AM-1220
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| Formula | C26H26N2O |
| Molar mass | 382.497 g/mol g·mol−1 |
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AM-1220 is a drug which acts as a potent and moderately selective agonist for the cannabinoid receptor CB1, with around 19x selectivity for CB1 over the related CB2 receptor.[1] It was originally invented in the early 1990s by a team led by Thomas D'Ambra at Sterling Winthrop,[2] but has subsequently been researched by many others, most notably the team led by Alexandros Makriyannis at the University of Connecticut. The (piperidin-2-yl)methyl side chain of AM-1220 contains a stereocenter, so there are two enantiomers with quite different potency, the (R) enantiomer having a Ki of 0.27nM at CB1 while the (S) enantiomer has a much weaker Ki of 217nM.[3] A number of related compounds are known with similar potent cannabinoid activity, with modifications such as substitution of the indole ring at the 2- or 6- positions, the naphthoyl ring substituted at the 4- position or replaced by substituted benzoyl rings or other groups, or the 1-(N-methylpiperidin-2-ylmethyl) group replaced by similar heterocyclic groups such as N-methylpyrrolidin-2-ylmethyl or N-methylmorpholin-3-ylmethyl.[4][5][6] AM-1220 was first detected as an ingredient of synthetic cannabis smoking blends in 2010.[7]
See also
References
- ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
- ^ US patent 5068234, Thomas E. D'Ambra et al, "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1016/0960-894X(95)00560-G, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1016/0960-894X(95)00560-Ginstead. - ^ Hongfeng Deng. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
- ^ Attention: This template ({{cite doi}}) is deprecated. To cite the publication identified by doi:10.1021/jm0502743, please use {{cite journal}} (if it was published in a bona fide academic journal, otherwise {{cite report}} with
|doi=10.1021/jm0502743instead. - ^ US patent 7820144, Alexandros Makriyannis et al, "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26
- ^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)
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