CAS 91-56-5|isatin
| 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 | ChineseUSA | Flash Point | 171.7±30.7 °C |
Names
| Name | isatin |
|---|---|
| Synonym | More Synonyms |
isatin BiologicalActivity
| 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 OxidaseNatural Products >>AlkaloidResearch Areas >>CancerResearch Areas >>Cardiovascular DiseaseResearch 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. |
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 |
| InChIKey | JXDYKVIHCLTXOP-UHFFFAOYSA-N |
| SMILES | O=C1Nc2ccccc2C1=O |
| Storage condition | Store at RT. |
Toxicological Information
CHEMICAL IDENTIFICATION |
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 |
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 |
