| Revision as of 20:15, 20 September 2011 editCheMoBot (talk | contribs)Bots141,565 edits Updating {{drugbox}} (no changed fields - added verified revid - updated 'UNII_Ref', 'ChEMBL_Ref', 'ChEBI_Ref', 'KEGG_Ref', 'ChEBI_Ref') per Chem/Drugbox validation (report errors or [[user← Previous edit |
Latest revision as of 16:39, 23 September 2024 edit undoJWBE (talk | contribs)Extended confirmed users10,127 edits removed Category:Phenol ethers; added Category:4-Methoxyphenyl compounds using HotCat |
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{{Short description|Chemical compound}} |
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{{Drugbox |
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{{Infobox drug |
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| verifiedrevid = 443354313 |
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| Verifiedfields = changed |
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⚫ |
| verifiedrevid = 451559315 |
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| IUPAC_name = 1--piperidine |
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| IUPAC_name = 1--piperidine |
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| image = 4-methoxyphencyclidine.png |
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| image = 4-MeO-PCP.svg |
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| width = 200 |
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| width = 200 |
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<!--Clinical data--> |
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<!--Clinical data--> |
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| tradename = |
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| tradename = |
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| legal_status = Not Currently Scheduled |
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| legal_status = <!--Not Currently Scheduled country?--> |
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| legal_CA = Schedule I |
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| legal_UK = Class B |
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| legal_DE = NpSG |
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<!--Identifiers--> |
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<!--Identifiers--> |
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| CAS_number_Ref = {{cascite|correct|??}} |
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| CAS_number = 2201-35-6 |
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| CAS_number = 2201-35-6 |
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| CAS_supplemental = <br /> 91164-58-8 (hydrochloride) |
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| CAS_supplemental = <br /> 91164-58-8 (hydrochloride) |
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| ATC_prefix = none |
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| ATC_prefix = none |
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| PubChem = 11778080 |
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| PubChem = 15100753 |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| DrugBank_Ref = {{drugbankcite|correct|drugbank}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} |
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| ChemSpiderID = 10526416 |
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| ChemSpiderID = 10526416 |
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| UNII_Ref = {{fdacite|changed|FDA}} |
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| UNII = OZM0C31BLL |
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<!--Chemical data--> |
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<!--Chemical data--> |
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| C=18 | H=27 | N=1 | O=1 |
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| C=18 | H=27 | N=1 | O=1 |
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| smiles = COc1ccc(cc1)C2(CCCCC2)N3CCCCC3 |
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| molecular_weight = 273.412 g/mol |
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| smiles = COc3cccc(c3)C1(CCCCC1)N2CCCCC2 |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI_Ref = {{stdinchicite|correct|chemspider}} |
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| StdInChI = 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 |
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| StdInChI = 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 |
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'''4-Methoxyphencyclidine''' ('''methoxydine''', '''4-MeO-PCP''') is a ] ] drug that has been sold online as a ]. The synthesis of 4-MeO-PCP was first reported in 1965 by the ] medicinal chemist Victor Maddox.<ref name=Morris>{{cite journal | vauthors = Morris H, Wallach J | title = From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs | journal = Drug Testing and Analysis | volume = 6 | issue = 7–8 | pages = 614–632 | year = 2014 | pmid = 24678061 | doi = 10.1002/dta.1620 }}</ref> 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.<ref name="Morris"/> 4-MeO-PCP was the first ] 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 as ] and ].<ref name="Morris"/><ref>{{cite conference | vauthors = King LA | title = New drugs coming our way - what are they and how do we detect them? | conference = EMCDDA Conference | location = Lisbon | date = 6–8 May 2009 | url = http://www.emcdda.europa.eu/attachements.cfm/att_78745_EN_4_King.pps }}</ref> 4-MeO-PCP has lower affinity for the ] than PCP, but higher affinity than ], it is orally active in a dosage range similar to ketamine, with some users requiring doses in excess of 100 mg for desired effects.<ref name="Morris"/><ref name=Roth>{{cite journal | vauthors = Roth BL, Gibbons S, Arunotayanun W, Huang XP, Setola V, Treble R, Iversen L | title = The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor | journal = PLOS ONE | volume = 8 | issue = 3 | pages = e59334 | year = 2013 | pmid = 23527166 | pmc = 3602154 | doi = 10.1371/journal.pone.0059334 | bibcode = 2013PLoSO...859334R | doi-access = free }}</ref> 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 the ].<ref name="Morris"/> 4-MeO-PCP has ] values of 404 nM for the ], 713 nM for the ], 844 nM for the ], 296 nM for the ] and 143 nM for the ].<ref name="Roth"/> |
