Arylcyclohexylamines

Substitutive structure of an arylcyclohexylamine molecule. Here the aryl is comprised of a phenyl ring.

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Arylcyclohexylamine refers to a class of compounds which typically produce dissociation, anesthesia and hallucinogenic effects.

Chemistry

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 methylamine or ethylamine, or tertiary cycloalkylamines such as piperidine and pyrrolidine, are the most commonly encountered N-substituents.

Pharmacology

Arylcyclohexylamines are believed to produce their effects primarily by antagonism of NMDA receptors.^[1]Antagonism of the NMDA receptor confers anesthetic, anticonvulsant (seizure-preventing), and dissociative effects. Contrary to popular belief, most arylcyclohexylamines do not significantly inhibit re-uptake of dopamine or agonise μ-opioid receptors.=

Representative pK_i values for ketamine, PCP and analogs. – pK_i ± SD, (K_i, nM)^[2]
Compound	NMDA^[3]	SERT^[4]	NET^[5]	Sigma1	Sigma2
Ketamine	6.18±0.07 (659)	-	-	-	-
Phencyclidine (PCP)	7.23±0.07 (59)	5.65±0.05 (2234)	-	-	6.82±0.09 (136)
Methoxetamine (MXE)	6.59±0.06 (259)	6.32±0.05 (481)	-	-	-
4-MeO-PCP	6.39±0.06 (404)	6.07±0.05 (844)	6.1±0.1 (713)	6.5±0.1 (296)	7.93±0.08 (143)
3-MeO-PCP	7.69±0.08 (20)	6.7±0.1 (216)	-	7.4±0.1 (42)	-
3-MeO-PCE	7.22±0.08 (61)	6.9±0.06 (115)	-	5.3±0.1 (4519)	6.31±0.1 (525)

List of substituted arylcyclohexylamines

Compound	R_N1	R_N2	R₂	R₃	R₄	R_2'
2-BDCK	Methyl	H	Br	H	H	Ketone
2-FDCK	Methyl	H	F	H	H	Ketone
2-TFMDCK	Methyl	H	CF₃	H	H	Ketone
3,4-MD-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	OCH-	O-	H
O-PCE	Ethyl	H	H	H	H	Ketone
Deschloroketamine (DCK, O-PCM)	Methyl	H	H	H	H	Ketone
3-Cl-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	Cl	H	H
3-F-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	F	H	H
3-HO-PCE	Ethyl	H	H	Hydoxy	H	H
3-HO-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	Hydroxy	H	H
3-Me-PCE	Ethyl	H	H	Methyl	H	H
3-Me-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	Methyl	H	H
3-Me-PCPy	CH₂CH₂-	CH₂CH₂-	H	Methyl	H	H
3-MeO-PCE	Ethyl	H	H	Methoxy	H	H
3-MeO-PCMo	CH₂CH₂O-	CH₂CH₂-	H	Methoxy	H	H
3-MeO-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	Methoxy	H	H
4-MeO-PCP	CH₂CH₂CH₂-	CH₂CH₂-	H	H	Methoxy	H
Eticyclidine (PCE)	Ethyl	H	H	H	H	H
HXE	Ethyl	H	H	Hydroxy	H	Ketone
Phencyclidine (PCP)	CH₂CH₂CH₂-	CH₂CH₂-	H	H	H	H
Ketamine	Methyl	H	Cl	H	H	Ketone
Methoxetamine	Ethyl	H	H	Methoxy	H	Ketone
MXiPr	Isopropyl	H	H	Methoxy	H	Ketone