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Methoxmetamine

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Chemical compound

Pharmaceutical compound

Methoxmetamine
Legal status

Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Class B
Identifiers
IUPAC name 2-(3-Methoxyphenyl)-2-(methylamino)cyclohexanone
CAS Number	1781829-56-8
PubChemCID	117067863
ChemSpider	58939253
UNII	U2B6L9JR4L
CompTox Dashboard(EPA)	DTXSID101045797
Chemical and physical data
Formula	C₁₄H₁₉NO₂
Molar mass	233.311 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC=CC(=C1)C2(CCCCC2=O)NC
InChI InChI=1S/C14H19NO2/c1-15-14(9-4-3-8-13(14)16)11-6-5-7-12(10-11)17-2/h5-7,10,15H,3-4,8-9H2,1-2H3 Key:ZGQWDAOLJNAADS-UHFFFAOYSA-N

Methoxmetamine (also known as3-MeO-2'-Oxo-PCM,MXM andMMXE) is adissociative anesthetic of thearylcyclohexylamine class that is closely related tomethoxetamine andmethoxyketamine, and has been sold online as adesigner drug.^[1]

References

[edit]

^Kaizaki-Mitsumoto A, Noguchi N, Yamaguchi S, Odanaka Y, Matsubayashi S, Kumamoto H, et al. (November 2015). "Three 25-NBOMe-type drugs, three other phenethylamine-type drugs (25I-NBMD, RH34, and escaline), eight cathinone derivatives, and a phencyclidine analog MMXE, newly identified in ingredients of drug products before they were sold on the drug market".Forensic Toxicology.34:108–114.doi:10.1007/s11419-015-0293-6.S2CID 45890497.

Hallucinogens

Psychedelics
(5-HT_2AR agonists)

Tryptamines (e.g.,DMT,psilocin,psilocybin,bufotenin,5-MeO-DMT,AMT)
Phenethylamines (e.g.,mescaline,2C-B,DOM,MDA,TMA,2C-B-FLY,25I-NBOMe)
Lysergamides (e.g.,LSD,ergine,isoergine)
Others (e.g.,quipazine,efavirenz)

For a full list of serotonergic psychedelics, see the navboxhere and the listhere instead.

Dissociatives
(NMDAR antagonists)

Arylcyclo‐ hexylamines	Ketamine-related: 2-Fluorodeschloroketamine Arketamine ((R)-ketamine) Deschloroketamine Ethketamine (N-Ethylnorketamine) Esketamine ((S)-ketamine) Ketamine Methoxetamine Methoxmetamine Methoxyketamine MXiPr Norketamine Tiletamine PCP-related: 2'-Oxo-PCE 3-HO-PCE 3-HO-PCP 3-MeO-PCE 3-MeO-PCMo 3-MeO-PCP 3-MeO-PCPr 3-MeO-PCPy 4-MeO-PCP BDPC Dieticyclidine (PCDE) Eticyclidine (PCE) PCPr Phencyclidine (PCP) Rolicyclidine (PCPy) Tenocyclidine (TCP) Others:BTCP Gacyclidine PRE-084
Adamantanes	Amantadine Memantine Rimantadine
Diarylethylamines	Diphenidine Ephenidine Fluorolintane Methoxphenidine
Morphinans	Dextrallorphan Dextromethorphan Dextrorphan Racemethorphan Racemorphan
Others	2-EMSB 2-MDP 8A-PDHQ Aptiganel Budipine Delucemine Dexoxadrol Dizocilpine Etoxadrol F-17475 Herkinorin Ibogaine Midafotel NEFA Neramexane Nitrous oxide Noribogaine Perzinfotel RB-64 Remacemide Selfotel Xenon

Deliriants
(mAChR antagonists)

Cannabinoids
(CB₁R agonists)

Natural

Synthetic

AM-x	AM-087 AM-251 AM-279 AM-281 AM-356 AM-374 AM-381 AM-404 AM-411 AM-630 AM-661 AM-678 AM-679 AM-694 AM-735 AM-855 AM-881 AM-883 AM-905 AM-906 AM-919 AM-926 AM-938 AM-1116 AM-1172 AM-1220 AM-1221 AM-1235 AM-1241 AM-1248 AM-1710 AM-1714 AM-1902 AM-2201 AM-2212 AM-2213 AM-2232 AM-2233 AM-2389 AM-3102 AM-4030 AM-4054 AM-4056 AM-4113 AM-6545
CPx	CP 47,497 CP 55,244 CP 55,940 (±)-CP 55,940 (+)-CP 55,940 (-)-CP 55,940
HU-x	HU-210 HU-211 HU-239 HU-243 HU-308 HU-320 HU-331 HU-336 HU-345
JWH-x	JWH-007 JWH-015 JWH-018 JWH-019 JWH-030 JWH-047 JWH-048 JWH-051 JWH-057 JWH-073 JWH-081 JWH-098 JWH-116 JWH-120 JWH-122 JWH-133 JWH-139 JWH-147 JWH-148 JWH-149 JWH-149 JWH-161 JWH-164 JWH-166 JWH-167 JWH-171 JWH-175 JWH-176 JWH-181 JWH-182 JWH-184 JWH-185 JWH-192 JWH-193 JWH-194 JWH-195 JWH-196 JWH-197 JWH-198 JWH-199 JWH-200 JWH-203 JWH-205 JWH-210 JWH-210 JWH-213 JWH-220 JWH-229 JWH-234 JWH-249 JWH-250 JWH-251 JWH-253 JWH-258 JWH-300 JWH-302 JWH-307 JWH-336 JWH-350 JWH-359 JWH-387 JWH-398 JWH-424
Misc.	4-HTMPIPO 5F-AB-FUPPYCA 5F-AB-PINACA 5F-ADB 5F-ADB-PINACA 5F-ADBICA 5F-AMB 5F-APINACA 5F-CUMYL-PINACA 5F-NNE1 5F-PB-22 5F-SDB-006 A-796,260 A-836,339 AB-001 AB-005 AB-CHFUPYCA AB-CHMINACA AB-FUBINACA AB-PINACA ADAMANTYL-THPINACA ADB-CHMINACA ADB-FUBINACA ADB-PINACA ADBICA ADSB-FUB-187 AMB-FUBINACA APICA APINACA APP-FUBINACA CB-13 CUMYL-PICA CUMYL-PINACA CUMYL-THPINACA DMHP EAM-2201 FAB-144 FDU-PB-22 FUB-144 FUB-APINACA FUB-JWH-018 FUB-PB-22 FUBIMINA JTE 7-31 JTE-907 Levonantradol MDMB-CHMICA MDMB-CHMINACA MDMB-FUBINACA MEPIRAPIM MAM-2201 MDA-19 MN-18 MN-25 NESS-0327 NESS-040C5 Nabilone Nabitan NM-2201 NNE1 Org 28611 Parahexyl PTI-1 PTI-2 PX-1 PX-2 PX-3 QUCHIC QUPIC RCS-4 RCS-8 SDB-005 SDB-006 STS-135 THC-O-acetate THC-O-phosphate THJ-018 THJ-2201 UR-144 WIN 55,212-2 XLR-11

