Pethidine intermediate A

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,[1] 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).[2]

Pethidine intermediate A
Clinical data
Routes of
administration		N/A
ATC code
  • none
Legal status
Legal status
  • 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
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.020.771
Chemical and physical data
FormulaC13H16N2
Molar mass200.285 g·mol−1
3D model (JSmol)
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)

See also

References
  1. 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.
  2. "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.