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Phencyclidine

Updated: Wikipedia source

Phencyclidine

Phencyclidine or phenylcyclohexyl piperidine (PCP), also known in its use as a street drug as angel dust among other names, is a dissociative anesthetic mainly used recreationally for its significant mind-altering effects. PCP may cause hallucinations, distorted perceptions of sounds, and psychotic behavior. As a recreational drug, it is typically smoked, but may be taken by mouth, snorted, or injected. It may also be mixed with cannabis or tobacco. Adverse effects may include paranoia, addiction, and an increased risk of suicide, as well as seizures and coma in cases of overdose. Flashbacks may occur despite stopping usage. Chemically, PCP is a member of the arylcyclohexylamine class. PCP works primarily as an NMDA receptor antagonist. PCP is most commonly used in the US. While usage peaked in the US in the 1970s, between 2005 and 2011, an increase in visits to emergency departments as a result of the drug occurred. As of 2022, in the US, about 0.7% of 12th-grade students reported using PCP in the prior year, while 1.7% of people in the US over age 25 reported using it at some point in their lives.

Infobox

Trade names
Sernyl, Sernylan (both discontinued)
Other names
CI-395; Phenylcyclohexylpiperidine; "Angel dust"
AHFS/Drugs.com
phencyclidine
Dependenceliability
Physical: Low Psychological: Moderate
Addictionliability
Variable, reported from low to high
Routes ofadministration
Smoking, injection, snorted, by mouth
Drug class
NMDA receptor antagonists; General anesthetics; Dissociative hallucinogens
ATC code
mw- None
Legal status
AU: S8 (Controlled drug) BR: Class A3 (Psychoactive drugs) CA: Schedule I DE: Anlage I (Authorized scientific use only) NZ: Class A UK: Class A US: Schedule II UN: Psychotropic Schedule II Tabella I in Italy
Metabolism
Oxidative hydroxylation in liver by CYP450 enzymes, glucuronidation
Metabolites
PCHP, PPC, PCAA
Onset of action
2–60 min
Elimination half-life
7–46 hours
Duration of action
6–48 hours
Excretion
Urine
CAS Number
77-10-1 Y
PubChem CID
6468
IUPHAR/BPS
4282
DrugBank
DB03575 Y
ChemSpider
6224 Y
UNII
J1DOI7UV76
KEGG
C07575 Y
ChEBI
CHEBI:8058 N
ChEMBL
ChEMBL275528 Y
CompTox Dashboard (EPA)
DTXSID6023446
ECHA InfoCard
100.150.427
Formula
C17H25N
Molar mass
243.394 g·mol−1
3D model (JSmol)
Interactive image
Melting point
46.5 °C (115.7 °F)
Boiling point
136 °C (277 °F)

