4-Hydroxy-3-methoxyamphetamine (HMA), also known as 3-''O''-methyl-α-methyldopamine, is an
active metabolite
An active metabolite, or pharmacologically active metabolite is a biologically active metabolite of a xenobiotic substance, such as a drug or environmental chemical. Active metabolites may produce therapeutic effects, as well as harmful effects. ...
of
3,4-methylenedioxymethamphetamine (MDMA).
It is substantially less potent than MDMA or
3,4-methylenedioxyamphetamine (MDA) as a
monoamine releasing agent
A monoamine releasing agent (MRA), or simply monoamine releaser, is a drug that induces the release of one or more monoamine neurotransmitters from the presynaptic neuron into the synapse, leading to an increase in the extracellular concentrati ...
''
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
A serotonin–norepinephrine–dopamine releasing agent (SNDRA), also known as a triple releasing agent (TRA), is a type of drug which induces the release of serotonin, norepinephrine/epinephrine, and dopamine in the brain and body. SNDRAs produc ...
(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
2,4,5-Trihydroxyamphetamine (THA) is a neurotoxin and a metabolite of MDMA. It comes from the ring-hydroxylation of 3,4-methylenedioxyamphetamine (MDA).
In one paper, it was shown to reduce hippocampal tryptophan hydroxylase activity by 54% afte ...
(THA)
*
2,4,5-Trihydroxymethamphetamine
2,4,5-Trihydroxymethamphetamine (THMA or THM) is a neurotoxin and a metabolite of MDMA. It has structural similarity to the dopamine neurotoxin 6-hydroxydopamine, and produces lasting serotonin deficits when administered centrally.
See also
* 2,4 ...
(THMA)
*
3,4-Dimethoxyamphetamine
3,4-Dimethoxyamphetamine (3,4-DMA), or simply dimethoxyamphetamine (DMA), is a psychedelic drug of the phenethylamine and amphetamine families. It is one of the dimethoxyamphetamine (DMA) series of positional isomers.
The drug has been assessed ...
(DMA)
*
3,4-Dihydroxymethcathinone (HHMC)
*
4-Hydroxy-3-methoxymethcathinone (HMMC)
References
Human drug metabolites
Methoxyphenethylamines
Phenols
Serotonin-norepinephrine-dopamine releasing agents
Substituted amphetamines
{{Psychoactive-stub