Furethidine

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-[2-(oxolan-2-ylmethoxy)ethyl]-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−1
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 ;
	(verify)

Furethidine^[2]^[3]^[4] is a 4-phenyl piperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine),^[5] but with around 25x higher potency.^[6] According to another source, Furethidine is 500/30 = 16.7 x the potency of pethidine (table VII).^[7]^[8]

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.^[9] In the United States it is a Schedule I Narcotic controlled substance with the ACSCN of 9626.^[10]

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.

External links

UNODC Bulletin on Narcotics 1961

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[1] 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.

[2] GB 797448, Frearson PM, Stern ES, "Novel piperidine compounds and their production", published 2 July 1958, assigned to J F Macfarlan & Co Ltd

[3] Frearson Peter Marshall; Stern Edward Severin, DE 1256219 (1967 to Glaxo Lab Ltd).

[4] 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.

[5] Maul C, Buschmann H, Sundermann B (2005). "Opioids: 3.3 Synthetic Opioids.". Analgesics. Wiley-VCH. pp. 159–169. ISBN 978-3-527-30403-5.

[6] Casy AF, Parfitt RY. Opioid analgesics, chemistry and receptors. 1986, Plenum Press, New York. pp 234-235. ISBN 0-306-42130-5

[7] 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.

[8] 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.

[pmid13689779-9] 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.

[10] "Controlled Substances - Alphabetical Order" (PDF). Diversion Control Division. Drug Enforcement Agency, U.S. Department of Justice. 2020. p. 9.

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