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;

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[]

^ 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.; Grélard, A.; Loquet, A.; Molimard, M. (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. ISSN 0379-0738. PMID 35151938.
^ "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

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[1] 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.

[2] Goncalves, R.; Castaing, N.; Richeval, C.; Ducint, D.; Titier, K.; Morvan, E.; Grélard, A.; Loquet, A.; Molimard, M. (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. ISSN 0379-0738. PMID 35151938.

[3] "EU Early Warning System Situation Report. Situation report 1" (PDF). European Monitoring Centre for Drugs and Drug Addiction (EMCDDA). June 2020.

[4] Valtioneuvoston asetus kuluttajamarkkinoilta kielletyistä psykoaktiivisista aineista

[1]

[2]

[3]

[4]

v t Sigma receptor modulators
σ₁	Agonists: 3-PPP 4-PPBP 5-MeO-DMT Alazocine (SKF-10047) Amantadine Arketamine BD-1052 Blarcamesine 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) Ketamine L-687384 MDMA (midomafetamine) Memantine Methamphetamine Methoxetamine Methylphenidate Nepinalone Neuropeptide Y Noscapine Opipramol Pentazocine Pentoxyverine (carbetapentane) PRE-084 Pregnenolone Pregnenolone sulfate Pridopidine Racemethorphan (methorphan) Racemorphan (morphanol) Antagonists: 3-PPP AC-927 BD-1008 BD-1031 BD-1047 BD-1060 BD-1063 BD-1067 BMY-14802 (BMS-181100) CM-156 E-52862 (S1RA) Haloperidol NE-100 Panamesine (EMD-57455) Pentazocine Progesterone Rimcazole (BW-234U) Sertraline Allosteric modulators: Phenytoin; Positive: Methylphenylpiracetam Unknown/unsorted: 3-MeO-PCP 4C-T-2 4-MeO-PCP 5-MeO-DALT 5-MeO-DiPT Amitriptyline Chlorpromazine Clemastine Clomipramine Clorgiline D-Deprenyl DiPT DPT Ibogaine Imipramine Nemonapride Noribogaine RS-67,333 RTI-55 Saffron Safinamide Selegiline Trifluoperazine W-18 YKP10A
σ₂	Agonists: 3-PPP Arketamine BD-1047 BD1063 Ditolylguanidine (DTG) Haloperidol Ifenprodil Ketamine MDMA (midomafetamine) Methamphetamine Opipramol PB-28 Phencyclidine Siramesine (Lu 28-179) Antagonists: AC-927 BD-1008 BD-1067 CM-156 MIN-101 Panamesine (EMD-57455) Unknown/unsorted: 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 W-18
Unsorted	Agonists: Berberine Ethylketazocine Fourphit Metaphit Naluzotan Tapentadol Tenocyclidine Antagonists: Lamotrigine Naloxone Allosteric modulators: SKF-83959 Unknown/unsorted: 18-Methoxycoronaridine Butaclamol Caramiphen Chlorphenamine (chlorpheniramine) Chlorpromazine Cinnarizine Clocapramine Dezocine Hypericin (St. John's wort) Fluphenazine Gevotroline (WY-47384) Mepyramine (pyrilamine) Molindone Perphenazine Pimozide Proadifen Promethazine Propranolol Quinidine Remoxipride Tiospirone (BMY-13859) Venlafaxine
See also: Receptor/signaling modulators

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
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

Methoxpropamine

See also[]

References[]