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MDMA

MDMA

Empathogen and stimulant

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Canonical SMILES
CC(CC1=CC2=C(C=C1)OCO2)NC
CAS Registry Number
42542-10-9
ChEMBL ID
CHEMBL43048
UNII
KE1SEN21RM
Wikidata ID
Q69488

c3,4-Methylenedioxymethamphetamine is a DEA Schedule I controlled substance. Substances in the DEA Schedule I have no currently accepted medical use in the United States, a lack of accepted safety for use under medical supervision, and a high potential for abuse.

3,4-Methylenedioxymethamphetamine is a ring-substituted amphetamine derivative, structurally related to the hallucinogen mescaline, with entactogenic, neurotoxic, and motor-stimulatory activities. 3,4-methylenedioxymethamphetamine (MDMA) produces an acute, rapid enhancement in both the release of serotonin from and the inhibition of serotonin reuptake by serotonergic nerve endings in the brain. Once within the cell, MDMA depletes stores of tryptophan hydroxylase (TPH) via acute oxidative inactivation; in turn, depleted stores of TPH leave cell terminals open to damage from oxidative stress, possibly a source of MDMA neurotoxicity. This agent also induces norepinephrine, dopamine, and acetylcholine release and can act directly on a number of receptors, including alpha 2-adrenergic and 5-hydroxytryptamine (5-HT) 2A receptors. MDMA may suppress the dyskinesia associated with long-term use of L-dopamine (L-DOPA) without affecting the efficacy of L-DOPA treatment.

3,4-methylenedioxymethamphetamine is a member of the class of benzodioxoles that is 1,3-benzodioxole substituted by a 2-(methylamino)propyl group at position 5. It has a role as a neurotoxin. It is a member of amphetamines and a member of benzodioxoles.

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