''meta''-Methoxyamphetamine (MMA), also known as 3-methoxyamphetamine (3-MA), is a
stimulant drug from the
amphetamine 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, 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 synapse, release of a monoamine neurotransmitter from the synapse, presynaptic neuron into the synapse, leading to an increase in the extracellular conc ...
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. D ...
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 desire ...
, 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 meta ...
. It produces
gepefrine, a
cardiac stimulant A cardiac stimulant is a substance which acts as a stimulant of the heart – e.g., via positive chronotropic or inotropic
An inotrope is an agent that alters the force or energy of muscular contractions. Negatively inotropic agents weaken the fo ...
, as one of its major
metabolites.
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, U ...
(MMA)
*
3-Methoxymethamphetamine
3-Methoxymethamphetamine (also known as ''meta''-methoxymethamphetamine or MMMA), which is most closely related to 3-methoxyamphetamine and PMMA and shares similar monoamine releasing effects, although its effects have not been studied so extens ...
(MMMA)
*
4-Ethoxyamphetamine (4-ETA)
References
{{DEFAULTSORT:Methoxyamphetamine, 3-
Substituted amphetamines
Phenol ethers
Serotonin-norepinephrine-dopamine releasing agents