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Isatin

Isatin structure

CAS No:
91-56-5
Formula:
C8H5NO2
Chemical Name:
Isatin
Synonyms:
1H-Indole-2,3-dione;Indole-2,3-dione;o-Aminobenzoylformic anhydride;2,3-Diketoindoline;2,3-Dioxoindoline;2,3-Indolinedione;Isatic acid lactam;Isatin;Isatinic acid anhydride;Pseudoisatin;2,3-Dioxo-2,3-dihydroindole;Isatine;2,3-Dihydro-1H-indole-2,3-dione;2,3-Indolindione;NSC 9262;2,3-Dihydroindole-2,3-dione;5815-00-9;84788-92-1
Categories:
Cosmetic Ingredient > Hair Dyeing

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].

Isatin or 1H-indole-2,3-dione is an indole derivative. The compound was first obtained by Erdmann and Laurent in 1841 as a product from the oxidation of indigo dye by nitric acid and chromic acids. The compound is found in many plants, such as Isatis tinctoria, Calanthe discolor and in Couroupita guianensis.

Isatin is an indoledione that is the 2,3-diketo derivative of indole. It has a role as an EC 1.4.3.4 (monoamine oxidase) inhibitor and a plant metabolite.|Isatin is an indole derivative first obtained by Erdman and Laurent in 1841 as an oxidation product of Indigo dye with nitric acid and chromic acids. The compound is found in many plants and Schiff bases of Isatin are have been investigated for pharmaceutical applications.|An indole-dione that is obtained by oxidation of indigo blue. It is a MONOAMINE OXIDASE INHIBITOR and high levels have been found in urine of PARKINSONISM patients.

Isatin Basic Attributes

Molecular Weight：

147.13

Exact Mass：

147.13

BRN：

383659

EC Number：

202-077-8

UNII：

82X95S7M06

NSC Number：

9262

DSSTox ID：

DTXSID3038694

HScode：

2933990090

Characteristics

PSA：

46.2

XLogP3：

0.8

Appearance：

Orange Powder

Density：

1.4±0.1 g/cm3

Melting Point：

203 °C (decomp)

Boiling Point：

360.3°C at 760 mmHg

Flash Point：

220 °C

Refractive Index：

1.679

Water Solubility：

soluble in water (1.9 g/L at 20°C).

Storage Conditions：

Store at RT.

Safety Information

Packing level：

III

Hazard category：

6.1(b)

Transport codes：

2811

wgk germany：

hazard class code：

36/37/38-20/21/22

safety instructions：

26-36-24/25

RTECS Number：

NL7873000

Marks：

Xi,Xn

Stability/Shelf Life：

Stable. Incompatible with strong acids.

Precautionary statement(s)：

P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, P501

Hazard Statements：

H302

RIDADR：

2811

GHS Classification：

|Warning|H302 (60%): Harmful if swallowed [Warning Acute toxicity, oral]|P261, P264, P270, P271, P280, P301+P312, P302+P352, P304+P340, P305+P351+P338, P312, P321, P330, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 151 companies from 10 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.|H317: May cause an allergic skin reaction [Warning Sensitization, Skin]|P261, P272, P280, P302+P352, P321, P333+P313, P363, and P501

Toxicity

Name	Type of Test	Exposure Route	Species Observed	Dose/Duration	Toxic Effects	Reference
ACUTE TOXICITY DATA	LDLo - Lowest published lethal dose	Oral	Rodent - rat	5 gm/kg	Peripheral Nerve and Sensation--flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral--changes in motor activity (specific assay)	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
ACUTE TOXICITY DATA	LD50 - Lethal dose, 50 percent kill	Intraperitoneal	Rodent - rat	7740 mg/kg	Details of toxic effects not reported other than lethal dose value--	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
ACUTE TOXICITY DATA	LD - Lethal dose	Intravenous	Rodent - rat	>800 mg/kg	Peripheral Nerve and Sensation--flaccid paralysis without anesthesia (usually neuromuscular blockage) Behavioral--changes in motor activity (specific assay)	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

Drug Information

MeSH Entry Terms：

2,3 Dioxoindoline

Isatin Use and Manufacturing

Methods of Manufacturing

The oxime acetanilide is prepared by condensation of aniline trichloroacetaldehyde oxime, and then isatin is obtained by cyclization and hydrolysis.

Uses

manufacture of vat dyes.In analytical chemistry as a reagent for cuprous ions, mercaptans, thiophene, and indican.

Manufacturing Info：

1H-Indole-2,3-dione: ACTIVE

Computed Properties

Molecular Weight:147.13
XLogP3:0.8
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:147.032028402
Monoisotopic Mass:147.032028402
Topological Polar Surface Area:46.2
Heavy Atom Count:11
Complexity:212
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes

Synthesis Route

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CAS No.: 91-56-5

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isatin 91-56-5

CAS No.: 91-56-5

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Isatin 91-56-5 orange-red single residual prism crystal molecular weight :147.13, melting point: 203.5 ℃

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Guide of Isatin

Description
Basic Attributes
Characteristics
Safety Information
Toxicity
Drug Information
Use and Manufacturing
Computed Properties
Synthesis Route
Recommended Suppliers
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Isatin

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