For a full list of cannabinoids, see the navboxhere and the listhere instead.

Inhalants
(mixed MoATooltip mechanism of action)

Others

Aminochromes (e.g.,adrenochrome,adrenolutin)
Carbogen
CertainGABA_A receptor positive allosteric modulators (nonbenzodiazepines/Z-drugs) (e.g.,eszopiclone,zaleplon,zolpidem,zopiclone)
CI-966
Cryogenine
Glaucine
Hallucinogenic bolete mushrooms (e.g.,Lanmaoa asiatica)
Harmala alkaloids/β-carbolines (e.g.,harmaline,6-methoxyharmalan)
Iboga alkaloids/azepinoindoles (e.g.,ibogaine)
Isoaminile
Noscapine
Nutmeg (e.g.,myristicin,elemicin)
Oneirogens (e.g.,Calea zacatechichi,galantamine,nicotine,Silene capensis)
Prenoxdiazine
Pukateine

Glutamate receptor modulators

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 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

Metabotropic glutamate receptor modulators

Group I

mGluR₁Tooltip Metabotropic glutamate receptor 1	Agonists:ACPD DHPG Glutamate Ibotenic acid Quisqualic acid Ro01-6128 Ro67-4853 Ro67-7476 VU-71 Theanine Antagonists:BAY 36-7620 CPCCOEt Cyclothiazide LY-367,385 LY-456,236 MCPG NPS-2390
mGluR₅Tooltip Metabotropic glutamate receptor 5	Agonists:ACPD ADX-47273 CDPPB CHPG DFB DHPG Glutamate Ibotenic acid Quisqualic acid VU-1545;Positive allosteric modulators:LSN2463359 Antagonists:CTEP DMeOB LY-344,545 Mavoglurant MCPG NPS-2390 Remeglurant SIB-1757 SIB-1893;Negative allosteric modulators:AZD9272 Basimglurant Dipraglurant Fenobam GRN-529 MPEP MTEP Raseglurant

Group II

mGluR₂Tooltip Metabotropic glutamate receptor 2

Agonists:BINA
CBiPES
DCG-IV
Eglumetad (LY-354740)
Glutamate
Ibotenic acid
LY-379,268
LY-487,379
LY-566,332
MGS-0028
Pomaglumetad (LY-404039)
Pomaglumetad methionil (LY-2140023)
Talaglumetad (LY-544344);Positive allosteric modulators:JNJ-40411813 (ADX-71149)

Antagonists:APICA
CECXG
EGLU
HYDIA
LY-307,452
LY-341,495
MCPG
MGS-0039
PCCG-4;Negative allosteric modulators:Decoglurant
RO4491533

mGluR₃Tooltip Metabotropic glutamate receptor 3

Antagonists:APICA
CECXG
EGLU
HYDIA
LY-307,452
LY-341,495
MCPG
MGS-0039;Negative allosteric modulators:Decoglurant
RO4491533

Group III

mGluR₄Tooltip Metabotropic glutamate receptor 4	Agonists:Glutamate L-AP4 LSP2-9166 PHCCC VU-001,171 VU-0155,041;Positive allosteric modulators:Foliglurax MPEP Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₆Tooltip Metabotropic glutamate receptor 6	Agonists:Glutamate L-AP4 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112
mGluR₇Tooltip Metabotropic glutamate receptor 7	Agonists:AMN082 Glutamate L-AP4 LSP2-9166 Antagonists:CPPG MAP4 MMPIP MPPG MSOP MTPG UBP-1112 XAP044;Negative allosteric modulators:ADX71743
mGluR₈Tooltip Metabotropic glutamate receptor 8	Agonists:DCPG Glutamate L-AP4;Positive allosteric modulators:AZ12216052 Antagonists:CPPG MAP4 MPPG MSOP MTPG UBP-1112

See also:Receptor/signaling modulators •Ionotropic 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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