SML1952

GAT228

≥98% (HPLC)

• Synonym(s): 3-[(1R)-2-nitro-1-phenylethyl]-2-phenyl-1H-Indole, R-(+)-3-(2-Nitro-1-phenylethyl)-2-phenyl-1H-indole
• Empirical Formula (Hill Notation): C₂₂H₁₈N₂O₂
• CAS Number: 1446648-15-2
• Molecular Weight: 342.39
• UNSPSC Code: 12352200
• NACRES: NA.77

Properties

• Quality Level: 100
• Assay: ≥98% (HPLC)
• form: powder
• optical activity: [α]/D 80 to 94°, c = 1 in methanol
• color: white to beige
• solubility: DMSO: 20 mg/mL, clear
• storage temp.: 2-8°C
• SMILES string: O=[N+]([O-])C[C@H](C1=CC=CC=C1)C2=C(C3=CC=CC=C3)NC4=CC=CC=C42

Description

Biochem/physiol Actions

GAT228 is the R-(+)-enantiomer of GAT211, a positive allosteric modulator (PAM) of cannabinoid CB1 receptor signaling that was found to amplify the therapeutic effect of endocannabinoids without the negative side effects of psychoactivity or tolerance. GAT228 was found to be an unbiased CB1 allosteric agonist, while the S-(-)-enantiomer, GAT229,was found to be a potent, Gαi/o-biased CB1 PAM without intrinsic activity. In radioligand binding assays, both GAT228 and GAT229 behaved as PAMs of orthosteric ligand binding. Allosteric CB1R activation by GAT211 and its enantiomers could be a better therapeutic strategy for enhancing endogenous cannabinergic activity than targeting endocannabinoid-degrading enzymes with small-molecule inhibitors, with a lower likelihood of tolerance and dependence.

Safety Information

• Storage Class Code: 11 - Combustible Solids
• WGK: WGK 3
• Flash Point(F): Not applicable
• Flash Point(C): Not applicable