Chemicals and Drugs

Buprenorphine

A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.

National Library of MedicineMedical Subject Headings2026

Structured Summary

Abstract

A derivative of the opioid alkaloid THEBAINE that is a more potent and longer lasting analgesic than MORPHINE. It appears to act as a partial agonist at mu and kappa opioid receptors and as an antagonist at delta receptors. The lack of delta-agonist activity has been suggested to account for the observation that buprenorphine tolerance may not develop with chronic use.

Chemical Identity

Chemical Information

Molecular Formula
C29H41NO4
Molecular Weight
467.6 g/mol
CAS Registry No.
52485-79-7
IUPAC Name
(1S,2S,6R,14R,15R,16R)-5-(cyclopropylmethyl)-16-[(2S)-2-hydroxy-3,3-dimethylbutan-2-yl]-15-methoxy-13-oxa-5-azahexacyclo[13.2.2.12,8.01,6.02,14.012,20]icosa-8(20),9,11-trien-11-ol
InChIKey
RMRJXGBAOAMLHD-IHFGGWKQSA-N
SMILES
C[C@]([C@H]1C[C@@]23CC[C@@]1([C@H]4[C@@]25CCN([C@@H]3CC6=C5C(=C(C=C6)O)O4)CC7CC7)OC)(C(C)(C)C)O
MeSH Unique ID
D002047
Source
PubChem CID 644073

MeSH Record

Classification

Broader headings

Narrower headings

Related Concepts

Knowledge Graph

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Drug Class

Pharmacological Action

MeSH Record

See Also

MeSH Record

Synonyms

14 entry terms
  • 6029-M
  • Buprenex
  • Buprenorphine Hydrochloride
  • Buprex
  • Prefin
  • RX-6029-M
  • Subutex
  • Temgesic
  • Temgésic
  • 6029 M
  • 6029M
  • Hydrochloride, Buprenorphine
  • RX 6029 M
  • RX6029M

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

Indexing Annotation

for buprenorphine maintenance treatment, coordinate with OPIATE SUBSTITUTION TREATMENT

MeSH Record

History Note

87(79); was see under MORPHINANS 1979-86

MeSH Record

Previous Indexing

  • Dihydromorphinone (1966-1968)
  • Morphinans (1969-1978)
  • Morphine (1966-1968)

MeSH Hierarchy

Tree Numbers

  1. D03w.132w.577.249.150w
  2. D03w.605.497.150w
  3. D03w.633.400.686.150w
  4. D04w.615w.723w.795.150w

MeSH Record

NLM Classification

QV 92

AMA Style

References

  1. National Library of Medicine. Buprenorphine. Medical Subject Headings (MeSH). 2026. Unique ID D002047. http://id.nlm.nih.gov/mesh/2026/D002047
  2. Buprenorphine. In: Wikipedia. https://en.wikipedia.org/wiki/Buprenorphine
  3. Buprenorphine. In: Wikidata. https://www.wikidata.org/wiki/Q407721
  4. Buprenorphine. In: PubChem Compound. CID 644073. https://pubchem.ncbi.nlm.nih.gov/compound/644073