Etoxeridine

Etoxeridine
Clinical data

Other names	Etoxeridine, Carbetidine, Atenos
ATC code	none
Legal status
Legal status	AU: S9 (Prohibited substance) CA: Schedule I DE: Anlage I (Authorized scientific use only) UK: Class A US: Schedule I
Identifiers
show IUPAC name Ethyl 1-[2-(2-hydroxyethoxy)ethyl]-4-phenylpiperidine-4-carboxylate
CAS Number	469-82-9^Y
PubChem CID	61122
DrugBank	DB01505^Y
ChemSpider	55070^Y
UNII	RHW35E1G7E
ChEMBL	ChEMBL2104254
CompTox Dashboard (EPA)	DTXSID30196980
ECHA InfoCard	100.006.750
Chemical and physical data
Formula	C₁₈H₂₇NO₄
Molar mass	321.417 g·mol⁻¹
3D model (JSmol)	Interactive image
show SMILES C1(CCN(CC1)CCOCCO)(C(=O)OCC)C2=CC=CC=C2
show InChI InChI=1S/C18H27NO4/c1-2-23-17(21)18(16-6-4-3-5-7-16)8-10-19(11-9-18)12-14-22-15-13-20/h3-7,20H,2,8-15H2,1H3^Y Key:KJTKYGFGPQSRRA-UHFFFAOYSA-N^Y

Etoxeridine (Carbetidine, Atenos) is a 4-phenylpiperidine derivative that is related to the clinically used opioid analgesic drug pethidine (meperidine).

Etoxeridine was developed in the 1950s^[1] and investigated for use in surgical anesthesia, however it was never commercialized and is not currently used in medicine.^[2]^[3]^[4] As with other opioids which were not in clinical use during the drafting of the Controlled Substances Act, it is categorized as a Schedule I narcotic.

References[]

^ BE 558883
^ Merlevede E, Levis S (1958). "Pharmacological study of carbetidine, a new synthetic analgesic". Archives Internationales de Pharmacodynamie et de Thérapie (in French). 115 (1–2): 213–232. PMID 13545901.
^ Sironi PG (1959). "Brief note on a new synthetic analgesic: carbetidine hydrochloride". Minerva Anestesiologica (in Italian). 25 (6): 251–254. PMID 13674097.
^ Crawford JS, Foldes FF (August 1959). "Studies on the respiratory and circulatory effects of carbetidine HCI used for supplementation of thiopentone sodium-nitrous oxide-oxygen anaesthesia". British Journal of Anaesthesia. 31 (8): 348–51. doi:10.1093/bja/31.8.348. PMID 13812715.

