Propoxyphene
Title: Propoxyphene
CAS Registry Number: 469-62-5
CAS Name: (aS)-a-[(1R)-2-(Dimethylamino)-1-methylethyl]-a-phenylbenzeneethanol propanoate (ester)
Additional Names: a-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; a-d-propoxyphene; dextropropoxyphene
Molecular Formula: C22H29NO2
Molecular Weight: 339.47
Percent Composition: C 77.84%, H 8.61%, N 4.13%, O 9.43%
Literature References: 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 a-dl- and d-diastereoisomers possess marked analgesic activity in contrast to the b-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).
Properties: Crystals from petr ether, mp 75-76°. [a]D25 +67.3° (c = 0.6 in chloroform).
Melting point: mp 75-76°
Optical Rotation: [a]D25 +67.3° (c = 0.6 in chloroform)
 
Derivative Type: Hydrochloride
CAS Registry Number: 1639-60-7
Trademarks: Darvon (AAI Pharma); Deprancol (Parke-Davis); Develin (Gecke)
Molecular Formula: C22H29NO2.HCl
Molecular Weight: 375.93
Percent Composition: 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°. [a]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).
Melting point: mp 163-168.5°
Optical Rotation: [a]D25 +59.8° (c = 0.6 in water)
Toxicity data: LD50 in mice, rats (mg/kg): 28, 15 i.v.; 111, 58 i.p.; 211, 134 s.c.; 282, 230 orally (Emerson)
 
Derivative Type: Napsylate monohydrate
CAS Registry Number: 26570-10-5
Trademarks: Darvon-N (AAI Pharma)
Molecular Formula: C22H29NO2.C10H8O3S.H2O
Molecular Weight: 565.72
Percent Composition: 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).
Toxicity data: 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 Type: a-l-Form see Levopropoxyphene
 
Derivative Type: a-dl-Form
Additional Names: Racemic propoxyphene; diméprotane
 
Derivative Type: a-dl-Form hydrochloride
Properties: Crystals from methanol + ethyl acetate, mp 170-171°. Soluble in water, alcohol, chloroform. Practically insol in benzene, ether.
Melting point: mp 170-171°
 
Derivative Type: b-dl-Form
Properties: Crystals from acetone + ether. mp 187-188°. More soluble than the a-form.
Melting point: mp 187-188°
 
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.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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