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{{SubstanceBox/Methylhexanamine}}
{{SubstanceBox/Methylhexanamine}}
Methylhexanamine (also known as methylhexamine, 1,3-dimethylamylamine, 1,3-DMAA, dimethylamylamine, and DMAA; trade names Forthane and Geranamine) is an indirect sympathomimetic drug.
'''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==
{{In April 1944, Eli Lilly and Company introduced methylhexanamine under the brand name Forthane as an inhaled nasal decongestant; Lilly voluntarily withdrew methylhexanamine from the market in 1983. The compound is an aliphatic amine; the pharmaceutical industry had a strong interest in compounds in this class as nasal decongestants in the early 20th century, which led to methylhexanamine and four other similar compounds being brought to market for that use: tuaminoheptane, octin, oenethyl (2-methylaminoheptane), and propylhexedrine; octin and oenethyl were eventually approved for use in keeping blood pressure sufficiently high for patients under anesthesia.
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>
Patrick Arnold reintroduced methylhexanamine in 2006 as a dietary supplement, after the final ban of ephedrine 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 (thermogenic or general-purpose stimulants) used the ingredient in concert with other substances such as caffeine, a combination similar to the combination of ephedrine and caffeine.}}
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==
{{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.}}
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]]'''
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|{{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]]'''
*'''[[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]]'''
*'''[[Effect::Focus enhancement]]'''
*'''[[Effect::Increased libido]]'''
*'''[[Effect::Increased libido]]'''
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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]]'''
*'''[[Effect::Depression]]'''
*'''[[Effect::Irritability]]'''
*'''[[Effect::Irritability]]'''
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*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Thought deceleration]]'''
*'''[[Effect::Wakefulness]]''' - According to anecdotal reports, residual feelings of wakefulness can persist for up to 6 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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==Legal status==
==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.}}
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.
It may contain incorrect information, particularly with respect to dosage, duration, subjective effects, toxicity and other risks. It may also not meet PW style and grammar standards.
WARNING: Always start with lower doses due to differences between individual body weight, tolerance, metabolism, and personal sensitivity. See responsible use section.
DISCLAIMER: PW's dosage information is gathered from users and resources for educational purposes only. It is not a recommendation and should be verified with other sources for accuracy.
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. It is thought to produce its effects by increasing levels of the neurotransmittersepinephrine, norepinephrine, and to a lesser extent, dopamine in the brain.
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.
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 PsychonautWikicontributors. 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
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 neurotransmittersnorepinephrine 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 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.
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:
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. Note: Always conduct independent research and use harm reduction practices if using this substance.
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.
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.
↑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.
