isatin

Names

[ CAS No. ]:
91-56-5

[ Name ]:
isatin

[Synonym ]:
Indolequinone
EINECS 202-077-8
MFCD00005718
indole-2,3-dione
indoline-2,3-dione
Indoquinone
2,3-Dioxoindoline
2,3-Dioxo-2,3-dihydroindole
2,3-Indolinedione
2,3-INDOLEDIONE
2H-Indol-2-one, 3-hydroxy-
3-hydroxy-2-oxoindole
ISATIC ANHYDRIDE
Isotin
2,3-Diketoindoline
2-methopropan-1-ol
3-Hydroxy-2H-indol-2-one
Isatin
2,3-KETOINDOLINE
5-21-10-00221 (Beilstein Handbook Reference)
2,3-dihydro-1H-indol-2,3-dione

Biological Activity

[Description]:

Isatin (Indoline-2,3-dione) is a potent inhibitor of monoamine oxidase (MAO) with an IC50 of 3 μM. Also binds to central benzodiazepine receptors (IC50 against clonazepam, 123 μM)[1]. Also acts as an antagonist of both atrial natriuretic peptide stimulated and nitric oxide-stimulated guanylate cyclase activity[2]. Shows effect on the serotonergic system[3].

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase

Natural Products >> Alkaloid

Research Areas >> Cancer

Research Areas >> Cardiovascular Disease

Research Areas >> Neurological Disease

[Target]

IC50: 3 μM (MAO B)[1]

[In Vitro]

In dopaminergic SH-SY5Y cells isatin (1-400 μM) induces cell death in dose- and time dependent manner. This death occurred as a continuum of survival, apoptosis and necrosis[2].

[In Vivo]

A single dose of isatin (80 mg/kg) has a rapid effect on the serotonergic system in the hypothalamus. Isatin significantly increases 5-HT concentrations in the hypothalamus and cortex but did not significantly alter 5-HIAA concentrations[3].

[References]

[1]. Glover V, et al. Isatin: Identity with the Purified Endogenous Monoamine Oxidase Inhibitor Tribulin. Journal of Neurochemistry, 51(2), 656–659.

[2]. Igosheva N, et al. Isatin, an endogenous monoamine oxidase inhibitor, triggers a dose- and time-dependent switch from apoptosis to necrosis in human neuroblastoma cells. Neurochem Int. 2005 Aug;47(3):216-24.

[3]. McIntyre IM, et al. Serotonergic effects of isatin: an endogenous MAO inhibitor related to tribulin. J Neural Transm Gen Sect. 1990;79(1-2):35-40.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
360.3±52.0 °C at 760 mmHg

[ Melting Point ]:
193-195 °C (dec.)(lit.)

[ Molecular Formula ]:
C₈H₅NO₂

[ Molecular Weight ]:
147.131

[ Flash Point ]:
171.7±30.7 °C

[ Exact Mass ]:
147.032028

[ PSA ]:
46.17000

[ LogP ]:
-0.17

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.679

[ Storage condition ]:
Store at RT.

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :: NL7873000

CHEMICAL NAME :: Indole-2,3-dione

CAS REGISTRY NUMBER :: 91-56-5

BEILSTEIN REFERENCE NO. :: 0383659

LAST UPDATED :: 199701

DATA ITEMS CITED :: 9

MOLECULAR FORMULA :: C8-H5-N-O2

MOLECULAR WEIGHT :: 147.14

WISWESSER LINE NOTATION :: T56 BMVVJ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LDLo - Lowest published lethal dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 5 gm/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay)

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 6,145,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 7740 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 27(8),54,1983

TYPE OF TEST :: LD - Lethal dose

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: >800 mg/kg

TOXIC EFFECTS :: Peripheral Nerve and Sensation - flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral - changes in motor activity (specific assay)

REFERENCE :: IJPPAZ Indian Journal of Physiology and Pharmacology. (All India Institute of Medical Sciences, Dept. of Physiology, Ansari Nagar, New Delhi 110 029, India) V.1- 1957- Volume(issue)/page/year: 6,145,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Unreported

