Pethidine intermediate A

Chemical compound

none

Legal statusLegal status

BR: Class A1 (Narcotic drugs)^[1]
DE: Anlage II (Authorized trade only, not prescriptible)
US: Schedule II
UN: Narcotic Schedule I

Identifiers

IUPAC name

1-methyl-4-phenylpiperidine-4-carbonitrile

CAS Number

3627-62-1

PubChem CID

62513

ChemSpider

56289

UNII

EL4L2474TY

KEGG

C22687

CompTox Dashboard (EPA)

DTXSID50189814

ECHA InfoCard100.020.771

Chemical and physical dataFormulaC₁₃H₁₆N₂Molar mass200.285 g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

CN1CCC(CC1)(C#N)c2ccccc2

InChI

InChI=1S/C13H16N2/c1-15-9-7-13(11-14,8-10-15)12-5-3-2-4-6-12/h2-6H,7-10H2,1H3
Key:ZLFQTZYFXYOGLS-UHFFFAOYSA-N

(verify)

Pethidine intermediate A is a 4-phenylpiperidine derivative that is a precursor to the opioid analgesic drug pethidine (meperidine). It is not known to have any analgesic activity in its own right, however other derivatives of pethidine with a 4-cyano group in place of the carboxylate ethyl ester have been found to be active,^[2] so pethidine intermediate A might also show opioid effects. It is scheduled by UN Single Convention on Narcotic Drugs. It is a Schedule II Narcotic controlled substance in the United States and has an ACSCN of 9232. The 2014 annual manufacturing quota was 6 grammes (as an end product, presumably for research use).^[3]

References

^ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
^ Lomenzo SA, Rhoden JB, Izenwasser S, Wade D, Kopajtic T, Katz JL, Trudell ML (March 2005). "Synthesis and biological evaluation of meperidine analogues at monoamine transporters". Journal of Medicinal Chemistry. 48 (5): 1336–43. doi:10.1021/jm0401614. PMID 15743177.
^ "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.