Hydroxypethidine

Title: Hydroxypethidine
CAS Registry Number: 468-56-4
CAS Name: 4-(3-Hydroxyphenyl)-1-methyl-4-piperidinecarboxylic acid ethyl ester
Additional Names: 4-(m-hydroxyphenyl)-1-methylisonipecotic acid ethyl ester; ethyl 4-(m-hydroxyphenyl)-1-methylisonipecotate; demidone; oxipethidine; oxypetidin
Manufacturers' Codes: Hoechst 10446; Win-771
Trademarks: Bemidone; Biphenal
Molecular Formula: C15H21NO3
Molecular Weight: 263.33
Percent Composition: C 68.42%, H 8.04%, N 5.32%, O 18.23%
Literature References: Prepn: Morrison, Rinderknecht, J. Chem. Soc. 1950, 1467; Eisleb, DE 752755 (1952 to I. G. Farben), C.A. 52, 7361e (1958).
Properties: Crystals from ethanol, mp 110°.
Melting point: mp 110°
Derivative Type: Hydrochloride
Molecular Formula: C15H21NO3.HCl
Molecular Weight: 299.79
Percent Composition: C 60.10%, H 7.40%, N 4.67%, O 16.01%, Cl 11.83%
Properties: Crystals, mp 173-174°. Soluble in water; slightly sol in alc.
Melting point: mp 173-174°
NOTE: This is a controlled substance (opiate): 21 CFR, 1308.11.
Therap-Cat: Analgesic (narcotic).
Keywords: Analgesic (Narcotic).
Hydroxyphenamate Hydroxyproline Hydroxypropyl Cellulose Hydroxypropyl Methylcellulose Hydroxystilbamidine

Hydroxypethidine
Hydroxypethidine.svg
Systematic (IUPAC) name
Ethyl 4-(3-hydroxyphenyl)-1-methyl-piperidine-4-carboxylate
Clinical data
Legal status  ?
Identifiers
CAS number 468-56-4
ATC code None
PubChem CID 61120
ChemSpider 55068 YesY
UNII W1J43H2B3K YesY
Chemical data
Formula C15H21NO3 
Mol. mass 263.332 g/mol
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Hydroxypethidine (Bemidone) is an opioid analgesic that is an analogue of pethidine (meperidine). Hydroxypethidine is significantly less potent than meperidine as an analgesic, (0.3x meperidine in potency) although it also has NMDA antagonist properties like its close relative ketobemidone.[1]

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.