Arylcyclohexylamine

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Substitutive structure of an arylcyclohexylamine molecule
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Arylcyclohexylamine refers to a class of compounds which typically produce dissociation, anesthesia and hallucinogenic effects.

Chemistry

Arylcyclohexylamines are comprised of an amine moiety and an aromatic ring attached to a cyclohexane ring.

Hydrogen atoms around the structure can be substituted for other functional groups to produce drugs of varying potency, affinity, efficacy and half-life.

Pharmacology

Arylcyclohexylamines are believed to produce their effects primarily by antagonism of NMDA receptors.[1]Antagonism of the NMDA receptor confers anesthetic, anticonvulsant, 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)

Examples

Legal status

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

See also

References

  1. Ahmadi, A.; Khalili, M.; Hajikhani, R.; Naserbakht, M. (2011). "New morpholine analogues of phencyclidine: Chemical synthesis and pain perception in rats". Pharmacology Biochemistry and Behavior 98 (2): 227–233. (ScienceDirect) | http://www.sciencedirect.com/science/article/pii/S0091305710004028
  2. http://journals.plos.org/plosone/article?id=10.1371/journal.pone.0059334
  3. N-methyl-D-aspartate receptor
  4. Serotonin transporter
  5. Norepinephrine transporter