3-MeO-PCP

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

3-Methoxyphencyclidine (3-MeO-PCP) is a dissociative anesthetic drug with hallucinogenic and sedative effects that has been sold as a research chemical. It is around the same potency as phencyclidine, but has slightly different effects due to its altered binding profile at various targets, particularly being somewhat more potent as an NMDA antagonist while having around the same potency as a dopamine reuptake inhibitor.[1][2][3][4]

The corresponding 4-methoxy derivative 4-MeO-PCP is also known, but is around 10 times less potent by weight than the 3-methoxy isomer, making it around the same potency as ketamine.

3-MeO-PCP has a Ki of 20 nM for the NMDA receptor, 216 nM for the SERT receptor and 42 for the sigma1 receptor[5]

On October 18, 2012 the ACMD 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.[5]

See also [edit]

References [edit]

  1. ^ Vignon J, Vincent JP, Bidard JN, Kamenka JM, Geneste P, Monier S, Lazdunski M (July 1982). "Biochemical properties of the brain phencyclidine receptor". European Journal of Pharmacology 81 (4): 531–42. doi:10.1016/0014-2999(82)90342-9. PMID 6214413. 
  2. ^ Manallack DT, Wong MG, Costa M, Andrews PR, Beart PM (December 1988). "Receptor site topographies for phencyclidine-like and sigma drugs: predictions from quantitative conformational, electrostatic potential, and radioreceptor analyses". Molecular Pharmacology 34 (6): 863–79. PMID 2849051. 
  3. ^ Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R (March 1989). "Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs". Pharmacology, Biochemistry, and Behavior 32 (3): 699–705. doi:10.1016/0091-3057(89)90020-8. PMID 2544905. 
  4. ^ Manallack DT, Davies JW, Beart PM, Saunders MR, Livingstone DJ (October 1993). "Analysis of the biological and molecular properties of phencyclidine-like compounds by chemometrics". Arzneimittel-Forschung 43 (10): 1029–32. PMID 8267664. 
  5. ^ a b "(ACMD) Methoxetamine Report (2012)" (PDF). UK Home Office. 2012-10-18. p. 14. Retrieved 2012-10-22.