Furethidine

Last updated
Furethidine
Furethidine.svg
Clinical data
Other namesethyl 4-phenyl-1-(2-tetrahydrofurfuryloxyethyl)piperidine-4-carboxylate
ATC code
  • none
Legal status
Legal status
Identifiers
  • ethyl 1-[2-(oxolan-2-ylmethoxy)ethyl]-4-phenylpiperidine-4-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
ECHA InfoCard 100.017.451 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C21H31NO4
Molar mass 361.482 g·mol−1
3D model (JSmol)
  • O=C(OCC)C3(c1ccccc1)CCN(CCOCC2OCCC2)CC3
  • 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 Yes check.svgY
  • Key:NNCOZXNZFLUYGG-UHFFFAOYSA-N Yes check.svgY
   (verify)

Furethidine [1] [2] [3] is a 4-phenyl piperidine 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 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]

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<span class="mw-page-title-main">Pyrrolidinylthiambutene</span> Chemical compound

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Morphine-N-oxide (genomorphine) is an active opioid metabolite of morphine. Morphine itself, in trials with rats, is 11–22 times more potent than morphine-N-oxide subcutaneously and 39–89 times more potent intraperitoneally. However, pretreatment with amiphenazole or tacrine increases the potency of morphine-N-oxide in relation to morphine. A possible explanation is that morphine-N-oxide is rapidly inactivated in the liver and impairment of inactivation processes or enzymes increases functionality.

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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.