A-834,735

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A-834,735
A-834735 structure.png
Systematic (IUPAC) name
{1-[(tetrahydro-2H-pyran-4-yl)methyl]-1H-indol-3-yl}-(2,2,3,3-tetramethylcyclopropyl)methanone
Identifiers
CAS Number 895155-57-4 N
PubChem CID: 11544639
ChemSpider 9719418 YesY
ChEMBL CHEMBL271158 YesY
Chemical data
Formula C22H29NO2
Molecular mass 339.48 g·mol−1
  • C4COCCC4Cn(c3)c2ccccc2c3C(=O)C1C(C)(C)C1(C)C
  • InChI=1S/C22H29NO2/c1-21(2)20(22(21,3)4)19(24)17-14-23(13-15-9-11-25-12-10-15)18-8-6-5-7-16(17)18/h5-8,14-15,20H,9-13H2,1-4H3 YesY
  • Key:NQTMRZNYLIGQCF-UHFFFAOYSA-N YesY
 NYesY (what is this?)  (verify)

A-834,735 is a drug developed by Abbott Laboratories that acts as a potent cannabinoid receptor full agonist at both the CB1 and CB2 receptors, with a Ki of 12nM at CB1 and 0.21nM at CB2. Replacing the aromatic 3-benzoyl or 3-naphthoyl group found in most indole derived cannabinoids, with the 3-tetramethylcyclopropylmethanone group of A-834,735 and related compounds, imparts significant selectivity for CB2, with most compounds from this group found to be highly selective CB2 agonists with little affinity for CB1. However low nanomolar CB1 binding affinity is retained with certain heterocyclic 1-position substituents such as (N-methylpiperidin-2-yl)methyl (cf. AM-1220, AM-1248), or the (tetrahydropyran-4-yl)methyl substituent of A-834,735, resulting in compounds that still show significant affinity and efficacy at both receptors despite being CB2 selective overall.[1][2][3][4][5]

Legal Status

As of October 2015 A-834,735 is a controlled substance in China.[6]

See also

References

  1. ↑ Dart M, et al. (2006). 1-Alkyl-3-keto-indoles: identification and in vitro characterization of a series of potent cannabinoid ligands. In 2006 Symposium on the Cannabinoids. International Cannabinoid Research Society: Burlington, VT.
  2. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  3. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  6. ↑ Lua error in package.lua at line 80: module 'strict' not found.


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