Structure via PubChem · Public domain (PubChem)
cis-(−)-metazocine
Sign in to saveMetazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects, mediated through a mixed agonist–antagonist action at the mu opioid receptor, its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors (where it is a high-efficacy agonist) and/or sigma receptors.
Chemical data
- Formula
- C15H21NO
- Molecular weight
- 231.33 g/mol
- IUPAC name
- (1R,9R,13R)-1,10,13-trimethyl-10-azatricyclo[7.3.1.02,7]trideca-2(7),3,5-trien-4-ol
- SMILES
- C[C@H]1[C@H]2CC3=C([C@@]1(CCN2C)C)C=C(C=C3)O
- InChIKey
- YGSVZRIZCHZUHB-COLVAYQJSA-N
- XLogP
- 1.8
- Polar surface area
- 23.5 Ų
- H-bond donors
- 1
- H-bond acceptors
- 2
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Wikidata facts
- Mass
- 231.162314292
Show 4 more facts
- Commons category
- Metazocine
- isomeric SMILES
- C[C@H]1[C@H]2CC3=C([C@@]1(CCN2C)C)C=C(C=C3)O
- chemical formula
- C₁₅H₂₁NO
- canonical SMILES
- CC1C2CC3=C(C1(CCN2C)C)C=C(C=C3)O
Sources (1)
via Wikidata · CC0
~2 min read
Encyclopedic overview
3 sectionsContents
- Syntheses
- See also
- References
Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects, mediated through a mixed agonist–antagonist action at the mu opioid receptor, its clinical use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors (where it is a high-efficacy agonist) and/or sigma receptors.
Metazocine is in Schedule II of the Controlled Substances Act 1970 of the United States as a Narcotic with ACSCN 9240 with a 19 gram aggregate manufacturing quota as of 2014. The free base conversion ratio for salts includes 0.81 for the hydrochloride and 0.74 for the hydrobromide. It is listed under the Single Convention for the Control of Narcotic Substances 1961 and is controlled in most countries in the same fashion as is morphine.
Excerpted from Wikipedia’s “cis-(−)-metazocine” article, available under the CC BY-SA 4.0 licence.