Arylcyclohexylamine

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File:Phencyclidine structure.svg
Phencyclidine, the prototypal arylcyclohexylamine derivative.

Arylcyclohexylamines, also known as arylcyclohexamines or arylcyclohexanamines, are a chemical class of pharmaceutical, designer, and experimental drugs.

History

The arylcyclohexylamines were originally developed as anesthetics in the 1960s with ketamine and phencyclidine (PCP) being the first members of the class to be synthesized. The 1970s saw the debut of these compounds, especially PCP and its analogues, as illicit drugs of abuse due to their dissociative hallucinogenic and euphoriant effects. Since, the class has been expanded by scientific research into stimulant, analgesic, and neuroprotective agents, and also by clandestine chemists in search of novel recreational drugs.

Chemistry

An arylcyclohexylamine is composed of a cyclohexylamine unit with an aryl moiety attachment. The aryl group is often positioned geminal to the amine. In the simplest cases, the aryl moiety is typically a phenyl ring, sometimes with additional substitution. The amine is usually not primary, piperidino and pyrrolidino are examples of tertiary cycloalkylamines.

Pharmacology

Arylcyclohexylaminess varyingly possess NMDA receptor antagonist, dopamine reuptake inhibitor, and μ-opioid receptor agonist properties. Additionally, σ receptor agonist, nACh receptor antagonist, and D2 receptor agonist actions have been reported for some of these agents. Antagonism of the NMDA receptor confers anesthetic, anticonvulsant, neuroprotective, and dissociative effects, blockade of the dopamine transporter mediates stimulant and euphoriant effects as well as psychosis in high amounts, and activation of the μ-opioid receptor causes analgesic and euphoriant effects. Stimulation of the σ and D2 receptors may also contribute to hallucinogenic and psychotic effects.

Versatile agents with a wide range of possible pharmacological activities depending on the extent and range to which chemical modifications are implemented. The various choice of substitutions that are made allows for "fine-tuning" of the pharmacological profile that results. As examples, BTCP is a selective dopamine reuptake inhibitor,[1] PCP is primarily an NMDA antagonist, and BDPC is a superpotent μ-opioid agonist. Thus, radically different pharmacology is possible through different structural configurations.

List of arylcyclohexylamines

Compound Aryl Substituent N Group Other
2-HO-PCP[2] Phenyl Piperidine 2-Hydroxy
2-Me-PCP[3] Phenyl Piperidine 2-Methyl(cyclohexyl)
2-MeO-PCP[4] Phenyl Piperidine 2-Methoxy
3-HO-PCP m-Hydroxyphenyl Piperidine -
3-MeO-PCP m-Methoxyphenyl Piperidine -
4-MeO-PCP p-Methoxyphenyl Piperidine -
Arketamine o-Chlorophenyl NHMe 2-Keto(cyclohexyl)
BDPC p-Bromophenyl NHMe2 4-Phenethyl-4-hydroxy
BTCP Benzothiophen-2-yl Piperidine -
Deschloroketamine Phenyl NHMe 2-Keto
Dieticyclidine Phenyl NEt2 -
Esketamine o-Chlorophenyl NHMe 2-Keto
Ethylketamine o-Chlorophenyl NHEt O
Eticyclidine Phenyl NHEt -
Gacyclidine 2-Thienyl Piperidine 2-Methyl(cyclohexyl)
Ketamine o-Chlorophenyl NHMe O
Methoxetamine m-Methoxyphenyl NHEt O
PCEEA[5] Phenyl NHC2H4OEt -
PCM Phenyl NHMe -
PCMEA[5] Phenyl NHCH2OEt -
PCPr[6] Phenyl PrnNH -
Phencyclamine Phenyl NH2 -
Phencyclidine Phenyl Piperidine -
Rolicyclidine Phenyl Pyrrolidine -
Tenocyclidine 2-Thienyl Piperidine -
Tiletamine 2-Thienyl NHEt O

References

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External links


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Others: AL-38022A • Ibogaine • Noribogaine • Voacangine
Dissociatives
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Adamantanes: Amantadine • Memantine • Rimantadine;
Arylcyclohexylamines: 3-MeO-PCP • 4-MeO-PCP • Dieticyclidine • Esketamine • Eticyclidine • Gacyclidine • Ketamine • Methoxetamine • Neramexane • Phencyclidine • PCPr • Rolicyclidine • Tenocyclidine • Tiletamine;
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  1. ↑ Chaudieu, I; Vignon; Chicheportiche; Kamenka; Trouiller; Chicheportiche (1989). "Role of the aromatic group in the inhibition of phencyclidine binding and dopamine uptake by PCP analogs". Pharmacology, biochemistry, and behavior. 32 (3): 699–705. doi:10.1016/0091-3057(89)90020-8. PMID 2544905.  More than one of |author2= and |last2= specified (help); More than one of |author3= and |last3= specified (help); More than one of |author4= and |last4= specified (help); More than one of |author5= and |last5= specified (help); More than one of |author6= and |last6= specified (help) edit
  2. ↑ Ahmadi, A; Mahmoudi (2005). "Synthesis and biological properties of 2-hydroxy-1-(1-phenyltetralyl)piperidine and some of its intermediates as derivatives of phencyclidine". Arzneimittel-Forschung. 55 (9): 528–32. PMID 16229117.  More than one of |author2= and |last2= specified (help) edit
  3. ↑ Iorio, MA; Tomassini, L; Mattson, MV; George, C; Jacobson, AE (1991). "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". Journal of Medicinal Chemistry. 34 (8): 2615–23. doi:10.1021/jm00112a041. PMID 1875352.  edit
  4. ↑ Ahmadi, A; Mahmoudi, A (2006). "Synthesis with improved yield and study on the analgesic effect of 2-methoxyphencyclidine". Arzneimittel-Forschung. 56 (5): 346–50. PMID 16821645.  edit
  5. ↑ 5.0 5.1 Sauer, C.; Peters, F.; Schwaninger, A.; Meyer, M.; Maurer, H. (2009). "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". Biochemical pharmacology. 77 (3): 444–450. doi:10.1016/j.bcp.2008.10.024. PMID 19022226.  edit
  6. ↑ Sauer, C.; Peters, F.; Staack, R.; Fritschi, G.; Maurer, H. (2008). "Metabolism and toxicological detection of a new designer drug, N-(1-phenylcyclohexyl)propanamine, in rat urine using gas chromatography-mass spectrometry". Journal of chromatography. A. 1186 (1-2): 380–390. doi:10.1016/j.chroma.2007.11.002. PMID 18035363.  edit
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