Phenazocine
Title: Phenazocine
CAS Registry Number: 127-35-5
CAS Name: 1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(2-phenethyl)-2,6-methano-3-benzazocin-8-ol
Additional Names: 2¢-hydroxy-2-(N,b-phenethyl)-5,9-dimethyl-6,7-benzomorphan; 2¢-hydroxy-5,9-dimethyl-2-phenethyl-6,7-benzmorphan; phenethylazocine; phenobenzorphan
Molecular Formula: C22H27NO
Molecular Weight: 321.46
Percent Composition: C 82.20%, H 8.47%, N 4.36%, O 4.98%
Literature References: Prepn: E. L. May, N. B. Eddy, J. Org. Chem. 24, 294, 1435 (1959); Ager, May, ibid. 25, 984 (1960); Gordon et al., US 2959594 (1960 to SK&F).
 
Derivative Type: (±)-Form
Properties: Rods from methanol, mp 181-182°.
Melting point: mp 181-182°
 
Derivative Type: (-)-Form
Properties: Needles from methanol, mp 159-159.5°. [a]D20 -122° (c = 0.74 in 95% ethanol).
Melting point: mp 159-159.5°
Optical Rotation: [a]D20 -122° (c = 0.74 in 95% ethanol)
 
Derivative Type: (±)-Hydrobromide
CAS Registry Number: 1239-04-9
Manufacturers' Codes: NIH-7519; SKF-6574
Trademarks: Narphen (Smith & Nephew); Prinadol (SK & F); Xenagol (Desbergers)
Molecular Formula: C22H27NO.HBr
Molecular Weight: 402.37
Percent Composition: 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).
Melting point: mp 166-170°
Toxicity data: LD50 s.c. in mice: 332 mg/kg (May, Eddy)
 
Derivative Type: (-)-Hydrobromide
Properties: Crystals, mp 284-287°. [a]D20 -84.1° (c = 1.12 in 95% ethanol). LD50 s.c. in mice: 147 mg/kg (May, Eddy).
Melting point: mp 284-287°
Optical Rotation: [a]D20 -84.1° (c = 1.12 in 95% ethanol)
Toxicity data: LD50 s.c. in mice: 147 mg/kg (May, Eddy)
 
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.12.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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