AM-905

AM-905
Identifiers
IUPAC name
  • (6aR,9R,10aR)-3-[(E)-hept-1-enyl]-9-(hydroxymethyl)-6,6-dimethyl-6a,7,8,9,10,10a-hexahydrobenzo[c]chromen-1-ol
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
Chemical and physical data
FormulaC23H34O3
Molar mass358.522 g·mol−1
3D model (JSmol)
SMILES
  • CCCCC/C=C/c(cc1O)cc(OC(C)(C)C2CC3)c1C2CC3CO
InChI
  • InChI=1S/C23H34O3/c1-4-5-6-7-8-9-16-13-20(25)22-18-12-17(15-24)10-11-19(18)23(2,3)26-21(22)14-16/h8-9,13-14,17-19,24-25H,4-7,10-12,15H2,1-3H3/b9-8+/t17-,18-,19-/m1/s1 checkY
  • Key:NJIKRWBGUIYKJM-OKMMTOMJSA-N checkY
  (verify)

AM-905 (part of the AM cannabinoid series) is an analgesic drug which is a cannabinoid agonist. It is conformationally restricted by virtue of the double bond on its side chain, leading an increased affinity for and selectivity between CB1 and CB2 receptors.[1] It is a potent and reasonably selective agonist for the CB1 cannabinoid receptor, with a Ki of 1.2 nM at CB1 and 5.3 nM at CB2.[2]

See also

  • AM-906 - The corresponding Z or cis isomer
  • HU-243 - Double bond replaced by geminal methyls for Thorpe–Ingold effect

References

  1. ↑ Busch-Petersen J, Hill WA, Fan P, Khanolkar A, Xie XQ, Tius MA, Makriyannis A (September 1996). "Unsaturated side chain beta-11-hydroxyhexahydrocannabinol analogs". Journal of Medicinal Chemistry. 39 (19): 3790–6. doi:10.1021/jm950934b. PMID 8809166.
  2. ↑ Papahatjis DP, Kourouli T, Abadji V, Goutopoulos A, Makriyannis A (March 1998). "Pharmacophoric requirements for cannabinoid side chains: multiple bond and C1'-substituted delta 8-tetrahydrocannabinols". Journal of Medicinal Chemistry. 41 (7): 1195–200. doi:10.1021/jm970277i. PMID 9544219.
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