Chemicals and Drugs

Cocaine

An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.

Chemical Identity

Chemical Information

Molecular Formula
C17H21NO4
Molecular Weight
303.35 g/mol
CAS Registry No.
50-36-2
IUPAC Name
methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate
InChIKey
ZPUCINDJVBIVPJ-LJISPDSOSA-N
SMILES
CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
MeSH Unique ID
D003042
Source
PubChem CID 446220

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

Synonyms

4 entry terms
  • Cocaine HCl
  • Cocaine Hydrochloride
  • HCl, Cocaine
  • Hydrochloride, Cocaine

MeSH Record

Aspects Covered

27 allowable subheadings

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

MeSH Record

Indexing Annotation

cocaine derivatives = COCAINE /analogs; CRACK COCAINE, COCAINE SMOKING and COCAINE-RELATED DISORDERS are available

MeSH Record

History Note

COCAINE DERIVATIVES was see under COCAINE 1975-77; was see under TROPANES 1969-74

MeSH Hierarchy

Tree Numbers

  1. D02w.145.074.722.388w
  2. D03w.132w.889.354w
  3. D03w.605.084.500.722.388w
  4. D03w.605.869.388w

AMA Style

References

  1. National Library of Medicine. Cocaine. Medical Subject Headings (MeSH). 2026. Unique ID D003042. http://id.nlm.nih.gov/mesh/2026/D003042
  2. Cocaine. In: Wikipedia. https://en.wikipedia.org/wiki/Cocaine
  3. Cocaine. In: Wikidata. https://www.wikidata.org/wiki/Q41576
  4. Cocaine. In: PubChem Compound. CID 446220. https://pubchem.ncbi.nlm.nih.gov/compound/446220