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Metazocine
Systematic (IUPAC) name
(2S,6R,11R)-3,6,11-trimethyl-1,2,3,4,5,6-hexahydro-2,6-methano-3-benzazocin-8-ol
Identifiers
CAS number 3734-52-9
ATC code none
PubChem 3037886
Chemical data
Formula C 15H21NO 
Mol. mass 231.333 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status  ? (US)
Routes Oral, Other R.O.A. Unknown

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]

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.
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