Exploring PCP. To explore a different substance…

Names:
PCP
CI-395
Phencyclidine
IUPAC name:
1-(1-Phenylcyclohexyl)piperidine
11011 · C17H25N · 243.387
Arylcycloalkylamine
InChI=1S/C17H25N/c1-4-10-16(11-5-1)17(12-6-2-7-13-17)18-14-8-3-9-15-18/h1,4-5,10-11H,2-3,6-9,12-15H2
JTJMJGYZQZDUJJ-UHFFFAOYSA-N This stereoisomer Any stereoisomer

Wallach, J; Kang, H; Colestock, T; Morris, H; Bortolotto, ZA; Collingridge, GL; Lodge, D; Halberstadt, AL; Brandt, SD; Adejare, A. Pharmacological investigations of the dissociative “Legal Highs” diphenidine, methoxphenidine and analogues. PLOS ONE, 17 Jun 2016, 11 (6), e0157021. 1.9 MB. https://doi.org/10.1371/journal.pone.0157021 #PCP GC,MS,NMR

Wallach, J; Kavanagh, PV; McLaughlin, G; Morris, N; Power, JD; Elliott, SP; Mercier, MS; Lodge, D; Morris, H; Dempster, NM; Brandt, SD. Preparation and characterization of the ‘research chemical’ diphenidine, its pyrrolidine analogue, and their 2,2-diphenylethyl isomers. Drug Test. Analysis, 1 May 2015, 7 (5), 358-367. 632 kB. https://doi.org/10.1002/dta.1689

Shulgin, AT; Helisten, C. Differentiation of PCP, TCP, and a contaminating precursor PCC, by thin layer chromatography [Reconstructed and searchable, with minor edits]. Microgram, 1 Jan 1975, 8, 171–172. 133 kB. The unretouched original scan, sans OCR. A clean, corrected version.

Morris, H; Wallach, J. From PCP to MXE: A comprehensive review of the non-medical use of dissociative drugs. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 614-632. 942 kB. https://doi.org/10.1002/dta.1620

Wallach, J; De Paoli, G; Adejare, A; Brandt, SD. Preparation and analytical characterization of 1-(1-phenylcyclohexyl)piperidine (PCP) and 1-(1-phenylcyclohexyl)pyrrolidine (PCPy) analogues. Drug Test. Analysis, 1 Jul 2014, 6 (7-8), 633-650. 874 kB. https://doi.org/10.1002/dta.1468

Shulgin, AT; MacLean, DE. Illicit synthesis of phencyclidine (PCP) and several of its analogs. Clin. Toxicol., 1 Jan 1976, 9 (4), 553–560. 352 kB. https://doi.org/10.3109/15563657608988157 #PCP Rhodium.

Bailey, K; Legault, D. Carbon-13 nuclear magnetic resonance spectra of aminocyclohexanecarbonitriles and comparison with phencyclidine analogues. Org. Magn. Resonance, 1 Jan 1981, 15 (1), 68–71. 407 kB. https://doi.org/10.1002/mrc.1270150114

Wallach, JV. Structure activity relationship (SAR) studies of arylcycloalkylamines as N-methyl-D-aspartate receptor antagonists. Ph. D. Thesis, 19 Dec 2014. #1

Kalir, A. Structure activity relationships of phencyclidine derivatives. In PCP (phencyclidine), historical and current perspectives; Domino, EF, Ed., NPP Books, Ann Arbor, MI, 1981; pp 31–46. 2.3 MB.

Meyers, FH; Rose, AJ; Smith, DE. Incidents involving the Haight-Ashbury population and some uncommonly used drugs. J. Psychedelic Drugs, 1 Apr 1968, 1 (2), 139–146. 842 kB. https://doi.org/10.1080/02791072.1968.10524531

Garey, RE. PCP (Phencyclidine): An Update. J. Psychedelic Drugs, 1 Oct 1979, 11 (4), 265–275. 6.6 MB. https://doi.org/10.1080/02791072.1979.10471408

Balster, RL; Pross, RS. Phencyclidine: A Bibliography of biomedical and behavioral research. J. Psychedelic Drugs, 1 Jan 1978, 10 (1), 1–15. 6.3 MB. https://doi.org/10.1080/02791072.1978.10471862

Garey, RE; Weisberg, LA; Heath, RG. Phencyclidine: An overview. J. Psychedelic Drugs, 1 Oct 1977, 9 (4), 280–285. 3.8 MB. https://doi.org/10.1080/02791072.1977.10472059

