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
Identifiers
CAS Number 137642-54-7 YesY (racemic)
134959-64-1 ((R) enantiomer)
PubChem CID: 9929889
ChemSpider 26231035 YesY
Chemical data
Formula C26H26N2O
Molecular mass 382.497 g/mol
  • O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53
  • InChI=1S/C26H26N2O/c1-27-16-7-6-11-20(27)17-28-18-24(22-13-4-5-15-25(22)28)26(29)23-14-8-10-19-9-2-3-12-21(19)23/h2-5,8-10,12-15,18,20H,6-7,11,16-17H2,1H3/t20-/m1/s1 YesY
  • Key:URKVBEKZCMUTQC-HXUWFJFHSA-N YesY
  (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

Legal Status

As of October 2015 AM-1220 is a controlled substance in China.[8]

See also

References

  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. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  4. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  5. ↑ Lua error in package.lua at line 80: module 'strict' not found.
  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)
  8. ↑ Lua error in package.lua at line 80: module 'strict' not found.
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