Methoxyketamine

Methoxyketamine
Names
	IUPAC name 2-(2-Methoxyphenyl)-2-(methylamino)cyclohexanone
Identifiers
CAS Number	7063-51-6 ; 6728-62-7 (HCl) ;
3D model (JSmol)	Interactive image;
ChemSpider	27470964;
PubChem CID	57483650;
UNII	U4I8JIS24N ; 2OVB5UO35R (HCl) ;
CompTox Dashboard (EPA)	DTXSID30990849 ;
	InChI 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;
	SMILES CNC1(CCCCC1=O)c2ccccc2OC;
Properties
Chemical formula	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). Infobox references

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.

References

^ BE 634208, Stevens, Calvin L., "Amino ketones", published 1963
^ 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.

[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.

[1]

[2]

See also

References