Reed, A; Kane, AW. Phencyclidine (PCP): Another illicit psychedelic drug. J. Psychedelic Drugs, 1 Sep 1972, 5 (1), 8–12. 3.0 MB. https://doi.org/10.1080/02791072.1972.10471463

Colestock, T; Wallach, J; Mansi, M; Filemban, N; Morris, H; Elliott, SP; Westphal, F; Brandt, SD; Adejare, A. Syntheses, analytical and pharmacological characterizations of the ‘legal high’ 4-[1-(3-methoxyphenyl)cyclohexyl]morpholine (3-MeO-PCMo) and analogues. Drug Test. Analysis, 26 Jul 2017, n/a-n/a. 1.6 MB. https://doi.org/10.1002/dta.2213

adder. PCP analogs (cumulative). Bluelight.org, 20 May 2010. 792 kB. #PCP From bluelight.org PCP analogs (Cumulative)

Morris, H; Wallach, J. Arylcyclohexylamines. Psymposium 2014, 27 Oct 2015. 39:47. Psymposia Big hug to W. Snow for providing the video. Unfortunately I just cannot seem to make it work. It may be a bug in my code. For now, the link points to YouTube.

Allen, AC; Robles, J; Dovenski, W; Calderon, S. PCP: A review of synthetic methods for forensic clandestine investigation. Forensic Sci. Int., 1 Oct 1993, 61 (2), 85–100. 1.1 MB. https://doi.org/10.1016/0379-0738(93)90217-X

Maddox, VH; Godefroi, EF; Parcell, RF. The synthesis of phencyclidine and other 1-arylcyclohexylamines. J. Med. Chem., 1 Mar 1965, 8 (2), 230–235. 696 kB. https://doi.org/10.1021/jm00326a019 #1

Itzhak, Y; Kalir, A; Weissman, BA; Cohen, S. New analgesic drugs derived from phencyclidine. J. Med. Chem., 1 May 1981, 24 (5), 496–499. 557 kB. https://doi.org/10.1021/jm00137a004 #1

Ahmadi, A; Kermani, M; Naderi, N; Hajikhani, R; Rezaee, N; Javadi, M; Niknafs, B. Synthesis and antinociceptive behaviors of new methyl and hydroxyl derivatives of phencyclidine. Curr. Med. Chem., 1 Feb 2012, 19 (5), 763–769. 431 kB. https://doi.org/10.2174/092986712798992057 #I

Roth, BL; Gibbons, S; Arunotayanun, W; Huang, X; Setola, V; Treble, R; Iversen, L. The ketamine analogue methoxetamine and 3- and 4-methoxy analogues of phencyclidine are high affinity and selective ligands for the glutamate NMDA receptor. PLoS ONE, 19 Mar 2013, 8 (3), e59334. 453 kB. https://doi.org/10.1371/journal.pone.0059334 #Phencyclidine

Domino, EF; Luby, ED. Phencyclidine/Schizophrenia: One view toward the past, the other to the future. Schizophr. Bull., 1 Sep 2012, 38 (5), 914–919. 181 kB. https://doi.org/10.1093/schbul/sbs011 #PCP

Hermle, L; Kraehenmann, R. Experimental psychosis research and schizophrenia—Similarities and dissimilarities in psychopathology. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 313-332. 446 kB. https://doi.org/10.1007/7854_2016_460

Halpern, JH; Lerner, AG; Passie, T. A review of hallucinogen persisting perception disorder (HPPD) and an exploratory study of subjects claiming symptoms of HPPD. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 333-360. 579 kB. https://doi.org/10.1007/7854_2016_457

Lladó-Pelfort, L; Celada, P; Riga, M; Troyano-Rodríguez,, E. Effect of hallucinogens on neuronal activity. In Behavioral Neurobiology of Psychedelic Drugs; Halberstadt, AL; Vollenweider, FX; Nichols, DE, Eds., Springer, 1 Jan 2017; pp 75-105. 902 kB. https://doi.org/10.1007/7854_2017_473

Moriarty, RM; Enache, LA; Zhao, L; Gilardi, R; Mattson, MV; Prakash, O. Rigid phencyclidine analogues. Binding to the phencyclidine and σ1 receptors. J. Med. Chem., 1 Feb 1998, 41 (4), 468–477. 313 kB. https://doi.org/10.1021/jm970059p #PCP

Shulgin, AT. Basic Pharmacology and Effects. In Hallucinogens. A Forensic Drug Handbook; Laing, R; Siegel, JA, Eds., Academic Press, London, 2003; pp 67–137. 6.3 MB.

