isatin

Modify Date: 2024-01-02 08:00:51

isatin Structure
isatin structure
Common Name isatin
CAS Number 91-56-5 Molecular Weight 147.131
Density 1.4±0.1 g/cm3 Boiling Point 360.3±52.0 °C at 760 mmHg
Molecular Formula C8H5NO2 Melting Point 193-195 °C (dec.)(lit.)
MSDS Chinese USA Flash Point 171.7±30.7 °C

 Use of isatin


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].

 Names

Name isatin
Synonym More Synonyms

 isatin 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
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.

 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.

 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

 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%

 Articles78

More 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 ...

 Synonyms

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
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  • Purity: 98.0%
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