stamina enhancement]]'''  
*'''[[Effect::Stamina enhancement]]''' - This effect is said to be more noticeable than on any other stimulant such as [[MDMA]].
*'''[[Effect::Teeth grinding]]'''  
*'''[[Effect::Teeth grinding]]'''  
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Temporary erectile dysfunction]]'''
*'''[[Effect::Vasoconstriction]]''' - Propylhexedrine has been noted by users as being particularly vasoconstrictive in comparison to other stimulants. It has been speculated that this is due to its higher affinity for [[noradrenaline]] relative to stimulants such as [[amphetamine]].
*'''[[Effect::Vasoconstriction]]'''


}}
|{{effects/cognitive|
|{{effects/cognitive|


*'''[[Effect::Disinhibition]]'''
*'''[[Effect::Disinhibition]]''' - The disihibiting effects of methylhexanamine are pronounced to a greater extent than on other stimulants such as [[Modafinil]] or [[MDMA]].
*'''[[Effect::Euphoria]]''' - The euphoria capable of being produced by propylhexedrine is reported to be similiar to that of [[methamphetamine]] at high doses.
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Analysis enhancement]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Compulsive redosing]]'''
*'''[[Effect::Ego inflation]]'''  
*'''[[Effect::Ego inflation]]'''  
*'''[[Effect::Cognitive euphoria|Euphoria]]'''
*'''[[Effect::Cognitive euphoria|Euphoria]]''' - This effect is mild.
*'''[[Effect::Focus enhancement]]''' - This component is most effective at low to moderate dosages as anything higher will usually impair concentration.
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased music appreciation]]'''
*'''[[Effect::Increased music appreciation]]'''
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*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought acceleration]]'''
*'''[[Effect::Thought organization]]'''
*'''[[Effect::Thought organization]]'''
*'''[[Effect::Time distortion]]''' - As with other stimulants, time can feel like it moves faster while on methylhexanamine.
*'''[[Effect::Wakefulness]]'''
*'''[[Effect::Wakefulness]]'''


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*'''[[Effect::Anxiety]]'''
*'''[[Effect::Anxiety]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Appetite suppression]]'''
*'''[[Effect::Cognitive fatigue]]'''
*'''[[Effect::Physical fatigue]]'''
*'''[[Effect::Depression]]''' - Due to depletion of the essential neurotransmitters [[serotonin]],[[dopamine]], and [[norepinephine]], propylhexedrine can cause moderate to strong feelings of depression after large doses.
*'''[[Effect::Depression]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Motivation suppression]]'''
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Thought deceleration]]'''  
*'''[[Effect::Wakefulness]]''' - According to anecdotal reports, residual feelings of wakefulness can persist for up to 12 hours after the initial high wears off.
*'''[[Effect::Wakefulness]]''' - According to anecdotal reports, residual feelings of wakefulness can persist for up to 6 hours after the initial high wears off.
 
The comedown experienced on methylhexanamine is rather more physical than cognitive due to the increase in [[epinephrine]].
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{{toxicity}}
{{toxicity}}
It is strongly recommended that one use [[responsible use|harm reduction practices]] when using this substance.
It is strongly recommended that one use [[responsible 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===
===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===
===Tolerance and addiction potential===
===Dangerous interactions===
===Dangerous interactions===
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==Legal status==
==Legal status==
{{LegalStub}}
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==
==See also==
*[[Responsible use]]
*[[Responsible use]]
*[[1,4-DMAA]]


==External links==
==External links==
(List along order below)
*[https://en.wikipedia.org/wiki/Methylhexanamine Methylhexanamine (Wikipedia)]
* [https://en.wikipedia.org/wiki/SUBSTANCE SUBSTANCE (Wikipedia)]
*[https://drugs-forum.com/wiki/Methylhexanamine Methylhexanamine (Drugs-Forum)]
* SUBSTANCE (Erowid Vault)
* SUBSTANCE ([''PiHKAL'' or ''TiHKAL''] / Isomer Design)
 
==Literature==
* APA formatted reference
 
Please see the [[citation formatting guide]] if you need assistance properly formatting citations.


==References==
==References==
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