Arylcyclohexylamines

from Wikipedia, the free encyclopedia
Phencyclidine (PCP), a well-known arylcyclohexylamine derivative.

Arylcyclohexylamines , also known as arylcyclohexamines or arylcyclohexanamines , are a chemical class of (experimental) medicinal products and designer drugs .

history

Phencyclidine (PCP) is believed to be the first arylcyclohexylamine discovered with recognized anesthetic properties. In the scientific literature, however, several arylcyclohexylamines have been described before PCP, starting with PCA (1-phenylcyclohexan-1-amine), the synthesis of which was first published in 1907. Eticyclidine (PCE) was discovered in 1953 and PCMo in 1954, the latter compound having been described as a potent sedative . Arylcyclohexylamine anesthetics were extensively studied by Parke-Davis , beginning with the synthesis of PCP and later the related compound ketamine in 1956. In the 1970s, these compounds, especially PCP and its analogues , were considered to be due to their dissociative , hallucinogenic and euphoric effects used illegal drugs . Since then, the group of substances has been expanded by scientific research on stimulants , analgesics and neuroprotectants, as well as by chemists looking for novel recreational drugs.

structure

General structure of arylcyclohexylamines

An arylcyclohexylamine consists of a cyclohexylamine which is substituted with an aryl group geminally to the amino group . In the simplest cases, the aryl unit is a phenyl ring , optionally with additional substituents.

The amino group is usually not primary ; the most common N -substituents in the secondary amines are the methyl or ethyl group and the tertiary amines are mostly piperidine and pyrrolidine derivatives .

Pharmacology and pharmacodynamics

Arylcyclohexylamines have different NMDA receptor - antagonistic , dopamine reuptake inhibiting , and μ-opioid receptor - agonistic properties. In addition, they have an agonistic effect on the sigma receptor , antagonistic on nicotine receptors and agonistic on dopamine D 2 receptors . Different pharmacological effects were observed depending on the active ingredients . The antagonism of the NMDA receptor confers anesthetic , antispasmodic , neuroprotective and dissociative effects; the blockade of the dopamine transporter mediates stimulating and euphoric effects as well as psychoses in high doses; and activation of the μ-opioid receptor causes analgesic and euphoric effects. The stimulation of the σ and D2 receptors can also contribute to hallucinogenic and psychotomimetic effects.

Arylcyclohexylamines are versatile active ingredients with a broad spectrum of possible pharmacological effects , depending on the scope and area in which structural chemical modifications have been carried out. The various possibilities of modification of the chemical structure allow a "fine tuning" of the resulting pharmacological and pharmacodynamic profile. z. B. Benocyclidine (BTCP) is a selective dopamine reuptake inhibitor , PCP is primarily an NMDA antagonist, and bromadol (BDPC) is a potent μ-opioid agonist, while PRE-084 is a selective sigma receptor agonist . Thus, radically different pharmacology and pharmacodynamics are possible through different structural combinations.

