Hydroxypethidine

Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of the more commonly used pethidine (meperidine). Hydroxypethidine is slightly more potent than meperidine as an analgesic, 1.5x meperidine in potency,[1] and it also has NMDA antagonist properties like its close relative ketobemidone.[2]

Hydroxypethidine

Clinical data
ATC code	none
Legal status
Legal status	CA: Schedule I DE: Anlage I (Authorized scientific use only) US: Schedule I
Identifiers
IUPAC name Ethyl 4-(3-hydroxyphenyl)-1-methyl-piperidine-4-carboxylate
CAS Number	468-56-4
PubChem CID	61120
ChemSpider	55068
UNII	W1J43H2B3K
ChEMBL	ChEMBL1182665
CompTox Dashboard (EPA)	DTXSID90196941
ECHA InfoCard	100.006.738
Chemical and physical data
Formula	C15H21NO3
Molar mass	263.337 g·mol^−1
3D model (JSmol)	Interactive image
SMILES O=C(OCC)C2(c1cccc(O)c1)CCN(C)CC2
InChI InChI=1S/C15H21NO3/c1-3-19-14(18)15(7-9-16(2)10-8-15)12-5-4-6-13(17)11-12/h4-6,11,17H,3,7-10H2,1-2H3 Key:WTJBNMUWRKPFRS-UHFFFAOYSA-N
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Hydroxypethidine has similar effects to other opioids, and produces analgesia, sedation and euphoria. Side effects can include itching, nausea and potentially serious respiratory depression which can be life-threatening.

Hydroxypethidine is under international control under the Single Convention on Narcotic Drugs 1961 and therefore controlled like morphine in most countries; in the United States it is a Schedule I Narcotic controlled substance with an ACSCN of 9627 and a 2014 annual aggregate manufacturing quota of 2 grams. The salt in use is the hydrochloride, with a free base conversion ratio of 0.878. [3]

See also

• 4-Fluoromeperidine

References

1. Beckett AH, Casy AF. Analgesics and their antagonists: biochemical aspects and structure-activity relationships. Prog Med Chem. 1965 Feb;4:171-218. doi:10.1016/s0079-6468(08)70169-3 PMID 5319798
2. Harris I (1949). "The addiction liability of some analogues of meperidine". Journal of Pharmacology and Experimental Therapeutics. 97 (2): 182–190.
3. "Conversion Factors for Controlled Substances". Diversion Control Division. Drug Enforcement Administration, U.S. Department of Justice.