3-MeO-PCP

3-MeO-PCP
Clinical data
ATC code
  • None
Legal status
Legal status
Identifiers
  • 1-[1-(3-methoxyphenyl)cyclohexyl]-piperidine
CAS Number
PubChem CID
ChemSpider
UNII
KEGG
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H27NO
Molar mass273.420 g·mol−1
3D model (JSmol)
  • COc3cccc(c3)C1(CCCCC1)N2CCCCC2
  • InChI=1S/C18H27NO/c1-20-17-10-8-9-16(15-17)18(11-4-2-5-12-18)19-13-6-3-7-14-19/h8-10,15H,2-7,11-14H2,1H3 checkY
  • Key:BQQSZHHKGPOXLN-UHFFFAOYSA-N checkY
 X markNcheckY (what is this?)  (verify)

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative anesthetic of the arylcyclohexylamine class structurally related to PCP. It has been sold online as a designer drug. It has been used across Europe and the United States. It acts mainly as an NMDA receptor antagonist, though it has also been found to interact with the sigma σ1 receptor and the serotonin transporter.

Pharmacology

Pharmacodynamics

3-MeO-PCP has a Ki of 20 nM for the PCP site of the NMDA receptor, which is higher than PCP or any other anisyl substition of PCP. It has secondary activity at multiple other receptors, with a Ki of 216 nM for the serotonin transporter (SERT), and 42 nM for the sigma σ1 receptor. It does not bind to the norepinephrine or dopamine transporter, nor to the sigma σ2 receptor (Ki >10,000 nM).

Based on structural similarity to 3-HO-PCP, it was initially expected that 3-MeO-PCP may have opioid activity. However, radioligand binding assays confirmed that the drug lacks significant activity at μ-, δ-, or κ-opioid receptors.

Pharmacokinetics

As of 2018, controlled clinical studies have not been performed in humans but the elimination half-life is estimated to be between 10 and 11 hours.

Chemistry

3-MeO-PCP hydrochloride is a white crystalline solid with a melting point of 204–205 °C.

History

3-MeO-PCP was first synthesized in 1979 to investigate the structure–activity relationships of phencyclidine (PCP) derivatives. The effects of 3-MeO-PCP in humans were not described until 1999 when a chemist using the pseudonym John Q. Beagle wrote that 3-MeO-PCP was qualitatively similar to PCP with comparable potency. Interest in gray-market dissociates accelerated in 2008, when an online research chemical vendor began offering the less potent 4-MeO-PCP. In 2009, a Swiss chemist described the effects of taking the drug on the Bluelight forums. 3-MeO-PCP first became available as a research chemical in 2011. The drug was first reported to the European Monitoring Centre for Drugs and Drug Addiction by the UK on March 29, 2012.

Society and culture

Recreational use

3-MeO-PCP has been more widely reported than many other similar grey market arylcyclohexylamines. 3-MeO-PCP has been available for purchase online as a research chemical. Use has been reported across Europe and the United States.

3-MeO-PCP is usually taken orally or nasally, but can also be injected or smoked. Duration and onset of effects varies depending on route of administration. When taken orally, onset takes 30–90 minutes and effects last 4–8 hours, generally peaking at 2-3 hours. Its effects are described as being similar to related dissociatives such as PCP.

Being slightly more potent than PCP, threshold doses starts at 1 mg, with substantial dissociative effects starting at 5 mg. Strong dissociative effects are seen at 10-20 mg. It has been described as producing more euphoria and mental clarity than similar drugs. Negative effects include hypertension, tachycardia, confusion, and disorientation. In one case of an individual taking a very large oral dose (300–500 mg), psychosis and aggressive behaviors, followed by amnesia were observed.

As of 2022, there has been two known deaths that can be attributed to 3-MeO-PCP alone; one in Sweden and one in the UK. There were 14 additional deaths where 3-MeO-PCP was detected in the blood post-mortem.

United Kingdom

On October 18, 2012, the Advisory Council on the Misuse of Drugs in the United Kingdom released a report about methoxetamine, saying that the "harms of methoxetamine are commensurate with Class B of the Misuse of Drugs Act (1971)". The report went on to suggest that all analogues of MXE should also become class B drugs and suggested a catch-all clause covering both existing and unresearched arylcyclohexylamines, including 3-MeO-PCP.

United States

3-MeO-PCP is not a controlled substance in the United States but possession or distribution of 3-MeO-PCP for human use could potentially be prosecuted under the Federal Analogue Act due to its structural and pharmacological similarities to PCP.

Canada

Canada's Controlled Drugs And Substances Act has placed all PCP analogues, derivatives, salts and further children thereof under a Schedule 1 prohibition, alongside opioids, cocaine and other top-ranked illegal psychoactive substances. As such, 3-MeO-PCP is automatically banned, although it is not mentioned by name in the schedule. Only PCP and Ketamine are specifically written in.

Sweden

3-MeO-PCP is a controlled substance in Sweden.

Czech Republic

3-MeO-PCP is banned in the Czech Republic.

Chile

As per Chile's Ley de drogas, aka Ley 20000, all esters and ethers of PCP are illegal. As 3-MeO-PCP is an ether of PCP, it is thus illegal.

Portugal

3-MeO-PCP is neither a salt nor an isomer of PCP, not making it illegal.

