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''meta''-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a
stimulant Stimulants (also often referred to as psychostimulants or colloquially as uppers) is an overarching term that covers many drugs including those that increase activity of the central nervous system and the body, drugs that are pleasurable and inv ...
drug A drug is any chemical substance that causes a change in an organism's physiology or psychology when consumed. Drugs are typically distinguished from food and substances that provide nutritional support. Consumption of drugs can be via inhal ...
from the
amphetamine Amphetamine (contracted from alpha- methylphenethylamine) is a strong central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. It is also commonly used ...
family. It has similar effects in animal drug discrimination tests to the more widely known derivative 4-methoxyamphetamine (PMA), although with a slightly different ratio of monoamine release, being a combined serotonin,
dopamine Dopamine (DA, a contraction of 3,4-dihydroxyphenethylamine) is a neuromodulatory molecule that plays several important roles in cells. It is an organic chemical of the catecholamine and phenethylamine families. Dopamine constitutes about 8 ...
, and
norepinephrine Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic chemical in the catecholamine family that functions in the brain and body as both a hormone and neurotransmitter. The name "noradrenaline" (from Latin '' ad ...
releasing agent A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of a monoamine neurotransmitter from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrations of the ...
rather than a fairly selective serotonin releaser like PMA. 3-Methoxyamphetamine has similarly appeared on the illicit market as a
designer drug A designer drug is a structural or functional analog of a controlled substance that has been designed to mimic the pharmacological effects of the original drug, while avoiding classification as illegal and/or detection in standard drug tests. Des ...
alternative to
MDMA 3,4-Methylenedioxymethamphetamine (MDMA), commonly seen in tablet form (ecstasy) and crystal form (molly or mandy), is a potent empathogen–entactogen with stimulant properties primarily used for recreational purposes. The desired ...
, although far more rarely than its infamous
positional isomer In chemistry, a structural isomer (or constitutional isomer in the IUPAC nomenclature) of a compound is another compound whose molecule has the same number of atoms of each element, but with logically distinct bonds between them. The term met ...
. It produces
gepefrine 3-Hydroxyamphetamine ( INN; trade names Pressionorm, Gepefrine, and Wintonin), also known as meta-hydroxyamphetamine, and α-methyl-''meta''-tyramine, is an antihypotensive or sympathomimetic agent of the amphetamine family that is marketed in c ...
, a
cardiac stimulant A cardiac stimulant is a substance which acts as a stimulant of the heart – e.g., via positive chronotropic or inotropic action. Examples of cardiac stimulant drugs are cocaine and methamphetamine Methamphetamine (contracted from ) is a p ...
, as one of its major
metabolite In biochemistry, a metabolite is an intermediate or end product of metabolism. The term is usually used for small molecules. Metabolites have various functions, including fuel, structure, signaling, stimulatory and inhibitory effects on enzymes, ...
s.


See also

* 2-Methoxyamphetamine (OMA) *
3-Methylamphetamine 3-Methylamphetamine (3-MeA; PAL-314) is a stimulant drug from the amphetamine family. It is self-administered by mice to a similar extent to 4-fluoroamphetamine and has comparable properties as a monoamine releaser, although with a more balanced ...
(3-MA) *
3-Fluoroamphetamine 3-Fluoroamphetamine (3-FA; PAL-353) is a stimulant drug from the amphetamine family which acts as a monoamine releaser with similar potency to methamphetamine but more selectivity for dopamine and norepinephrine release over serotonin. It is se ...
(3-FA) * 3-Trifluoromethylamphetamine (Norfenfluramine) *
3-Methoxy-4-methylamphetamine 3-Methoxy-4-methylamphetamine (MMA) is an entactogen and psychedelic drug of the phenethylamine and amphetamine classes. It was first synthesized in 1970 and was encountered as a street drug in Italy in the same decade.de Zorzi C, Cavalli A, Un ...
(MMA) * 3-Methoxymethamphetamine (MMMA) * 4-Ethoxyamphetamine (4-ETA)


References

{{DEFAULTSORT:Methoxyamphetamine, 3- Substituted amphetamines Phenol ethers Serotonin-norepinephrine-dopamine releasing agents