Hydroxypethidine

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;
ChEBI	CHEBI:135085;
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 ;
	(verify)

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 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]

References

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

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[pmid5319798-1] Beckett AH, Casy AF (February 1965). "Analgesics and their antagonists: biochemical aspects and structure-activity relationships". Progress in Medicinal Chemistry. 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.

[1]

[2]

[3]

See also

References