ADSB-FUB-187

Summary

ADSB-FUB-187 is an indazole-based synthetic cannabinoid. It is a potent agonist of the CB1 receptor with a binding affinity of Ki = 0.09 nM and an EC50 of 1.09 nM.[1] It was originally developed by Pfizer in 2009, being example 187 from patent WO 2009/106982. While it is the most tightly binding compound from this patent in terms of Ki, it is not the most potent compound at producing a CB1 mediated pharmacological effect, with at least 17 other compounds from the patent having lower EC50 values.[2]

ADSB-FUB-187
Legal status
Legal status
Identifiers
  • 7-chloro-N-[(2S)-1-[2-(cyclopropylsulfonylamino)ethylamino]-3,3-dimethyl-1-oxobutan-2-yl]-1-[(4-fluorophenyl)methyl]indazole-3-carboxamide
CAS Number
  • 1185283-97-9 checkY
PubChem CID
  • 44186812
ChemSpider
  • 65322246
UNII
  • L6K9PBL5EO
Chemical and physical data
FormulaC26H31ClFN5O4S
Molar mass564.07 g·mol−1
3D model (JSmol)
  • Interactive image
  • CC(C)(C)[C@@H](C(=O)NCCNS(=O)(=O)C1CC1)NC(=O)C2=NN(C3=C2C=CC=C3Cl)CC4=CC=C(C=C4)F
  • InChI=1S/C26H31ClFN5O4S/c1-26(2,3)23(25(35)29-13-14-30-38(36,37)18-11-12-18)31-24(34)21-19-5-4-6-20(27)22(19)33(32-21)15-16-7-9-17(28)10-8-16/h4-10,18,23,30H,11-15H2,1-3H3,(H,29,35)(H,31,34)/t23-/m1/s1
  • Key:UANJTRHQSBHCID-HSZRJFAPSA-N

Legality edit

Sweden's public health agency suggested classifying ADSB-FUB-187 as hazardous substance on November 10, 2014, following its use as an ingredient in grey-market synthetic cannabis products.[3]

See also edit

References edit

  1. ^ Banister SD, Connor M (2018). "The Chemistry and Pharmacology of Synthetic Cannabinoid Receptor Agonist New Psychoactive Substances: Evolution". New Psychoactive Substances. Handbook of Experimental Pharmacology. Vol. 252. pp. 191–226. doi:10.1007/164_2018_144. ISBN 978-3-030-10560-0. PMID 30105473.
  2. ^ WO 2009106982, Buchler IP, Hayes MJ, Hedge SG, Landis S, Hockerman SL, Jones DE, Kortum SW, Rico JG, Tenbrink RE, Wu KW, "Indazole derivatives", published 3 September 2009, assigned to Pfizer Inc.. 
  3. ^ "Cannabinoider föreslås bli klassade som hälsofarlig vara" [Cannabinoids are proposed to be classified as hazardous to health] (in Swedish). Folkhälsomyndigheten (The Swedish Public Health Agency). Archived from the original on 25 March 2015. Retrieved 8 July 2015.