AB-001

AB-001
Systematic (IUPAC) name
1-pentyl-3-(adamant-1-oyl)indole
Clinical data
Pregnancy cat.  ?
Legal status  ?
Identifiers
CAS number 1345973-49-0 N
ATC code  ?
ChemSpider 26286891 Y
Chemical data
Formula C24H31NO 
Mol. mass 349.508 g/mol
SMILES eMolecules & PubChem
 N(what is this?)  (verify)

AB-001 or 1-pentyl-3-(1-adamantoyl)indole is a designer drug which was found as an ingredient in synthetic cannabis smoking blends in Ireland in 2010 and Hungary and Germany in 2011.[1][2][3] It is unclear who AB-001 was originally developed by, and no information has been published on its receptor binding or pharmacological profile, but it is structurally related to compounds such as AM-1248 and its corresponding 1-(tetrahydropyran-4-ylmethyl) analogue, which are known to be potent cannabinoid agonists with moderate to high selectivity for CB2 over CB1.[4][5]

See also

References

  1. ^ Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (August 2011). "Detection and identification of the new potential synthetic cannabinoids 1-pentyl-3-(2-iodobenzoyl)indole and 1-pentyl-3-(1-adamantoyl)indole in seized bulk powders in Hungary". Forensic Science International. doi:10.1016/j.forsciint.2011.07.011. PMID 21813254. 
  2. ^ Research on Head Shop drugs in Dublin: Part 2
  3. ^ Grigoryev A, Kavanagh P, Melnik A. The detection of the urinary metabolites of 3-[(adamantan-1-yl)carbonyl]-1-pentylindole (AB-001), a novel cannabimimetic, by gas chromatography-mass spectrometry. Drug Testing and Analysis. 2011 Nov 18. DOI 10.1002/dta.350 PMID 22102533
  4. ^ US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26  
  5. ^ Frost, J. M.; Dart, M. J.; Tietje, K. R.; Garrison, T. R.; Grayson, G. K.; Daza, A. V.; El-Kouhen, O. F.; Yao, B. B. et al. (2010). "Indol-3-ylcycloalkyl Ketones: Effects of N1 Substituted Indole Side Chain Variations on CB2 Cannabinoid Receptor Activity". Journal of Medicinal Chemistry 53 (1): 295. doi:10.1021/jm901214q. PMID 19921781.  edit