AM-2233

AM-2233
Legal status
Legal status	CA: Schedule II; DE: Anlage II (Authorized trade only, not prescriptible); NZ: Temporary Class; UK: Class B;
Identifiers
	IUPAC name 1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole;
CAS Number	444912-75-8 ;
PubChem CID	10226340;
ChemSpider	8401830 ;
UNII	Z489688DK3;
ChEMBL	ChEMBL364266 ;
CompTox Dashboard (EPA)	DTXSID401014171 ;
ECHA InfoCard	100.233.382
Chemical and physical data
Formula	C22H23IN2O
Molar mass	458.343 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Ic3ccccc3C(=O)c1cn(CC2CCCCN2C)c4c1cccc4;
	InChI InChI=1S/C22H23IN2O/c1-24-13-7-6-8-16(24)14-25-15-19(17-9-3-5-12-21(17)25)22(26)18-10-2-4-11-20(18)23/h2-5,9-12,15-16H,6-8,13-14H2,1H3 ; Key:KSLCYQTUSSEGPT-UHFFFAOYSA-N ;
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AM-2233 is a drug that acts as a highly potent full agonist for the cannabinoid receptors, with a K_i of 1.8 nM at CB₁ and 2.2 nM at CB₂ as the active (R) enantiomer. It was developed as a selective radioligand for the cannabinoid receptors and has been used as its ¹³¹I derivative for mapping the distribution of the CB₁ receptor in the brain. AM-2233 was found to fully substitute for THC in rats, with a potency lower than that of JWH-018 but higher than WIN 55,212-2.

It is notable for inducing tinnitus, though the reasons for this are unclear and may provide valuable insight into tinnitus research.

Legal status

Legal status	CA: Schedule II DE: Anlage II (Authorized trade only, not prescriptible) NZ: Temporary Class UK: Class B
Identifiers
IUPAC name 1-[(N-methylpiperidin-2-yl)methyl]-3-(2-iodobenzoyl)indole
CAS Number	444912-75-8^N
PubChem CID	10226340
ChemSpider	8401830^Y
UNII	Z489688DK3
ChEMBL	ChEMBL364266^Y
CompTox Dashboard (EPA)	DTXSID401014171
ECHA InfoCard	100.233.382
Chemical and physical data
Formula	C₂₂H₂₃IN₂O
Molar mass	458.343 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES Ic3ccccc3C(=O)c1cn(CC2CCCCN2C)c4c1cccc4
InChI InChI=1S/C22H23IN2O/c1-24-13-7-6-8-16(24)14-25-15-19(17-9-3-5-12-21(17)25)22(26)18-10-2-4-11-20(18)23/h2-5,9-12,15-16H,6-8,13-14H2,1H3^Y Key:KSLCYQTUSSEGPT-UHFFFAOYSA-N^Y
^NY (what is this?) (verify)