Metazocine

Metazocine
	File:Metazocine.png
Clinical data
Synonyms	Metazocine
Identifiers
	IUPAC name (2α,6α,11R*)-1,2,3,4,5,6-Hexahydro-3,6,11-trimethyl-2,6-methano-3-benzazocin-8-ol;
CAS Number	3734-52-9;
PubChem CID	3037886;
E number	{{#property:P628}}
ECHA InfoCard	{{#property:P2566}}Lua error in Module:EditAtWikidata at line 36: attempt to index field 'wikibase' (a nil value).
Chemical and physical data
Formula	C15H21NO
Molar mass	231.333 g/mol

Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects,^[1] mediated through a mixed agonist-antagonist action^[2] at the mu opioid receptor,^[3] its clincial use is limited by dysphoric and hallucinogenic effects which are most likely caused by activity at kappa opioid receptors^[4] and sigma receptors.^[5]^[6]

References

↑ Hori M, Ban M, Imai E, Iwata N, Suzuki Y, Baba Y, Morita T, Fujimura H, Nozaki M, Niwa M. Novel nonnarcotic analgesics with an improved therapeutic ratio. Structure-activity relationships of 8-(methylthio)- and 8-(acylthio)-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocines. Journal of Medicinal Chemistry. 1985 Nov;28(11):1656-61.
↑ Berzetei-Gurske I, Loew GH. The novel antagonist profile of (-)metazocine. Progress in Clinical and Biological Research. 1990;328:33-6.
↑ Gharagozlou P, Demirci H, David Clark J, Lameh J. Activity of opioid ligands in cells expressing cloned mu opioid receptors. BMC Pharmacology. 2003 Jan 4;3:1.
↑ Gharagozlou P, Hashemi E, DeLorey TM, Clark JD, Lameh J. Pharmacological profiles of opioid ligands at kappa opioid receptors. BMC Pharmacology. 2006 Jan 25;6:3.
↑ Shannon HE. Pharmacological analysis of the phencyclidine-like discriminative stimulus properties of narcotic derivatives in rats. Journal of Pharmacology and Experimental Therapeutics. 1982 Jul;222(1):146-51.
↑ Slifer BL, Balster RL, May EL. Reinforcing and phencyclidine-like stimulus properties of enantiomers of metazocine. Pharmacology, Biochemistry and Behaviour. 1986 Oct;25(4):785-9.