Phencyclidine, the prototypal arylcyclohexylamine derivative.

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



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.


An arylcyclohexylamine is composed of a cyclohexylamine unit with an aryl moiety attachment. The aryl group is 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, secondary amines such as methylamino or ethylamino, or tertiary cycloalkylamines such as piperidino and pyrrolidino, are the most commonly encountered N-substituents.

General structure of arylcyclohexylamines


Arylcyclohexylamines 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, while PRE-084 is a selective sigma receptor agonist. Thus, radically different pharmacology is possible through different structural combinations.

List of arylcyclohexylamines

Compound Aryl Substituent N Group Cyclohexyl ring
PCA Phenyl NH2 -
PCM Phenyl Methylamino -
Eticyclidine Phenyl Ethylamino -
PCPr[2] Phenyl n-Propylamino -
PCiP Phenyl Isopropylamino -
PCBu Phenyl n-Butylamino -
PCEOH Phenyl Hydroxyethylamino -
PCMEA[3] Phenyl Methoxyethylamino -
PCEEA Phenyl Ethoxyethylamino -
PCMPA Phenyl Methoxypropylamino -
PCDM Phenyl Dimethylamino -
Dieticyclidine Phenyl Diethylamino -
2-HO-PCP[4] Phenyl Piperidine 2-Hydroxy
2-Me-PCP[5] Phenyl Piperidine 2-Methyl
2-MeO-PCP[6] Phenyl Piperidine 2-Methoxy
2-Keto-PCP Phenyl Piperidine 2-Keto
2-Keto-PCE Phenyl Ethylamino 2-Keto
4-Methyl-PCP Phenyl Piperidine 4-Methyl
4-Keto-PCP Phenyl Piperidine 4-Keto
2'-Cl-PCP o-Chlorophenyl Piperidine -
2'-MeO-PCP o-Methoxyphenyl Piperidine -
3'-F-PCP m-Fluorophenyl Piperidine -
3'-Me-PCP m-Methylphenyl Piperidine -
3'-NH2-PCP m-Aminophenyl Piperidine -
3'-HO-PCP m-Hydroxyphenyl Piperidine -
3-MeO-PCP m-Methoxyphenyl Piperidine -
3'-MeO-PCE m-Methoxyphenyl Ethylamino -
3'-MeO-PCPr m-Methoxyphenyl n-Propylamino -
3'-MeO-PCPy m-Methoxyphenyl Pyrrolidine -
4'-OH-PCP p-Hydroxyphenyl Piperidine -
Methoxydine (4-MeO-PCP) p-Methoxyphenyl Piperidine -
4'-F-PCP p-Fluorophenyl Piperidine -
Arketamine o-Chlorophenyl Methylamino 2-Keto
Deschloroketamine Phenyl Methylamino 2-Keto
Esketamine o-Chlorophenyl Methylamino 2-Keto
Ethketamine o-Chlorophenyl Ethylamino 2-Keto
Ketamine o-Chlorophenyl Methylamino 2-Keto
Methoxyketamine o-Methoxyphenyl Methylamino 2-Keto
Fluoroketamine o-Fluorophenyl Methylamino 2-Keto
Bromoketamine o-Bromophenyl Methylamino 2-Keto
Methoxetamine m-Methoxyphenyl Ethylamino 2-Keto
Phencyclidine (PCP) Phenyl Piperidine -
PC3MP Phenyl 3-Methylpiperidine -
PC4MP Phenyl 4-Methylpiperidine -
Rolicyclidine (PCPy) Phenyl Pyrrolidine -
PCDMPy Phenyl 3,3-Dimethylpyrrolidine -
PCMo Phenyl Morpholine -
Methoxy-PCM[7] o-Methoxyphenyl Morpholine -
Methyl-PCM[8] p-Methylphenyl Morpholine -
Hydroxy-methyl-PCM 2-Methyl-4-hydroxyphenyl Morpholine -
TCM 2-Thienyl Methylamino -
TCE 2-Thienyl Ethylamino -
Tenocyclidine (TCP) 2-Thienyl Piperidine -
TCPy 2-Thienyl Pyrrolidine -
Tiletamine 2-Thienyl Ethylamino 2-Keto
Gacyclidine 2-Thienyl Piperidine 2-Methyl
BDPC p-Bromophenyl Dimethylamino 4-Phenethyl-4-hydroxy
Dimetamine p-Methylphenyl Dimethylamino 4-Keto
BTCP Benzothiophen-2-yl Piperidine -
PRE-084 Phenyl Morpholinylethylcarboxylate -

See also

  • Substituted cathinone


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