Methoxyketamine
Names
IUPAC name
2-(2-Methoxyphenyl)-2-(methylamino)cyclohexanone
Identifiers
3D model (JSmol)
ChemSpider
UNII
  • InChI=1S/C14H19NO2/c1-15-14(10-6-5-9-13(14)16)11-7-3-4-8-12(11)17-2/h3-4,7-8,15H,5-6,9-10H2,1-2H3
    Key: OYAUVHORXFUVAJ-UHFFFAOYSA-N
  • InChI=1/C14H19NO2/c1-15-14(10-6-5-9-13(14)16)11-7-3-4-8-12(11)17-2/h3-4,7-8,15H,5-6,9-10H2,1-2H3
    Key: OYAUVHORXFUVAJ-UHFFFAOYAM
  • CNC1(CCCCC1=O)c2ccccc2OC
Properties
C14H19NO2
Molar mass 233.311 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Methoxyketamine or 2-MeO-2-deschloroketamine is a designer drug of the arylcyclohexylamine class first reported in 1963.[1] It is an analog of ketamine in which the chlorine atom has been replaced with a methoxy group. Its synthesis by rearrangement of an amino ketone has been reported.[2] As an arylcyclohexylamine, methoxyketamine most likely functions as an NMDA receptor antagonist. It produces sedative, hallucinogenic, and (at high doses) anesthetic effects, but with a lower potency than ketamine itself.

See also

References

  1. ^ BE 634208, Stevens, Calvin L., "Amino ketones", published 1963 
  2. ^ Stevens, Calvin L.; Thuillier, Andre; Taylor, K. Grant; Daniher, Francis A.; Dickerson, James P.; Hanson, Harry T.; Nielsen, Norman A.; Tikotkar, N. A.; Weier, Richard M. (1966). "Amino Ketone Rearrangements. VII.1 Synthesis of 2-Methylamino-2-Substituted Phenylcyclohexanones". The Journal of Organic Chemistry. 31 (8): 2601. doi:10.1021/jo01346a034.



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