AM-1220

AM-1220
Legal status
Legal status	AU: S9 (Prohibited substance); CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B; US: Schedule I;
Identifiers
	IUPAC name (R)-(1-((1-Methylpiperidin-2-yl)methyl)-1H-indol-3-yl)(naphthalen-1-yl)methanone;
CAS Number	137642-54-7 (racemic) ; 134959-64-1 ((R)-enantiomer);
PubChem CID	9929889;
ChemSpider	26231035 ;
UNII	05850M72P2; (R)-enantiomer: 44NQ9RBE1B ;
CompTox Dashboard (EPA)	DTXSID50433001 ;
Chemical and physical data
Formula	C26H26N2O
Molar mass	382.507 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(C1=CC=CC2=C1C=CC=C2)C3=CN(C[C@@H]4N(C)CCCC4)C5=CC=CC=C53;
	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 ; Key:URKVBEKZCMUTQC-HXUWFJFHSA-N ;
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AM-1220 is a drug that acts as a potent and moderately selective agonist for the cannabinoid receptor CB₁, with around 19 times selectivity for CB₁ over the related CB₂ receptor. It was originally invented in the early 1990s by a team led by Thomas D'Ambra at Sterling Winthrop, 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 0.27 nM at CB₁ while the (S)-enantiomer has a much weaker K_i of 217 nM.

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