Piminodine - Misplaced Pages

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Piminodine
Clinical data

ATC code	none
Legal status
Legal status	US: Schedule II
Identifiers
IUPAC name ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
CAS Number	13495-09-5
PubChem CID	21950
ChemSpider	20628
UNII	3IIX447HWS
CompTox Dashboard (EPA)	DTXSID60159149
ECHA InfoCard	100.033.455
Chemical and physical data
Formula	C₂₃H₃₀N₂O₂
Molar mass	366.497 g/mol g·mol
3D model (JSmol)	Interactive image
SMILES O=C(OCC)C3(c1ccccc1)CCN(CCCNc2ccccc2)CC3
InChI InChI=1S/C23H30N2O2/c1-2-27-22(26)23(20-10-5-3-6-11-20)14-18-25(19-15-23)17-9-16-24-21-12-7-4-8-13-21/h3-8,10-13,24H,2,9,14-19H2,1H3 Key:PXXKIYPSXYFATG-UHFFFAOYSA-N
(verify)

Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine). It was used in medicine briefly during the 1960s and 70s, but has largely fallen out of clinical use. It was used particularly for obstetric analgesia and in dental procedures and, like pethidine, could be combined with hydroxyzine to intensify the effects. The duration of action is 2 to 4 hours and 7.5 to 10 mg via the subcutaneous route is the most common starting dose, being equal to 80 to 100 mg of pethidine, 40 to 60 mg of alphaprodine and 10 mg of morphine. Oral formulations were also available.

Piminodine 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.

References

Sim E, Dimoglo A, Shvets N, Ahsen V. Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics. Current Medicinal Chemistry. 2002 Aug;9(16):1537-45.
Dekornfeld TJ, Lasagna L. The analgesic potency of piminodine (alvodine). Journal of Chronic Diseases. 1960 Aug;12:252-7.
Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH. A comparison of the pharmacology of two potent analgesic agents, piminodine (Win 14,098-2) and Win 13,797, with morphine and meperidine. Toxicology and Applied Pharmacology. 1961 May;3:358-79.