Alphaprodine

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).
alpha-Ribazole alpha-Santonin alpha-Spinasterol alpha-Terpineol alpha-Terthienyl

Prodine
Alphaprodine.svg
Systematic (IUPAC) name
(1,3-Dimethyl-4-phenylpiperidin-4-yl) propanoate
Clinical data
Legal status Controlled (S8) (AU) Schedule II (US)
Identifiers
CAS number 77-20-3 N
468-59-7 (beta)
ATC code None
PubChem CID 204163
ChemSpider 176845 YesY
ChEMBL CHEMBL14309 YesY
Chemical data
Formula C16H23NO2 
Mol. mass 261.359 g/mol
 N (what is this?)  (verify)

Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analog of pethidine (meperidine).

There are two isomers of prodine, alphaprodine and betaprodine.[1] Betaprodine is some 5x more potent than alphaprodine,[2] but is metabolised more rapidly, and only alphaprodine was developed for medicinal use. It has similar activity to pethidine, but with a faster onset of action and shorter duration.[3]

Prodine isomers.png

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was mainly used for pain relief in childbirth[4] and dentistry,[5] as well as for minor surgical procedures. Alphaprodine has a duration of action of 1 to 2 hours and 40 to 60 mg is equal to 10 mg of morphine via the subcutaneous route.

Prodine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening. Respiratory depression can be a problem with alphaprodine even at normal therapeutic doses.[6] Unlike pethidine, prodine does not produce toxic metabolites and is therefore more suitable for high dose therapy.[medical citation needed]