Piminodine

Piminodine (Alvodine) is an opioid analgesic that is an analogue of pethidine (meperidine).[1] 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
Clinical data
ATC code
  • none
Identifiers
IUPAC name
  • ethyl 1-(3-anilinopropyl)-4-phenylpiperidine-4-carboxylate
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.033.455
Chemical and physical data
FormulaC23H30N2O2
Molar mass366.505 g·mol−1
3D model (JSmol)
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 Y

  • InChI=1/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-UHFFFAOYAI Y
 NY (what is this?)  (verify)

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]

References
  1. Sim E, Dimoglo A, Shvets N, Ahsen V (August 2002). "Electronic-topological study of the structure-activity relationships in a series of piperidine morphinomimetics". Current Medicinal Chemistry. 9 (16): 1537–45. doi:10.2174/0929867023369510. PMID 12171562.
  2. Dekornfeld TJ, Lasagna L (August 1960). "The analgesic potency of piminodine (alvodine)". Journal of Chronic Diseases. 12 (2): 252–7. doi:10.1016/0021-9681(60)90102-8. PMID 13815493.
  3. Woods LA, Deneau GA, Bennett DR, Domino EF, Seevers MH (May 1961). "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. 3: 358–79. doi:10.1016/0041-008x(61)90072-2. hdl:2027.42/32367. PMID 13786579.
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