3-MeO-PCP

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3-MeO-PCP
3-methoxyphencyclidine.png
Systematic (IUPAC) name
1-[1-(3-methoxyphenyl)cyclohexyl]-piperidine
Clinical data
Legal status
?
Identifiers
CAS number 72242-03-6 N
91164-58-8 (hydrochloride)
ATC code None
PubChem CID 11778080
ChemSpider 9952762 YesY
Chemical data
Formula C18H27NO 
Mol. mass 273.412 g/mol
 N (what is this?)  (verify)

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative anesthetic drug that has been sold online as a research chemical. The compound was first synthesized in 1979 to investigate the structure-activity relationship of phencyclidine derivatives. The activity of 3-MeO-PCP in man was 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] 3-MeO-PCP binds to the NMDA receptor with higher affinity than PCP and has the highest affinity of the three isomeric anisyl-substitutions, followed by 2-MeO-PCP and 4-MeO-PCP. Though 3-MeO-PCP is often described as having opioid or dopaminergic activity,[2] this supposition is contradicted by data showing 3-MeO-PCP to be a potent and selective ligand for the NMDA receptor without appreciable affinity for the µ-opioid receptor or dopamine transporter.[3][4] 3-MeO-PCP was preceded by the less potent dissociative 4-MeO-PCP and first became available as a research chemical in 2011.[1]

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

3-MeO-PCP has a Ki of 20 nM for the NMDA receptor, 216 nM for the serotonin transporter and 42 for the sigma1 receptor[3]

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)", despite the fact that the act does not classify drugs based on harm. 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 arylcyclohexamines, including 3-MeO-PCP.[3]

See also[edit]

References[edit]

  1. ^ a b Morris, H.; Wallach, J. (2014). "From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs". Drug Testing and Analysis. 
  2. ^ Morris, H. (2011-02-11). "Interview with a ketamine chemist: or to be more precise, an arylcyclohexylamine chemist". Vice Magazine. Retrieved 2012-01-23. 
  3. ^ a b c "(ACMD) Methoxetamine Report (2012)" (PDF). UK Home Office. 2012-10-18. p. 14. Retrieved 2012-10-22. 
  4. ^ Roth, B.; Gibbons, S. (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". 
  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.