// Workers AI · dad joke modeWhat did 3-HO-PCP say to its friend? "You're a compound friend.
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| Other names | 3-Hydroxyphencyclidine; 3-OH-PCP; PCP-3-OH |
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| Formula | C17H25NO |
| Molar mass | 259.393 g·mol−1 |
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3-Hydroxyphencyclidine (3-HO-PCP) is a dissociative of the arylcyclohexylamine class derived from PCP. It has been sold online as a designer drug.[1][2]
3-HO-PCP primarily acts as an NMDA antagonist. However, it also has strong activity at opioid receptors compared to related drugs, and has significant activity at the σ1 receptor.[1][3][4][5]
Pharmacology
[edit]Pharmacodynamics
[edit]3-HO-PCP acts as a high-affinity uncompetitive NMDA receptor antagonist via the PCP site with a Ki of 30 nM.[1][3] It has a higher affinity than PCP, which has a Ki of 250 nM for this site (eight-fold higher).[3]
Unlike many other arylcyclohexylamines, including close analogues such as 3-Chloro-PCP and 3-MeO-PCP, 3-HO-PCP has a high affinity for various opioid receptors.[6] It has a Ki value of 39–60 nM for the μ-opioid receptor, 140 nM for the κ-opioid receptor, and 42 nM for the σ1 receptor. It has weaker activity at the δ-opioid receptor, with a Ki of 2,300 nM.[3][4][5]
Pharmacokinetics
[edit]Four primary metabolic pathways of 3-HO-PCP have been identified. These include piperidine hydroxylation, N-dealkylation, O-glucuronidation, and O-sulfate-conjugation. In urine samples, the N-dealkylated-COOH metabolite was the main metabolite detected.[2]
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.[7][8] 3-HO-PCP is a metabolite of 3-MeO-PCP.[9]
Chemistry
[edit]3-HO-PCP is an arylcyclohexylamine which is derived from PCP and closely structurally related to 3-MeO-PCP, 3-MeO-PCMo, and 4-MeO-PCP, among others[1]
History
[edit]3-HO-PCP was mentioned by a chemist under the pseudonym "John Q. Beagle" in 1999 in a post on The Hive.[1] The psychoactive effects of 3-HO-PCP have been described by Bluelight users even before its availability as a research chemical in 2009.[1]
Society and culture
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Legal status
[edit]United Kingdom
[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.[10]
Sweden
[edit]Switzerland
[edit]3-HO-PCP is illegal in Switzerland.[12]
See also
[edit]References
[edit]- 1 2 3 4 5 6 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.
- 1 2 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.
- 1 2 3 4 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.
- 1 2 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.
- 1 2 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.
- ↑ Jiang Q (2026). "Structural basis of opioid receptor activation by PCP and ketamine". Nature Structural & Molecular Biology. doi:10.1038/s41594-026-01839-y. PMID 42332075.
- ↑ 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.
- ↑ Wallach J, Brandt SD (2018). "Phencyclidine-Based New Psychoactive Substances". In Maurer HH, Brandt SD (eds.). Handbook of Experimental Pharmacology. Vol. 252. Cham: Springer International Publishing=. pp. 261–303. doi:10.1007/164_2018_124. ISBN 978-3-030-10561-7. PMID 30105474.
- ↑ "(ACMD) Methoxetamine Report (2012)" (PDF). UK Home Office. 2012-10-18. p. 14. Retrieved 2015-06-24.
- ↑ "SFS 1992:1554/konsolidering/2025:77 – Förordning om kontroll av narkotika". lagen.nu (in Swedish). Retrieved 2026-09-20.
- ↑ "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.