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'''4-Methoxyphencyclidine''' ('''methoxydine''', '''4-MeO-PCP''') is a ] ] drug with ]ic and ] effects. It is around the same potency as ], but has slightly different effects due to its altered binding profile at various targets, particularly being somewhat more potent as an ] while having around the same potency as a ].<ref name="pmid6214413">{{cite journal |author=Vignon J, Vincent JP, Bidard JN, Kamenka JM, Geneste P, Monier S, Lazdunski M |title=Biochemical properties of the brain phencyclidine receptor |journal=European Journal of Pharmacology |volume=81 |issue=4 |pages=531–42 |year=1982 |month=July |pmid=6214413 |doi= 10.1016/0014-2999(82)90342-9|url=}}</ref><ref name="pmid2849051">{{cite journal |author=Manallack DT, Wong MG, Costa M, Andrews PR, Beart PM |title=Receptor site topographies for phencyclidine-like and sigma drugs: predictions from quantitative conformational, electrostatic potential, and radioreceptor analyses |journal=Molecular Pharmacology |volume=34 |issue=6 |pages=863–79 |year=1988 |month=December |pmid=2849051 |doi= |url=}}</ref><ref name="pmid2544905">{{cite journal |author=Chaudieu I, Vignon J, Chicheportiche M, Kamenka JM, Trouiller G, Chicheportiche R |title=Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs |journal=Pharmacology, Biochemistry, and Behavior |volume=32 |issue=3 |pages=699–705 |year=1989 |month=March |pmid=2544905 |doi= 10.1016/0091-3057(89)90020-8|url=}}</ref><ref name="pmid8267664">{{cite journal |author=Manallack DT, Davies JW, Beart PM, Saunders MR, Livingstone DJ |title=Analysis of the biological and molecular properties of phencyclidine-like compounds by chemometrics |journal=Arzneimittel-Forschung |volume=43 |issue=10 |pages=1029–32 |year=1993 |month=October |pmid=8267664 |doi= |url=}}</ref> |
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4-MeO-PCP hydrochloride is a white crystalline solid with a melting point of 181-182 °C<ref name="PMID23554350">{{cite journal | vauthors = Wallach J, De Paoli G, Adejare A, Brandt SD | title = Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues | journal = Drug Testing and Analysis | volume = 6 | issue = 7–8 | pages = 633–650 | date = 2013 | pmid = 23554350 | doi = 10.1002/dta.1468 }}</ref> |
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The positional isomer ] is also known. Being around 10 times more potent by weight than the 4-methoxy isomer it has around the same potency as ]. 4-Meo-PCP was reportedly first sold within the UK from 2008 as a ] and ] by a company trading under the name CBAY.<ref></ref> |
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==See also== |
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==Side effects== |
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4-MeO-PCP has caused a fatality in combination with ], ], ], ] and ].<ref>{{cite journal | vauthors = McIntyre IM, Trochta A, Gary RD, Storey A, Corneal J, Schaber B | title = A Fatality Related to Two Novel Hallucinogenic Compounds: 4-Methoxyphencyclidine and 4-Hydroxy-N-methyl-N-ethyltryptamine | journal = Journal of Analytical Toxicology | volume = 39 | issue = 9 | pages = 751–755 | date = August 2015 | pmid = 26265285 | doi = 10.1093/jat/bkv089 | doi-access = free }}</ref> |
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==Legality== |
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On October 18, 2012, the ] in the ] released a about ], saying that the "harms of methoxetamine are commensurate with ] of the ]", 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.<ref name='ACMD MXE report'>{{ cite web | url = http://www.homeoffice.gov.uk/publications/agencies-public-bodies/acmd1/methoxetamine2012 | title = Methoxetamine Report (2012) | access-date = 2012-10-22 | date = 2012-10-18 | format = PDF | pages = 14 | work = Advisory Council on the Misuse of Drugs (ACMD) | publisher = UK Home Office}}</ref> |
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Sweden's public health agency suggested classifying 4-MeO-PCP as hazardous substance on November 10, 2014.<ref>{{cite web | url=http://www.folkhalsomyndigheten.se/nyheter-och-press/nyhetsarkiv/2014/november/cannabinoider-foreslas-bli-klassade-som-halsofarlig-vara/ | title=Cannabinoider föreslås bli klassade som hälsofarlig vara | trans-title = Cannabinoids are proposed to be classified as a health hazard | work = Folkhälsomyndigheten | trans-work = The Public Health Authority | language = Swedish | access-date=29 June 2015}}</ref> |
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As per Chile's ], aka Ley 20000,<ref>{{cite web | url=https://www.leychile.cl/Navegar?idNorma=235507 | title=Sustituye La Ley Nº 19.366, Que Sanciona el Trafico Ilicito de Estupefacientes y Sustancias Sicotropicas | trans-title = Substitutes Law No. 19,366, which Sanctions Illicit Trafficking of Narcotic Drugs and Psychotropic Substances | work = Bibloteca Del Congreso Nacional | trans-work = National Library of Congress | date=22 October 2015 | language=es | access-date=6 February 2018}}</ref> all esters and ethers of PCP are illegal. As 4-MeO-PCP is an ] of PCP, it is thus illegal. |
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== See also == |
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==References== |
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== References == |
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{{Reflist}} |
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{{Depressants}} |
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{{Hallucinogens}} |
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{{Hallucinogens}} |
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{{Ionotropic glutamate receptor modulators}} |
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{{Glutamatergics}} |
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{{Sigma receptor modulators}} |
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{{hallucinogen-stub}} |
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