Tables

Phencyclidine[36][37] · Pharmacology › Pharmacodynamics
NMDATooltip N-Methyl-D-aspartate receptor
NMDATooltip N-Methyl-D-aspartate receptor
Site
NMDATooltip N-Methyl-D-aspartate receptor
Ki (nM)
59
Action
Antagonist
Species
Human
MORTooltip μ-Opioid receptor
MORTooltip μ-Opioid receptor
Site
MORTooltip μ-Opioid receptor
Ki (nM)
>10,000
Action
ND
Species
Human
DORTooltip δ-Opioid receptor
DORTooltip δ-Opioid receptor
Site
DORTooltip δ-Opioid receptor
Ki (nM)
>10,000
Action
ND
Species
Human
KORTooltip κ-Opioid receptor
KORTooltip κ-Opioid receptor
Site
KORTooltip κ-Opioid receptor
Ki (nM)
>10,000
Action
ND
Species
Human
NOPTooltip Nociceptin receptor
NOPTooltip Nociceptin receptor
Site
NOPTooltip Nociceptin receptor
Ki (nM)
>10,000
Action
ND
Species
Human
σ1
σ1
Site
σ1
Ki (nM)
>10,000
Action
Agonist
Species
Guinea pig
σ2
σ2
Site
σ2
Ki (nM)
136
Action
Agonist
Species
Rat
D2
D2
Site
D2
Ki (nM)
>10,000
Action
ND
Species
Human
D2High
D2High
Site
D2High
Ki (nM)
2.7–4.3144 (EC50)
Action
Partial Agonist
Species
Rat/humanHuman
5-HT2A
5-HT2A
Site
5-HT2A
Ki (nM)
>10,000
Action
ND
Species
Human
5-HT2AHigh
5-HT2AHigh
Site
5-HT2AHigh
Ki (nM)
≥5,000
Action
Partial Agonist
Species
Rat
SERTTooltip Serotonin transporter
SERTTooltip Serotonin transporter
Site
SERTTooltip Serotonin transporter
Ki (nM)
2,234
Action
Inhibitor
Species
Human
NETTooltip Norepinephrine transporter
NETTooltip Norepinephrine transporter
Site
NETTooltip Norepinephrine transporter
Ki (nM)
>10,000
Action
Inhibitor
Species
Human
DATTooltip Dopamine transporter
DATTooltip Dopamine transporter
Site
DATTooltip Dopamine transporter
Ki (nM)
>10,000
Action
Inhibitor
Species
Human
PCP2
PCP2
Site
PCP2
Ki (nM)
154
Action
agonist
Species
Human
[3H]5-HT uptake
[3H]5-HT uptake
Site
[3H]5-HT uptake
Ki (nM)
1,424 (IC50)
Action
Inhibitor
Species
Rat
[3H]NIS binding
[3H]NIS binding
Site
[3H]NIS binding
Ki (nM)
16,628 (IC50)
Action
Inhibitor
Species
Rat
[3H]DA uptake
[3H]DA uptake
Site
[3H]DA uptake
Ki (nM)
347 (IC50)
Action
Inhibitor
Species
Rat
[3H]CFT binding
[3H]CFT binding
Site
[3H]CFT binding
Ki (nM)
1,547 (IC50)
Action
Inhibitor
Species
Rat
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.
Site
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.
Site
Ki (nM)
Action
Species
Ref
NMDATooltip N-Methyl-D-aspartate receptor
59
Antagonist
Human
MORTooltip μ-Opioid receptor
>10,000
ND
Human
DORTooltip δ-Opioid receptor
>10,000
ND
Human
KORTooltip κ-Opioid receptor
>10,000
ND
Human
NOPTooltip Nociceptin receptor
>10,000
ND
Human
σ1
>10,000
Agonist
Guinea pig
σ2
136
Agonist
Rat
D2
>10,000
ND
Human
D2High
2.7–4.3144 (EC50)
Partial Agonist
Rat/humanHuman
5-HT2A
>10,000
ND
Human
5-HT2AHigh
≥5,000
Partial Agonist
Rat
SERTTooltip Serotonin transporter
2,234
Inhibitor
Human
NETTooltip Norepinephrine transporter
>10,000
Inhibitor
Human
DATTooltip Dopamine transporter
>10,000
Inhibitor
Human
PCP2
154
agonist
Human
[3H]5-HT uptake
1,424 (IC50)
Inhibitor
Rat
[3H]NIS binding
16,628 (IC50)
Inhibitor
Rat
[3H]DA uptake
347 (IC50)
Inhibitor
Rat
[3H]CFT binding
1,547 (IC50)
Inhibitor
Rat
Values are Ki (nM). The smaller the value, the more strongly the drug binds to the site.

