3-HO-PCP acts as a high-affinityuncompetitive antagonist of the NMDA receptor via the dizocilpine (MK-801) site (Ki = 30 nM).[3][4] It has much higher affinity than PCP for this site (Ki = 250 nM, for comparison; 8-fold difference).[4] The drug also has high affinity for the μ-opioid receptor (MOR) (Ki = 39–60 nM) in animal test subjects,[3][4][5][6] the κ-opioid receptor (KOR) (Ki = 140 nM),[5] and the sigmaσ1 receptor (Ki = 42 nM; IC50 = 19 nM),[5][7][8][9] whereas it has only low affinity for the δ-opioid receptor (Ki = 2,300 nM).[5] The high affinity of 3-HO-PCP for opioid receptors is unique among arylcyclohexylamines and is in contrast to PCP, which has only very low affinity for the MOR (Ki = 11,000–26,000 nM; 282- to 433-fold difference) and the other opioid receptors (Ki = 4,100 nM for the KOR and 73,000 nM for the DOR).[4][5]
Although it was hypothesized that 3-HO-PCP might be a metabolite of PCP in humans, there is no evidence that this is the case.[10][11]
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-HO-PCP.[12]
3-HO-PCP is banned in Sweden[13][14] and Switzerland.[15]
^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.
^Davidsen AB, Mardal M, Johansen SS, Dalsgaard PW, Linnet K (July 2020). "In vitro and in vivo metabolism and detection of 3-HO-PCP, a synthetic phencyclidine, in human samples and pooled human hepatocytes using high resolution mass spectrometry". Drug Testing and Analysis. 12 (7): 987–993. doi:10.1002/dta.2807. PMID 32311838. S2CID 216047397.
^ abcdMorris 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.
^ abcdKamenka JM, Chiche B, Goudal R, Geneste P, Vignon J, Vincent JP, Lazdunski M (April 1982). "Chemical synthesis and molecular pharmacology of hydroxylated 1-(1-phenylcyclohexyl-piperidine derivatives". Journal of Medicinal Chemistry. 25 (4): 431–435. doi:10.1021/jm00346a019. PMID 6279847.
^ abcdeJohnson N, Itzhak Y, Pasternak GW (June 1984). "Interaction of two phencyclidine opiate-like derivatives with 3H-opioid binding sites". European Journal of Pharmacology. 101 (3–4): 281–284. doi:10.1016/0014-2999(84)90171-7. PMID 6088255.
^Itzhak Y, Kalir A, Sarne Y (July 1981). "On the opioid nature of phencyclidine and its 3-hydroxy derivative". European Journal of Pharmacology. 73 (2–3): 229–233. doi:10.1016/0014-2999(81)90097-2. PMID 6273187.
^Itzhak Y, Hiller JM, Simon EJ (January 1985). "Characterization of specific binding sites for [3H](d)-N-allylnormetazocine in rat brain membranes". Molecular Pharmacology. 27 (1): 46–52. PMID 3965930.
^Itzhak Y (April 1987). "[3H]PCP-3-OH and (+)[3H]SKF 10047 binding sites in rat brain membranes: evidence of multiplicity". European Journal of Pharmacology. 136 (2): 231–234. doi:10.1016/0014-2999(87)90715-1. PMID 3036548.
^Itzhak Y (1988). "Pharmacological specificity of some psychotomimetic and antipsychotic agents for the sigma and PCP binding sites". Life Sciences. 42 (7): 745–752. doi:10.1016/0024-3205(88)90646-7. PMID 2893238.
^Holsztynska EJ, Domino EF (1985). "Biotransformation of phencyclidine". Drug Metabolism Reviews. 16 (3): 285–320. doi:10.3109/03602538508991437. PMID 3914938.
^Holsztynska EJ, Domino EF (1986). "Quantitation of phencyclidine, its metabolites, and derivatives by gas chromatography with nitrogen-phosphorus detection: application for in vivo and in vitro biotransformation studies". Journal of Analytical Toxicology. 10 (3): 107–115. doi:10.1093/jat/10.3.107. PMID 3724069.
