Arylcyclohexylamines

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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 pKi values for ketamine, PCP and analogs. – pKi ± SD, (Ki, 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 RN1 RN2 R2 R3 R4 R2' Structure
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
 

Legal status

 

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  • United Kingdom - The arylcyclohexylamine family became illegal in the United Kingdom 2013.[citation needed]

See also

External links

References

  1. ↑ Ahmadi, A., Khalili, M., Hajikhani, R., Naserbakht, M. (1 April 2011). "New morpholine analogues of phencyclidine: Chemical synthesis and pain perception in rats". Pharmacology Biochemistry and Behavior. 98 (2): 227–233. doi:10.1016/j.pbb.2010.12.019. ISSN 0091-3057. 
  2. ↑ Roth, B. L., Gibbons, S., Arunotayanun, W., Huang, X.-P., Setola, V., Treble, R., Iversen, L. (19 March 2013). "The Ketamine Analogue Methoxetamine and 3- and 4-Methoxy Analogues of Phencyclidine Are High Affinity and Selective Ligands for the Glutamate NMDA Receptor". PLOS ONE. 8 (3): e59334. doi:10.1371/journal.pone.0059334. ISSN 1932-6203. 
  3. ↑ N-methyl-D-aspartate receptor
  4. ↑ Serotonin transporter
  5. ↑ Norepinephrine transporter


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