3-MeO-PCMo

3-MeO-PCMo
Legal status
Legal status	CA: Schedule I ; DE: NpSG (Industrial and scientific use only) ; UK: Under Psychoactive Substances Act ;
Identifiers
	IUPAC name 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine;
CAS Number	138873-80-0;
PubChem CID	132605908;
ChemSpider	58191437;
Chemical and physical data
Formula	C17H25NO2
Molar mass	275.392 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES COC1=CC(C2(N3CCOCC3)CCCCC2)=CC=C1;
	InChI InChI=1S/C17H25NO2/c1-19-16-7-5-6-15(14-16)17(8-3-2-4-9-17)18-10-12-20-13-11-18/h5-7,14H,2-4,8-13H2,1H3; Key:BOGOEDFWPOXWQE-UHFFFAOYSA-N;

3-MeO-PCMo is a dissociative anesthetic drug which is similar in structure to phencyclidine^[1]^[2] and been sold online as a designer drug.^[3]^[4] The inhibitory effect of 3-MeO-PCMo on the reduction in the density of the drebrin clusters by NMDAR stimulation with glutamic acid is lower than that of PCP or 3-MeO-PCP, with half maximal inhibitory concentration (IC₅₀) values of 26.67 μM (3-MeO-PCMo), 2.02 μM (PCP) and 1.51 μM (3-MeO-PCP).^[5]

References[]

^ Ahmadi A, Khalili M, Hajikhani R, Naserbakht M (April 2011). "New morpholine analogues of phencyclidine: chemical synthesis and pain perception in rats". Pharmacology, Biochemistry, and Behavior. 98 (2): 227–33. doi:10.1016/j.pbb.2010.12.019. PMID 21215770. S2CID 24650035.
^ Abiero A, Botanas CJ, Custodio RJ, Sayson LV, Kim M, Lee HJ, et al. (March 2020). "4-MeO-PCP and 3-MeO-PCMo, new dissociative drugs, produce rewarding and reinforcing effects through activation of mesolimbic dopamine pathway and alteration of accumbal CREB, deltaFosB, and BDNF levels". Psychopharmacology. 237 (3): 757–772. doi:10.1007/s00213-019-05412-y. PMID 31828394. S2CID 209169410.
^ Colestock T, Wallach J, Mansi M, Filemban N, Morris H, Elliott SP, et al. (February 2018). "Syntheses, analytical and pharmacological characterizations of the 'legal high' 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo) and analogues". Drug Testing and Analysis. 10 (2): 272–283. doi:10.1002/dta.2213. PMID 28513099.
^ "3-MeO-PCMo". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-02-09.
^ Mitsuoka T, Hanamura K, Koganezawa N, Kikura-Hanajiri R, Sekino Y, Shirao T (September–October 2019). "Assessment of NMDA receptor inhibition of phencyclidine analogues using a high-throughput drebrin immunocytochemical assay". Journal of Pharmacological and Toxicological Methods. 99: 106583. doi:10.1016/j.vascn.2019.106583. PMID 31082488.

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[1] Ahmadi A, Khalili M, Hajikhani R, Naserbakht M (April 2011). "New morpholine analogues of phencyclidine: chemical synthesis and pain perception in rats". Pharmacology, Biochemistry, and Behavior. 98 (2): 227–33. doi:10.1016/j.pbb.2010.12.019. PMID 21215770. S2CID 24650035.

[2] Abiero A, Botanas CJ, Custodio RJ, Sayson LV, Kim M, Lee HJ, et al. (March 2020). "4-MeO-PCP and 3-MeO-PCMo, new dissociative drugs, produce rewarding and reinforcing effects through activation of mesolimbic dopamine pathway and alteration of accumbal CREB, deltaFosB, and BDNF levels". Psychopharmacology. 237 (3): 757–772. doi:10.1007/s00213-019-05412-y. PMID 31828394. S2CID 209169410.

[3] Colestock T, Wallach J, Mansi M, Filemban N, Morris H, Elliott SP, et al. (February 2018). "Syntheses, analytical and pharmacological characterizations of the 'legal high' 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo) and analogues". Drug Testing and Analysis. 10 (2): 272–283. doi:10.1002/dta.2213. PMID 28513099.

[4] "3-MeO-PCMo". New Synthetic Drugs Database. Archived from the original on 2016-07-03. Retrieved 2016-02-09.

[5] Mitsuoka T, Hanamura K, Koganezawa N, Kikura-Hanajiri R, Sekino Y, Shirao T (September–October 2019). "Assessment of NMDA receptor inhibition of phencyclidine analogues using a high-throughput drebrin immunocytochemical assay". Journal of Pharmacological and Toxicological Methods. 99: 106583. doi:10.1016/j.vascn.2019.106583. PMID 31082488.

