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GAT228

SIGMA/SML1952 - ≥98% (HPLC)

Synonym: 3-[(1R)-2-nitro-1-phenylethyl]-2-phenyl-1H-Indole; R-(+)-3-(2-Nitro-1-phenylethyl)-2-phenyl-1H-indole

CAS Number: 1446648-15-2
Empirical Formula (Hill Notation): C22H18N2O2
Molecular Weight: 342.39
Linear Formula: C22H18N2O2
Product Type: Chemical
Catalog Number PKG Qty. Price Quantity
45-SML1952-5MG 5 mg
 $111.00
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assay ≥98% (HPLC)
color white to beige
form powder
InChI 1S/C22H18N2O2/c25-24(26)15-19(16-9-3-1-4-10-16)21-18-13-7-8-14-20(18)23-22(21)17-11-5-2-6-12-17/h1-14,19,23H,15H2/t19-/m1/s1
InChI key OHZDCJJHWPHZJD-LJQANCHMSA-N
optical activity [α]/D 80 to 94°, c = 1 in methanol
Quality Level 100 
SMILES string O=[N+]([O-])C[C@H](C1=CC=CC=C1)C2=C(C3=CC=CC=C3)NC4=CC=CC=C42
solubility DMSO: 20 mg/mL, clear
storage temp. 2-8°C
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.
Biochem/physiol Actions: Unbiased cannabinoid CB1 allosteric agonist
RIDADR NONH for all modes of transport
WGK Germany WGK 3
Flash Point(F) Not applicable
Flash Point(C) Not applicable
Purity ≥98% (HPLC)
Storage Temp. 2-8°C
UNSPSC 12352200

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