N-Acetyl-L-cysteine

Iupac Name：(2R)-2-acetamido-3-sulfanylpropanoic acid

Molecular Weight：163.19500

Modify Date.: 2022-11-05 04:05

Introduction: N-acetylcysteine amide is a kind of membrane penetrating antioxidant. It has anti-inflammatory activity through regulating the activation of NF-κB and HIF-1α as well as modulation of ROS. It can penetrate across the membrane, replenishes intracellular and glutathione and GSH to help the cell fight against oxidative stress. For these reasons, it has the potential for the treatment of neurodegeneration (such as Parkinson’s disease), radiation exposure and other disorders caused by oxidation. Moreover, it can also attenuate the allergic airway diseases. View more+

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1. Names and Identifiers

1.1 Name: N-Acetyl-L-cysteine
1.2 Synonyms: (2R)-2-acetylamino-2-carboxyethanethiol (R)-2-Acetamido-3-mercaptopropanoic acid (S)-ALPHA-AMINO-2-NAPHTHALENEPROPIONIC ACID 2-(acetylamino)-3-sulfanylpropanoic acid AC-ASP-GLU AC-ASP-GLU H2O AC-ASP-GLU-OH Acetylcysteine ACETYL-D-E AC-L-CYS-OH Cysteine, N-acetyl- EINECS 210-498-3 Isospaglumic acid L-N-acetyl-cysteine MFCD00004880 NAAG NAAGA Naaxia N-ACETYL CYSTEINE N-acetyl-(R)-cysteine N-ACETYL-3-MERCAPTOALANINE N-acetyl-aspartatylglutamate N-acetylcycteine N-Acetylcysteine N-Acetyl-cysteine N-ACETYL-L-(+)-CYSTEINE N-acetyl-L-aspartyl-L-glutamate N-acetyl-L-aspartyl-L-glutamic acid N-ALPHA-ACETYL-L-CYSTEINE RARECHEM BK PT 0097 SPAGLUMIC ACID

1.3 CAS No.: 616-91-1

1.4 CID: 12035

1.5 EINECS(EC#): 210-498-3

1.6 Molecular Formula: C5H9NO3S (isomer)

1.7 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

1.8 InChkey: PWKSKIMOESPYIA-BYPYZUCNSA-N

1.9 Canonical Smiles: CC(=O)NC(CS)C(=O)O

1.10 Isomers Smiles: CC(=O)N[C@@H](CS)C(=O)O

2. Properties

2.1 Density: 1.294 g/cm3

2.1 Melting point: 106-108°C(lit.)

2.1 Boiling point: 407.7ºC at 760 mmHg

2.1 Refractive index: 24 ° (C=JPC Method)

2.1 Flash Point: 200.4ºC

2.1 Precise Quality: 163.03000

2.1 PSA: 105.20000

2.1 logP: -0.10360

2.1 Solubility: H2O: 100?mg/mL with heating

2.2 AnalyticLaboratory Methods: THREE N-SUBSTITUTED MALEIMIDES, INCLUDING ACETYLCYSTEINE;, WERE TESTED AS DERIVATIZING REAGENTS. N-ACETYLCYSTEINE; WAS READILY CONVERTED INTO THE ADDUCT WITH N-(4-ANILINOPHENYL)MALEIMIDE;. PICROGRAM LEVELS WERE SEPARATED & QUANTIFIED.

2.3 Appearance: White crystalline powder

2.4 Storage: Ambient temperatures.

2.5 Chemical Properties: White or almost white, crystalline powder or colourless crystals

2.6 Color/Form: Crystals from water
WHITE, CRYSTALLINE POWDER

2.7 Odor: SLIGHT ACETIC ODOR

2.8 PH: 2 TO 2.75 (1 IN 100 ML)

2.9 Physical: Solid

2.10 pKa: pK1: 9.52 (30°C)

2.11 Water Solubility: 200 g/L

2.12 Spectral Properties: Specific optical rotation: +5 deg at 20 deg C (concn = 3 g/100 mL water)
MASS: 75327 (NIST/EPA/MSDC Mass Specral Database 1990 Version)

2.13 Stability: Stable. Incompatible with strong oxidizing agents.

2.14 StorageTemp: 2-8°C

3. Use and Manufacturing

3.1 Definition: ChEBI: An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.

3.2 GHS Classification: Signal: Warning
GHS Hazard Statements
Aggregated GHS information provided by 40 companies from 7 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Reported as not meeting GHS hazard criteria by 24 of 40 companies. For more detailed information, please visit ECHA C&L website

Of the 6 notification(s) provided by 16 of 40 companies with hazard statement code(s):

H315 (93.75%): Causes skin irritation [Warning Skin corrosion/irritation]
H319 (93.75%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]
H335 (93.75%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

Precautionary Statement Codes
P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501

