Metazocine

Metazocine

Systematic (IUPAC) name
1,2,​3,4,5,6-h​exahydro-​3,6,11-tr​imethyl-2​,6-methan​o-3-benza​zocin-8-ol or 2'-hydrox​y-2,5,9-t​rimethyl-​6,7-benzo​morphan
Clinical data
Pregnancy cat.	?
Legal status	Uncontrolled
Routes	?
Identifiers
CAS number	3734-52-9 Y
ATC code	None
PubChem	CID 62518
ChemSpider	56292 Y
UNII	XD53YGT34W N
ChEMBL	CHEMBL257661 N
Chemical data
Formula	C15H21NO
Mol. mass	231.333 g/mol
SMILES	eMolecules & PubChem
InChI 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
N(what is this?)  (verify)

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 clinical 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]

See also

• Benzomorphans

References

1. ^ 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.
2. ^ Berzetei-Gurske I, Loew GH. The novel antagonist profile of (-)metazocine. Progress in Clinical and Biological Research. 1990;328:33-6.
3. ^ 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.
4. ^ 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.
5. ^ 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.
6. ^ 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.