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
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About This Item
Empirical Formula (Hill Notation):
C22H18N2O2
CAS Number:
Molecular Weight:
342.39
UNSPSC Code:
12352200
NACRES:
NA.77
Assay:
≥98% (HPLC)
Form:
powder
Quality Segment
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
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
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.
Unbiased cannabinoid CB1 allosteric agonist
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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