List of arylcyclohexylamines

structure connection Aryl group Amine group Cyclohexyl ring
1-Phenylcyclohexylamine.svg PCA Phenyl NH 2 -
N-methyl-1-phenylcyclohexylamine.svg PCM Phenyl Methylamine -
N-Ethyl-1-phenylcyclohexylamine.svg Eticyclidine Phenyl Ethylamine -
N-Propyl-1-phenylcyclohexylamine.svg PCPr Phenyl n -propylamine -
N-Isopropyl-1-phenylcyclohexylamine.svg PCiP Phenyl Isopropylamine -
N-Allyl-1-phenylcyclohexylamine.svg PCAL Phenyl Allylamine -
N-Butyl-1-phenylcyclohexylamine.svg PCBu Phenyl n -butylamine -
N- (2-Hydroxyethyl) -1-phenylcyclohexylamine.svg PCEOH Phenyl Hydroxyethylamine -
N- (2-methoxyethyl) -1-phenylcyclohexylamine.svg PCMEA Phenyl Methoxyethylamine -
N- (2-ethoxyethyl) -1-phenylcyclohexylamine.svg PCEEA Phenyl Ethoxyethylamine -
N- (3-methoxypropyl) -1-phenylcyclohexylamine.svg PCMPA Phenyl Methoxypropylamine -
N, N-Dimethyl-1-phenylcyclohexylamine.svg PCDM Phenyl Dimethylamine -
N, N-Diethyl-1-phenylcyclohexylamine.svg Dieticyclidine Phenyl Diethylamine -
2-phenyl-2- (1-piperidinyl) cyclohexanol.svg 2-HO-PCP Phenyl Piperidine 2-hydroxy
1- (2-Methyl-1-phenylcyclohexyl) piperidine.svg 2-Me-PCP Phenyl Piperidine 2-methyl
1- (2-Methoxy-1-phenylcyclohexyl) piperidine.svg 2-MeO-PCP Phenyl Piperidine 2-methoxy
2-phenyl-2- (1-piperidinyl) cyclohexanone.svg 2-keto-PCP Phenyl Piperidine 2-oxo
2-Ethylamino-2-phenylcyclohexanone.svg Eticyclidone ("O-PCE") Phenyl Ethylamine 2-oxo
2-Propylamino-2-phenylcyclohexanone.svg 2-keto-PCPr Phenyl n -propylamine 2-oxo
1- (4-Methyl-1-phenylcyclohexyl) piperidine.svg 4-methyl-PCP Phenyl Piperidine 4-methyl
4-phenyl-4- (1-piperidinyl) cyclohexanone.svg 4-keto-PCP Phenyl Piperidine 4-oxo
1- (1- (2-chlorophenyl) cyclohexyl) piperidine.svg 2'-Cl-PCP o -chlorophenyl Piperidine -
1- (1- (2-methoxyphenyl) cyclohexyl) piperidine.svg 2'-MeO-PCP o -methoxyphenyl Piperidine -
1- (1- (3-fluorophenyl) cyclohexyl) piperidine.svg 3'-F-PCP m -fluorophenyl Piperidine -
1- (1- (3-methylphenyl) cyclohexyl) piperidine.svg 3'-Me-PCP m -Tolyl Piperidine -
1- (1- (3-methylphenyl) cyclohexyl) pyrrolidine.svg 3'-Me-PCPy m -Tolyl Pyrrolidine -
1- (1- (3-aminophenyl) cyclohexyl) piperidine.svg 3'-NH 2 -PCP m -aminophenyl Piperidine -
1- (1- (3-Hydroxyphenyl) cyclohexyl) piperidine.svg 3'-HO-PCP m -hydroxyphenyl Piperidine -
1- (1- (3-methoxyphenyl) cyclohexyl) piperidine.svg 3'-MeO-PCP m -methoxyphenyl Piperidine -
