Benzethidine

Benzethidine is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine, or Demerol).[1]

Benzethidine
Clinical data
ATC code
  • none
Legal status
Legal status
  • AU: S9 (Prohibited substance)
  • CA: Schedule I
  • DE: Anlage I (Authorized scientific use only)
  • UK: Class A
  • US: Schedule I
Identifiers
IUPAC name
  • ethyl 1-[2-(benzyloxy)ethyl]- 4-phenylpiperidine- 4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC23H29NO3
Molar mass367.489 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC)C3(c1ccccc1)CCN(CCOCc2ccccc2)CC3
InChI
  • InChI=1S/C23H29NO3/c1-2-27-22(25)23(21-11-7-4-8-12-21)13-15-24(16-14-23)17-18-26-19-20-9-5-3-6-10-20/h3-12H,2,13-19H2,1H3 Y
  • Key:UVTBZAWTRVBTMK-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Benzethidine is not currently used in medicine and is a Class A/Schedule I drug which is controlled under UN drug conventions. It has similar effects to other opioid derivatives, such as analgesia, sedation, nausea and respiratory depression.[2] In the United States, the drug is a Schedule I Narcotic Controlled Substance with a DEA ACSCN of 9606 and 2014 annual aggregate manufacturing quota of nil.[3] The most common salt in use is the hydrochloride, free base conversion ratio of 0.910

Australia

Benzethidine is considered a Schedule 9 prohibited substance in Australia under the Poisons Standard (February 2017).[4] A Schedule 9 substance is a substance which may be abused or misused, the manufacture, possession, sale or use of which should be prohibited by law except when required for medical or scientific research, or for analytical, teaching or training purposes with approval of Commonwealth and/or State or Territory Health Authorities.[4]

References
  1. Maul C, Buschmann H, Sundermann B (2005). "Opioids: 3.3 Synthetic Opioids.". Analgesics. pp. 159–169. ISBN 978-3-527-30403-5.
  2. Cahal DA, Dare JG, Keith D (February 1961). "A sequential trial of analgesics in labour". The Journal of Obstetrics and Gynaecology of the British Commonwealth. 68: 88–93. doi:10.1111/j.1471-0528.1961.tb02689.x. PMID 13689779. S2CID 27397119.
  3. "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice.
  4. "Poisons Standard". Australian Government. October 2015.



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