Furethidine - Misplaced Pages

Chemical compound

Pharmaceutical compound

Furethidine
Clinical data

Other names	ethyl 4-phenyl-1-(2-tetrahydrofurfuryloxyethyl)piperidine-4-carboxylate
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) BR: Class A1 (Narcotic drugs) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
IUPAC name ethyl 1--4-phenylpiperidine-4-carboxylate
CAS Number	2385-81-1
PubChem CID	61306
DrugBank	DB01464
ChemSpider	55245
UNII	6U9XA4JOD4
KEGG	D12682
ChEMBL	ChEMBL2105078
CompTox Dashboard (EPA)	DTXSID10862914
ECHA InfoCard	100.017.451
Chemical and physical data
Formula	C₂₁H₃₁NO₄
Molar mass	361.482 g·mol
3D model (JSmol)	Interactive image
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 Key:NNCOZXNZFLUYGG-UHFFFAOYSA-N
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Furethidine is a 4-phenyl piperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine), but with around 25x higher potency. According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine (table VII).

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. In the United States it is a Schedule I Narcotic controlled substance with the ACSCN of 9626.

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.
GB 797448, Frearson PM, Stern ES, "Novel piperidine compounds and their production", published 2 July 1958, assigned to J F Macfarlan & Co Ltd
Frearson Peter Marshall; Stern Edward Severin, DE 1256219 (1967 to Glaxo Lab Ltd).
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.
Maul C, Buschmann H, Sundermann B (2005). "Opioids: 3.3 Synthetic Opioids.". Analgesics. Wiley-VCH. pp. 159–169. ISBN 978-3-527-30403-5.
Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 234-235. ISBN 0-306-42130-5
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.
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.
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.
"Controlled Substances - Alphabetical Order" (PDF). Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. 2020. p. 9.