1- (1- (1,3-Benzodioxol-5-yll) cyclohexyl) piperidine.svg 3 ', 4'-MD-PCP 3,4-methylenedioxyphenyl Piperidine -
N-Ethyl-1- (3-methoxyphenyl) cyclohexylamine.svg 3'-MeO-PCE m -methoxyphenyl Ethylamine -
N-Ethyl-1- (3-hydroxyphenyl) cyclohexylamine.svg 3'-HO-PCE m -hydroxyphenyl Ethylamine -
1- (3-Methoxyphenyl) -N-propylcyclohexylamine.svg 3'-MeO-PCPr m -methoxyphenyl n -propylamine -
1- (3-Hydroxyphenyl) -N-propylcyclohexylamine.svg 3'-HO-PCPr m -hydroxyphenyl n -propylamine -
1- (1,3-Benzodioxol-5-yl) -N-propylcyclohexylamine.svg 3 ', 4'-MD-PCPr 3,4-methylenedioxyphenyl n -propylamine -
1- (1- (3-methoxyphenyl) cyclohexyl) pyrrolidine.svg 3'-MeO-PCPy m -methoxyphenyl Pyrrolidine -
1- (1- (4-Hydroxyphenyll) cyclohexyl) piperidine.svg 4'-HO-PCP p -hydroxyphenyl Piperidine -
1- (1- (4-methoxyphenyll) cyclohexyl) piperidine.svg Methoxydine (4'-MeO-PCP) p -methoxyphenyl Piperidine -
N-Ethyl-1- (4-methoxyphenyl) cyclohexylamine.svg 4'-MeO-PCE p -methoxyphenyl Ethylamine -
1- (1- (4-fluorophenyll) cyclohexyl) piperidine.svg 4'-F-PCP p -fluorophenyl Piperidine -
1- (1- (4-fluorophenyll) cyclohexyl) pyrrolidine.svg 4'-F-PCPy p -fluorophenyl Pyrrolidine -
(R) -2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Arketamine o -chlorophenyl Methylamine 2-oxo
2-methylamino-2-phenylcyclohexanone.svg Deschloroketamine Phenyl Methylamine 2-oxo
(S) -2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Esketamine o -chlorophenyl Methylamine 2-oxo
2- (2-Chlorophenyl) -2-methylaminocyclohexanone.svg Ketamine o -chlorophenyl Methylamine 2-oxo
2-Amino-2- (2-chlorophenyl) -6-hydroxycyclohexanone.svg Hydroxynorketamine o -chlorophenyl NH 2 2-oxo, 6-hydroxy
2- (2-Chlorophenyl) -2-ethylamino-cyclohexanone.svg Ethketamine o -chlorophenyl Ethylamine 2-oxo
2- (2-Chlorophenyl) -2-propylaminocyclohexanone.svg NPNK o -chlorophenyl n -propylamine 2-oxo
2- (2-Methoxyphenyl) -2-methyllaminocyclohexanone.svg Methoxyketamine o -methoxyphenyl Methylamine 2-oxo
2-methylamino-2- (2-methylphenyl) cyclohexanone.svg oMDCK o -Tolyl Methylamine 2-oxo
2-methylamino-2- (3-methylphenyl) cyclohexanone.svg mMDCK m -Tolyl Methylamine 2-oxo
2- (3-Chlorophenyl) -2-methylaminocyclohexanone.svg meta- ketamine m -chlorophenyl Methylamine 2-oxo
4- (2-chlorophenyl) -4-methylaminocyclohexanone.svg iso -ketamines o -chlorophenyl Methylamine 4-oxo
2- (2-Fluorophenyl) -2-methylaminocyclohexanone.svg 2-fluorodeschloroketamine o -fluorophenyl Methylamine 2-oxo
