Levopropoxyphene
Title: Levopropoxyphene
CAS Registry Number: 2338-37-6
CAS Name: (aR)-a-[(1S)-2-(Dimethylamino)-1-methylethyl]-a-phenylbenzeneethanol propanoate (ester)
Additional Names: a-l-4-dimethylamino-3-methyl-1,2-diphenyl-2-butanol propionate; a-l-4-dimethylamino-1,2-diphenyl-3-methyl-2-butanol propionate; l-propoxyphene
Molecular Formula: C22H29NO2
Molecular Weight: 339.47
Percent Composition: C 77.84%, H 8.61%, N 4.13%, O 9.43%
Literature References: Prepn: Pohland, Sullivan, J. Am. Chem. Soc. 77, 3400 (1955). Stereoselective synthesis: Pohland et al., J. Org. Chem. 28, 2483 (1963). Toxicity data: E. I. Goldenthal, Toxicol. Appl. Pharmacol. 18, 185 (1971). See also Propoxyphene.
Properties: Crystals from petr ether, mp 75-76°. [a]D25 -68.2° (c = 0.6 in chloroform).
Melting point: mp 75-76°
Optical Rotation: [a]D25 -68.2° (c = 0.6 in chloroform)
 
Derivative Type: Hydrochloride
CAS Registry Number: 1596-70-9
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: Crystals from methanol + ethyl acetate, mp 163-164°. [a]D25 -60.1° (c = 0.7).
Melting point: mp 163-164°
Optical Rotation: [a]D25 -60.1° (c = 0.7)
 
Derivative Type: 2-Naphthalenesulfonate
CAS Registry Number: 5714-90-9
Additional Names: Levopropoxyphene napsylate
Trademarks: Novrad (Lilly); Letusin; Contratuss
Molecular Formula: C22H29NO2.C10H8SO3
Molecular Weight: 547.70
Percent Composition: C 70.17%, H 6.81%, N 2.56%, O 14.61%, S 5.85%
Properties: LD50 orally in female rats: 1455 ±77 mg/kg (Goldenthal).
Toxicity data: LD50 orally in female rats: 1455 ±77 mg/kg (Goldenthal)
 
Therap-Cat: Antitussive.
Keywords: Antitussive.

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