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616-91-1

Basic Information
CAS No.: 616-91-1
Name: N-Acetyl-cysteine
Article Data: 45
Cas Database
Molecular Structure:
Molecular Structure of 616-91-1 (N-Acetyl-cysteine)
Formula: C5H9NO3S
Molecular Weight: 163.197
Synonyms: Sodium 2-acetamido-3-mercaptopropionate;Mucolytikum Lappe;Acetein;Fluatox;(2R)-2-acetamido-3-sulfanyl-propanoic acid;Fabrol;Fluibiotic;Flumicil;Airbron;Mucosolvin;Tixair;Fluimucetin;N- Acetyl -L- Cysteine;Brunac;Ac-Cys;N-Acetyl Cysteine;Acetyl-L-cysteine;(R)-N-Acetylcysteine;Mercapturic acid, (R)-;L-Acetylcysteine;Mucomyst (TN);Mucofilin;(2R)-2-acetamido-3-sulfanyl-propanoate;N-Acetyl-L-Cysteine(NAC);Mucomyst;L-Cysteine, N-acetyl-;N-Acetyl-L-cysteine;N-Acetylcysteine;Flumucetin;Mucolyticum;Respaire;Mercapturic acid;Acetylcysteine (JAN/USP);L-Cysteine,N-acetyl-;Sodium N-acetyl-L-cysteinate;Cysteine, N-acetyl-, L-;Broncholysin;Parvolex;Broncholysin (mucolytic);Fluimucil;L-Cysteine, N-acetyl-,;
EINECS: 210-498-3
Density: 1.295 g/cm3
Melting Point: 106-108 °C
Boiling Point: 407.678 °C at 760 mmHg
Flash Point: 200.357 °C
Solubility: Soluble in water, ethanol, methanol, dimethyl sulfoxide, hot isopropyl alcohol, methyl acetate and ethyl acetate. Insoluble in chloroform and ether.
Appearance: White crystalline powder
Hazard Symbols: N/A
Risk Codes: 36/37/38
Safety: 22-24/25
Transport Information: N/A
PSA: 105.20000
LogP: -0.10360
Synthetic route
108-24-7

acetic anhydride

7048-04-6

L-cysteine hydrochloride monohydrate

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With sodium acetate In tetrahydrofuran; water at 10 - 60℃; for 37h; pH=4 - 5; Inert atmosphere;85%
463-51-4

Ketene

56-89-3

L-cystine

616-91-1

N-acetylcystein

Conditions
ConditionsYield
durch Erwaermen des Reaktionsprodukts mit Zink und Essigsaeure auf 50-60grad; Reinigung ueber das Kupfer(I)-Salz;
56-89-3

L-cystine

108-24-7

acetic anhydride

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With sodium hydroxide durch Erwaermen des Reaktionsprodukts mit Zink und Essigsaeure auf 50-60grad; Reinigung ueber das Kupfer(I)-Salz;
108-22-5

Isopropenyl acetate

52-90-4

L-Cysteine

616-91-1

N-acetylcystein

Conditions
ConditionsYield
In water

Sodium; (R)-2-methyl-4,5-dihydro-thiazole-4-carboxylate

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With hydrogenchloride
86124-83-6

N-Acetyl-S-<2-(4-ethoxycarbonylphenylsulfonyl)ethyl>cystein

A

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With sodium hydroxide Ambient temperature; reaction times, various conc. of NaOH, add. of N-Acetyl-S-<2-(phenylsulfonyl)ethyl>-cystein;

N-Acetyl-L-cysteine disulfide radical anion

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With water; dinitrogen monoxide at 22℃; Equilibrium constant; Rate constant; Irradiation; various pH;
60-24-2

2-hydroxyethanethiol

675587-70-9

Nα-acetyl-S-(2,4-dinitro-5-(dimethylaminomethyl)phenyl)-L-cysteine

A

616-91-1

N-acetylcystein

B

N,N-dimethyl-2,4-dinitro-5-((2-hydroxyethyl)thio)benzylamine

Conditions
ConditionsYield
With sodium phosphate buffer for 1h; pH=8.0;
1222442-92-3

2-acetamido-3-(3-hydroxy-2-isopropyl-4-methoxy-4-oxobutanoylthio)propanoic acid

A

616-91-1

N-acetylcystein

Conditions
ConditionsYield
With water; sodium hydroxide at 40℃; for 1h;
72-18-4

L-valine

1415322-55-2

N-acetyl-S-[[4-(4-aminobenzyl)phenyl]carbamoyl]-cysteine

A

616-91-1

N-acetylcystein

B

1415322-26-7

N-([4-(4-aminobenzyl)-phenyl]carbamoyl)-valine

C

1,3-bis{4-[4-aminobenzyl]-phenyl}urea

Conditions
ConditionsYield
In aq. phosphate buffer at 37℃; for 5h; pH=7.4;
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    N-Acetyl-cysteine CAS No.:616-91-1 Name: N-Acetyl-cysteine Synonyms: N-Acetyl-L-(+)-cysteine Molecular Structure Molecular Formula: C5H9NO3S Molecular Weight: 163.19 CAS Registry Number: 616-91-1

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Consensus Reports

Reported in EPA TSCA Inventory.

