Piminodine

Piminodine
Clinical data
ATC code	none;
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule I; DE: Anlage I (Authorized scientific use only); 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−1
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).^[1] It was used in medicine briefly during the 1960s and 1970s, 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.^[2]^[3]

Piminodine is currently a Schedule II controlled substance in the United States. It has a DEA ACSCN of 9730 and in 2013 the aggregate annual manufacturing quota for the US was zero.^[4]

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.
^ http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm

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[1] 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.

[2] Dekornfeld TJ, Lasagna L. The analgesic potency of piminodine (alvodine). Journal of Chronic Diseases. 1960 Aug;12:252-7.

[3] 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.

[4] ttp://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0620.htm

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