7121. Pentazocine

Nomenclature

CAS number: 359-83-1
(2R,6R,11R)-rel-1,2,3,4,5,6-Hexahydro-6,11-dimethyl-3-(3-methyl-2-buten-1-yl)-2,6-methano-3-benzazocin-8-ol; (±)-cis-1,2,3,4,5,6-hexahydro-3-(3-methyl-2-butenyl)-6,11-dimethyl-8-hydroxy-2,6-methano-3-benzazocine; (±)-cis-2-dimethylallyl-5,9-dimethyl-2′-hydroxybenzomorphan; NSC-107430; Win-20228.
C19H27NO; mol wt 285.42.
C 79.95%, H 9.53%, N 4.91%, O 5.61%.

Description and references

Mixed opioid agonist-antagonist. Prepn: BE 611000; S. Archer, US 4105659 (1962, 1978 both to Sterling Drug); idem et al., J. Med. Chem. 7, 123 (1964). Prepn and activity of isomers: B. F. Tullar et al., ibid. 10, 383 (1967). Enantioselective synthesis of (-)-form: B. M. Trost, W. Tang, J. Am. Chem. Soc. 125, 8744 (2003). GC/MS determn in blood and urine: H. Seno et al., J. Mass Spectrom. 35, 33 (2000). Review of pharmacology and clinical experience: G. Goldstein, Drug Alcohol Depend. 14, 313-324 (1985).

Chemical structure

Properties

White or very pale, tan-colored powder. Crystals from methanol + water, mp 145.4-148.6°. Freely sol in chloroform; sol in alcohol, acetone, ether; sparingly sol in benzene, ethyl actate. Practically insol in water. LD50 s.c. in male rats: 175±36 mg/kg. See: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971).

Derivative

Hydrochloride.

Nomenclature

CAS number: 64024-15-3
Fortalgesic (tabl.) (Sanofi-Synthelabo); Fortral (cap.) (Sanofi-Synthelabo); Talwin (tabl.) (Sanofi-Synthelabo).
C19H27NO.HCl; mol wt 321.88.
C 70.90%, H 8.77%, N 4.35%, O 4.97%, Cl 11.01%.

Description and references

Component of Talacen.

Properties

White crystalline powder. mp 245-247° (dec). Freely sol in chloroform; sol in alcohol; sparingly sol in water; very slightly sol in acetone, ether. Practically insol in benzene.

Derivative

Lactate.

Nomenclature

CAS number: 17146-95-1
Fortalgesic (inj.) (Sanofi-Synthelabo); Fortralin (Sanofi-Aventis); Pentagin (Sankyo); Sosegon (Sanofi-Aventis); Talwin (inj.) (Hospira).
C19H27NO.C3H6O3; mol wt 375.50.
C 70.37%, H 8.86%, N 3.73%, O 17.04%.

Properties

White crystalline solid. Sol in acidic aq solns.

Derivative

2R,6R,11R-Form.

Nomenclature

CAS number: 7488-49-5
α-(-)-Pentazocine; cis-(-)-pentazocine.

Properties

mp 180.6-182.2°. [α]D25 -138.0° (c = 1.0 in CHCl3).

Derivative

2S,6S,11S-Form.

Nomenclature

CAS number: 7361-76-4
α-(+)-Pentazocine; cis-(+)-pentazocine.

Properties

mp 180.4-182.0°. [α]D25 +135.5° (c = 1.0 in CHCl3).

Note

This is a controlled substance: 21 CFR, 1308.14.

Therapeutic Category

Analgesic.

Therapeutic Category (Veterinary)

Analgesic.

Keywords

Analgesic; Opioids; Benzomorphan Derivatives