Furethidine

Furethidine[1][2][3] is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine),[4] but with around 25x higher potency.[5] According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine (table VII).[6][7]

Furethidine
Clinical data
Other namesethyl 4-phenyl-1-(2-tetrahydrofurfuryloxyethyl)piperidine-4-carboxylate
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-(oxolan-2-ylmethoxy)ethyl]-4-phenylpiperidine-4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
ECHA InfoCard100.017.451
Chemical and physical data
FormulaC21H31NO4
Molar mass361.482 g·mol−1
3D model (JSmol)
SMILES
  • O=C(OCC)C3(c1ccccc1)CCN(CCOCC2OCCC2)CC3
InChI
  • InChI=1S/C21H31NO4/c1-2-25-20(23)21(18-7-4-3-5-8-18)10-12-22(13-11-21)14-16-24-17-19-9-6-15-26-19/h3-5,7-8,19H,2,6,9-17H2,1H3 Y
  • Key:NNCOZXNZFLUYGG-UHFFFAOYSA-N Y
  (verify)

Furethidine 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.[8] In the United States it is a Schedule I Narcotic controlled substance with the ACSCN of 9626.[9]

References
  1. GB 797448, Frearson PM, Stern ES, "Novel piperidine compounds and their production", published 2 July 1958, assigned to J F Macfarlan & Co Ltd
  2. Frearson Peter Marshall; Stern Edward Severin, DE 1256219 (1967 to Glaxo Lab Ltd).
  3. Frearson, P. M., Hardy, D. G., Stern, E. S. (1960). "426. Some new analogues of pethidine. Part IV. Substituents at the 1-position incorporating cyclic ether groups". Journal of the Chemical Society (Resumed): 2103. doi:10.1039/jr9600002103. ISSN 0368-1769.
  4. Maul C, Buschmann H, Sundermann B (2005). "Opioids: 3.3 Synthetic Opioids.". Analgesics. pp. 159–169. ISBN 978-3-527-30403-5.
  5. Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 234-235. ISBN 0-306-42130-5
  6. Blair, A. M. J. N.; Stephenson, R. P. (1960). "ANALGESIC ACTION OF ETHYL 4-PHENYLPIPERIDINE-4-CARBOXYLATES WITH OXYGENATED 1-SUBSTITUENTS". British Journal of Pharmacology and Chemotherapy. 15 (2): 247–253. doi:10.1111/j.1476-5381.1960.tb01239.x.
  7. Lister, R. E. (1960). "PHARMACOLOGICAL ACTIONS OF TWO NEW PETHIDINE ANALOGUES". British Journal of Pharmacology and Chemotherapy. 15 (2): 254–259. doi:10.1111/j.1476-5381.1960.tb01240.x.
  8. 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.
  9. "Controlled Substances - Alphabetical Order" (PDF). Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. 2020. p. 9.



This article is issued from Wikipedia. The text is licensed under Creative Commons - Attribution - Sharealike. Additional terms may apply for the media files.