^"(ACMD) Methoxetamine Report (2012)" (PDF). UK Home Office. 2012-10-18. p. 14. Retrieved 2015-06-24.
^"Elva nya ämnen klassas som narkotika eller hälsofarlig vara" [Eleven new substances are classified as narcotics or dangerous goods] (in Swedish). Folkhälsomyndigheten. 28 June 2018.
^"Förordning (1992:1554) om kontroll av narkotika" [Ordinance (1992:1554) on the control of narcotics]. Riksdagsförvaltningen (in Swedish).
^"Verordnung des EDI vom 30. Mai 2011 über die Verzeichnisse der Betäubungsmittel, psychotropen Stoffe, Vorläuferstoffe und Hilfschemikalien (Betäubungsmittelverzeichnisverordnung, BetmVV-EDI)" [EDI ordinance of May 30, 2011 on the lists of narcotics, psychotropic substances, precursors and auxiliary chemicals (narcotics list ordinance, BetmVV-EDI)] (in German). Der Bundesrat.
April 20, 2023
hydroxyphencyclidine, dissociative, arylcyclohexylamine, class, related, phencyclidine, that, been, sold, online, designer, drug, clinical, dataother, names3, hydroxyphencyclidine, ohlegal, statuslegal, statusca, schedule, npsg, industrial, scientific, only, c. 3 Hydroxyphencyclidine 3 HO PCP is a dissociative of the arylcyclohexylamine class related to phencyclidine PCP that has been sold online as a designer drug 1 2 3 HO PCPClinical dataOther names3 Hydroxyphencyclidine 3 OH PCP PCP 3 OHLegal statusLegal statusCA Schedule I DE NpSG Industrial and scientific use only UK Class B Illegal in Sweden and SwitzerlandIdentifiersIUPAC name 3 1 Piperidin 1 yl cyclohexyl phenolCAS Number79787 43 2 Y 79295 51 5 hydrochloride PubChem CID133277ChemSpider117583UNIIV886QLHNA6CompTox Dashboard EPA DTXSID20229918Chemical and physical dataFormulaC 17H 25N OMolar mass259 393 g mol 13D model JSmol Interactive imageSMILES c1cc cc c1 O C2 CCCCC2 N3CCCCC3InChI InChI 1S C17H25NO c19 16 9 7 8 15 14 16 17 10 3 1 4 11 17 18 12 5 2 6 13 18 h7 9 14 19H 1 6 10 13H2Key AMSXTZUCNOKUEN UHFFFAOYSA N Contents 1 Pharmacology 2 Chemistry 3 Society and culture 3 1 Legal status 4 See also 5 ReferencesPharmacology Edit3 HO PCP acts as a high affinity uncompetitive antagonist of the NMDA receptor via the dizocilpine MK 801 site Ki 30 nM 3 4 It has much higher affinity than PCP for this site Ki 250 nM for comparison 8 fold difference 4 The drug also has high affinity for the m opioid receptor MOR Ki 39 60 nM in animal test subjects 3 4 5 6 the k opioid receptor KOR Ki 140 nM 5 and the sigma s1 receptor Ki 42 nM IC50 19 nM 5 7 8 9 whereas it has only low affinity for the d opioid receptor Ki 2 300 nM 5 The high affinity of 3 HO PCP for opioid receptors is unique among arylcyclohexylamines and is in contrast to PCP which has only very low affinity for the MOR Ki 11 000 26 000 nM 282 to 433 fold difference and the other opioid receptors Ki 4 100 nM for the KOR and 73 000 nM for the DOR 4 5 Although it was hypothesized that 3 HO PCP might be a metabolite of PCP in humans there is no evidence that this is the case 10 11 Chemistry Edit3 HO PCP is an arylcyclohexylamine 3 Close analogues of 3 HO PCP include PCP 3 MeO PCP 4 MeO PCP 3 MeO PCMo and somewhat more distantly ketamine methoxyketamine 3 MeO PCE methoxetamine and dimetamine 3 Society and culture EditLegal status Edit 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 