Article · Wikipedia archive · Last revised Jul 21, 2026

Methoxyketamine

Methoxyketamine or 2-MeO-2-deschloroketamine is a designer drug of the arylcyclohexylamine class first reported in 1963. 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. As an arylcyclohexylamine, methoxyketamine most likely functions as an NMDA receptor antagonist. It produces sedative, hallucinogenic, and anesthetic effects, but with a lower potency than ketamine itself.

Last revised
Jul 21, 2026
Read time
≈ 1 min
Length
210 w
Citations
2
Source
Wikipedia ↗
Methoxyketamine
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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
Pharmacology
Legal status
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

See also

References

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.