7839. Propoxyphene

Nomenclature

CAS number: 469-62-5
(αS)-α-[(1R)-2-(Dimethylamino)-1-methylethyl]-α-phenylbenzeneethanol propanoate (ester); α-d-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol propionate; (+)-1,2-diphenyl-2-propionoxy-3-methyl-4-dimethylaminobutane; (+)-4-dimethylamino-1,2-diphenyl-3-methyl-2-propionyloxybutane; α-d-propoxyphene; dextropropoxyphene.
C22H29NO2; mol wt 339.47.
C 77.84%, H 8.61%, N 4.13%, O 9.43%.

Description and references

Opioid analgesic. Prepn of racemate: Pohland, Sullivan, J. Am. Chem. Soc. 75, 4458 (1953); Pohland, US 2728779 (1955 to Lilly). Prepn of (+)-form: Pohland, Sullivan, J. Am. Chem. Soc. 77, 3400 (1955). Stereochemistry: Sullivan et al., J. Org. Chem. 28, 2381 (1963); Casy, Myers, J. Pharm. Pharmacol. 16, 455 (1964). Stereospecific synthesis: Pohland et al., J. Org. Chem. 28, 2483 (1963). Metabolism: S. L. Due et al., Biomed. Mass Spectrom. 3, 217 (1976). The α-dl- and d-diastereoisomers possess marked analgesic activity in contrast to the β-diastereoisomers which are substantially inactive. Toxicity: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971); J. L. Emerson et al., ibid. 19, 445 (1971). Comprehensive description: B. McEwan, Anal. Profiles Drug Subs. 1, 301-318 (1972). Symposium on pharmacology, toxicology, and clinical efficacy of propoxyphene alone and in combination with acetaminophen: Hum. Toxicol. 3, Suppl., 1S-238S (1984).

Chemical structure

Properties

Crystals from petr ether, mp 75-76°. [α]D25 +67.3° (c = 0.6 in chloroform).

Derivative

Hydrochloride.

Nomenclature

CAS number: 1639-60-7
Darvon (AAI Pharma); Deprancol (Parke-Davis); Develin (G"odecke).
C22H29NO2.HCl; mol wt 375.93.
C 70.29%, H 8.04%, N 3.73%, O 8.51%, Cl 9.43%.

Properties

Bitter crystals from methanol + ethyl acetate, mp 163-168.5°. [α]D25 +59.8° (c = 0.6 in water). Sol in water, alc, chloroform, acetone. Practically insol in benzene, ether. LD50 in mice, rats (mg/kg): 28, 15 i.v.; 111, 58 i.p.; 211, 134 s.c.; 282, 230 orally (Emerson).

Derivative

Napsylate monohydrate.

Nomenclature

CAS number: 26570-10-5
Darvon-N (AAI Pharma).
C22H29NO2.C10H8O3S.H2O; mol wt 565.72.
C 67.94%, H 6.95%, N 2.48%, O 16.97%, S 5.67%.

Properties

Odorless, white crystalline powder; bitter taste. Sol in methanol, ethanol, chloroform, acetone; very slightly sol in water. LD50 orally in female rats: 990 mg/kg (Goldenthal).

Derivative

α-l-Form see Levopropoxyphene.

Derivative

α-dl-Form.

Nomenclature

Racemic propoxyphene; diméprotane.

Derivative

α-dl-Form hydrochloride.

Properties

Crystals from methanol + ethyl acetate, mp 170-171°. Soluble in water, alcohol, chloroform. Practically insol in benzene, ether.

Derivative

β-dl-Form.

Properties

Crystals from acetone + ether. mp 187-188°. More soluble than the α-form.

Note

Bulk dextropropoxyphene (non-dosage forms) is a controlled substance (opiate): 21 CFR, 1308.12; dextropropoxyphene is a controlled substance (narcotic): 21 CFR, 1308.14.

Therapeutic Category

Analgesic.

Keywords

Analgesic; Opioids; Diphenylpropylamine Derivatives