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v t Ionotropic glutamate receptor modulators
AMPAR	Agonists: Main site agonists: 5-Fluorowillardiine AMPA Domoic acid Glutamate Ibotenic acid Proline Quisqualic acid Willardiine; Positive allosteric modulators: Aniracetam BIIB-104 (PF-04958242) Cyclothiazide CX-516 CX-546 CX-614 Farampator (CX-691, ORG-24448) CX-717 CX-1739 Diazoxide Hydrochlorothiazide (HCTZ) IDRA-21 LY-404187 LY-503430 Mibampator (LY-451395) Nooglutyl ORG-26576 Oxiracetam PEPA Piracetam Pramiracetam S-18986 Tulrampator (S-47445, CX-1632) Antagonists: Becampanel Caroverine CNQX Dasolampanel DNQX Fanapanel (MPQX) Kaitocephalin Kynurenic acid Kynurenine Licostinel (ACEA-1021) NBQX Selurampanel Tezampanel Theanine Topiramate Zonampanel; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Cyclopropane Enflurane Ethanol (alcohol) Evans blue GYKI-52466 Halothane Irampanel Isoflurane Perampanel Pregnenolone sulfate Sevoflurane Talampanel; Unknown/unsorted antagonists: Minocycline
KAR	Agonists: Main site agonists: 5-Iodowillardiine AMPA Domoic acid Glutamate Ibotenic acid Kainic acid Proline Quisqualic acid ; Positive allosteric modulators: Cyclothiazide Diazoxide Enflurane Halothane Isoflurane Antagonists: CNQX Dasolampanel DNQX Kaitocephalin Kynurenic acid Licostinel (ACEA-1021) NBQX NS102 Selurampanel Tezampanel Theanine Topiramate UBP-302; Negative allosteric modulators: Barbiturates (e.g., pentobarbital, sodium thiopental) Enflurane Ethanol (alcohol) Evans blue Pregnenolone sulfate
NMDAR	Agonists: Main site agonists: Aspartate Glutamate Homocysteic acid (L-HCA) Homoquinolinic acid Ibotenic acid NMDA Proline Quinolinic acid Tetrazolylglycine Theanine; Glycine site agonists: ACC (ACPC) ACPD Apimostinel (NRX-1074) D-Alanine D-Cycloserine D-Serine Dimethylglycine Glycine HA-966 L-Alanine L-Serine Milacemide Neboglamine (nebostinel) Rapastinel (GLYX-13) Sarcosine; Polyamine site agonists: Neomycin Spermidine Spermine; Other positive allosteric modulators: 24S-Hydroxycholesterol DHEA (prasterone) DHEA sulfate (prasterone sulfate) Pregnenolone sulfate Antagonists: Competitive antagonists: AP5 (APV) AP7 CGP-37849 Kaitocephalin LY-235959 Midafotel (d-CPPene) PEAQX Perzinfotel Selfotel; Glycine site antagonists: 4-Cl-KYN (AV-101) 5,7-DCKA 7-CKA ACC Apimostinel (NRX-1074) AV-101 Carisoprodol CNQX D-Cycloserine DNQX Felbamate Gavestinel Kynurenic acid Kynurenine Licostinel (ACEA-1021) Meprobamate Rapastinel (GLYX-13) ; Polyamine site antagonists: 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 Arketamine Budipine Coronaridine Delucemine (NPS-1506) Dexoxadrol Dextrallorphan Dextromethadone Dextromethorphan Dextrorphan Dieticyclidine Diphenidine Dizocilpine Ephenidine Esketamine Etoxadrol Eticyclidine 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) Eliprodil Haloperidol Isoxsuprine Rislenemdaz (CERC-301, MK-0657) Traxoprodil (CP-101606); NR2A-selective antagonists: ; 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: Bumetanide Caroverine Conantokin D-αAA Dexanabinol Flufenamic acid Flupirtine Furosemide Hodgkinsine 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

Legal status

Legal status	CA: Schedule I DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act
Identifiers
IUPAC name 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine
CAS Number	138873-80-0
PubChem CID	132605908
ChemSpider	58191437
Chemical and physical data
Formula	C₁₇H₂₅NO₂
Molar mass	275.392 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES COC1=CC(C2(N3CCOCC3)CCCCC2)=CC=C1
InChI InChI=1S/C17H25NO2/c1-19-16-7-5-6-15(14-16)17(8-3-2-4-9-17)18-10-12-20-13-11-18/h5-7,14H,2-4,8-13H2,1H3 Key:BOGOEDFWPOXWQE-UHFFFAOYSA-N

3-MeO-PCMo

See also[]

References[]