Ahmadi, A; Khalili, M; Abbassi, S; Javadi, M; Mahmoudi, A; Hajikhani, R. Synthesis and study on analgesic effects of l-[l-(4-methylphenyl) (cyclohexyl)] 4-piperidinol and l-[l-(4-methoxyphenyl) (cyclohexyl)] 4-piperidinol as two new phencyclidine derivatives. Arzneim. Forsch., 1 Apr 2009, 59 (04), 202–206. 231 kB. https://doi.org/10.1055/s-0031-1296386 #I MS,NMR,IR

Shulgin, AT. Chemistry of psychotomimetics. In Handbook of Experimental Pharmacology. Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs; Hoffmeister, F; Stille, G, Eds., Springer-Verlag, Berlin, 1982; Vol. 55 (3), pp 3–29. 29.7 MB. #16a

Shulgin, AT. Hallucinogens. In Burger’s Medicinal Chemistry, 4th ed., Part III; Wolff, ME, Ed., Wiley & Co., 1981; pp 1109–1137. 4.7 MB. #46

Shulgin, AT. Psychotomimetic agents. In Psychopharmacological Agents; Gordon, M, Ed., Academic Press, New York, 1976; Vol. 4, pp 59–146. 3.1 MB. #CII

Ahmadi, A; Khalili, M; Hajikhani, R; Hosseini, H; Afshin, N; Nahri-Niknafs, B. Synthesis and study the analgesic effects of new analogues of ketamine on female Wistar rats. Med. Chem., 29 Feb 2012, 8 (2), n/a. 132 kB. https://doi.org/10.2174/157340612800493683 #II

Ahmadi, A; Solati, J; Hajikhani, R; Onagh, M; Javadi, M. Synthesis and analgesic effects of 1-[1-(2-methylphenyl)(cyclohexyl)]-3-piperidinol as a new derivative of phencyclidine in mice. Arzneim. Forsch., 1 Aug 2010, 60 (08), 492–496. 244 kB. https://doi.org/10.1055/s-0031-1296317 #I

Hajikhani, R; Ahmadi, A; Naderi, N; Yaghoobi, K; Shirazizand, Z; Rezaee, NM; Niknafs, BN. Effect of phencyclidine derivatives on anxiety-like behavior using an elevated-plus maze test in mice. Adv. Clin. Exp. Med., 1 Jan 2012, 21 (3), 307–312. 218 kB. #I

Ahmadi, A; Solati, J; Hajikhani, R; Pakzad, S. Synthesis and analgesic effects of new pyrrole derivatives of phencyclidine in mice. Arzneim. Forsch., 1 May 2011, 61 (05), 296–300. 285 kB. https://doi.org/10.1055/s-0031-1296202 #I

Ahmadi, A; Khalili, M; Hajikhani, R; Barghi, L; Mihandoust, F. Synthesis and determination of chronic and acute thermal and chemical pain activities of a new derivative of phencyclidine in rats. Iran J. Pharm. Res., 1 Jan 2010, 9 (4), 379–385. 314 kB. #I

Ahmadi, A; Khalili, M; Mihandoust, F; Barghi, L. Synthesis and determination of acute and chronic pain activities of 1-[1-(3-methylphenyl) (tetralyl)]piperidine as a new derivative of phencyclidine via tail immersion and formalin tests. Arzneim. Forsch., 1 Jan 2010, 60 (01), 30–35. 251 kB. https://doi.org/10.1055/s-0031-1296245 #I

Hoffer, A; Osmond, H. The Hallucinogens, Academic Press, New York, 1967. 3.9 MB. #Sernyl

Wallach, J; Brandt, SD. Phencyclidine-based new psychoactive substances. In Handbook of Experimental Pharmacology; , Springer, Berlin, Heidelberg, 1 Jan 2018; pp 1–43. 510 kB. https://doi.org/10.1007/164_2018_124 #PCP

Wallach, J; Brandt, SD. 1,2-Diarylethylamine- and ketamine-based new psychoactive substances. In Handbook of Experimental Pharmacology; , Springer Berlin Heidelberg, 1 Jan 2018; . 570 kB. https://doi.org/10.1007/164_2018_148 #PCP

PCHEPy
N-Allyl-PCE
3-Me-PCPy
3-Me-PBCHPr
23 September 2018 · Creative Commons BY-NC-SA ·