HO PCP 12 3 HO PCP is banned in Sweden 13 14 and Switzerland 15 See also Edit2 FDCK 4 Keto PCP Delucemine Desmetramadol Hydroxetamine DimetamineReferences Edit 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 Davidsen AB Mardal M Johansen SS Dalsgaard PW Linnet K July 2020 In vitro and in vivo metabolism and detection of 3 HO PCP a synthetic phencyclidine in human samples and pooled human hepatocytes using high resolution mass spectrometry Drug Testing and Analysis 12 7 987 993 doi 10 1002 dta 2807 PMID 32311838 S2CID 216047397 a b c d 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 a b c d Kamenka JM Chiche B Goudal R Geneste P Vignon J Vincent JP Lazdunski M April 1982 Chemical synthesis and molecular pharmacology of hydroxylated 1 1 phenylcyclohexyl piperidine derivatives Journal of Medicinal Chemistry 25 4 431 435 doi 10 1021 jm00346a019 PMID 6279847 a b c d e Johnson N Itzhak Y Pasternak GW June 1984 Interaction of two phencyclidine opiate like derivatives with 3H opioid binding sites European Journal of Pharmacology 101 3 4 281 284 doi 10 1016 0014 2999 84 90171 7 PMID 6088255 Itzhak Y Kalir A Sarne Y July 1981 On the opioid nature of phencyclidine and its 3 hydroxy derivative European Journal of Pharmacology 73 2 3 229 233 doi 10 1016 0014 2999 81 90097 2 PMID 6273187 Itzhak Y Hiller JM Simon EJ January 1985 Characterization of specific binding sites for 3H d N allylnormetazocine in rat brain membranes Molecular Pharmacology 27 1 46 52 PMID 3965930 Itzhak Y April 1987 3H PCP 3 OH and 3H SKF 10047 binding sites in rat brain membranes evidence of multiplicity European Journal of Pharmacology 136 2 231 234 doi 10 1016 0014 2999 87 90715 1 PMID 3036548 Itzhak Y 1988 Pharmacological specificity of some psychotomimetic and antipsychotic agents for the sigma and PCP binding sites Life Sciences 42 7 745 752 doi 10 1016 0024 3205 88 90646 7 PMID 2893238 Holsztynska EJ Domino EF 1985 Biotransformation of phencyclidine Drug Metabolism Reviews 16 3 285 320 doi 10 3109 03602538508991437 PMID 3914938 Holsztynska EJ Domino EF 1986 Quantitation of phencyclidine its metabolites and derivatives by gas chromatography with nitrogen phosphorus detection application for in vivo and in vitro biotransformation studies Journal of Analytical Toxicology 10 3 107 115 doi 10 1093 jat 10 3 107 PMID 3724069 ACMD Methoxetamine Report 2012 PDF UK Home Office 2012 10 18 p 14 Retrieved 2015 06 24 Elva nya amnen klassas som narkotika eller halsofarlig vara Eleven new substances are classified as narcotics or dangerous goods in Swedish Folkhalsomyndigheten 28 June 2018 Forordning 1992 1554 om kontroll av narkotika Ordinance 1992 1554 on the control of narcotics Riksdagsforvaltningen in Swedish Verordnung des EDI vom 30 Mai 2011 uber die Verzeichnisse der Betaubungsmittel psychotropen Stoffe Vorlauferstoffe und Hilfschemikalien Betaubungsmittelverzeichnisverordnung BetmVV EDI EDI ordinance of May 30 2011 on the lists of narcotics psychotropic substances precursors and auxiliary chemicals narcotics list ordinance BetmVV EDI in German Der Bundesrat Retrieved from https en wikipedia org w index php title 3 HO PCP amp oldid 1148769966, wikipedia, wiki, book, books, library,