See also

References

  1. ↑ Drug Enforcement Administration (23 March 2026). "Schedules of Controlled Substances: Placement of 3-Methoxyphencyclidine (1-(1-(3-Methoxyphenyl)cyclohexyl)piperidine) in Schedule I". Federal Register. 91: 13733–13736. Document no. 2026-05618; Docket No. DEA-1146. Retrieved 23 October 2026.
  2. 1 2 3 4 5 6 7 8 9 10 11 Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 6 (7–8): 614–632. doi:10.1002/dta.1620. PMID 24678061.
  3. 1 2 3 4 5 Roth BL, Gibbons S, Arunotayanun W, Huang XP, Setola V, Treble R, et al. (2013). "The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor". PLOS ONE. 8 (3) e59334. Bibcode:2013PLoSO...859334R. doi:10.1371/journal.pone.0059334. PMC 3602154. PMID 23527166.
  4. 1 2 3 4 Advisory Council on the Misuse of Drugs (2012-10-18). "(ACMD) Methoxetamine Report (2012)" (PDF). GOV.UK. GOV.UK. p. 14. Retrieved 2012-10-22.
  5. ↑ Morris H (2011-02-11). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". VICE. Vice Magazine. Retrieved 2012-01-23.{{cite web}}: CS1 maint: deprecated archival service (link)
  6. 1 2 3 Wallach J, Brandt SD (2018). "Phencyclidine-Based New Psychoactive Substances". In Maurer HH, Brandt SD (eds.). Handbook of Experimental Pharmacology. Vol. 252. Cham: Springer International Publishing=. pp. 261–303. doi:10.1007/164_2018_124. ISBN 978-3-030-10561-7. PMID 30105474.
  7. ↑ Wallach J, De Paoli G, Adejare A, Brandt SD (2013). "Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues". Drug Testing and Analysis. 6 (7–8): 633–650. doi:10.1002/dta.1468. PMID 23554350.
  8. ↑ De Paoli G, Brandt SD, Wallach J, Archer RP, Pounder DJ (June 2013). "From the street to the laboratory: analytical profiles of methoxetamine, 3-methoxyeticyclidine and 3-methoxyphencyclidine and their determination in three biological matrices". Journal of Analytical Toxicology. 37 (5): 277–283. doi:10.1093/jat/bkt023. PMID 23552616.
  9. 1 2 Copeland CS, Hudson S, Treble R, Hamnett HJ (May 2022). "The First Fatal Intoxication with 3-MeO-PCP in the UK and a Review of the Literature". Journal of Analytical Toxicology. 46 (5): 461–470. doi:10.1093/jat/bkac015. PMID 35246686.
  10. 1 2 Expert Committee on Drug Dependence 43rd Meeting (20 October 2020). "Critical Review Report: 3-Methoxyphencyclidine (3-MeO-PCP)" (PDF). World Health Organization.
  11. ↑ Pepe M, Di Nicola M, Cocciolillo F, Chiappini S, Martinotti G, Calcagni ML, et al. (March 2024). "3-Methoxy-Phencyclidine Induced Psychotic Disorder: A Literature Review and an 18F-FDG PET/CT Case Report". Pharmaceuticals. 17 (4). Basel, Switzerland: 452. doi:10.3390/ph17040452. PMC 11053433. PMID 38675413.
  12. ↑ "Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012". GOV.UK. Advisory Council on the Misuse of Drugs. 18 October 2012.
  13. ↑ Food and Drug Administration (August 4, 2020). International Drug Scheduling; Convention on Psychotropic Substances; Single Convention on Narcotic Drugs; Isotonitazene; MDMB-4en-PINACA; CUMYL-PEGACLONE; Flubromazolam; Clonazolam; Diclazepam; 3-MeO-PCP; DIPHENIDINE; 2-MEO-DIPHENIDINE; 5-MEO-DALT; and 3-FLUOROPHENMETRAZINE (3-FPM); Request for Comments (Report). pp. 47217–47220. FDA-2020-N-1680. Retrieved June 15, 2024. If intended for human consumption, 3-MeO-PCP may be treated as a "controlled substance analogue
  14. ↑ "Controlled Drugs And Substances Act". Government of Canada Justice Laws. 18 March 2021. Retrieved 25 April 2021.
  15. ↑ "SFS 1992:1554/konsolidering/2025:77 – Förordning om kontroll av narkotika". lagen.nu (in Swedish). Retrieved 2026-09-20.
  16. ↑ "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" [Substances added to list No. 4 of psychotropic substances (Annex No. 4 to Government Regulation No. 463/2013 Coll.)] (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
  17. ↑ Nacional BD (22 October 2015). "Sustituye La Ley Nº 19.366, Que Sanciona El Trafico Ilicito De Estupefacientes Y Sustancias Sicotropicas" [Replaces Law No. 19,366, Which Punishes Illicit Trafficking in Narcotic Drugs and Psychotropic Substances]. www.bcn.cl/leychile (in Spanish). Bibloteca Del Congreso Nacional. Retrieved 6 February 2018.
  18. ↑ "Legislação de Combate à Droga, Tabela II-A" [Anti-Drug Legislation, Table II-A]. Procuradoria-Geral Distrital de Lisboa (in Portuguese). Ministério Público.