Prodine

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IUPAC_name = (1,3-dimethyl-4-phenylpiperidin-4-yl) propanoate

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CAS_number = 77-20-3
CAS_supplemental = 468-59-7 (beta)
synonyms = Prodine, Prisilidine, Nisentil
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PubChem = 6471
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C = 16 | H = 23 | N = 1 | O = 2
molecular_weight = 261.359 g/mol
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Prodine (Prisilidine, Nisentil) is an opioid analgesic that is an analogue of pethidine (meperidine).

There are two isomers of prodine, Alphaprodine and Betaprodine. [Beckett AH, Walker J. The configuration of alphaprodine and betaprodine. Journal of Pharmacy and Pharmacology. 1955 Dec;7(12):1039-45.] Betaprodine is some 5x more potent than alphaprodine, [John Bedford Stenlake. Foundations of Molecular Pharmacology. ISBN 0-485-11171-3] 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. [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.]

Alphaprodine was sold under several brand names, mainly Nisentil and Prisilidine. It was mainly used for pain relief in childbirth [Burnett RG, White CA. Alphaprodine for continuous intravenous obstetric analgesia. "Obstetrics and Gynecology". 1966 Apr;27(4):472-7.] and dentistry, [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.] as well as for minor surgical procedures.

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. [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.]

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