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Methoxpropamine

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Chemical compound

Pharmaceutical compound

Methoxpropamine
Legal status

Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 2-(3-Methoxyphenyl)-2-(propylamino)cyclohexanone
CAS Number	2504100-71-2^Y
PubChemCID	155817932
ChemSpider	128909942
UNII	LTF83AU3X8
CompTox Dashboard(EPA)	DTXSID501336500
Chemical and physical data
Formula	C₁₆H₂₃NO₂
Molar mass	261.365 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COc1cccc(c1)C2(NCCC)CCCCC2=O
InChI InChI=1S/C16H23NO2/c1-3-11-17-16(10-5-4-9-15(16)18)13-7-6-8-14(12-13)19-2/h6-8,12,17H,3-5,9-11H2,1-2H3 Key:AAVOSBAXDRASAH-UHFFFAOYSA-N

Methoxpropamine (MXPr,2-Oxo-3'-methoxy-PCPr) is adissociative anesthetic drug of thearylcyclohexylamine class andNMDA receptor antagonist^[1] that is closely related to substances such asmethoxetamine andPCPr.^[2] It has been sold online as adesigner drug, first being identified in Denmark in October 2019,^[3] and is illegal in Finland.^[4]

References

[edit]

^Irie T, Yamazaki D, Kikura-Hanajiri R (July 2021). "A potential of methoxpropamine to be a widespread recreational drug: it blocks NMDA receptors and inhibits NMDA receptor-mediated synaptic transmission in a brain preparation of mice".Forensic Toxicology.39 (2):474–80.doi:10.1007/s11419-021-00571-0.S2CID 232273277.
^Goncalves R, Castaing N, Richeval C, Ducint D, Titier K, Morvan E, et al. (April 2022)."Methoxpropamine (MXPr) in powder, urine and hair samples: Analytical characterization and metabolite identification of a new threat".Forensic Science International.333 111215.doi:10.1016/j.forsciint.2022.111215.PMID 35151938.S2CID 246685658.
^"EU Early Warning System Situation Report. Situation report 1"(PDF).European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020.
^"Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" [Government decree on psychoactive substances banned from the consumer market].Finlex Data Bank (in Finnish). Finnish Ministry of Justice.

v t e Dissociatives
Arylcyclo‐ hexylamines	Ketamine-related:2-Bromodeschloroketamine (2-BDCK; bromoketamine) 2-Fluorodeschloroketamine (2-FDCK) 2-FXPr 3-Fluorodeschloroketamine (3-FDCK) A-NK Arketamine ((R)-ketamine) Blixeprodil (GM-1020; (R)-4-FDCK) Deoxymethoxetamine (DMXE) Deschloroketamine (DXE, DCK) Ethketamine (N-ethylnorketamine, NENK) Esketamine ((S)-ketamine) Fluorexetamine (3-FXE) Hydroxetamine (HXE) Ketamine (K) Methoxetamine (MXE) Methoxmetamine (MXM, MXME) Methoxypropamine (MXPr) Methoxyketamine Methoxisopropamine (MXiPr) Norketamine (NK) SN-35210 TFMDCK Tiletamine Tilmetamine XW10508 PCP-related:2-Oxo-PCE 3-Chloro-PCP 3-Fluoro-PCP 3-HO-PCP 3-Me-PCE 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 3-Methyl-PCP 3-Methyl-PCPy 4-Keto-PCP 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) MDPCP PCPEP PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) TCTHP Tenocyclidine (TCP) Others:Gacyclidine
Adamantanes	Amantadine Memantine
Diarylethylamines	Diphenidine (1,2-DEP, DPD) Ephenidine (NEDPA, EPE) Fluorolintane (2-FPPP) Methoxphenidine (MXP) NPDPA (isopropylphenidine, isophenidine) Remacemide
Morphinans	Dextrallorphan (DXA) Dextromethorphan (DXM) Dextrorphan (DXO) Racemethorphan (methorphan) Racemorphan (morphanol)
Inhalants	Aliphatic hydrocarbons Butane Gasoline Kerosene Propane Ethers Diethyl ether Enflurane Isoflurane Haloalkanes Chlorofluorocarbons Chloroform Nitrous oxide (N₂O) Xenon (Xe)
Others	2-MDP (U-23807A) 8A-PDHQ Alkyl nitrites/poppers (e.g.,amyl nitrite) Aptiganel (Cerestat; CNS-1102) CNS-5161 Delucemine Dexoxadrol Dizocilpine (MK-801) Etoxadrol F-17475 Midafotel (CPPene) NEFA Neramexane PD-137889 Perzinfotel Selfotel (CGS-19755)
See also:Hallucinogens Ionotropic glutamate receptor modulators List of hallucinogens

