| 词条 | 3-HO-PCP |
| 释义 |
| Verifiedfields = | verifiedrevid = | IUPAC_name = 3-[1-(Piperidin-1-yl)cyclohexyl]phenol | image = 3-HO-PCP.png | width = 250px | tradename = | legal_status = | legal_CA = Schedule I | legal_UK = Class B | CAS_number_Ref = | CAS_number = 79787-43-2 | CAS_number2_Ref = | CAS_number2 = 79295-51-5 (hydrochloride) | ATC_prefix = | PubChem = 133277 | ChemSpiderID_Ref = | ChemSpiderID = 117583 | synonyms = 3-Hydroxyphencyclidine; 3-OH-PCP; PCP-3-OH | C=17 | H=25 | N=1 | O=1 | molecular_weight = 259.39 g/mol | SMILES = c1cc(cc(c1)O)C2(CCCCC2)N3CCCCC3 | StdInChI = 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,1-6,10-13H2 | StdInChIKey = AMSXTZUCNOKUEN-UHFFFAOYSA-N }}3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative hallucinogen of the arylcyclohexylamine class related to phencyclidine (PCP) that has been sold online as a designer drug.[1]{{TOC limit|3}} Pharmacology3-HO-PCP acts as a high-affinity uncompetitive antagonist of the NMDA receptor via the dizocilpine (MK-801) site (Ki = 30 nM).[2][3] It has much higher affinity than PCP for this site (Ki = 250 nM, for comparison; 8-fold difference).[3] The drug also has high affinity for the μ-opioid receptor (MOR) (Ki = 39–60 nM),[2][3][4][5] the κ-opioid receptor (KOR) (Ki = 140 nM),[4] and the sigma σ1 receptor (Ki = 42 nM; IC50 = 19 nM),[4][6][7][8] whereas it has only low affinity for the δ-opioid receptor (Ki = 2,300 nM).[4] 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).[3][4] 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.[9][10] Chemistry3-HO-PCP is an arylcyclohexylamine.[2] 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, and methoxetamine.[2] Society and cultureLegal statusLegal in Germany United KingdomOn 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.[11] United States3-HO-PCP is a close analogue of PCP. Hence, possession or distribution for use in humans could potentially be prosecuted under the Federal Analogue Act. References1. ^{{cite journal|first1=H.|last1=Morris|first2=J.|last2=Wallach|title=From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs|journal=Drug Testing and Analysis|year=2014|doi=10.1002/dta.1620|volume=6|issue=7–8|pages=614–632|pmid=24678061}} {{Hallucinogens}}{{Ionotropic glutamate receptor modulators}}{{Opioid receptor modulators}}{{Sigma receptor modulators}}{{hallucinogen-stub}}2. ^1 2 3 {{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 Test Anal | volume = 6 | issue = 7–8 | pages = 614–32 | year = 2014 | pmid = 24678061 | doi = 10.1002/dta.1620 | url = }} 3. ^1 2 3 {{cite journal | vauthors = Kamenka JM, Chiche B, Goudal R, Geneste P, Vignon J, Vincent JP, Lazdunski M | title = Chemical synthesis and molecular pharmacology of hydroxylated 1-(1-phenylcyclohexyl-piperidine derivatives | journal = J. Med. Chem. | volume = 25 | issue = 4 | pages = 431–5 | year = 1982 | pmid = 6279847 | doi = 10.1021/jm00346a019| url = }} 4. ^1 2 3 4 {{cite journal | vauthors = Johnson N, Itzhak Y, Pasternak GW | title = Interaction of two phencyclidine opiate-like derivatives with 3H-opioid binding sites | journal = Eur. J. Pharmacol. | volume = 101 | issue = 3–4 | pages = 281–4 | year = 1984 | pmid = 6088255 | doi = 10.1016/0014-2999(84)90171-7| url = }} 5. ^{{cite journal | vauthors = Itzhak Y, Kalir A, Sarne Y | title = On the opioid nature of phencyclidine and its 3-hydroxy derivative | journal = Eur. J. Pharmacol. | volume = 73 | issue = 2–3 | pages = 229–33 | year = 1981 | pmid = 6273187 | doi = 10.1016/0014-2999(81)90097-2| url = }} 6. ^{{cite journal | vauthors = Itzhak Y, Hiller JM, Simon EJ | title = Characterization of specific binding sites for [3H](d)-N-allylnormetazocine in rat brain membranes | journal = Mol. Pharmacol. | volume = 27 | issue = 1 | pages = 46–52 | year = 1985 | pmid = 3965930 | doi = | url = }} 7. ^{{cite journal | vauthors = Itzhak Y | title = [3H]PCP-3-OH and (+)[3H]SKF 10047 binding sites in rat brain membranes: evidence of multiplicity | journal = Eur. J. Pharmacol. | volume = 136 | issue = 2 | pages = 231–4 | year = 1987 | pmid = 3036548 | doi = 10.1016/0014-2999(87)90715-1| url = }} 8. ^{{cite journal | vauthors = Itzhak Y | title = Pharmacological specificity of some psychotomimetic and antipsychotic agents for the sigma and PCP binding sites | journal = Life Sci. | volume = 42 | issue = 7 | pages = 745–52 | year = 1988 | pmid = 2893238 | doi = 10.1016/0024-3205(88)90646-7| url = }} 9. ^{{cite journal | vauthors = Holsztynska EJ, Domino EF | title = Biotransformation of phencyclidine | journal = Drug Metab. Rev. | volume = 16 | issue = 3 | pages = 285–320 | year = 1985 | pmid = 3914938 | doi = 10.3109/03602538508991437 | url = }} 10. ^{{cite journal | vauthors = Holsztynska EJ, Domino EF | title = Quantitation of phencyclidine, its metabolites, and derivatives by gas chromatography with nitrogen-phosphorus detection: application for in vivo and in vitro biotransformation studies | journal = J Anal Toxicol | volume = 10 | issue = 3 | pages = 107–15 | year = 1986 | pmid = 3724069 | doi = 10.1093/jat/10.3.107| url = }} 11. ^{{ cite web | url = https://www.gov.uk/government/publications/advisory-council-on-the-misuse-of-drugs-acmd-methoxetamine-report-2012 | title = (ACMD) Methoxetamine Report (2012) | accessdate = 2015-06-24 | date = 2012-10-18 | format = PDF | pages = 14 | work = UK Home Office}} 8 : Designer drugs|Dissociative drugs|NMDA receptor antagonists|Opioid receptor ligands|Phenols|Piperidines|Sigma receptor ligands|Synthetic opioids |
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