Chemicals and Drugs

N-Methyl-3,4-methylenedioxyamphetamine

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.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

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.

Chemical Identity

Chemical Information

Molecular Formula
C11H15NO2
Molecular Weight
193.24 g/mol
CAS Registry No.
42542-10-9
IUPAC Name
1-(1,3-benzodioxol-5-yl)-N-methylpropan-2-amine
InChIKey
SHXWCVYOXRDMCX-UHFFFAOYSA-N
SMILES
CC(CC1=CC2=C(C=C1)OCO2)NC
MeSH Unique ID
D018817
Source
PubChem CID 1615

MeSH Record

Classification

Broader headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

7 entry terms
  • Ecstasy (Drug)
  • MDMA
  • Methylenedioxymethamphetamine
  • N Methyl 3,4 methylenedioxyamphetamine
  • N-Methyl-3,4-methylenedioxyamphetamine Hydrochloride
  • Hydrochloride, N-Methyl-3,4-methylenedioxyamphetamine
  • N Methyl 3,4 methylenedioxyamphetamine Hydrochloride

MeSH Record

Aspects Covered

25 allowable subheadings

Indexed with the subheadings administration & dosage, adverse effects, agonists, analogs & derivatives, analysis, antagonists & inhibitors, blood, cerebrospinal fluid, chemical synthesis, chemistry, classification, economics, history, immunology, isolation & purification, metabolism, pharmacokinetics, pharmacology, poisoning, radiation effects, standards, supply & distribution, therapeutic use, toxicity, urine.

MeSH Record

History Note

95; was N-METHYL-3,4-METHYLENEDIOXYAMPHETAMINE (NM) 1984-94

MeSH Record

Previous Indexing

  • 3,4-Methylenedioxyamphetamine/analogs & derivatives (1984-1994)

MeSH Hierarchy

Tree Number

  1. D02w.092w.471.683w.152w.670w

AMA Style

References

  1. National Library of Medicine. N-Methyl-3,4-methylenedioxyamphetamine. Medical Subject Headings (MeSH). 2026. Unique ID D018817. http://id.nlm.nih.gov/mesh/2026/D018817
  2. N-Methyl-3,4-methylenedioxyamphetamine. In: Wikipedia. https://en.wikipedia.org/wiki/MDMA
  3. N-Methyl-3,4-methylenedioxyamphetamine. In: Wikidata. https://www.wikidata.org/wiki/Q69488
  4. N-Methyl-3,4-methylenedioxyamphetamine. In: PubChem Compound. CID 1615. https://pubchem.ncbi.nlm.nih.gov/compound/1615