Methoxyketamine

Methoxyketamine
Names
IUPAC name
2-(2-Methoxyphenyl)-2-(methylamino)cyclohexanone
Identifiers
CAS Number
  • 7063-51-6 checkY
  • 6728-62-7 (HCl) checkY
3D model (JSmol)
  • Interactive image
ChemSpider
  • 27470964
PubChem CID
  • 57483650
UNII
  • U4I8JIS24N checkY
  • 2OVB5UO35R (HCl) checkY
CompTox Dashboard (EPA)
  • DTXSID30990849 Edit this at Wikidata
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
  • 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
Chemical compound

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.


  • v
  • t
  • e
Psychedelics
(5-HT2A
agonists)
Benzofurans
Lyserg‐
amides
Phenethyl‐
amines
2C-x
25x-NBx
25x-NB
25x-NB3OMe
  • 25B-NB3OMe
  • 25C-NB3OMe
  • 25D-NB3OMe
  • 25E-NB3OMe
  • 25H-NB3OMe
  • 25I-NB3OMe
  • 25N-NB3OMe
  • 25P-NB3OMe
  • 25T2-NB3OMe
  • 25T4-NB3OMe
  • 25T7-NB3OMe
  • 25TFM-NB3OMe
25x-NB4OMe
  • 25B-NB4OMe
  • 25C-NB4OMe
  • 25D-NB4OMe
  • 25E-NB4OMe
  • 25H-NB4OMe
  • 25I-NB4OMe
  • 25N-NB4OMe
  • 25P-NB4OMe
  • 25T2-NB4OMe
  • 25T4-NB4OMe
  • 25T7-NB4OMe
  • 25TFM-NB4OMe
25x-NBF
25x-NBMD
  • 25B-NBMD
  • 25C-NBMD
  • 25D-NBMD
  • 25E-NBMD
  • 25F-NBMD
  • 25H-NBMD
  • 25I-NBMD
  • 25P-NBMD
  • 25T2-NBMD
  • 25T7-NBMD
  • 25TFM-NBMD
25x-NBOH
25x-NBOMe
Atypical structures
25x-NMx
  • 25B-NMe7BF
  • 25B-NMe7BT
  • 25B-NMe7Bim
  • 25B-NMe7Box
  • 25B-NMe7DHBF
  • 25B-NMe7Ind
  • 25B-NMe7Indz
  • 25B-NMePyr
  • 25I-NMe7DHBF
  • 25I-NMeFur
  • 25I-NMeTHF
  • 25I-NMeTh
N-(2C)-fentanyl
  • N-(2C-B) fentanyl
  • N-(2C-C) fentanyl
  • N-(2C-D) fentanyl
  • N-(2C-E) fentanyl
  • N-(2C-G) fentanyl
  • N-(2C-H) fentanyl
  • N-(2C-I) fentanyl
  • N-(2C-IP) fentanyl
  • N-(2C-N) fentanyl
  • N-(2C-P) fentanyl
  • N-(2C-T) fentanyl
  • N-(2C-T-2) fentanyl
  • N-(2C-T-4) fentanyl
  • N-(2C-T-7) fentanyl
  • N-(2C-TFM) fentanyl
3C-x
4C-x
DOx
HOT-x
MDxx
Mescaline (subst.)
TMAs
  • TMA
  • TMA-2
  • TMA-3
  • TMA-4
  • TMA-5
  • TMA-6
Others
Piperazines
Tryptamines
alpha-alkyltryptamines
x-DALT
x-DET
x-DiPT
x-DMT
x-DPT
Ibogaine-related
x-MET
x-MiPT
Others
Others
Dissociatives
(NMDAR
antagonists)
Arylcyclo‐
hexylamines
Ketamine-related
PCP-related
Others
Adamantanes
Diarylethylamines
Morphinans
Others
Deliriants
(mAChR
antagonists)
Others
Cannabinoids
(CB1 agonists)
Natural
Synthetic
AM-x
CP x
HU-x
JWH-x
Misc. designer cannabinoids
D2 agonists
GABAA
enhancers
Inhalants
(Mixed MOA)
κOR agonists
Oneirogens
Others
  • v
  • t
  • e
AMPARTooltip α-Amino-3-hydroxy-5-methyl-4-isoxazolepropionic acid receptor
KARTooltip Kainate receptor
NMDARTooltip N-Methyl-D-aspartate receptor
  • See also: Receptor/signaling modulators
  • Metabotropic glutamate receptor modulators
  • Glutamate metabolism/transport modulators
  • v
  • t
  • e
Group I
mGluR1Tooltip Metabotropic glutamate receptor 1
mGluR5Tooltip Metabotropic glutamate receptor 5
Group II
mGluR2Tooltip Metabotropic glutamate receptor 2
mGluR3Tooltip Metabotropic glutamate receptor 3
Group III
mGluR4Tooltip Metabotropic glutamate receptor 4
  • Antagonists: CPPG
  • MAP4
  • MPPG
  • MSOP
  • MTPG
  • UBP-1112
mGluR6Tooltip Metabotropic glutamate receptor 6
  • Antagonists: CPPG
  • MAP4
  • MPPG
  • MSOP
  • MTPG
  • UBP-1112
mGluR7Tooltip Metabotropic glutamate receptor 7
  • Antagonists: CPPG
  • MAP4
  • MMPIP
  • MPPG
  • MSOP
  • MTPG
  • UBP-1112
  • XAP044; Negative allosteric modulators: ADX71743
mGluR8Tooltip Metabotropic glutamate receptor 8
  • Antagonists: CPPG
  • MAP4
  • MPPG
  • MSOP
  • MTPG
  • UBP-1112
See also: Receptor/signaling modulators • Ionotropic glutamate receptor modulators • Glutamate metabolism/transport modulators


Stub icon

This article about an organic compound is a stub. You can help Wikipedia by expanding it.

  • v
  • t
  • e