3-MeO-PCP

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 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]

3-MeO-PCP
Clinical data
ATC code
  • None
Legal status
Legal status
  • CA: Schedule I
  • DE: Anlage II (Authorized trade only, not prescriptible)
  • UK: Class B
  • Illegal in the Czech Republic and Sweden
Identifiers
IUPAC name
  • 1-[1-(3-methoxyphenyl)cyclohexyl]-piperidine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC18H27NO
Molar mass273.420 g·mol−1
3D model (JSmol)
SMILES
  • COc3cccc(c3)C1(CCCCC1)N2CCCCC2
InChI
  • 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 Y
  • Key:BQQSZHHKGPOXLN-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

Pharmacology

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]

Chemistry

3-MeO-PCP hydrochloride is a white crystalline solid with a melting point of 204–205 °C.[5]

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.[6] 3-MeO-PCP was preceded by the less potent dissociative 4-MeO-PCP and first became available as a research chemical in 2011.[6]

Society and culture

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)".[7] 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

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 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.[8]

Sweden

Sweden's public health agency suggested classifying 3-MeO-PCP as hazardous substance on November 10, 2014.[9]

Czech Republic

3-MeO-PCP is banned in the Czech Republic.[10]

Chile

As per Chile's Ley de drogas, aka Ley 20000,[11] 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,[12] not making it illegal.

See also

References
  1. Morris H, Wallach J (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Test Anal. 6 (7–8): 614–32. doi:10.1002/dta.1620. PMID 24678061.
  2. Roth BL, Gibbons S, Arunotayanun W, Huang XP, Setola V, Treble R, Iversen L (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. "(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. Wallach J, De Paoli G, Adejare A, Brandt S (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.
  6. 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.
  7. "Advisory Council on the Misuse of Drugs (ACMD) Methoxetamine report, 2012". Advisory Council on the Misuse of Drugs. 18 October 2012.
  8. "Controlled Drugs And Substances Act". Government of Canada Justice Laws. 18 March 2021. Retrieved 25 April 2021.
  9. "Cannabinoider föreslås bli klassade som hälsofarlig vara". Retrieved 29 June 2015.
  10. "Látky, o které byl doplněn seznam č. 4 psychotropních látek (příloha č. 4 k nařízení vlády č. 463/2013 Sb.)" (PDF) (in Czech). Ministerstvo zdravotnictví. Archived from the original (PDF) on 2016-03-09. Retrieved 2016-02-06.
  11. "SUSTITUYE LA LEY Nº 19.366, QUE SANCIONA EL TRAFICO ILICITO DE ESTUPEFACIENTES Y SUSTANCIAS SICOTROPICAS" (in Spanish). Bibloteca Del Congreso Nacional. 22 October 2015. Retrieved 6 February 2018.
  12. "Legislação de Combate à Droga, Tabela II-A"
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