Arylcyclohexylamine

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Phencyclidine, the prototypal arylcyclohexylamine derivative.

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

History[edit]

Phencyclidine (PCP) is believed to be the first arylcyclohexylamine with recognized anesthetic properties, but several arylcyclohexylamines were described before PCP in the scientific literature, beginning with PCA (1-phenylcyclohexan-1-amine) the synthesis of which was first published in 1907. PCE was reported in 1953 and PCMo in 1954, with the latter compound described as a potent sedative.[1] Arylcyclohexylamine anesthetics were intensively investigated at Parke-Davis, beginning with the 1956 synthesis of phencyclidine and later the related compound ketamine.[1] The 1970s saw the debut of these compounds, especially PCP and its analogues, as illicitly used recreational drugs 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.[2][3][4]

Structure[edit]

General structure of arylcyclohexylamines

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.

Pharmacology[edit]

Arylcyclohexylamines varyingly possess NMDA receptor antagonistic,[5][6] dopamine reuptake inhibitory,[7] and μ-opioid receptor agonistic[8] properties. Additionally, σ receptor agonistic,[9] nACh receptor antagonistic,[10] and D2 receptor agonistic[11] 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 psychomimetic effects.[11]

These are versatile agents with a wide range of possible pharmacological activities depending on the extent and range to which chemical modifications are implemented.[12][13][14][15][16][17][18][19][20] 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,[7] PCP is primarily an NMDA antagonist,[5] and BDPC is a potent μ-opioid agonist,[21] while PRE-084 is a selective sigma receptor agonist.[22] Thus, radically different pharmacology is possible through different structural combinations.

List of arylcyclohexylamines[edit]