2- (3-Fluorophenyl) -2-methylaminocyclohexanone.svg 3-fluorodeschloroketamine m -fluorophenyl Methylamine 2-oxo
2- (2-bromophenyl) -2-methylaminocyclohexanone.svg Bromoketamine o -Bromophenyl Methylamine 2-oxo
2- (2-Trifluoromethylphenyl) -2-methylaminocyclohexanone.svg TFMDCK o -trifluoromethylphenyl Methylamine 2-oxo
SN35210.svg SN 35210 o -chlorophenyl Carbomethoxybutylamine 2-oxo
2-Ethylamino-2- (3-methoxyphenyl) cyclohexanone.svg Methoxetamine (MXE) m -methoxyphenyl Ethylamine 2-oxo
2- (3-Methoxyphenyl) -2-methylaminocyclohexanone.svg Methoxmetamine m -methoxyphenyl Methylamine 2-oxo
MXPr structure.png MXPr m -methoxyphenyl n -propylamine 2-oxo
HXE structure.png HXE m -hydroxyphenyl Ethylamine 2-oxo
HXM structure.png HXM m -hydroxyphenyl Methylamine 2-oxo
FXE structure.png FXE m -fluorophenyl Ethylamine 2-oxo
Phencyclidine structure.svg Phencyclidine (PCP) Phenyl Piperidine -
PC3MP structure.png PC3MP Phenyl 3-methylpiperidine -
PC4MP structure.png PC4MP Phenyl 4-methylpiperidine -
Rolicyclidine.svg Rolicyclidine (PCPy) Phenyl Pyrrolidine -
PCDMPy structure.png PCDMPy Phenyl 3,3-dimethylpyrrolidine -
PCMo structure.png PCMo Phenyl Morpholine -
2'-MeO-PCMo structure.png Methoxy-PCM (2'-MeO-PCMo) o -methoxyphenyl Morpholine -
3-MeO-PCMo.png 3'-MeO-PCMo m -methoxyphenyl Morpholine -
4'-MeO-PCMo structure.png 4'-MeO-PCMo p -methoxyphenyl Morpholine -
4'-Me-PCMo structure.png Methyl-PCM (4'-Me-PCMo) p -tolyl Morpholine -
2'-Me-4'-HO-PCMo structure.png Hydroxy-methyl-PCM 2-methyl-4-hydroxyphenyl Morpholine -
PYCP structure.png PYCP 2-pyridinyl Piperidine -
TCM structure.png TCM 2-thienyl Methylamine -
TCE structure.png TCE 2-thienyl Ethylamine -
TCPr structure.png TCPr 2-thienyl Propylamine -
Tenocyclidine.svg Tenocyclidine (TCP) 2-thienyl Piperidine -
TCPy structure.png TCPy 2-thienyl Pyrrolidine -
Tiletamine.svg Tiletamine 2-thienyl Ethylamine 2-oxo
Gacyclidine.png Gacyclidine 2-thienyl Piperidine 2-methyl
Bromadol Skeletal.png BDPC p -bromophenyl Dimethylamine 4-phenethyl-4-hydroxy
C-8813.svg C-8813 p -bromophenyl Dimethylamine 4- (thiophen-2-yl) ethyl-4-hydroxy
Dimetamine structure.png Dimetamine p -tolyl Dimethylamine 4-oxo
Ahmadi pcp 2010.svg 3 "-OH-2'-Me-PCP o -Tolyl 3-hydroxypiperidine -
1- (1-PhCHX) -4-Ph-4-OH-piperidine structure.png 4 "- Ph-4" - OH-PCP Phenyl 4-phenyl-4-hydroxypiperidine -
BTCP structure.png BTCP Benzothiophen-2-yl Piperidine -
BTCPy structure.png BTCPy Benzothiophen-2-yl Pyrrolidine -

