Metazocine

Metazocine
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • (2R,6R,11R)-3,6,11-Trimethyl-1,2,3,4,5,6-hexahydro-2,6-methanobenzo[d]azocin-8-ol
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.020.998
Chemical and physical data
FormulaC15H21NO
Molar mass231.339 g·mol−1
3D model (JSmol)
  • OC1=CC([C@@](C)([C@@]2([H])C)CCN(C)[C@]2([H])C3)=C3C=C1
  • InChI=1S/C15H21NO/c1-10-14-8-11-4-5-12(17)9-13(11)15(10,2)6-7-16(14)3/h4-5,9-10,14,17H,6-8H2,1-3H3 Y
  • Key:YGSVZRIZCHZUHB-UHFFFAOYSA-N Y

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.

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