References

  1. justice.gov
    https://web.archive.org/web/20210814124326/https://www.justice.gov/archive/ndic/pubs4/4440/
  2. The Principles and Practice of Medicine
    https://books.google.com/books?id=aA9mMB3lDh4C
  3. Molecular Neuropharmacology: A Foundation for Clinical Neuroscience
  4. Handbook of Substance Abuse: Neurobehavioral Pharmacology
    https://books.google.com/books?id=-0r0BwAAQBAJ&pg=PA579
  5. drugabuse.gov
    http://drugabuse.gov/infofacts/hallucinogens.html
  6. Manual of forensic emergency medicine: a guide for clinicians
    https://books.google.com/books?id=keng9ELAE2IC&pg=PA41
  7. The CBHSQ Report
    https://pubmed.ncbi.nlm.nih.gov/27656747
  8. "Hallucinogens"
    https://www.drugabuse.gov/publications/drugfacts/hallucinogens
  9. Drugs in American Society: An Encyclopedia of History, Politics, Culture, and the Law
    https://books.google.com/books?id=c5PgBQAAQBAJ&pg=PA732
  10. Forensic Pharmacology
    https://books.google.com/books?id=tyBE3F5ACK4C&pg=PA97
  11. ginad.org
    https://web.archive.org/web/20180910002927/http://www.ginad.org/en/drugs/drugs/306/pcp-
  12. cesar.umd.edu
    https://web.archive.org/web/20100312005219/http://www.cesar.umd.edu/cesar/drugs/pcp.asp
  13. drugabuse.gov
    https://web.archive.org/web/20200603125635/https://www.drugabuse.gov/drugs-abuse/hallucinogens
  14. The European Journal of Neuroscience
    https://doi.org/10.1046%2Fj.1460-9568.1999.00858.x
  15. Diaz, Jaime. How Drugs Influence Behavior. Englewood Cliffs: Prentice Hall, 1996.
  16. Neuroscience for Kids
    http://faculty.washington.edu/chudler/pcp.html
  17. The California Journal of Emergency Medicine
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2859735
  18. The War on Drugs II
  19. Journal of Psychedelic Drugs
    https://doi.org/10.1080%2F02791072.1980.10471426
  20. Journal of Clinical Psychopharmacology
    https://doi.org/10.1097%2F00004714-198812000-00003
  21. NIDA Research Monograph
    https://pubmed.ncbi.nlm.nih.gov/3086733
  22. Eur Neuropsychopharmacol
    https://doi.org/10.1016%2Fj.euroneuro.2019.06.005
  23. NIDA Research Monograph
    https://archives.drugabuse.gov/sites/default/files/monograph21.pdf
  24. California Medicine
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1518731
  25. Drugs of Abuse
  26. Philos. Trans. R. Soc. Lond. B Biol. Sci
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2607320
  27. Methods and Findings in Experimental and Clinical Pharmacology
    https://doi.org/10.1358%2Fmf.1998.20.7.485726
  28. Schizophrenia Bulletin
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7147575
  29. ACS Chemical Neuroscience
    https://doi.org/10.1021%2Facschemneuro.8b00266
  30. "Fry Fast Facts"
    https://web.archive.org/web/20210417111038/https://www.justice.gov/archive/ndic/pubs11/12208/
  31. eMedicine
    http://www.emedicine.com/med/TOPIC1813.HTM
  32. Goldfrank's Toxicologic Emergencies
    https://books.google.com/books?id=HVYyRsuUEc0C&pg=PA1041
  33. American Family Physician
    https://pubmed.ncbi.nlm.nih.gov/2008817
  34. Medical Times
  35. Journal of Clinical Pharmacology
    https://doi.org/10.1002%2Fj.1552-4604.1984.tb01831.x
  36. Psychoactive Drug Screening Program (PDSP)
    https://kidbdev.med.unc.edu/databases/pdsp.php?knowID=0&kiKey=&receptorDD=&receptor=&speciesDD=&species=&sourcesDD=&source=&hotLigandDD=&hotLigand=&testLigandDD=&testFreeRadio=testFreeRadio&testLigand=phencyclidine&referenceDD=&reference=&KiGreater=&KiLess=&kiAllRadio=all&doQuery=Submit+Query
  37. ACS Chem Neurosci
    https://doi.org/10.1021%2Facschemneuro.8b00266
  38. PLOS ONE
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3602154
  39. Neurotoxicol Teratol
    https://zenodo.org/record/1258623
  40. J. Psychopharmacol. (Oxford)
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4133098
  41. Synapse
    https://doi.org/10.1002%2Fsyn.20561
  42. Mol. Psychiatry
    https://doi.org/10.1038%2Fsj.mp.4001093
  43. Synapse
    https://doi.org/10.1002%2Fsyn.20647
  44. Int. J. Neuropsychopharmacol
    https://doi.org/10.1017%2FS1461145700002091
