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4-MeO-PCP

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
4-MeO-PCP
Clinical data
ATC code
  • none
Legal status
Legal status
Identifiers
  • 1-[1-(4-methoxyphenyl)cyclohexyl]-piperidine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC18H27NO
Molar mass273.420 g·mol−1
3D model (JSmol)
  • COc1ccc(cc1)C2(CCCCC2)N3CCCCC3
  • InChI=1S/C18H27NO/c1-20-17-10-8-16(9-11-17)18(12-4-2-5-13-18)19-14-6-3-7-15-19/h8-11H,2-7,12-15H2,1H3 checkY
  • Key:MUZGGFNYVLGUFS-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

4-Methoxyphencyclidine (methoxydine,4-MeO-PCP) is adissociativeanesthetic drug that has been sold online as aresearch chemical. The synthesis of 4-MeO-PCP was first reported in 1965 by theParke-Davis medicinal chemist Victor Maddox.[1] A 1999 review published by a chemist using the pseudonym John Q. Beagle suggested the potency of 4-MeO-PCP in man was reduced relative to PCP, two years later Beagle published a detailed description of the synthesis and qualitative effects of 4-MeO-PCP, which he said possessed 70% the potency of PCP.[1] 4-MeO-PCP was the firstarylcyclohexylamine research chemical to be sold online, it was introduced in late 2008 by a company trading under the name CBAY and was followed by several related compounds such as3-MeO-PCP andmethoxetamine.[1][2] 4-MeO-PCP has lower affinity for theNMDA receptor than PCP, but higher affinity thanketamine, it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects.[1][3] Users have reported substantial differences in active dose, these discrepancies can be partially explained by the presence of unreacted PCC and other impurities in samples sold on thegrey market.[1] 4-MeO-PCP hasKi values of 404 nM for theNMDA receptor, 713 nM for thenorepinephrine transporter, 844 nM for theserotonin transporter, 296 nM for theσ1 receptor and 143 nM for theσ2 receptor.[3]

4-MeO-PCP hydrochloride is a white crystalline solid with a melting point of 181-182 °C[4]

Side effects

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4-MeO-PCP has caused a fatality in combination with4-HO-MET,venlafaxine,olanzapine,lorazepam andhydroxyzine.[5]

Legality

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On October 18, 2012, theAdvisory Council on the Misuse of Drugs in theUnited Kingdom released areport aboutmethoxetamine, saying that the "harms of methoxetamine are commensurate withClass B of theMisuse 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 4-MeO-PCP.[6]

Sweden's public health agency suggested classifying 4-MeO-PCP as hazardous substance on November 10, 2014.[7]

As per Chile'sLey de drogas, aka Ley 20000,[8] all esters and ethers of PCP are illegal. As 4-MeO-PCP is anether of PCP, it is thus illegal.

See also

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References

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  1. ^abcdeMorris 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. ^King LA (6–8 May 2009).New drugs coming our way - what are they and how do we detect them?. EMCDDA Conference. Lisbon. Archived fromthe original on 14 May 2013. Retrieved11 October 2010.
  3. ^abRoth 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.
  4. ^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.
  5. ^McIntyre IM, Trochta A, Gary RD, Storey A, Corneal J, Schaber B (August 2015)."A Fatality Related to Two Novel Hallucinogenic Compounds: 4-Methoxyphencyclidine and 4-Hydroxy-N-methyl-N-ethyltryptamine".Journal of Analytical Toxicology.39 (9):751–755.doi:10.1093/jat/bkv089.PMID 26265285.
  6. ^"Methoxetamine Report (2012)"(PDF).Advisory Council on the Misuse of Drugs (ACMD). UK Home Office. 2012-10-18. p. 14. Retrieved2012-10-22.
  7. ^"Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as a health hazard].Folkhälsomyndigheten [The Public Health Authority] (in Swedish). Retrieved29 June 2015.
  8. ^"Sustituye La Ley Nº 19.366, Que Sanciona el Trafico Ilicito de Estupefacientes y Sustancias Sicotropicas" [Substitutes Law No. 19,366, which Sanctions Illicit Trafficking of Narcotic Drugs and Psychotropic Substances].Bibloteca Del Congreso Nacional [National Library of Congress] (in Spanish). 22 October 2015. Retrieved6 February 2018.
Arylcyclo‐
hexylamines
Adamantanes
Diarylethylamines
Morphinans
Inhalants
Others
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
σ1
σ2
Unsorted
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