v t e Ionotropic glutamate receptor modulators
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor	Agonists:Main site agonists:5-Fluorowillardiine Acromelic acid (acromelate) AMPA BOAA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine;Positive allosteric modulators:Aniracetam Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 CX-1942 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-392098 LY-395153 LY-404187 LY-451646 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Pesampator (BIIB-104, PF-04958242) Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists:ACEA-1011 ATPO Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) GAMS Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX PNQX Selurampanel Tezampanel Theanine Topiramate YM90K Zonampanel;Negative allosteric modulators:Barbiturates (e.g.,pentobarbital,sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 GYKI-53655 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel;Unknown/unsorted antagonists:Minocycline
KARTooltip Kainate receptor	Agonists:Main site agonists:5-Bromowillardiine 5-Iodowillardiine Acromelic acid (acromelate) AMPA ATPA Domoic acid Glutamate Ibotenic acid Kainic acid LY-339434 Proline Quisqualic acid SYM-2081;Positive allosteric modulators:Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists:ACEA-1011 CNQX Dasolampanel DNQX GAMS Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) LY-382884 NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302;Negative allosteric modulators:Barbiturates (e.g.,pentobarbital,sodium thiopental) Enflurane Ethanol (alcohol) Evans blue NS-3763 Pregnenolone sulfate
NMDARTooltip N-Methyl-D-aspartate receptor	Agonists:Main site agonists:AMAA Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine;Glycine site agonists:β-Fluoro-D-alanine ACBD ACC (ACPC) ACPD AK-51 Apimostinel (NRX-1074) B6B21 CCG D-Alanine D-Cycloserine D-Serine DHPG Dimethylglycine Glycine HA-966 L-687,414 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine;Polyamine site agonists:Neomycin Spermidine Spermine;Other positive allosteric modulators:24S-Hydroxycholesterol DHEATooltip Dehydroepiandrosterone (prasterone) DHEA sulfate (prasterone sulfate) Epipregnanolone sulfate Plazinemdor Pregnenolone sulfate SAGE-201 SAGE-301 SAGE-718 Antagonists:Competitive antagonists:AP5 (APV) AP7 CGP-37849 CGP-39551 CGP-39653 CGP-40116 CGS-19755 CPP Kaitocephalin LY-233053 LY-235959 LY-274614 MDL-100453 Midafotel (d-CPPene) NPC-12626 NPC-17742 PBPD PEAQX Perzinfotel PPDA SDZ-220581 Selfotel;Glycine site antagonists:4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC ACEA-1011 ACEA-1328 Apimostinel (NRX-1074) AV-101 Carisoprodol CGP-39653 CNQX D-Cycloserine DNQX Felbamate Gavestinel GV-196771 Harkoseride Kynurenic acid Kynurenine L-689560 L-701324 Licostinel (ACEA-1021) LU-73068 MDL-105519 Meprobamate MRZ 2/576 PNQX Rapastinel (GLYX-13) ZD-9379;Polyamine site antagonists:Arcaine Co 101676 Diaminopropane Diethylenetriamine Huperzine A Putrescine;Uncompetitive pore blockers (mostly dizocilpine site):2-MDP 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 4-MeO-PCP 8A-PDHQ 18-MC α-Endopsychosin Alaproclate Alazocine (SKF-10047) Amantadine Aptiganel Argiotoxin-636 Arketamine ARL-12495 ARL-15896-AR ARL-16247 Budipine CNS-5161 Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine F-17475 Fluorolintane Gacyclidine Ibogaine Ibogamine Indantadol Ketamine Ketobemidone Lanicemine Levomethadone Levomethorphan Levomilnacipran Levorphanol Loperamide Memantine Methadone Methorphan Methoxetamine Methoxphenidine Milnacipran Morphanol NEFA Neramexane Nitromemantine Noribogaine Norketamine Orphenadrine PCPr PD-137889 Pethidine (meperidine) Phencyclamine Phencyclidine Propoxyphene Remacemide Rhynchophylline Rimantadine Rolicyclidine Sabeluzole Tabernanthine Tenocyclidine Tiletamine Tramadol;Ifenprodil (NR2B) site antagonists: Besonprodil Buphenine (nylidrin) CO-101244 (PD-174494) Eliprodil Haloperidol Isoxsuprine Radiprodil (RGH-896) Rislenemdaz (CERC-301, MK-0657) Ro 8-4304 Ro 25-6981 Safaprodil Traxoprodil (CP-101606);NR2A-selective antagonists:MPX-004 MPX-007 TCN-201 TCN-213;Cations:Hydrogen Magnesium Zinc;Alcohols/volatile anesthetics/related:Benzene Butane Chloroform Cyclopropane Desflurane Diethyl ether Enflurane Ethanol (alcohol) Halothane Hexanol Isoflurane Methoxyflurane Nitrous oxide Octanol Sevoflurane Toluene Trichloroethane Trichloroethanol Trichloroethylene Urethane Xenon Xylene;Unknown/unsorted antagonists:ARR-15896 Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine FPL-12495 FR-115427 Furosemide Hodgkinsine Ipenoxazone (MLV-6976) MDL-27266 Metaphit Minocycline MPEP Niflumic acid Pentamidine Pentamidine isethionate Piretanide Psychotridine Transcrocetin (saffron) Unsorted:Allosteric modulators:AGN-241751
See also:Receptor/signaling modulators Metabotropic glutamate receptor modulators Glutamate metabolism/transport modulators