Specification

1. Introduction of N-Acetyl-cysteine

N-Acetyl-cysteine, with the IUPAC Name of (2R)-2-acetamido-3-sulfanylpropanoic acid, is one kind of white crystalline powder. This product belongs to the Product Categories which include Phenylalanine analogs and other aromatic alpha amino acids; Amino; Amino Acids; Cysteine [Cys, C];Ac-Amino Acids; Amino Acids (N-Protected); Antioxidant; Biochemistry; Nutritional Supplements; Pharmaceutical Intermediates; N-Acetyl-Amino acid series; Miscellaneous Compounds.

2. Properties of N-Acetyl-cysteine

N-Acetyl-cysteine has the following property datas: (1)Freely Rotating Bonds: 4; (2)Polar Surface Area: 71.91 ?2; (3)Index of Refraction: 1.518; (4)Molar Refractivity: 38.25 cm3; (5)Molar Volume: 126 cm3; (6)Surface Tension: 49.9 dyne/cm; (7)Density: 1.294 g/cm3; (8)Flash Point: 200.4 °C; (9)Enthalpy of Vaporization: 72.37 kJ/mol; (10)Boiling Point: 407.7 °C at 760 mmHg; (11)Vapour Pressure: 8.68E-08 mmHg at 25°C; (12)EINECS: 210-498-3; (13)Melting point: 106-108 °C; (14)alpha: -35.1 oC (c=2,H2O); (15)Storage temp: 2-8°C; (16)Solubility: H2O: 100 mg/mL with heating.

3. Structure Descriptors of N-Acetyl-cysteine

You could convert the following datas into the molecular structure:
(1)InChI: InChI=1S/C5H9NO3S/c1-3(7)6-4(2-10)5(8)9/h4,10H,2H2,1H3,(H,6,7)(H,8,9)/t4-/m0/s1 
(2)InChIKey: InChIKey=PWKSKIMOESPYIA-BYPYZUCNSA-N 
(3)Smiles: [C@@H](NC(=O)C)(C(=O)O)CS

4. Toxicity of N-Acetyl-cysteine

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
child TDLo multiple routes 8480mg/kg/3D- (8480mg/kg) LIVER: LIVER FUNCTION TESTS IMPAIRED Pediatrics. Vol. 79, Pg. 281, 1987.
 
dog LD50 intraperitoneal 700mg/kg (700mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
dog LD50 intravenous 700mg/kg (700mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
dog LD50 oral > 1gm/kg (1000mg/kg)   Pharmacological and Biochemical Properties of Drug Substances. Vol. 2, Pg. 479, 1979.
mouse LD50 intraperitoneal 400mg/kg (400mg/kg)   National Technical Information Service. Vol. AD691-490,
mouse LD50 intravenous 3800mg/kg (3800mg/kg) BRAIN AND COVERINGS: RECORDINGS FROM SPECIFIC AREAS OF CNS

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Medicinal Chemistry. Vol. 10, Pg. 1172, 1967.
mouse LD50 oral 4400mg/kg (4400mg/kg)   European Patent Application. Vol. #0192191,
rat LD50 intravenous 1140mg/kg (1140mg/kg) GASTROINTESTINAL: OTHER CHANGES European Journal of Respiratory Diseases. Vol. 61(Suppl,
rat LD50 oral 5050mg/kg (5050mg/kg)   Toxicology and Applied Pharmacology. Vol. 18, Pg. 185, 1971.
 

5. Safety Information of N-Acetyl-cysteine

Poison by intraperitoneal route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NOx and SOx.
Risk Statements: 36/37/38
36/37/38: Irritating to eyes, respiratory system and skin 
Safety Statements: 22-24/25
22: Do not breathe dust
24/25: Avoid contact with skin and eyes
F 10-23: Keep under argon. Sensitive to air
WGK Germany: 3

6. Use of N-Acetyl-cysteine (CAS NO.616-91-1)
 
N-Acetyl-cysteine is a pharmaceutical drug used mainly as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. Oral N-Acetyl-cysteine is used for the prevention of radiocontrast-induced nephropathy. Besides can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis.