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AB-001

From Wikipedia, the free encyclopedia
Chemical compound
Pharmaceutical compound
AB-001
Legal status
Legal status
Identifiers
  • 1-Pentyl-3-(adamant-1-oyl)indole
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
Chemical and physical data
FormulaC24H31NO
Molar mass349.518 g·mol−1
3D model (JSmol)
  • CCCCCn1cc(c2c1cccc2)C(=O)C34CC5CC(C3)CC(C5)C4
  • InChI=1S/C24H31NO/c1-2-3-6-9-25-16-21(20-7-4-5-8-22(20)25)23(26)24-13-17-10-18(14-24)12-19(11-17)15-24/h4-5,7-8,16-19H,2-3,6,9-15H2,1H3 checkY
  • Key:SHWDYCMMUPPWQM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

AB-001 (1-pentyl-3-(1-adamantoyl)indole) is adesigner drug that was found as an ingredient insynthetic 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 asAM-1248 and its corresponding 1-(tetrahydropyran-4-ylmethyl) analogue, which are known to be potent cannabinoid agonists with moderate to a high selectivity forCB2 overCB1.[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 the carboxamide analogueAPICA, which possesses potent cannabimimetic activity at doses of 3 mg/kg.[6]

See also

[edit]

References

[edit]
  1. ^Jankovics P, Váradi A, Tölgyesi L, Lohner S, Németh-Palotás J, Balla J (January 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.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 (June 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):519–24.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 JM, Dart MJ, Tietje KR, Garrison TR, Grayson GK, Daza AV, El-Kouhen OF, Yao BB, Hsieh GC, Pai M, Zhu CZ, Chandran P, Meyer MD (January 2010). "Indol-3-ylcycloalkyl ketones: effects of N1 substituted indole side chain variations on CB(2) cannabinoid receptor activity".Journal of Medicinal Chemistry.53 (1):295–315.doi:10.1021/jm901214q.PMID 19921781.
  6. ^abBanister SD, Wilkinson SM, Longworth M, Stuart J, Apetz N, English K, Brooker L, Goebel C, Hibbs DE, Glass M, Connor M, McGregor IS, Kassiou M (July 2013)."The synthesis and pharmacological evaluation of adamantane-derived indoles: cannabimimetic drugs of abuse".ACS Chemical Neuroscience.4 (7):1081–92.doi:10.1021/cn400035r.PMC 3715837.PMID 23551277.
Phytocannabinoids
(comparison)
Cannabibutols
Cannabichromenes
Cannabicyclols
Cannabidiols
Cannabielsoins
Cannabigerols
Cannabiphorols
Cannabinols
Cannabitriols
Cannabivarins
Delta-8-tetrahydrocannabinols
Delta-9-tetrahydrocannabinols
Delta-10-Tetrahydrocannabinols
Miscellaneous cannabinoids
Active metabolites
Endocannabinoids
Synthetic
cannabinoid
receptor
agonists /
neocannabinoids
Classical cannabinoids
(dibenzopyrans)
Non-classical
cannabinoids
Adamantoylindoles
Benzimidazoles
Benzoylindoles
Cyclohexylphenols
Eicosanoids
Indazole-3-
carboxamides
Indole-3-carboxamides
Indole-3-carboxylates
Naphthoylindazoles
Naphthoylindoles
Naphthoylpyrroles
Naphthylmethylindenes
Naphthylmethylindoles
Phenylacetylindoles
Pyrazolecarboxamides
Tetramethylcyclo-
propanoylindazoles
Tetramethylcyclo-
propanoylindoles
Others
AllostericCBRTooltip Cannabinoid receptorligands
Endocannabinoid
enhancers

(inactivation inhibitors)
Anticannabinoids
(antagonists/inverse
agonists/antibodies)
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