Title: Alphaprodine
CAS Registry Number: 77-20-3
CAS Name: (cis)-1,3-Dimethyl-4-phenyl-4-piperidinol propanoate
Additional Names: (±)-a-1,3-dimethyl-4-phenyl-4-piperidinyl propionate; dl-a-1,3-dimethyl-4-phenyl-4-propionoxypiperidine; (±)-a-prodine
Molecular Formula: C16H23NO2
Molecular Weight: 261.36
Percent Composition: C 73.53%, H 8.87%, N 5.36%, O 12.24%
Literature References: Mixture of the two cis isomers of prodine; betaprodine is the mixture of trans isomers. Prepn: J. Lee, A. Ziering, US 2498433 (1950 to Hoffmann-La Roche); A. H. Beckett et al., J. Pharm. Pharmacol. 9, 939 (1957); A. Ziering et al., J. Org. Chem. 22, 1521 (1957). Configurational studies: F. R. Ahmed et al., Chem. Ind. (London) 1959, 485; eidem, ibid. 1962, 97. Stereostructure-activity studies: M. M. Abdel-Monem et al., J. Med. Chem. 15, 494 (1972). Pharmacology and toxicology: G. M. Gruber et al., J. Pharmacol. Exp. Ther. 99, 312 (1950). Review of clinical experience: R. C. Lunt, H. E. Howard, Pediatr. Dent. 10, 121-126 (1988).
Derivative Type: Hydrochloride
CAS Registry Number: 561-78-4
Manufacturers' Codes: Nu-1196
Trademarks: Nisentil (Roche)
Molecular Formula: C16H23NO2.HCl
Molecular Weight: 297.82
Percent Composition: C 64.53%, H 8.12%, N 4.70%, O 10.74%, Cl 11.90%
Properties: Crystals from acetone, mp 220-221°. Slightly saline taste. Freely sol in water, alc, chloroform. Practically insol in ether. pH of 1% aq soln 4.5-5.2. LD50 in mice: 54 mg/kg i.v., 73 mg/kg i.p.; in rats: 22 mg/kg i.p. (Gruber).
Melting point: mp 220-221°
Toxicity data: LD50 in mice: 54 mg/kg i.v., 73 mg/kg i.p.; in rats: 22 mg/kg i.p. (Gruber)
Derivative Type: Betaprodine hydrochloride
CAS Registry Number: 49638-23-5
Additional Names: (±)-b-Prodine hydrochloride
Manufacturers' Codes: Nu-1779
Properties: Crystals from methyl ethyl ketone, mp 195-196° (Beckett); from acetone + methanol, mp 199-200° (Ziering).
Melting point: mp 195-196° (Beckett); mp 199-200° (Ziering)
NOTE: These are controlled substances (opiates): 21 CFR, 1308.11 (betaprodine) and 1308.12 (alphaprodine).
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).

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