Analog connections

The structure dependence of the hallucinogenic effects of phencyclidine was investigated by varying the size of the cycloalkane ring. It turns out that the corresponding cyclopentyl compound has about 1/10 of the hallucinogenic activity, while the cycloheptyl and cyclooctyl derivatives are inactive. The homologous compounds are obtained by reacting the respective cycloalkyl ketones with phenylmagnesium bromide . The resulting alcohol is then reacted with sodium azide and then reduced to the amine with lithium aluminum hydride . In the last step the piperidine ring is then built up with 1-5-dibromopentane.

Web links

Individual evidence

  1. ^ H. Morris, J. Wallach: From PCP to MXE: a comprehensive review of the non-medical use of dissociative drugs . In: Drug Testing and Analysis . 6, No. 7-8, 2014, pp. 614-32. doi : 10.1002 / dta.1620 . PMID 24678061 .
  2. ^ Jason Wallach, Simon D. Brandt: Phencyclidine-Based New Psychoactive Substances . In: Hans H. Maurer, Simon D. Brandt (Eds.): New Psychoactive Substances. Handbook of Experimental Pharmacology . tape 252 . Springer, Cham 2018, ISBN 978-3-03010560-0 , pp. 261-303 .
  3. Jason Wallach, Simon D. Brandt: 1,2-Diarylethylamine- and Ketamine-Based New Psychoactive Substances . In: Hans H. Maurer, Simon D. Brandt (Eds.): New Psychoactive Substances. Handbook of Experimental Pharmacology . tape 252 . Springer, Cham 2018, ISBN 978-3-03010560-0 , pp. 305-352 .
  4. a b c Abbas Ahmadi, Ali Mahmoudi: Synthesis and Biological Properties of 2-Hydroxy-1- (1-phenyltetralyl) piperidine and Some of its Intermediates as Derivatives of Phencyclidine . In: drug research . tape 55 , no. September 09 , 2005, p. 528 , doi : 10.1055 / s-0031-1296900 .
  5. a b c Abbas Ahmadi, Ali Mahmoudi, Ramin Hajikhani, Moslem Naserbakht: New morpholine analogues of phencyclidine: Chemical synthesis and pain perception in rats . In: Pharmacology Biochemistry and Behavior . tape 98 , no. 2 , April 2011, p. 227–233 , doi : 10.1016 / j.pbb.2010.12.019 .
  6. a b Isabelle Chaudieu, Jacques Vignon, Michèle Chicheportiche, Jean-Marc Kamenka, Gérard Trouiller, Robert Chicheportiche: Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs . In: Pharmacology Biochemistry and Behavior . tape 32 , no. 3 , March 1989, p. 699 , doi : 10.1016 / 0091-3057 (89) 90020-8 .
  7. ^ Y. Itzhak, Simon: A novel phencyclidine analog interacts selectively with mu opioid receptors . In: The Journal of Pharmacology and Experimental Therapeutics . 230, No. 2, 1984, pp. 383-386. PMID 6086884 .
  8. XS He, LP Raymon: Synthesis and biological evaluation of 1-1- (2-benzobthienyl) cyclohexylpiperidine homologues at dopamine-uptake and phencyclidine and sigma-binding sites . In: Journal of Medicinal Chemistry . 36, No. 9, 1993, pp. 1188-1193. doi : 10.1021 / jm00061a009 . PMID 8098066 .
  9. VA Eterović, R. Lu: Determinants of phencyclidine potency on the nicotinic acetylcholine receptors from muscle and electric organ . In: Cellular and Molecular Neurobiology . 19, No. 6, 1999, pp. 745-757. doi : 10.1023 / A: 1006905106834 . PMID 10456235 .
  10. P. Seeman, F. Ko: Dopamine receptor contribution to the action of PCP, LSD and ketamine psychotomimetics . In: Molecular Psychiatry . 10, No. 9, 2005, pp. 877-883. doi : 10.1038 / sj.mp.4001682 . PMID 15852061 .
  11. ^ OA al-Deeb: New analgesics derived from the phencyclidine analogue thienylcyclidine . In: drug research . 46, No. 5, May 1996, pp. 505-8. PMID 8737636 .