Structure Compound Aryl Substituent N Group Cyclohexyl ring
PCA structure.png PCA[23] Phenyl NH2 -
PCM structure.png PCM[23] Phenyl Methylamino -
Eticyclidine.svg Eticyclidine Phenyl Ethylamino -
PCPr structure.png PCPr [24] Phenyl n-Propylamino -
PCiP structure.png PCiP Phenyl Isopropylamino -
PCAL structure.png PCAL [25] Phenyl Allylamino -
PCBu structure.png PCBu Phenyl n-Butylamino -
PCEOH structure.png PCEOH Phenyl Hydroxyethylamino -
PCMEA structure.png PCMEA[26] Phenyl Methoxyethylamino -
PCEEA structure.png PCEEA Phenyl Ethoxyethylamino -
PCMPA structure.png PCMPA Phenyl Methoxypropylamino -
PCDM structure.png PCDM[23] Phenyl Dimethylamino -
Dieticyclidine.svg Dieticyclidine Phenyl Diethylamino -
2-HO-PCP structure.png 2-HO-PCP[5] Phenyl Piperidine 2-Hydroxy
2-Me-PCP structure.png 2-Me-PCP[27] Phenyl Piperidine 2-Methyl
2-MeO-PCP structure.png 2-MeO-PCP[28] Phenyl Piperidine 2-Methoxy
O-PCP structure.png 2-Keto-PCP Phenyl Piperidine 2-Keto
O-PCE structure.png Eticyclidone ("O-PCE") Phenyl Ethylamino 2-Keto
O-PCPr structure.png 2-Keto-PCPr Phenyl n-Propylamino 2-Keto
4-Me-PCP structure.png 4-Methyl-PCP Phenyl Piperidine 4-Methyl
4-Keto-PCP structure.png 4-Keto-PCP Phenyl Piperidine 4-Keto
2'-Cl-PCP structure.png 2'-Cl-PCP o-Chlorophenyl Piperidine -
2'-MeO-PCP structure.png 2'-MeO-PCP o-Methoxyphenyl Piperidine -
3'-F-PCP structure.png 3'-F-PCP[29] m-Fluorophenyl Piperidine -
3'-Me-PCP structure.png 3'-Me-PCP[30] m-Tolyl Piperidine -
3'-Me-PCPy structure.png 3'-Me-PCPy m-Tolyl Pyrrolidine -
3'-NH2-PCP structure.png 3'-NH2-PCP m-Aminophenyl Piperidine -
3-HO-PCP.png 3'-HO-PCP m-Hydroxyphenyl Piperidine -
3-MeO-PCP structure.svg 3'-MeO-PCP m-Methoxyphenyl Piperidine -
MDPCP structure.png 3',4'-MD-PCP 3,4-Methylenedioxyphenyl Piperidine -
3-MeO-PCE.svg 3'-MeO-PCE m-Methoxyphenyl Ethylamino -
3'-OH-PCE structure.png 3'-HO-PCE m-Hydroxyphenyl Ethylamino -
3'-MeO-PCPr structure.png 3'-MeO-PCPr m-Methoxyphenyl n-Propylamino -
3'-OH-PCPr structure.png 3'-HO-PCPr m-Hydroxyphenyl n-Propylamino -
MDPCPr structure.png 3',4'-MD-PCPr 3,4-Methylenedioxyphenyl n-Propylamino -
3'-MeO-PCPy structure.png 3'-MeO-PCPy[30] m-Methoxyphenyl Pyrrolidine -
4'-HO-PCP structure.png 4'-HO-PCP p-Hydroxyphenyl Piperidine -
4-methoxyphencyclidine.png Methoxydine (4'-MeO-PCP) p-Methoxyphenyl Piperidine -
4'-MeO-PCE structure.png 4'-MeO-PCE p-Methoxyphenyl Ethylamino -
4'-F-PCP structure.png 4'-F-PCP[29] p-Fluorophenyl Piperidine -
4'-F-PCPy structure.png 4'-F-PCPy p-Fluorophenyl Pyrrolidine -
Arketamine structure.svg Arketamine o-Chlorophenyl Methylamino 2-Keto
Deschloroketamine.png Deschloroketamine Phenyl Methylamino 2-Keto
Esketamine2DCSD.svg Esketamine o-Chlorophenyl Methylamino 2-Keto
Ketamine2DCSD.svg Ketamine o-Chlorophenyl Methylamino 2-Keto
(2R,6R)-Hydroxynorketamine Formula V1.svg Hydroxynorketamine o-Chlorophenyl NH2 2-Keto, 6-Hydroxy
N-Ethylnorketamine structure.png Ethketamine o-Chlorophenyl Ethylamino 2-Keto
NPNK structure.png NPNK o-Chlorophenyl n-Propylamino 2-Keto
Methoxyketamine.svg Methoxyketamine o-Methoxyphenyl Methylamino 2-Keto
OMDCK structure.png oMDCK o-Tolyl Methylamino 2-Keto
MMDCK structure.png mMDCK m-Tolyl Methylamino 2-Keto
Meta-ketamine structure.png meta-Ketamine m-Chlorophenyl Methylamino 2-Keto
Isoketamine structure.png iso-Ketamine o-Chlorophenyl Methylamino 4-Keto
2-Fluorodeschloroketamine.svg 2-Fluorodeschloroketamine o-Fluorophenyl Methylamino 2-Keto
Bromoketamine structure.png Bromoketamine o-Bromophenyl Methylamino 2-Keto
TFMDCK structure.png TFMDCK o-Trifluoromethylphenyl Methylamino 2-Keto
SN35210 structure.png SN 35210 [31] o-Chlorophenyl Carbomethoxybutylamino 2-Keto
Methoxetamine2DCSD.svg Methoxetamine m-Methoxyphenyl Ethylamino 2-Keto
Methoxmetamine.png Methoxmetamine m-Methoxyphenyl Methylamino 2-Keto
MXPr structure.png MXPr m-Methoxyphenyl n-Propylamino 2-Keto
HXE structure.png HXE m-Hydroxyphenyl Ethylamino 2-Keto
HXM structure.png HXM m-Hydroxyphenyl Methylamino 2-Keto
FXE structure.png FXE m-Fluorophenyl Ethylamino 2-Keto
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[6] (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[32] (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 [33] 2-Pyridinyl Piperidine -
TCM structure.png TCM 2-Thienyl Methylamino -
TCE structure.png TCE 2-Thienyl Ethylamino -
TCPr structure.png TCPr [34] 2-Thienyl Propylamino -
Tenocyclidine.svg Tenocyclidine (TCP) 2-Thienyl Piperidine -
TCPy structure.png TCPy 2-Thienyl Pyrrolidine -
Tiletamine.svg Tiletamine 2-Thienyl Ethylamino 2-Keto
Gacyclidine.png Gacyclidine 2-Thienyl Piperidine 2-Methyl
Bromadol Skeletal.png BDPC p-Bromophenyl Dimethylamino 4-Phenethyl-4-hydroxy
C-8813.png C-8813 p-Bromophenyl Dimethylamino 4-(thiophen-2-yl)ethyl-4-hydroxy
Dimetamine structure.png Dimetamine [35] p-Tolyl Dimethylamino 4-Keto
Ahmadi pcp 2010.svg 3''-OH-2'-Me-PCP [36] o-Tolyl 3-Hydroxypiperidine -
1-(1-PhCHX)-4-Ph-4-OH-piperidine structure.png 4''-Ph-4''-OH-PCP [37] Phenyl 4-Phenyl-4-hydroxypiperidine -
BTCP structure.png BTCP[38] Benzothiophen-2-yl Piperidine -
PRE-084 SVG file.svg PRE-084 Phenyl Morpholinylethylcarboxylate -

Other cycloalkane ring sizes have been experimented with than just purely thinking in terms of the cyclohexylamine. The cyclopentyl homologue of PCP is active with around 1/10th the potency, while the cycloheptyl and cyclooctyl derivatives are inactive. The requisite cycloalkylketone is reacted with PhMgBr; 3° alcohol is then reacted with NaN3; azide then reduced with LAH. Then in the final step the piperidine ring is constructed with 1-5-dibromo-pentane.[39]

Rigid[edit]

Conformationally constrained analogs have also been prepared and researched by Morieti et al.[40]

References[edit]

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