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 725 mg/kg

TOXIC EFFECTS :: Behavioral - somnolence (general depressed activity)

REFERENCE :: RPTOAN Russian Pharmacology and Toxicology (English Translation). Translation of FATOAO. (Euromed Pub., 33, Woodlands Rd., Surbiton, Surrey, UK) V.30- 1967- Volume(issue)/page/year: 41,146,1978

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 330 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: NYKZAU Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. (Nippon Yakuri Gakkai, c/o Kyoto Daigaku Igakubu Yakurigaku Kyoshitsu, Konoe-cho, Yoshida, Sakyo-ku, Kyoto 606, Japan) V.40- 1944- Volume(issue)/page/year: 55,1514,1959 ** OTHER MULTIPLE DOSE TOXICITY DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - rat

DOSE/DURATION :: 43500 mg/kg/6W-I

TOXIC EFFECTS :: Blood - pigmented or nucleated red blood cells Blood - changes in serum composition (e.g. TP, bilirubin, cholesterol) Blood - changes in erythrocyte (RBC) count

REFERENCE :: GTPZAB Gigiena Truda i Professional'nye Zabolevaniya. Labor Hygiene and Occupational Diseases. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.1-36, 1957-1992. For publisher information, see MTPEEI Volume(issue)/page/year: 27(3),52,1983 ** REPRODUCTIVE DATA **

TYPE OF TEST :: TDLo - Lowest published toxic dose

ROUTE OF EXPOSURE :: Oral

DOSE :: 200 mg/kg

SEX/DURATION :: male 1 day(s) pre-mating

TOXIC EFFECTS :: Reproductive - Paternal Effects - other effects on male

REFERENCE :: IJMRAQ Indian Journal of Medical Research. (Indian Council of Medical Research, Ansari Nagar, New Delhi 110 029, India) V.1- 1913- Volume(issue)/page/year: 67,73,1978 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - A1765 No. of Facilities: 3 (estimated) No. of Industries: 1 No. of Occupations: 1 No. of Employees: 198 (estimated) No. of Female Employees: 151 (estimated)

Safety Information

[ Personal Protective Equipment ]:
dust mask type N95 (US);Eyeshields;Gloves

[ Hazard Codes ]:
Xi,Xn

[ Risk Phrases ]:
R36/37/38

[ Safety Phrases ]:
S26-S36-S24/25

[ RIDADR ]:
2811

[ WGK Germany ]:
1

[ RTECS ]:
NL7873000

[ Packaging Group ]:
III

[ Hazard Class ]:
6.1(b)

[ HS Code ]:
2933990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2933990090

[ Summary ]:
2933990090. heterocyclic compounds with nitrogen hetero-atom(s) only. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

Articles

Unprecedented one-pot, domino tertiary alcohol protection-Michael type addition of halides to Morita-Baylis-Hillman adduct of isatin with RCOX/K2CO3: diastereoselective synthesis of oxindole appended β-halo esters.

Org. Lett. 15(6) , 1186-9, (2013)

A facile method utilizing RCOX/K2CO3 as a novel reagent for conjugate addition of hydrogen halide, in addition to tertiary (3°)-hydroxyl protection that leads to the synthesis of functionalized β-halo...

Tryptophan 2,3-dioxygenase (TDO) inhibitors. 3-(2-(pyridyl)ethenyl)indoles as potential anticancer immunomodulators.

J. Med. Chem. 54 , 5320, (2011)

Tryptophan catabolism mediated by indoleamine 2,3-dioxygenase (IDO) is an important mechanism of peripheral immune tolerance contributing to tumoral immune resistance. IDO inhibition is thus an active...

Reactivity of dinuclear copper(II) complexes towards melanoma cells: Correlation with its stability, tyrosinase mimicking and nuclease activity.

J. Inorg. Biochem. 149 , 49-58, (2015)

In this work, the influence of two new dinuclear copper(II) complexes in the viability of melanoma cells (B16F10 and TM1MNG3) was investigated, with the aim of verifying possible correlations between ...