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QuickView for MDMA (compound)


PubChem
Name: N-Methyl-3,4-methylenedioxyamphetamine
PubChem Compound ID: 1615
Description: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.
Molecular formula: C11H15NO2
Molecular weight: 193.242 g/mol
Synonyms:
Ecstasy; (+-)-(3,4-Methylenedioxy)methamphetamine; DivK1c_000962; MDMA (unspecified); XTC; (+-)-N-Methyl-3,4-(methylenedioxy)amphetamine; 1,3-Benzodioxole-5-ethanamine, N,.alpha.-dimethyl-, hydrochloride; 54946-52-0; Phenethylamine, N,alpha-dimethyl-3,4-methylenedioxy-; MDMA.
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DrugBank
Identification
Name: N-Methyl-3,4-methylenedioxyamphetamine
Name (isomeric): DB01454
Drug Type: small molecule
Description: An N-substituted amphetamine analog. It is a widely abused drug classified as a hallucinogen and causes marked, long-lasting changes in brain serotonergic systems. It is commonly referred to as MDMA or ecstasy.
Synonyms:
Ecstasy; MDMA
Category: Serotonin Agents, Adrenergic Uptake Inhibitors, Hallucinogens
CAS number: 42542-10-9
Pharmacology
Indication: Clinical trials are now testing the therapeutic potential of MDMA for post-traumatic stress disorder (PTSD) and anxiety associated with terminal cancer. MDMA is one of the four most widely used illicit drugs in the U.S.
Pharmacology: MDMA acts as a releasing agent of serotonin, norepinephrine, and dopamine.
Mechanism of Action:
It enters neurons via carriage by the monoamine transporters. Once inside, MDMA inhibits the vesicular monoamine transporter, which results in increased concentrations of serotonin, norepinephrine, and dopamine into the cytoplasm, and induces their release by reversing their respective transporters through a process known as phosphorylation. It als...
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Biotransformation: Hepatic: CYP450 extensively involved, especially CYP2D6 MDMA is known to be metabolized by two main metabolic pathways: (1) O-demethylenation followed by catechol-O-methyltransferase (COMT)-catalyzed methylation and/or glucuronide/sulfate conjugation; and (2) N-dealkylation, deamination, and oxidation to the corresponding benzoic acid derivatives conjugated with glycine. The metabolism may be primarily by cytochrome P450 (CYP450) enzymes (CYP2D6 (in humans, but CYP2D1 in mice), and CYP3A4) and COMT. Complex, nonlinear pharmacokinetics arise via autoinhibition of CYP2D6 and CYP2D8, resulting in zeroth order kinetics at higher doses. It is thought that this can result in sustained and higher concentrations of MDMA if the user takes consecutive doses of the drug.
Route of elimination: renal
Half Life: 6–10 (though duration of effects is typically actually 3–5 hours)

Targets