Prodine - Misplaced Pages

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Prodine
Clinical data

ATC code	none
Legal status
Legal status	US: Schedule II
Identifiers
IUPAC name (1,3-dimethyl-4-phenylpiperidin-4-yl) propanoate
CAS Number	77-20-3 468-59-7 (beta)
PubChem CID	204163
ChemSpider	176845
ChEMBL	ChEMBL14309
CompTox Dashboard (EPA)	DTXSID70859103
Chemical and physical data
Formula	C₁₆H₂₃NO₂
Molar mass	261.359 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(O2(c1ccccc1)CCN(C)C2C)CC
InChI InChI=1S/C16H23NO2/c1-4-15(18)19-16(14-8-6-5-7-9-14)10-11-17(3)12-13(16)2/h5-9,13H,4,10-12H2,1-3H3/t13-,16+/m1/s1 Key:UVAZQQHAVMNMHE-CJNGLKHVSA-N
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Prodine (trade names Prisilidine and Nisentil) is an opioid analgesic that is an analogue of pethidine (meperidine).

There are two isomers of prodine, Alphaprodine and Betaprodine. Betaprodine is some 5x more potent than alphaprodine, 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.

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was mainly used for pain relief in childbirth and dentistry, 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.

References

Beckett AH, Walker J. The configuration of alphaprodine and betaprodine. Journal of Pharmacy and Pharmacology. 1955 Dec;7(12):1039-45.
John Bedford Stenlake. Foundations of Molecular Pharmacology. ISBN 0-485-11171-3
Fung DL, Asling JH, Eisele JH, Martucci R. A comparison of alphaprodine and meperidine pharmacokinetics. Journal of Clinical Pharmacology. 1980 Jan;20(1):37-41.
Burnett RG, White CA. Alphaprodine for continuous intravenous obstetric analgesia. Obstetrics and Gynecology. 1966 Apr;27(4):472-7.
Carter WJ, Bogert JA. An effective pre-medication procedure for dental patients. Journal of the Missouri Dental Association. 1966 Jun-Jul;46(6):8-9.
Fuller JD, Crombleholme WR. Respiratory arrest and prolonged respiratory depression after one low, subcutaneous dose of alphaprodine for obstetric analgesia. A case report. Journal of Reproductive Medicine. 1987 Feb;32(2):149-51.