3.3 Methods of Manufacturing: Direct acetylation of naturally occurring L-cysteine;

3.4 Usage: Paracetamol overdose Intravenous acetylcysteine is indicated for the treatment of paracetamol (acetaminophen) overdose. When paracetamol is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. It is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to inactivate the toxic NAPQI. This metabolite is then free to react with key hepatic enzymes, therefore damaging hepatocytes. This may lead to severe liver damage and even death by fulminant liver failure. For this indication, acetylcysteine acts to augment the glutathione reserves in the body and, together with glutathione, directly bind to toxic metabolites. These actions serve to protect hepatocytes in the liver from NAPQI toxicity. Mucolytic therapy ?Inhaled acetylcysteine is indicated for mucolytic (""mucusdissolving"") therapy as an adjuvant in respiratory conditions with excessive and / or thick mucus production. Such conditions include emphysema, bronchitis, tuberculosis, bronchiectasis, amyloidosis, pneumonia, cystic fibrosis, chronic obstructive pulmonary disease, and pulmonary fibrosis. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. It may be considered ineffective in cystic fibrosis.For this indication, acetylcysteine acts to reduce mucus viscosity by splitting disulfide bonds linking proteins present in the mucus (mucoproteins). Nephroprotective agent Oral acetylcysteine is used for the prevention of radiocontrastinduced nephropathy (a form of acute renal failure). Some studies show that prior administration of acetylcysteine markedly decreases radiocontrast nephropathy, whereas others appear to cast doubt on its efficacy. Treatment of cyclo phosphamide - induced hemorrhagic cystitis Acetylcysteine has been used for cyclophosphamide-induced hemorrhagic cystitis, although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide. Microbiological use Acetylcysteine can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis. Interstitial lung disease Acetylcysteine is used in the treatment of interstitial lung disease to prevent disease progression. Psychiatry Acetylcysteine has been shown to reduce the symptoms of both schizophrenia and bipolar disorder in two placebo controlled trials conducted at Melbourne University. It is thought to act via modulation of NMDA glutamate receptors or by increasing glutathione. Poly cystic ovary syndrome In a small prospective trial comparing acetylcysteine to metformin (which is the standard drug treatment for PCOS), both treatments resulted in a significant decrease in body mass index, hirsutism score, fasting insulin, HOMA index, free testosterone and menstrual irregularity compared with baseline values, and both treatments had equal efficacy.

4. Safety and Handling

4.1 Risk Statements: R36/37/38

4.1 Safety Statements: S22-S24/25

4.1 Exposure Standards and Regulations: The Approved Drug Products with Therapeutic Equivalence Evaluations List identifies currently marketed prescription drug products, incl acetylcysteine, approved on the basis of safety and effectiveness by FDA under sections 505 of the Federal Food, Drug, and Cosmetic Act.

4.2 Octanol/Water Partition Coefficient: log Kow = -0.66 /Estimated/

4.3 DisposalMethods: SRP: The most favorable course of action is to use an alternative chemical product with less inherent propensity for occupational exposure or environmental contamination. Recycle any unused portion of the material for its approved use or return it to the manufacturer or supplier. Ultimate disposal of the chemical must consider: the material's impact on air quality; potential migration in soil or water; effects on animal, aquatic, and plant life; and conformance with environmental and public health regulations.

4.4 RIDADR: NONH for all modes of transport

4.4 Safety Profile: Poison by intraperitoneal route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO, and SOx,

4.5 Formulations/Preparations: Parenteral: For injection concentrate, for IV infusion: 200 mg/mL Acetadote (Cumberland).
Oral inhalation, intratracheal instillation, and oral: Solution: 100 mg (of acetylcysteine) per mL (10%), Acetylcysteine Sodium Solution, (Abbott, American Regent, Bedford, Dey, Mayne, Roxane); Mucomyst (Sandoz); 200 mg (of acetylcysteine) per mL (20%) Acetylcysteine Sodium Solution (Abbott, American Regent, Bedford, Dey, Mayne, Roxane); Mucomyst (Sandoz). /Acetylcysteine sodium/

4.6 WGK Germany: 3

4.6 RTECS: HA1660000

4.6 Reactivities and Incompatibilities: Acetylcysteine is a reducing agent and is incompatible with oxidizing agents. Solutions of acetylcysteine become discolored and liberate hydrogen sulfide upon contact with rubber, some metals, particularly iron and copper, and/or when subjected to autoclaving. ... Solutions containing amphotericin B, tetracyclines, erythromycin lactobionate, or ampicillin sodium. ... Acetylcysteine solutions are also physically imcompatible with iodized oil, trypsin, hydrogen peroxide.

4.7 Report: Reported in EPA TSCA Inventory.

4.8 Safety: Poison by intraperitoneal route. Moderately toxic by other routes. Mutation data reported. When heated to decomposition it emits very toxic fumes of NO_x and SO_x.
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

4.9 Specification: ? N-Acetyl-cysteine , with CAS number of 616-91-1, can be called (2R)-2-(acetylamino)-3-sulfanylpropanoic acid ; (2R)-2-Acetamido-3-sulfanylpropanoic acid ; 2-Acetylamino-3-mercapto-propionate ; Acetylcysteinum ; Acetilcisteina . It is a?white crystalline powder. N-Acetyl-cysteine (CAS NO.616-91-1) 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.

