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
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, c ...
of
3,4-methylenedioxy-''N''-methylamphetamine (MDMA).
It is formed from MDMA by ''O''-
demethylation
Demethylation is the chemical process resulting in the removal of a methyl group (CH3) from a molecule. A common way of demethylation is the replacement of a methyl group by a hydrogen atom, resulting in a net loss of one carbon and two hydrogen at ...
via
cytochrome P450
Cytochromes P450 (P450s or CYPs) are a Protein superfamily, superfamily of enzymes containing heme as a cofactor (biochemistry), cofactor that mostly, but not exclusively, function as monooxygenases. However, they are not omnipresent; for examp ...
enzyme
An enzyme () is a protein that acts as a biological catalyst by accelerating chemical reactions. The molecules upon which enzymes may act are called substrate (chemistry), substrates, and the enzyme converts the substrates into different mol ...
s including
CYP2D6 as well as
CYP1A2 and
CYP3A4
Cytochrome P450 3A4 (abbreviated CYP3A4) () is an important enzyme in the body, mainly found in the liver and in the intestine, which in humans is encoded by ''CYP3A4'' gene. It organic redox reaction, oxidizes small foreign organic molecules ( ...
.
Like MDMA, HHMA is a
monoamine releasing agent.
Along with
3,4-dihydroxyamphetamine (HHA; α-methyldopamine), HHMA may be involved in the
serotonergic neurotoxicity of MDMA.
However, findings in this regard are conflicting, and the neurotoxicity of MDMA and related agents may instead be based on their
mechanism of action
In pharmacology, the term mechanism of action (MOA) refers to the specific biochemical Drug interaction, interaction through which a Medication, drug substance produces its pharmacological effect. A mechanism of action usually includes mention o ...
without involvement of metabolites.
See also
*
3,4-Dihydroxyamphetamine (HHA; α-methyldopamine)
*
4-Hydroxy-3-methoxyamphetamine (HMA)
*
4-Hydroxy-3-methoxymethamphetamine (HMMA)
*
2,4,5-Trihydroxyamphetamine (THA)
*
2,4,5-Trihydroxymethamphetamine (THMA)
*
3,4-Dihydroxymethcathinone (HHMC)
*
4-Hydroxy-3-methoxymethcathinone (HMMC)
References
{{DEFAULTSORT:Dihydroxymethamphetamine, 3,4-
Catecholamines
Human drug metabolites
Human pathological metabolites
Methamphetamines
Monoaminergic neurotoxins
Norepinephrine-dopamine releasing agents