AB-001

AB-001

AB-001
Systematic (IUPAC) name
1-pentyl-3-(adamant-1-oyl)indole
Clinical data
Legal status
  • Illegal in Russia
Identifiers
CAS number  N
ATC code ?
PubChem
ChemSpider  YesY
Chemical data
Formula C24H31NO 
Mol. mass 349.508 g/mol
 N   

AB-001 or 1-pentyl-3-(1-adamantoyl)indole is a designer drug that 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, 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] The first published synthesis and pharmacological evaluation of AB-001 revealed that it acts as a full agonist at CB1 (EC50 = 35 nM) and CB2 receptors (EC50 = 48 nM).[6] However, AB-001 was found to possess only weak cannabimimetic effects in rats at doses up to 30 mg/kg, making it less potent than carboxamide analogue SDB-001, which possesses potent cannabimimetic activity at doses of 3 mg/kg.[6]

See also

References

  1. ^ Jankovics, P. T.; Váradi, A. S.; Tölgyesi, L. S.; Lohner, S.; Németh-Palotás, J. L.; Balla, J. Z. (2012). "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 214 (1–3): 27–32.  
  2. ^ Research on Head Shop drugs in Dublin: Part 2
  3. ^ Grigoryev, A.; Kavanagh, P.; Melnik, A. (2012). "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 4 (6): 519–524.  
  4. ^ US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  5. ^ Frost, J. M., 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): 295–315.  
  6. ^ a b Banister, S. D.; Wilkinson, S. M.; Longworth, M.; Stuart, J.; Apetz, N.; English, K.; Brooker, L.; Goebel, C.; Hibbs, D. E.; Glass, M.; Connor, M.; McGregor, I. S.; Kassiou, M. (2013). "The synthesis and pharmacological evaluation of adamantane-derived indoles: Novel cannabimimetic drugs of abuse". ACS Chemical Neuroscience 4 (7): 130403084729007.