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Metazocine
Metazocine is an opioid analgesic related to pentazocine. While metazocine has significant analgesic effects,〔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.〕 mediated through a mixed agonist–antagonist action〔Berzetei-Gurske I, Loew GH. The novel antagonist profile of (-)metazocine.
''Progress in Clinical and Biological Research''. 1990;328:33-6.〕 at the mu opioid receptor,〔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.〕 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)〔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.〕 and/or sigma receptors.〔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.〕
==Syntheses==
The prototype benzomorphan, metazocine (5), can be obtained from a variation of the morphinan synthesis.
Thus, Rxn of the Grignard reagent from ''p''-methoxybenzyl chloride (1) with the lutidine methiodide (2) affords the benzylated dihydropyridine (3). (The addition to the most hindered position is rather puzzling.) Reduction of the enamine π-bond leads to the tetrahydropyridine (4). Cyclization by means of acid leads directly to the benzomorphan ring system (5). Demethylation of the aromatic ring system affords the phenol. Although this last compound is in fact a relatively potent analgesic, it is not available commercially as a drug.
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