AM-1221

AM-1221
Legal status
Legal status	CA: Schedule II; DE: NpSG (Industrial and scientific use only); UK: Under Psychoactive Substances Act; US: Schedule I;
Identifiers
	IUPAC name 1-[(N-Methylpiperidin-2-yl)methyl]-2-methyl-3-(naphthalen-1-oyl)-6-nitroindole;
CAS Number	335160-53-7 ;
PubChem CID	11604318;
ChemSpider	26286945 ;
UNII	SHC6SNM293;
CompTox Dashboard (EPA)	DTXSID701009967 ;
Chemical and physical data
Formula	C27H27N3O3
Molar mass	441.531 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CN1CCCCC1CN2C=C(C3=C2C=C(C=C3)[N+](=O)[O-])C(=O)C4=CC=CC5=CC=CC=C54;
	InChI InChI=1S/C27H27N3O3/c1-18-26(27(31)23-12-7-9-19-8-3-4-11-22(19)23)24-14-13-20(30(32)33)16-25(24)29(18)17-21-10-5-6-15-28(21)2/h3-4,7-9,11-14,16,21H,5-6,10,15,17H2,1-2H3 ; Key:QGNIEJBBHMMNOZ-UHFFFAOYSA-N ;
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AM-1221 is a drug that acts as a potent and selective agonist for the cannabinoid receptor CB₂, with a K_i of 0.28 nM at CB₂ and 52.3 nM at the CB₁ receptor, giving it around 180 times selectivity for CB₂.^[1] The 2-methyl and 6-nitro groups on the indole ring both tend to increase CB₂ affinity while generally reducing affinity at CB₁, explaining the high CB₂ selectivity of AM-1221. However, despite this relatively high selectivity for CB₂, its CB₁ affinity is still too strong to make it useful as a truly selective CB₂ agonist, so the related compound AM-1241 is generally preferred for research purposes.^[2]^[3]

In the United States, all CB₁ receptor agonists of the 3-(1-naphthoyl)indole class such as AM-1221 are Schedule I Controlled Substances.^[4]

^ WO patent 200128557, Makriyannis A, Deng H, "Cannabimimetic indole derivatives", granted 2001-06-07
^ Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (Ph.D. Dissertation). University of Connecticut. ProQuest 304624325.
^ Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.
^ 21 U.S.C. § 812: Schedules of controlled substances

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

[2] Deng H (2000). Design and synthesis of selective cannabinoid receptor ligands: Aminoalkylindole and other heterocyclic analogs (Ph.D. Dissertation). University of Connecticut. ProQuest 304624325.

[3] Manera C, Tuccinardi T, Martinelli A (April 2008). "Indoles and related compounds as cannabinoid ligands". Mini Reviews in Medicinal Chemistry. 8 (4): 370–87. doi:10.2174/138955708783955935. PMID 18473928.

[4] 21 U.S.C. § 812: Schedules of controlled substances

[1]

[2]

[3]

[4]

Legal status

Legal status	CA: Schedule II DE: NpSG (Industrial and scientific use only) UK: Under Psychoactive Substances Act US: Schedule I
Identifiers
IUPAC name 1-[(N-Methylpiperidin-2-yl)methyl]-2-methyl-3-(naphthalen-1-oyl)-6-nitroindole
CAS Number	335160-53-7^N
PubChem CID	11604318
ChemSpider	26286945^Y
UNII	SHC6SNM293
CompTox Dashboard (EPA)	DTXSID701009967
Chemical and physical data
Formula	C₂₇H₂₇N₃O₃
Molar mass	441.531 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CN1CCCCC1CN2C=C(C3=C2C=C(C=C3)[N+](=O)[O-])C(=O)C4=CC=CC5=CC=CC=C54
InChI InChI=1S/C27H27N3O3/c1-18-26(27(31)23-12-7-9-19-8-3-4-11-22(19)23)24-14-13-20(30(32)33)16-25(24)29(18)17-21-10-5-6-15-28(21)2/h3-4,7-9,11-14,16,21H,5-6,10,15,17H2,1-2H3^Y Key:QGNIEJBBHMMNOZ-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)

AM-1221

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