AB-001

AB-001
Legal status
Legal status	CA: Schedule II ; DE: Anlage II (Authorized trade only, not prescriptible) ; UK: Under Psychoactive Substances Act ;
Identifiers
	IUPAC name 1-Pentyl-3-(adamant-1-oyl)indole;
CAS Number	1345973-49-0 ;
PubChem CID	57404070;
ChemSpider	26286891 ;
UNII	H657DIA015;
CompTox Dashboard (EPA)	DTXSID90158822 ;
Chemical and physical data
Formula	C24H31NO
Molar mass	349.518 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CCCCCn1cc(c2c1cccc2)C(=O)C34CC5CC(C3)CC(C5)C4;
	InChI 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 ; Key:SHWDYCMMUPPWQM-UHFFFAOYSA-N ;
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AB-001 (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 the carboxamide analogue APICA, which possesses potent cannabimimetic activity at doses of 3 mg/kg.[6]

References

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.
Research on Head Shop drugs in Dublin: Part 2
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.
US patent 7820144, Makriyannis A, Deng H, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
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.
Banister 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.

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[pmid21813254-1] 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

[Grigoryev-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.

[US_7820144-4] 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.

[Banister-6] Banister 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.

AB-001

See also

References