3-Methyl-PCP

3'-Me-PCP
Legal status
Legal status	CA: Schedule I; DE: NpSG (Industrial and scientific use only); UK: Class B;
Identifiers
	IUPAC name 1-[1-(3-methylphenyl)cyclohexyl]piperidine;
CAS Number	2201-30-1 ;
PubChem CID	611899;
ChemSpider	531905;
UNII	Y9XHS38QLZ;
CompTox Dashboard (EPA)	DTXSID801336878 ;
Chemical and physical data
Formula	C18H27N
Molar mass	257.421 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC1=CC(=CC=C1)C2(CCCCC2)N3CCCCC3;
	InChI InChI=1S/C18H27N/c1-16-9-8-10-17(15-16)18(11-4-2-5-12-18)19-13-6-3-7-14-19/h8-10,15H,2-7,11-14H2,1H3; Key:BMFKUCGCXMDGBK-UHFFFAOYSA-N;

3-Methyl-PCP (3'-Methyl-PCP, meta-Methyl-PCP, 3-Me-PCP) is a recreational designer drug with dissociative effects. It is an arylcyclohexylamine derivative, related to drugs such as 3'-MeO-PCP and 3'-Me-PCPy.^[1]^[2] It was first synthesised in the 1960s,^[3] but was only identified on the illicit market in Hungary in September 2020,^[4] and was made illegal in Hungary in April 2021.^[5]

References

^ Linders J, Furlano DC, Mattson MV, Jacobson AE, Rice KC (February 2010). "Synthesis and preliminary biochemical evaluation of novel derivatives of PCP". Letters in Drug Design & Discovery. 7 (2): 79–87. doi:10.2174/157018010790225813.
^ Wallach J, De Paoli G, Adejare A, Brandt SD (2014). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–50. doi:10.1002/dta.1468. PMID 23554350.
^ Maddox VH, Godefroi EF, Parcell RF (March 1965). "The synthesis of phencyclidine and other 1-arylcyclohexylamines". Journal of Medicinal Chemistry. 8 (2): 230–5. doi:10.1021/jm00326a019. PMID 14332667.
^ Jankovic M (28 January 2021). "EU Early Warning System" (PDF). Der Koordinator für Psychiatrie, Sucht- und Drogenfragen und der Beauftragte für Sucht- und Drogenfragen der Stadt Wien.
^ Minister for Human Capacities. "Amendment of Minister for Human Capacities Decree No 55/2014 of 30 December 2014 on substances or groups of compounds classified as new psychoactive substances, 2021/225/HU". European Commission.

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[1] Linders J, Furlano DC, Mattson MV, Jacobson AE, Rice KC (February 2010). "Synthesis and preliminary biochemical evaluation of novel derivatives of PCP". Letters in Drug Design & Discovery. 7 (2): 79–87. doi:10.2174/157018010790225813.

[pmid23554350-2] Wallach J, De Paoli G, Adejare A, Brandt SD (2014). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–50. doi:10.1002/dta.1468. PMID 23554350.

[pmid14332667-3] Maddox VH, Godefroi EF, Parcell RF (March 1965). "The synthesis of phencyclidine and other 1-arylcyclohexylamines". Journal of Medicinal Chemistry. 8 (2): 230–5. doi:10.1021/jm00326a019. PMID 14332667.

[4] Jankovic M (28 January 2021). "EU Early Warning System" (PDF). Der Koordinator für Psychiatrie, Sucht- und Drogenfragen und der Beauftragte für Sucht- und Drogenfragen der Stadt Wien.

[5] Minister for Human Capacities. "Amendment of Minister for Human Capacities Decree No 55/2014 of 30 December 2014 on substances or groups of compounds classified as new psychoactive substances, 2021/225/HU". European Commission.

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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 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 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

See also

References