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3-MeO-PCP

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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
 ☒NcheckY (what is this?)  (verify)

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) which has been sold online as a designer drug.[1][2][3] It has been used across Europe and the United States. In some cases, consumption has been known to be fatal. 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.[2][3] The drug does not possess any opioid activity nor does it act as a dopamine reuptake inhibitor.[1][2][3]

Pharmacology

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3-MeO-PCP has a Ki of 20 nM for the dizocilpine (MK-801) site of the NMDA receptor, 216 nM for the serotonin transporter (SERT), and 42 nM for the sigma σ1 receptor.[3][2] It does not bind to the norepinephrine or dopamine transporter nor to the sigma σ2 receptor (Ki >10,000 nM).[2] Based on its structural similarity to 3-hydroxy-PCP (3-HO-PCP), which uniquely among arylcyclohexylamines has high affinity for the μ-opioid receptor in addition to the NMDA receptor, it was initially expected that 3-MeO-PCP would have opioid activity.[1][4] However, radioligand binding assays with human proteins have shown that, contrary to common belief, the drug also does not interact with the μ-, δ-, or κ-opioid receptors at concentrations of up to 10,000 nM.[2] As such, the notion that 3-MeO-PCP has opioid activity has been described as a myth.[1]

3-MeO-PCP binds to the NMDA receptor with higher affinity than PCP and has the highest affinity of the three isomeric anisyl-substitutions of PCP, followed by 2-MeO-PCP and 4-MeO-PCP.[2][3]

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.[5]

Chemistry

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3-MeO-PCP hydrochloride is a white crystalline solid with a melting point of 204–205 °C.[6]

History

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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.[1] Interest in gray-market dissociates accelerated in 2008, when an online research chemical vendor began offering the less potent 4-MeO-PCP.[1] In 2009, a Swiss chemist described the effects of taking the drug on the Bluelight forums.[1] 3-MeO-PCP first became available as a research chemical in 2011.[1] The drug was first reported to the European Monitoring Centre for Drugs and Drug Addiction by the UK on March 29, 2012.[1]

Society and culture

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Recreational use

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Based on the number of reported intoxications, 3-MeO-PCP is likely more popular than other similar grey market arylcyclohexylamines.[5] 3-MeO-PCP has been available for purchase online as a research chemical.[7] It has been found in drug samples in the United Kingdom and Italy. It is also known to be used in France, The Netherlands, Sweden, The United States, Spain, and the Czech Republic.[8]

3-MeO-PCP is usually taken orally or nasally, but can also be injected or smoked.[9] Duration and onset of effects varies depending on route of administration. When taken orally, onset takes 30-90 minutes and effects last 4-12 hours.[8] Its effects are described as a dissociative hallucinogen, similar to PCP. Being slightly more potent than PCP, threshold activity is exhibited at 3-5mg, with dissociative effects starting at 5mg.[1] Strong dissociative effects are seen at 10mg-20mg.[1] The effects are generally reported as positive, with more euphoria and mental clarity than similar drugs.[1] Negative effects include hypertension, tachycardia, confusion, and disorientation.[5] In one case of an individual taking a very large oral dose (300-500mg), psychosis and aggressive behaviors, followed by amnesia were observed.[10]

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.[8]

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United Kingdom

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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)".[11] 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.[3]

United States

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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.[12]

Canada

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Canada's Controlled Drugs And Substances Act has for years placed all PCP analogues, derivatives, salts and further children thereof under a Schedule 1 prohibition, alongside opioids, cocaine and other top-ranked illegal psychoactives. 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.[13]

Sweden

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Sweden's public health agency suggested classifying 3-MeO-PCP as hazardous substance on November 10, 2014.[14]

Czech Republic

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3-MeO-PCP is banned in the Czech Republic.[15]

Chile

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As per Chile's Ley de drogas, aka Ley 20000,[16] all esters and ethers of PCP are illegal. As 3-MeO-PCP is an ether of PCP, it is thus illegal.

Portugal

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3-MeO-PCP is neither a salt nor an isomer of PCP,[17] not making it illegal.

See also

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References

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  1. ^ a b c d e f g h i j k l 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.
  2. ^ a b c d e f g 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.
  3. ^ a b c d e f "(ACMD) Methoxetamine Report (2012)" (PDF). UK Home Office. 2012-10-18. p. 14. Retrieved 2012-10-22.
  4. ^ Morris H (2011-02-11). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2012-01-23.
  5. ^ a b c Wallach J, Brandt SD (2018). Maurer HH, Brandt SD (eds.). "Phencyclidine-Based New Psychoactive Substances". Handbook of Experimental Pharmacology. 252. Cham: Springer International Publishing=: 261–303. doi:10.1007/164_2018_124. ISBN 978-3-030-10561-7. PMID 30105474.
  6. ^ 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.
  7. ^ 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.
  8. ^ a b c 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.
  9. ^ Expert Committee on Drug Dependence 43rd Meeting (20 October 2020). "Critical Review Report: 3-Methoxyphencyclidine (3-MeO-PCP)" (PDF). World Health Organization.
  10. ^ 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): 452. doi:10.3390/ph17040452. PMC 11053433. PMID 38675413.
  11. ^ "Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012". Advisory Council on the Misuse of Drugs. 18 October 2012.
  12. ^ 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
  13. ^ "Controlled Drugs And Substances Act". Government of Canada Justice Laws. 18 March 2021. Retrieved 25 April 2021.
  14. ^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard]. Folkhalsomyndigheten (The Public Health Agency of Sweden). Retrieved 29 June 2015.
  15. ^ "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.
  16. ^ "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] (in Spanish). Bibloteca Del Congreso Nacional. 22 October 2015. Retrieved 6 February 2018.
  17. ^ "Legislação de Combate à Droga, Tabela II-A" [Anti-Drug Legislation, Table II-A]. Procuradoria-Geral Distrital de Lisboa (in Portuguese). Ministério Público.
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