4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-''O''-methyl-α-methyldopamine, is an
active metabolite of
3,4-methylenedioxymethamphetamine (MDMA).
It is substantially less potent than MDMA or
3,4-methylenedioxyamphetamine (MDA) as a
monoamine releasing agent ''
in vitro
''In vitro'' (meaning ''in glass'', or ''in the glass'') Research, studies are performed with Cell (biology), cells or biological molecules outside their normal biological context. Colloquially called "test-tube experiments", these studies in ...
''.
Nonetheless, HMA has been found to induce the release of
serotonin
Serotonin (), also known as 5-hydroxytryptamine (5-HT), is a monoamine neurotransmitter with a wide range of functions in both the central nervous system (CNS) and also peripheral tissues. It is involved in mood, cognition, reward, learning, ...
,
norepinephrine
Norepinephrine (NE), also called noradrenaline (NA) or noradrenalin, is an organic compound, organic chemical in the catecholamine family that functions in the brain and human body, body as a hormone, neurotransmitter and neuromodulator. The ...
, and
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. It is an amine synthesized ...
with values of 897nM, 694nM, and 1450–3423nM, respectively, and hence acts as a lower-potency
serotonin–norepinephrine–dopamine releasing agent (SNDRA).
The predicted
log P of HMA is 0.6.
See also
*
4-Hydroxy-3-methoxymethamphetamine
4-Hydroxy-3-methoxymethamphetamine (HMMA) is an active metabolite of 3,4-methylenedioxymethamphetamine (MDMA). It is a slightly more potent stimulant than MDMA in rodents. The drug is substantially less potent than MDMA as a monoamine releasi ...
(HMMA)
*
3,4-Dihydroxyamphetamine (HHA; α-methyldopamine)
*
3,4-Dihydroxymethamphetamine
3,4-Dihydroxymethamphetamine (HHMA, 3,4-DHMA), or 3,4-dihydroxy-''N''-methylamphetamine, also known as α-methylepinine or α,''N''-dimethyldopamine, is the major metabolite of 3,4-methylenedioxy-''N''-methylamphetamine (MDMA). It is formed fro ...
(HHMA; α-methylepinine)
*
2,4,5-Trihydroxyamphetamine (THA)
*
2,4,5-Trihydroxymethamphetamine (THMA)
*
3,4-Dimethoxyamphetamine (DMA)
*
3,4-Dihydroxymethcathinone (HHMC)
*
4-Hydroxy-3-methoxymethcathinone (HMMC)
References
Human drug metabolites
Methoxyphenethylamines
Phenols
Serotonin-norepinephrine-dopamine releasing agents
Substituted amphetamines
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