Hydroxypethidine

Chemical compound

none

Legal statusLegal status

BR: Class A1 (Narcotic drugs)^[1]
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^Y

PubChem CID

61120

ChemSpider

55068^Y

UNII

W1J43H2B3K

KEGG

D12681^Y

ChEBI

CHEBI:135085

ChEMBL

ChEMBL1182665

CompTox Dashboard (EPA)

DTXSID90196941

ECHA InfoCard100.006.738

Chemical and physical dataFormulaC₁₅H₂₁NO₃Molar mass263.337 g·mol⁻¹3D 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^Y
Key:WTJBNMUWRKPFRS-UHFFFAOYSA-N^Y

(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,^[2] and it also has NMDA antagonist properties like its close relative ketobemidone.^[3]

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. ^[4]

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.
^ 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. ISBN 9780444533234. 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. Archived from the original on 2016-03-02. Retrieved 2016-02-27.

Opioid receptor modulators

μ-opioid
(MOR)

Agonists (abridged; full list)	3-HO-PCP 7-Acetoxymitragynine 7-Hydroxymitragynine ψ-Akuammigine α-Chlornaltrexamine α-Narcotine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Akuammidine Alfentanil Anileridine Apparicine β-Endorphin BAM-12P BAM-18P BAM-22P Benzhydrocodone Benzylmorphine Bezitramide Biphalin BU08070 Buprenorphine Butorphan Butorphanol Butyrfentanyl BW373U86 Carfentanil Casokefamide Cebranopadol Chloroxymorphamine Codeine DADLE DAMGO (DAGO) Dermorphin Desmetramadol (desmethyltramadol) Desomorphine Dextromoramide Dextropropoxyphene (propoxyphene) Dezocine Dimenoxadol Dimethylaminopivalophenone Eluxadoline Diamorphine (heroin) Dihydrocodeine Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diphenoxylate Dipipanone Dynorphin A Embutramide Endomorphin-1 Endomorphin-2 Eseroline Ethylmorphine Etorphine Fentanyl Fluorophen Frakefamide Furanylfentanyl Hemorphin-4 Herkinorin Hodgkinsine Hydrocodone Hydromorphinol Hydromorphone IBNtxA Ketamine Ketobemidone Kratom Laudanosine Lefetamine Leu-enkephalin Levacetylmethadol Levomethorphan Levorphanol Lexanopadol Loperamide Loxicodegol LS-115509 Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine NalBzOH Nalmexone Naltalimide Neopine NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine Oxycodegol OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphonazine Oxymorphone Oxymorphone phenylhydrazone OxyPNPH Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide PL-017 Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil Salsolinol SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline TH-030418 Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 Tubotaiwine U-47700 Valorphin Viminol Xorphanol
Antagonists	(3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 3CS-nalmefene 4-Caffeoyl-1,5-quinide 4′-Hydroxyflavanone 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC α-Gliadin β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP CTOP Cyclofoxy Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Ginsenoside R Hyperoside Ibogaine JDTic Levallorphan Lobeline LY-255582 LY-2196044 Methocinnamox Methylnaltrexone Methylsamidorphan chloride Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexazone Naltrexonazine Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin

Agonists
(abridged;
full list)

Antagonists

δ-opioid
(DOR)

Agonists	3CS-nalmefene 6'-GNTI 7-SIOM ADL-5747 (PF-04856881) ADL-5859 Alazocine (SKF-10047) Amoxapine AR-M100390 (ARM390) AZD2327 β-Endorphin BAM-18P Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Deltorphin II Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 DSLET Ethylketazocine Etorphine Fentanyl FIT Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone JNJ-20788560 KNT-127 Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lexanopadol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine NalBzOH Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SB-235863 SNC-80 SNC-162 TAN-67 (SB-205,607) TH-030418 Thebaine Thiobromadol (C-8813) Tonazocine Tramadol TRV250 Xorphanol Zenazocine
Antagonists	4',7-Dihydroxyflavone 5'-NTII 6β-Naltrexol 6β-Naltrexol-d4 α-Santolol β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran BNTX Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin ICI-154129 ICI-174864 LY-255582 LY-2196044 Methylnaltrexone Methylnaltrindole N-Benzylnaltrindole Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SDM25N SoRI-9409 Taxifolin Thienorphine

Agonists

Antagonists

κ-opioid
(KOR)