show v t Opioid receptor modulators
MOR	Agonists (abridged; see here for a full list): 3-HO-PCP 7-Hydroxymitragynine α-Chlornaltrexamine Acetyldihydrocodeine Acetylfentanyl Acrylfentanyl Adrenorphin (metorphamide) AH-7921 Akuammicine Alfentanil Anileridine Apparicine β-Endorphin Benzhydrocodone Benzylmorphine Bezitramide Biphalin 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 Loperamide LS-115509 Matrine Meptazinol Met-enkephalin (metenkefalin) Methadone Metkefamide Metopon Mitragynine Mitragynine pseudoindoxyl Morphiceptin Morphine Nalbuphine Nalmexone Naltalimide NFEPP Nicocodeine Nicodicodine Nicomorphine Norketamine Nufenoxole Octreotide Oliceridine OM-3-MNZ Oripavine Oxycodone Oxymorphazone Oxymorphone Papaver somniferum (opium) Pentazocine Pericine Pethidine (meperidine) Phenazocine Phencyclidine Piminodine Piritramide Prodine Propiram PZM21 Racemethorphan Racemorphan Remifentanil SC-17599 Sinomenine Sufentanil Tapentadol Tetrahydropapaveroline Thebaine Thienorphine Tianeptine Tilidine Tramadol Trimebutine TRIMU 5 TRV734 U-47700 Valorphin Viminol Xorphanol PAMs: Antagonists: (3S,4S)-Picenadol 2-(S)-N,N-(R)-Viminol 4-Caffeoyl-1,5-quinide 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 18-MC β-Chlornaltrexamine β-Funaltrexamine Akuammine Alvimopan AM-251 Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox CTAP Cyprodime Diacetylnalorphine Diprenorphine ECG EGC Epicatechin Eptazocine Gemazocine Hyperoside Ibogaine Levallorphan Lobeline LY-255582 Methylnaltrexone Naldemedine Nalmefene Nalodeine (N-allylnorcodeine) Nalorphine Nalorphine dinicotinate Naloxazone Naloxegol Naloxol Naloxonazine Naloxone Naltrexone Naltrindole Naringenin Noribogaine Oxilorphan Pawhuskin A Rimonabant Quadazocine Samidorphan Taxifolin Unknown/unsorted: Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
DOR	Agonists: 6'-GNTI 7-SIOM Alazocine (SKF-10047) Amoxapine β-Endorphin Biphalin BU-48 Butorphan Butorphanol BW373U86 Casokefamide Cebranopadol Codeine Cyclazocine DADLE Deltorphin A Deltorphin I Desmethylclozapine Desmetramadol (desmethyltramadol) Dezocine Diamorphine (heroin) Dihydroetorphine Dihydromorphine DPDPE DPI-221 DPI-3290 Ethylketazocine Etorphine Fentanyl Fluorophen Hemorphin-4 Hydrocodone Hydromorphone Ibogaine Isomethadone Kratom Laudanosine Leu-enkephalin Levomethorphan Levorphanol Lofentanil Met-enkephalin (metenkefalin) Metazocine Metkefamide Mitragynine Mitragynine pseudoindoxyl Morphine N-Phenethyl-14-ethoxymetopon Norbuprenorphine Oripavine Oxycodone Oxymorphone Pethidine (meperidine) Proglumide Racemethorphan Racemorphan RWJ-394674 Samidorphan SNC-80 TAN-67 (SB-205,607) Thebaine Thiobromadol (C-8813) Tonazocine Tramadol Xorphanol Zenazocine Antagonists: 4',7-Dihydroxyflavone 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Apigenin AT-076 Axelopran Bevenopran Catechin Catechin gallate Clocinnamox Diacetylnalorphine Diprenorphine ECG EGC Eluxadoline Epicatechin LY-255582 Methylnaltrexone Nalmefene Nalorphine Naltrexone Naltriben Naltrindole Naloxone Naringenin Noribogaine Pawhuskin A Quadazocine SoRI-9409 Taxifolin Thienorphine Unknown/unsorted: 18-MC Cannabidiol Coronaridine Cyproterone acetate Tabernanthine Tetrahydrocannabinol
KOR	Agonists: 6'-GNTI 8-CAC 18-MC 14-Methoxymetopon β-Chlornaltrexamine β-Funaltrexamine Adrenorphin (metorphamide) Alazocine (SKF-10047) Asimadoline 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 Ethylketazocine Etorphine Fedotozine Fentanyl Gemazocine GR-89696 Hemorphin-4 Herkinorin HS665 Hydromorphone HZ-2 Ibogaine ICI-199,441 ICI-204,448 Ketamine Ketazocine Laudanosine Leumorphin (dynorphin B-29) Levallorphan Levomethorphan Levorphanol Lofentanil LPK-26 Lufuradom Matrine Menthol Metazocine Metkefamide Mianserin Mirtazapine Morphine Moxazocine Nalbuphine 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) Thienorphine Tifluadom Tricyclic antidepressants (e.g., amitriptyline, desipramine, imipramine, nortriptyline) U-50488 U-69,593 Xorphanol Antagonists: 4',7-Dihydroxyflavone 5'-GNTI 6'-GNTI 6β-Naltrexol 6β-Naltrexol-d4 β-Chlornaltrexamine Buprenorphine/samidorphan Amentoflavone Apigenin AT-076 Aticaprant Axelopran Binaltorphimine BU09059 Buprenorphine Catechin Catechin gallate CERC-501 (LY-2456302) Clocinnamox Dezocine EGC ECG Epicatechin Hyperoside JDTic LY-255582 LY-2459989 Methylnaltrexone Naloxone Naltrexone Naltrindole Naringenin Norbinaltorphimine Noribogaine Pawhuskin A PF-4455242 RB-64 Quadazocine Taxifolin Zyklophin Unknown/unsorted: Akuammicine Akuammine Coronaridine Cyproterone acetate Ibogamine Tabernanthine
NOP	Agonists: Buprenorphine Cebranopadol Dihydroetorphine Etorphine Levomethorphan Levorphanol MCOPPB NNC 63-0532 Nociceptin (orphanin FQ) Norbuprenorphine Racemethorphan Racemorphan Ro64-6198 SR-16435 Antagonists: AT-076 BTRX-246040 (LY-2940094) J-113,397 JTC-801 SB-612,111 Thienorphine
Unsorted	β-Casomorphins Amidorphin Cytochrophin-4 Gliadorphin (gluteomorphin) Gluten exorphins Hemorphins Kava constituents NEM Neoendorphins Nepetalactone (catnip) Rubiscolins
Others	Enkephalinase inhibitors: Amastatin Candoxatril D -Phenylalanine Ecadotril (sinorphan) Kelatorphan Racecadotril (acetorphan) RB-101 RB-120 RB-3007 Selank Semax Spinorphin Thiorphan Tynorphin Ubenimex (bestatin) Propeptides: β-Lipotropin (proendorphin) Prodynorphin Proenkephalin Proopiomelanocortin (POMC) Others: Kyotorphin (met-enkephalin releaser/degradation stabilizer)

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