AM-2389

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AM-2389
AM-2389 structure.png
Systematic (IUPAC) name
(6aR,9R,10aR)-3-(1-hexyl-cyclobut-1-yl)-6a,7,8,9,10,10a-hexahydro-6,6-dimethyl-6H-dibenzo[b,d]pyran-1,9 diol
Clinical data
Legal status
?
Identifiers
CAS number 1256842-49-5 N
ATC code ?
PubChem CID 49783410
ChemSpider 26333264 YesY
Chemical data
Formula C25H38O3 
Mol. mass 386.566 g/mol
 N (what is this?)

AM-2389 is a classical cannabinoid derivative which acts as a potent and reasonably selective agonist for the CB1 receptor, with a Ki of 0.16 nM, and 26x selectivity over the related CB2 receptor. It has high potency in animal tests of cannabinoid activity, and a medium duration of action.[1][2] Replacing the 1',1'-dimethyl substitution of the dimethylheptyl side chain of classical cannabinoids with cyclopropyl or cyclopentyl results in higher potency than cyclobutyl, but only the cyclobutyl derivatives show selectivity for CB1 over CB2.[3] High selectivity for CB1 over CB2 is difficult to achieve (cf. AM-906, AM-1235), as almost all commonly used CB1 agonists have similar or greater affinity for CB2 than CB1, and the only truly highly selective CB1 agonists known as of 2012 are eicosanoid derivatives such as O-1812.

See also[edit]

References[edit]

  1. ^ Nikas SP, et al. Novel 1',1'-chain substituted hexahydrocannabinols: 9β-hydroxy-3-(1-hexyl-cyclobut-1-yl)-hexahydrocannabinol (AM2389) a highly potent cannabinoid receptor 1 (CB1) agonist. Journal of Medicinal Chemistry. 2010 Oct 14;53(19):6996-7010. PMID 20925434
  2. ^ Järbe TU, et al. AM2389, a high-affinity, in vivo potent CB(1)-receptor-selective cannabinergic ligand as evidenced by drug discrimination in rats and hypothermia testing in mice. Psychopharmacology (Berlin). 2011 Oct 12. PMID 21989802
  3. ^ Papahatjis DP, et al. C1'-cycloalkyl side chain pharmacophore in tetrahydrocannabinols. Journal of Medicinal Chemistry. 2007 Aug 23;50(17):4048-60. PMID 17672444