7218. Phenazocine

Nomenclature

CAS number: 127-35-5
1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-phenylethyl)-2,6-methano-3-benzazocin-8-ol; 2′-hydroxy-5,9-dimethyl-2-phenethyl-6,7-benzmorphan; phenethylazocine; phenobenzorphan.
C22H27NO; mol wt 321.46.
C 82.20%, H 8.47%, N 4.36%, O 4.98%.

Description and references

Synthetic opioid analgesic. Prepn of (±)-cis-form from metazocine, q.v.: E. L. May, N. B. Eddy, J. Org. Chem. 24, 294 (1959). Optical resolution and pharmacology: eidem, ibid. 1435. Improved syntheses: J. H. Ager, E. L. May, ibid. 25, 984 (1960); G. A. Brine et al., J. Heterocycl. Chem. 27, 2139 (1990).

Chemical structure

Derivative

cis-(±)-Form.

Nomenclature

CAS number: 58073-76-0
(±)-α-Phenazocine.

Properties

Rods from methanol, mp 181-182°.

Derivative

cis-(±)-Form hydrobromide.

Nomenclature

CAS number: 70878-79-4; 1239-04-9 (unspecified stereo)
NIH-7519; Narphen (Napp); Prinadol.
C22H27NO.HBr; mol wt 402.37.
C 65.67%, H 7.01%, N 3.48%, O 3.98%, Br 19.86%.

Properties

Rods from acetone or abs alc + ether, mp 166-170°. LD50 s.c. in mice: 332 mg/kg (May, Eddy).

Derivative

cis-(-)-Form.

Nomenclature

CAS number: 58640-87-2
α-(-)-Phenazocine.

Properties

Needles from methanol, mp 159-159.5°. [α]D20 -122° (c = 0.74 in 95% ethanol).

Derivative

cis-(-)-Form hydrobromide.

Properties

Crystals, mp 284-287°. [α]D20 -84.1° (c = 1.12 in 95% ethanol). LD50 s.c. in mice: 147 mg/kg (May, Eddy).

Note

This is a controlled substance (opiate): 21 CFR, 1308.12.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Benzomorphan Derivatives