  45. Synapse
    https://zenodo.org/record/1229378
  46. The Journal of Pharmacology and Experimental Therapeutics
    https://doi.org/10.1124%2Fjpet.110.178475
  47. British Journal of Pharmacology
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2044888
  48. Drug Testing and Analysis
    https://doi.org/10.1002%2Fdta.1620
  49. Therapeutic Advances in Psychopharmacology
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3952483
  50. Brain Research
    https://doi.org/10.1016%2F0006-8993%2888%2990265-X
  51. Substance Abuse and Rehabilitation
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3931656
  52. Molecular Pharmacology
    https://pubmed.ncbi.nlm.nih.gov/6287200
  53. Bioorganic & Medicinal Chemistry Letters
    https://doi.org/10.1016%2Fj.bmcl.2011.02.009
  54. Proceedings of the National Academy of Sciences of the United States of America
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2944730
  55. Neuropharmacology
    https://doi.org/10.1016%2Fs0028-3908%2800%2900102-7
  56. PLOS ONE
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3669396
  57. Molecular Psychiatry
    https://doi.org/10.1038%2Fsj.mp.4001682
  58. Journal of Toxicology. Clinical Toxicology
    https://doi.org/10.3109%2F15563658408992586
  59. Molecular Pharmacology
    https://pubmed.ncbi.nlm.nih.gov/2557536
  60. Psychopharmacology
    https://doi.org/10.1007%2FBF00470593
  61. www.drugbank.ca
    https://www.drugbank.ca/drugs/DB03575
  62. Pharmacology, Biochemistry, and Behavior
    https://doi.org/10.1016%2F0091-3057%2888%2990346-2
  63. Anesthesia and Analgesia
    https://doi.org/10.1097%2F00000539-199811000-00039
  64. Journal of Medicinal Chemistry
    https://doi.org/10.1021%2Fjm9704412
  65. European Journal of Pharmacology
    https://doi.org/10.1016%2F0922-4106%2890%2990044-X
  66. Science
    https://ui.adsabs.harvard.edu/abs/1989Sci...244.1360O
  67. Brain Edema IX
    https://doi.org/10.1007%2F978-3-7091-9334-1_4
  68. Jansen, Karl. Ketamine: Dreams and Realities. MAPS, 2004. ISBN 0-9660019-7-4
  69. Schizophrenia Research
    https://doi.org/10.1016%2Fj.schres.2004.02.003
  70. The Journal of Psychology
    https://doi.org/10.1080%2F00223980209604159
  71. British Journal of Pharmacology
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4556466
  72. Schizophrenia Bulletin
    https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3446214
  73. Journal of Medicinal Chemistry
    https://doi.org/10.1021%2Fjm00137a004
  74. Pharmacology Biochemistry and Behavior
    https://doi.org/10.1016%2F0091-3057%2889%2990020-8
  75. Journal für Praktische Chemie
    https://doi.org/10.1002%2Fprac.19261130107
  76. Neuropsychopharmacology: Proceedings of the XVIth C.I.N.P. Congress, Munich, August, 15-19, 1988
    https://books.google.com/books?id=tX7nCAAAQBAJ&pg=PA717
  77. Toxicology in the Use, Misuse, and Abuse of Food, Drugs, and Chemicals
    https://doi.org/10.1007%2F978-3-642-69083-9_10
  78. Psychiatry, 2 Volume Set
    https://books.google.com/books?id=l2KRBgAAQBAJ&pg=PT4843
  79. deadiversion.usdoj.gov
    https://www.deadiversion.usdoj.gov/schedules/orangebook/d_cs_drugcode.pdf
  80. deadiversion.usdoj.gov
    https://web.archive.org/web/20140417130426/http://www.deadiversion.usdoj.gov/fed_regs/quotas/2013/fr0909.htm
  81. legislation.gov.uk
    http://www.legislation.gov.uk/uksi/1979/299/article/2/made#text%253DPhencyclidine
  82. The Economic Times
    https://economictimes.indiatimes.com/christies-evening-auction-to-present-a-major-painting-by-jean-michel-basquiat/articleshow/19496301.cms?from=mdr
  83. Anime News Network
    https://www.animenewsnetwork.com/news/2023-06-13/new-city-hunter-anime-film-trailer-unveils-more-cast-theme-songs-september-8-debut/.199110
  84. press.amazonstudios.com
    http://press.amazonstudios.com/us/en/press-release/prime-video-debuts-teaser-of-an-original-song-and-
  85. HAZBIN HOTEL Animation Cleanup Pt. 7 Ft. Michael Kovach and Vivziepop (2:31:28) – via YouTube.
    https://www.youtube.com/watch?v=qtIJvv70hoo&t=9088s
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