Chemistry:Methoxpropamine

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 ;
PubChem CID	155817932;
UNII	LTF83AU3X8;
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;

Short description: Chemical compound

Methoxpropamine (MXPr, 2-Oxo-3'-methoxy-PCPr) is a dissociative anesthetic drug of the arylcyclohexylamine class and NMDA receptor antagonist^[1] that is closely related to substances such as methoxetamine and PCPr.^[2] It has been sold online as a designer drug, first being identified in Denmark in October 2019,^[3] and is illegal in Finland.^[4]

References

↑ "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. July 2021. doi:10.1007/s11419-021-00571-0.
↑ "Methoxpropamine (MXPr) in powder, urine and hair samples: Analytical characterization and metabolite identification of a new threat". Forensic Science International 333: 111215. April 2022. doi:10.1016/j.forsciint.2022.111215. PMID 35151938.
↑ "EU Early Warning System Situation Report. Situation report 1". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020. https://www.aekwien.at/documents/263869/449604/200629_EU+EARLY+WARNING+SYSTEM+SITUATION+REPORT+June.pdf.
↑ "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" (in fi). Finlex Data Bank. Finnish Ministry of Justice. https://finlex.fi/fi/laki/ajantasa/2014/20141130#a12.11.2020-764.

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[1] "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. July 2021. doi:10.1007/s11419-021-00571-0.

[2] "Methoxpropamine (MXPr) in powder, urine and hair samples: Analytical characterization and metabolite identification of a new threat". Forensic Science International 333: 111215. April 2022. doi:10.1016/j.forsciint.2022.111215. PMID 35151938.

[3] "EU Early Warning System Situation Report. Situation report 1". European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020. https://www.aekwien.at/documents/263869/449604/200629_EU+EARLY+WARNING+SYSTEM+SITUATION+REPORT+June.pdf.

[4] "Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista" (in fi). Finlex Data Bank. Finnish Ministry of Justice. https://finlex.fi/fi/laki/ajantasa/2014/20141130#a12.11.2020-764.

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v t e Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine ANAVEX2-73 Arketamine BD-737 BD-1052 Captodiame Citalopram CGRP 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 DiPT DPT 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 CT-1812 LR-172 MIN-101 Panamesine (EMD-57455) SAS-0132 Unknown/unsorted: 3-Methoxydextrallorphan 3-MeO-PCE 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Clemastine DiPT DPT Ibogaine Nemonapride Nepinalone Noribogaine Pentazocine RS-67,333 Safinamide TMA 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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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
PubChem CID	155817932
UNII	LTF83AU3X8
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

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