Agonists	3CS-nalmefene 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Akuammicine Alazocine (SKF-10047) Allomatrine Apadoline Asimadoline BAM-12P BAM-18P BAM-22P Big dynorphin Bremazocine BRL-52537 Butorphan Butorphanol BW373U86 Cebranopadol Ciprefadol CR665 Cyclazocine Cyclorphan Cyprenorphine Desmetramadol (desmethyltramadol) Diamorphine (heroin) Diacetylnalorphine Difelikefalin Dihydroetorphine Dihydromorphine Dinalbuphine sebacate Diprenorphine Dynorphin A Dynorphin B (rimorphin) Eluxadoline Enadoline Eptazocine Erinacine E Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 GR-103545 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lexanopadol Lofentanil LPK-26 Lufuradom Matrine MB-1C-OH Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine MR-2034 N-MPPP Nalbuphine NalBzOH Nalfurafine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Naltriben Niravoline Norbuprenorphine Norbuprenorphine-3-glucuronide Noribogaine Norketamine Oripavine Oxilorphan Oxycodone Pentazocine Pethidine (meperidine) Phenazocine Proxorphan Racemethorphan Racemorphan RB-64 Salvinorin A (salvia) Salvinorin B ethoxymethyl ether Salvinorin B methoxymethyl ether Samidorphan Spiradoline (U-62,066) TH-030418 Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-54,494A U-69,593 Xorphanol
Antagonists	4′-Hydroxyflavanone 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone ANTI Apigenin Arodyne AT-076 Aticaprant Axelopran AZ-MTAB Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox CVL-354 Cyclofoxy Dezocine DIPPA EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2196044 LY-2444296 LY-2459989 LY-2795050 MeJDTic Methylnaltrexone ML190 ML350 MR-2266 N-Fluoropropyl-JDTic Naloxone Naltrexone Naltrindole Naringenin Navacaprant Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin UPHIT Zyklophin

Agonists

3CS-nalmefene
6'-GNTI
8-CAC
18-MC
14-Methoxymetopon
β-Chlornaltrexamine
β-Funaltrexamine
Adrenorphin (metorphamide)
Akuammicine
Alazocine (SKF-10047)
Allomatrine
Apadoline
Asimadoline
BAM-12P
BAM-18P
BAM-22P
Big dynorphin
Bremazocine
BRL-52537
Butorphan
Butorphanol
BW373U86
Cebranopadol
Ciprefadol
CR665
Cyclazocine
Cyclorphan
Cyprenorphine
Desmetramadol (desmethyltramadol)
Diamorphine (heroin)
Diacetylnalorphine
Difelikefalin
Dihydroetorphine
Dihydromorphine
Dinalbuphine sebacate
Diprenorphine
Dynorphin A
Dynorphin B (rimorphin)
Eluxadoline
Enadoline
Eptazocine
Erinacine E
Ethylketazocine
Etorphine
Fedotozine
Fentanyl
Gemazocine
GR-89696
GR-103545
Hemorphin-4
Herkinorin
HS665
Hydromorphone
HZ-2
Ibogaine
ICI-199,441
ICI-204,448
Ketamine
Ketazocine
Laudanosine
Leumorphin (dynorphin B-29)
Levallorphan
Levomethorphan
Levorphanol
Lexanopadol
Lofentanil
LPK-26
Lufuradom
Matrine
MB-1C-OH
Menthol
Metazocine
Metkefamide
Mianserin
Mirtazapine
Morphine
Moxazocine
MR-2034
N-MPPP
Nalbuphine
NalBzOH
Nalfurafine
Nalmefene
Nalodeine (N-allylnorcodeine)
Nalorphine
Naltriben
Niravoline
Norbuprenorphine
Norbuprenorphine-3-glucuronide
Noribogaine
Norketamine
Oripavine
Oxilorphan
Oxycodone
Pentazocine
Pethidine (meperidine)
Phenazocine
Proxorphan
Racemethorphan
Racemorphan
RB-64
Salvinorin A (salvia)
Salvinorin B ethoxymethyl ether
Salvinorin B methoxymethyl ether
Samidorphan
Spiradoline (U-62,066)
TH-030418
Thienorphine
Tifluadom
Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline)
U-50488
U-54,494A
U-69,593
Xorphanol

Antagonists

Nociceptin
(NOP)

Agonists	(Arg14,Lys15)Nociceptin ((pF)Phe⁴)Nociceptin(1-13)NH₂ (Phe¹Ψ(CH₂-NH)Gly²)Nociceptin(1-13)NH₂ Ac-RYYRWK-NH₂ Ac-RYYRIK-NH₂ BU08070 Buprenorphine Cebranopadol Dihydroetorphine Etorphine JNJ-19385899 Levomethorphan Levorphanol Lexanopadol MCOPPB MT-7716 NNC 63-0532 Nociceptin (orphanin FQ) Nociceptin (1-11) Nociceptin (1-13)NH₂ Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 Ro65-6570 SCH-221510 SCH-486757 SR-8993 SR-16435 Sunobinop (S-117957) TH-030418
Antagonists	(Nphe¹)Nociceptin(1-13)NH₂ AT-076 BAN-ORL-24 BTRX-246040 (LY-2940094) J-113,397 JTC-801 NalBzOH Nociceptin (1-7) Nocistatin SB-612,111 SR-16430 Thienorphine Trap-101 UFP-101

Agonists