v t e Sigma receptor modulators
σ₁	Agonists:3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-737 BD-1052 Blarcamesine Captodiame Citalopram CGRPTooltip Calcitonin gene-related peptide Cloperastine Cocaine Cutamesine (SA-4503) Cyclazocine Dehydroepiandrosterone (DHEA) (prasterone) Dehydroepiandrosterone sulfate (DHEA-S) (prasterone sulfate) Dextrallorphan Dextromethorphan (DXM) Dextrorphan (DXO) Dimemorfan Dimethyltryptamine (DMT) Ditolylguanidine (DTG) Donepezil Eliprodil Escitalopram Fabomotizole (afobazole) Fluoxetine Fluvoxamine Ifenprodil Igmesine (JO-1784) IPAB Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine OPC-14523 Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) UMB-23 UMB-82 Antagonists:3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 Dup-734 E-5842 E-52862 (S1RA) Haloperidol LR-132 LR-172 MS-377 NE-100 NPC-16377 Panamesine (EMD-57455) PD-144418 Pentazocine Progesterone Rimcazole (BW-234U) Sertraline SR-31742A Allosteric modulators:Phenytoin;Positive:Methylphenylpiracetam SOMCL-668 Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCP 4C-T-2 4-IBP 4-IPBS 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Azidopamil Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Imipramine KCR-12-83.1 Nemonapride Noribogaine RHL-033 RS-67,333 RTI-55 Saffron Safinamide Selegiline Spipethiane Trifluoperazine W-18 YKP10A
σ₂	Agonists:3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) DKR-1005 DKR-1051 Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine OPC-14523 Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) UKH-1114 Antagonists:AC-927 BD-1008 BD-1067 CM-156 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Zervimesine (CT-1812) Unknown/unsorted:3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPTTooltip N,N-Diisopropyltryptamine DPTTooltip N,N-Dipropyltryptamine Ibogaine Lu 29-252 Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMATooltip 3,4,5-Trimethoxyamphetamine UMB-23 UMB-82 W-18
Unsorted	Agonists:Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists:AHD1 AZ66 Lamotrigine Naloxone SM-21 UMB-100 UMB-101 UMB-103 UMB-116 YZ-011 YZ-069 YZ-185 Allosteric modulators:SKF-83959 Unknown/unsorted:18-Methoxycoronaridine BMY-13980 Butaclamol Caramiphen Carvotroline Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Cinuperone Clocapramine Dezocine EMD-59983 Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride SL 82.0715 SR-31747A Tiospirone (BMY-13859) Venlafaxine
See also:Receptor/signaling modulators

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