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 ;
	(verify)

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.^[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 0.27 nM at CB₁ while the (S)-enantiomer has a much weaker K_i of 217 nM.^[3]

^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^ US patent 5068234, D'Ambra TE, et al., "3-arylcarbonyl-1-(C-attached-N-heteryl)-1H-indoles", granted 1991-11-26
^ D'ambra, T. (1996). "C-Attached aminoalkylindoles: potent cannabinoid mimetics". Bioorganic & Medicinal Chemistry Letters. 6 (1): 17–22. doi:10.1016/0960-894X(95)00560-G.

[WO_2001_28557_A1-1] WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07

[US_5068234-2] US patent 5068234, D'Ambra TE, 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 (1): 17–22. doi:10.1016/0960-894X(95)00560-G.

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[2]

[3]

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^Y (racemic) 134959-64-1 ((R)-enantiomer)
PubChem CID	9929889
ChemSpider	26231035^Y
UNII	05850M72P2 (R)-enantiomer: 44NQ9RBE1B^Y
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^Y Key:URKVBEKZCMUTQC-HXUWFJFHSA-N^Y
(verify)