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Details

Stereochemistry ACHIRAL
Molecular Formula C8H5NO2
Molecular Weight 147.1308
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ISATIN

SMILES

O=C1NC2=C(C=CC=C2)C1=O

InChI

InChIKey=JXDYKVIHCLTXOP-UHFFFAOYSA-N
InChI=1S/C8H5NO2/c10-7-5-3-1-2-4-6(5)9-8(7)11/h1-4H,(H,9,10,11)

HIDE SMILES / InChI

Description

Isatin (1H-indole-2,3-dione) is a naturally occurring heterocycle that was first synthesised by Erdmann and Laurent in 1840. Isatin possesses a wide range of biological activities. Isatin has anxiogenic, sedative, anticonvulsant activities and acts as a potent antagonist on atrial natriuretic peptide receptors in vitro. Isatin is an endogenous monoamine oxidase (MAO) inhibitor involved in stress and anxiety. Additionally, isatin inhibits alkaline phosphatase (ALP), nitric oxide (NO)-stimulated soluble guanylate cyclase, and other enzymes.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
7.94 µM [IC50]
31.8 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Rats: Isatin (100 mg/kg, i.p.) inhibited APO-induced rotations of Parkinsonian rats to 39.1+/-3.7% of the control (n=12), while it had no apparent effects on electrical stimuli-induced DA release either in normal rats or in model rats. In addition, the content of 5-hydroxytryptamine but not DA was increased in both normal rats and model rats after isatin (100 mg/kg, i.p.) was administered.
Route of Administration: Intraperitoneal
In Vitro Use Guide
In vitro 10 and 100 uM isatin reduced irreversible inhibition of MAO A and MAO B assayed after rat mitochondria wash.