AM-1220

AM-1220

Systematic (IUPAC) name
(R)-(1-((1-methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone
Clinical data
Pregnancy cat.	?
Legal status	banned under analog laws in some US states, Temporary Class Drug (NZ)
Identifiers
CAS number	137642-54-7 Y (racemic) 134959-64-1 ((R) enantiomer)
ATC code	?
PubChem	CID 9929889
ChemSpider	26231035 Y
Chemical data
Formula	C26H26N2O
Mol. mass	382.497 g/mol
SMILES	eMolecules & PubChem
InChI 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 Y Key:URKVBEKZCMUTQC-HXUWFJFHSA-N Y
Y (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 K_i of 0.27nM at CB₁ while the (S) enantiomer has a much weaker K_i 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

• A-834,735
• AM-1221
• AM-1248
• AM-2201
• AM-2233
• Cannabipiperidiethanone

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. ^ 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. Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs. PhD Dissertation, University of Connecticut, 2000.
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. 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)

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