AM-1220

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AM-1220
AM-1220 structure.png
Systematic (IUPAC) name
(R)-(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone
Clinical data
Legal status
  • AU: Prohibited (S9)
  • banned under analog laws in some US states, Temporary Class Drug (NZ)
Identifiers
CAS number 137642-54-7 YesY (racemic)
134959-64-1 ((R) enantiomer)
ATC code ?
PubChem CID 9929889
ChemSpider 26231035 YesY
Chemical data
Formula C26H26N2O 
Mol. mass 382.497 g/mol
 YesY (what is this?)  (verify)

AM-1220 is a drug that 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]

Related 1-(N-methylpyrrolidin-2-ylmethyl) and 1-(N-methylmorpholin-3-ylmethyl) derivatives

See also[edit]

References[edit]

  1. ^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07 
  2. ^ US patent 5068234, Thomas E. D'Ambra et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26 
  3. ^ D'ambra, T. (1996). "C-Attached aminoalkylindoles: potent cannabinoid mimetics". Bioorganic & Medicinal Chemistry Letters 6: 17–14. doi:10.1016/0960-894X(95)00560-G.  edit
  4. ^ Hongfeng Deng (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (PhD. Dissertation). University of Connecticut. 
  5. ^ Willis, P. G.; Pavlova, O. A.; Chefer, S. I.; Vaupel, D. B.; Mukhin, A. G.; Horti, A. G. (2005). "Synthesis and Structure−Activity Relationship of a Novel Series of Aminoalkylindoles with Potential for Imaging the Neuronal Cannabinoid Receptor by Positron Emission Tomography". Journal of Medicinal Chemistry 48 (18): 5813–22. doi:10.1021/jm0502743. PMID 16134948.  edit
  6. ^ US patent 7820144, Alexandros Makriyannis, et al., "Receptor selective cannabimimetic aminoalkylindoles", granted 2010-10-26 
  7. ^ Head Shop ‘Legal Highs’ Active Constituents Identification Chart (July - August 2010)