1,4‑DMAA
Experimental sympathomimetic stimulant, a positional isomer of DMAA, banned in competitive sport.
Pharmacology
Contents
WHAT IS 1,4-DMAA?
Detailed overview
1,4-DMAA (1,4-dimethylamylamine, or 5-methylhexan-2-amine) is a positional isomer of the notorious 1,3-DMAA: an aliphatic amine stimulant detected in pre-workout and weight-loss supplements, often to sidestep regulatory bans. Its presumed mechanism is that of an indirect sympathomimetic, promoting the release of norepinephrine and dopamine, which accounts for the expected wakefulness, energy and appetite-suppressant effects along with vasoconstriction and raised blood pressure. There are no human efficacy or safety studies, and the mechanism is inferred from related compounds rather than established. The available literature is almost entirely analytical detection in supplements rather than drug development; the compound is an unapproved stimulant prohibited in competitive sport.
Mechanism
Indirect sympathomimetic (norepinephrine/dopamine release)
Evidence
Analytical detection only, no human clinical data
Legal status
Unapproved stimulant, prohibited in competitive sport
Receptor profile
- Norepinephrine and dopamine releaseStrong
- Sympathetic nervous systemModerate
- Blood pressure / heart rateStrong
Safety
Side effects, stop signs, contraindications
Side effects · 6
- Elevated blood pressure, sometimes markedly
- Rapid heart rate, palpitations
- Jitteriness, anxiety, tremor
- Headache
- Sleep disruption, especially with late dosing
- Unknown human safety: the closely related 1,3-DMAA has been linked to cerebral hemorrhage, heart attack and deaths, and the cardiovascular risk applies here too
Contraindications · 4
- Cardiovascular disease, hypertension, arrhythmia
- Pregnancy and breastfeeding: avoid
- Concurrent MAO inhibitors or other stimulants: risk of hypertensive crisis
- Competitive athletes: a WADA-prohibited substance that causes an anti-doping violation
Related Nootropics
Same therapeutic category
Studies
Related research and clinical findings
Nine prohibited stimulants found in sports and weight loss supplements: deterenol, phenpromethamine (Vonedrine), oxilofrine, octodrine, beta-methylphenylethylamine (BMPEA), 1,3-dimethylamylamine (1,3-DMAA), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylbutylamine (1,3-DMBA) and higenamine
Cohen PA, Travis JC, Vanhee C, Ohana D, Venhuis BJ
Four experimental stimulants found in sports and weight loss supplements: 2-amino-6-methylheptane (octodrine), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylamylamine (1,3-DMAA) and 1,3-dimethylbutylamine (1,3-DMBA)
Cohen PA, Travis JC, Keizers PHJ, Deuster P, Venhuis BJ
Analysis and Confirmation of 1,3-DMAA and 1,4-DMAA in Geranium Plants Using High Performance Liquid Chromatography with Tandem Mass Spectrometry at ng/g Concentrations
Fleming HL, Ranaivo PL, Simone PS
Differentiation of isomeric heptylamines by in-source collision-induced dissociation of [M + H]+ ions
Zaremba I, Frański R, Kasperkowiak M
FAQ
FAQ
Experimental sympathomimetic stimulant, a positional isomer of DMAA, banned in competitive sport.
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Structure & chemistry
The information here is strictly for educational and scientific purposes. It does not replace medical advice or clinical consultation, and it does not encourage illegal substance or pharmaceutical use. Data is sourced. When in doubt, consult your doctor.