  12. A Ahmadi: Synthesis and study the analgesic effects of new analogues of ketamine on female wistar rats . In: Medicinal Chemistry . 8, No. 2, September, pp. 246-51. PMID 22385170 .
  13. A Ahmadi: Synthesis and study on analgesic effects of 1-1- (4-methylphenyl) (cyclohexyl) 4-piperidinol and 1-1- (4-methoxyphenyl) (cyclohexyl) 4-piperidinol as two new phencyclidine derivatives . In: drug research . 59, No. 4, September, pp. 202-6. PMID 19517897 .
  14. A Ahmadi: Synthesis and pain perception of new analogues of phencyclidine in NMRI male mice . In: Mini Reviews in Medicinal Chemistry . 14, No. 1, September, pp. 64-71. PMID 24251803 .
  15. A Ahmadi: Synthesis and analgesic effects of new pyrrole derivatives of phencyclidine in mice . In: drug research . 61, No. 5, September, pp. 296-300. PMID 21755813 .
  16. A Ahmadi: Synthesis and determination of chronic and acute thermal and chemical pain activities of a new derivative of phencyclidine in rats . In: Iranian Journal of Pharmaceutical Research . 9, No. 4, September, pp. 379-85. PMID 24381602 .
  17. A Ahmadi: 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 . In: drug research . 60, No. 1, September, pp. 30-5. PMID 20184224 .
  18. R Hajikhani: Effect of phencyclidine derivatives on anxiety-like behavior using at elevated plus maze test in mice . In: Advances in Clinical and Experimental Medicine . 21, No. 3, September, pp. 307-12. PMID 23214193 .
  19. A Ahmadi: Synthesis and Antinociception Activities of Some Novel Derivatives of Phencyclidine with Substituted Aminobenzothiazoles . In: Mini Rev Med Chem . 17, No. 1, September, pp. 78-84. PMID 27121715 .
  20. D. Lednicer: 4- (p-Bromophenyl) -4- (dimethylamino) -1-phenethylcyclohexanol, an extremely potent representative of a new analgesic series . In: Journal of Medicinal Chemistry . 22, No. 10, September, pp. 1157-1158. PMID 513062 .
  21. T. Maurice: PRE-084, a sigma selective PCP derivative, attenuates MK-801-induced impairment of learning in mice . In: Pharmacology Biochemistry and Behavior . 49, No. 4, September, pp. 859-869. PMID 7886099 .
  22. A. Thurkauf, B. De Costa, S. Yamaguchi, MV Mattson, AE Jacobson, KC Rice, MA Rogawski: Synthesis and anticonvulsant activity of 1-phenylcyclohexylamine analogs . In: Journal of Medicinal Chemistry . 33, No. 5, 1990, pp. 1452-8. doi : 10.1021 / jm00167a027 . PMID 2329567 .
  23. C. Sauer, F. Peters, R. Staack, G. Fritschi, H. Maurer: Metabolism and toxicological detection of a new designer drug, N- (1-phenylcyclohexyl) propanamine, in rat urine using gas chromatography-mass spectrometry . In: Journal of Chromatography A . 1186, No. 1-2, 2008, pp. 380-390. doi : 10.1016 / j.chroma.2007.11.002 . PMID 18035363 .
  24. A Kalir, S Teomy, A Amir, P Fuchs, SA Lee, EJ Holsztynska, W Rocki: N-allyl analogues of phencyclidine: chemical synthesis and pharmacological properties . In: J Med Chem . 27, No. 10, September, pp. 1267-71. doi : 10.1021 / jm00376a006 . PMID 6481761 .
  25. C. Sauer, F. Peters, A. Schwaninger, M. Meyer, H. Maurer: Investigations on the cytochrome P450 (CYP) isoenzymes involved in the metabolism of the designer drugs N- (1-phenyl cyclohexyl) -2-ethoxyethanamine and N- (1-phenylcyclohexyl) -2-methoxyethanamine . In: Biochemical Pharmacology . 77, No. 3, 2009, pp. 444-450. doi : 10.1016 / j.bcp.2008.10.024 . PMID 19022226 .
  26. ^ MA Iorio, L. Tomassini, MV Mattson, C. George, AE Jacobson: Synthesis, stereochemistry, and biological activity of the 1- (1-phenyl-2-methylcyclohexyl) piperidines and the 1- (1-phenyl-4- methylcyclohexyl) piperidines. Absolute configuration of the potent trans - (-) - 1- (1-phenyl-2-methylcyclohexyl) piperidine . In: Journal of Medicinal Chemistry . 34, No. 8, 1991, pp. 2615-2623. doi : 10.1021 / jm00112a041 . PMID 1875352 .
  27. A. Ahmadi, A. Mahmoudi: Synthesis with improved yield and study on the analgesic effect of 2-methoxyphencyclidine . In: drug research . 56, No. 5, 2006, pp. 346-350. doi : 10.1055 / s-0031-1296732 . PMID 16821645 .
  28. AM Ogunbadeniyi, A. Adejare: Syntheses of fluorinated phencyclidine analogs . In: Journal of Fluorine Chemistry . 114, 2002, pp. 39-42. doi : 10.1016 / S0022-1139 (01) 00565-6 .
  29. ^ J. Wallach, GD Paoli, A. Adejare, SD Brandt: Preparation and analytical characterization of 1- (1-phenylcyclohexyl) piperidine (PCP) and 1- (1-phenylcyclohexyl) pyrrolidine (PCPy) analogues . In: Drug Testing and Analysis . 6, No. 7-8, 2013, pp. 633-50. doi : 10.1002 / dta.1468 . PMID 23554350 .
  30. M Harvey, J Sleigh, L Voss, F Pruijn, J Jose, S Gamage, W Denny: Determination of the Hypnotic Potency in Rats of the Novel Ketamine Ester Analogue SN 35210 . In: Pharmacology . 96, No. 5-6, 2015, pp. 226-32. doi : 10.1159 / 000439598 . PMID 26352278 .
  31. Synthesis and determination of acute and chronic pain activities of 1- [1- (4-methylphenyl) (cyclohexyl)] morpholine as a new phencyclidine derivative in rats . In: drug research . 61, No. 2, 2011, pp. 92-7. doi : 10.1055 / s-0031-1296173 . PMID 21428243 .
  32. P Zarantonello, E Bettini, A Paio, C Simoncelli, S Terreni, F Cardullo: Novel analogues of ketamine and phencyclidine as NMDA receptor antagonists . In: Bioorg Med Chem Lett . 21, No. 7, September, pp. 2059-63. doi : 10.1016 / j.bmcl.2011.02.009 . PMID 21334205 .
  33. J Wallach, T Cole floor, B Cicali, SP Elliott, PV Kavanagh, A Adejare, NM Dempster: Syntheses and analytical characterizations of N-alkyl-arylcyclohexylamines . In: Drug Test Anal . 8, No. 8, 2016, pp. 801–815. doi : 10.1002 / dta.1861 . PMID 26360516 .
  34. D Lednicer, PF VonVoigtlander, DE Emmert: 4-Amino-4-arylcyclohexanones and their derivatives, a novel class of analgesics. 1. Modification of the aryl ring . In: J Med Chem . 23, No. 4, September, pp. 424-30. doi : 10.1021 / jm00178a014 . PMID 7381841 .
  35. A Ahmadi, J Solati, R Hajikhani, M Onagh, M Javadi: Synthesis and analgesic effects of 1-1- (2-methylphenyl) (cyclohexyl) -3-piperidinol as a new derivative of phencyclidine in mice . In: drug research . 60, No. 8, 2010, pp. 492-6. doi : 10.1055 / s-0031-1296317 . PMID 20863005 .
  36. Y Itzhak, A Kalir, BA Weissman, S Cohen: New analgesic drugs derived from phencyclidine . In: J Med Chem . 24, No. 5, 1981, pp. 496-9. doi : 10.1021 / jm00137a004 . PMID 7241506 .
  37. Jump up ↑ J. Vignon, V. Pinet, C. Cerruti, JM Kamenka, R. Chicheportiche: 3HN-1- (2-benzo (b) thiophenyl) cyclohexylpiperidine (3HBTCP): A new phencyclidine analog selective for the dopamine uptake complex . In: European Journal of Pharmacology . 148, No. 3, 1988, pp. 427-436. doi : 10.1016 / 0014-2999 (88) 90122-7 . PMID 3384005 .
  38. XS He, LP Raymon, MV Mattson, ME Eldefrawi, BR de Costa: Synthesis and biological evaluation of 1- [1- (2-benzo [b] thienyl) cyclohexyl] piperidine homologues at dopamine-uptake and phencyclidine- and sigma- binding sites . In: J Med Chem . 36, No. 9, September, pp. 1188-93. doi : 10.1021 / jm00061a009 . PMID 8098066 .
  39. ^ Roy L. McQuinn, Edward J. Cone, Harlan E. Shannon, Tsung-Ping Su: Structure-activity relationships of the cycloalkyl ring of phencyclidine . In: Journal of Medicinal Chemistry . tape 24 , no. December 12 , 1981, pp. 1429 , doi : 10.1021 / jm00144a011 .