4.10 Toxicity

1.	???	mma-sat 8?μg/plate	???	CRNGDP ?? Carcinogenesis. 7 (1986),431.
2.	???	orl-rat LD50:5050?mg/kg	???	TXAPA9 ?? Toxicology and Applied Pharmacology. 18 (1971),185.
3.	???	ivn-rat LD50:1140?mg/kg	???	EJRDD2 ?? European Journal of Respiratory Diseases. 61 (Suppl 111),(1980),45.
4.	???	orl-mus LD50:7888?mg/kg	???	THEWA6 ?? Therapiewoche. 30 (1980),1926.
5.	???	ipr-mus LD50:400?mg/kg	???	NTIS** ?? National Technical Information Service. (Springfield, VA 22161) (Formerly U.S. Clearinghouse for Scientific and Technical Information) AD691-490 .
6.	???	ivn-mus LD50:3800?mg/kg	???	JMCMAR ?? Journal of Medicinal Chemistry. 10 (1967),1172.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Not classified.

2.2 GHS label elements, including precautionary statements

Pictogram(s)	No symbol.
Signal word	No signal word.
Hazard statement(s)	none
Precautionary statement(s)
Prevention	none
Response	none
Storage	none
Disposal	none

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

Mass spectrum (electron ionization)

7. Synthesis Route

616-91-1Total: 5 Synthesis Route

86124-83-6

616-91-1 506 Suppliers

5535-48-8 129 Suppliers

Literatures:
Liebigs Annalen der Chemie, , # 1 p. 22 - 33
Yield: null

1222442-92-3

616-91-1 506 Suppliers

16048-89-8

Literatures:
Journal of Antibiotics, , vol. 63, # 2 p. 95 - 96
Yield: null

463-51-4 10 Suppliers

56-89-3 541 Suppliers

616-91-1 506 Suppliers

Literatures:
Biochemical Journal, , vol. 25, p. 619 Biochemical Journal, , vol. 27, p. 1716
Yield: null

View all

8. Precursor and Product

precursor:

1222442-92-3

56-89-3

463-51-4

108-22-5

86124-83-6

52-90-4

product :

56577-02-7

23127-41-5

921-01-7

27486-87-9

16637-59-5

4775-80-8

15060-26-1

35356-70-8

19216-62-7

192227-89-7

5545-17-5

59587-09-6

19547-88-7

35897-25-7

19542-74-6

19542-77-9

14402-54-1

52-90-4

View all

9. Other Information

9.0 Merck: 14,88

9.1 BRN: 1724426

9.2 Description: N-acetylcysteine amide is a kind of membrane penetrating antioxidant. It has anti-inflammatory activity through regulating the activation of NF-κB and HIF-1α as well as modulation of ROS. It can penetrate across the membrane, replenishes intracellular and glutathione and GSH to help the cell fight against oxidative stress. For these reasons, it has the potential for the treatment of neurodegeneration (such as Parkinson’s disease), radiation exposure and other disorders caused by oxidation. Moreover, it can also attenuate the allergic airway diseases.

9.3 Chemical Properties: White or almost white, crystalline powder or colourless crystals

9.4 Chemical Properties: Acetylcysteine also known as N-acetylcysteine or N-acetyl-Lcysteine (abbreviated NAC), is a pharma ceutical drug and nutritional supplement used primarily as a mucolytic agent and in the management of paracetamol (acetaminophen) overdose. Other uses include sulfate repletion in conditions, such as autism, where cysteine and related sulfur amino acids may be depleted.
Acetylcysteine is a derivative of cysteine; an acetyl group is attached to the nitrogen atom. This compound is sold as a dietary supplement commonly claiming antioxidant and liver protecting effects. It is used as a cough medicine because it breaks disulfide bonds in mucus and liquefies it, making it easier to cough up. It is also this action of breaking disulfide bonds that makes it useful in thinning the abnormally thick mucus in cystic and pulmonary fibrosis patients. In India it is marketed by Intas under the trade name 'Efetil'.

9.5 Chemical Properties: Acetylcysteine is the N-acetyl derivative of the amino acid Lcysteine, and is a precursor in the formation of the antioxidant glutathione in the body. The thiol (sulfhydryl) group confers antioxidant effects and is able to reduce free radicals.

9.6 Originator: Mucomyst ,Mead Johnson,US

9.7 Uses: Paracetamol overdose
Intravenous acetylcysteine is indicated for the treatment of paracetamol (acetaminophen) overdose. When paracetamol is taken in large quantities, a minor metabolite called N-acetyl-p-benzoquinone imine (NAPQI) accumulates within the body. It is normally conjugated by glutathione, but when taken in excess, the body's glutathione reserves are not sufficient to inactivate the toxic NAPQI. This metabolite is then free to react with key hepatic enzymes, therefore damaging hepatocytes. This may lead to severe liver damage and even death by fulminant liver failure.
For this indication, acetylcysteine acts to augment the glutathione reserves in the body and, together with glutathione, directly bind to toxic metabolites. These actions serve to protect hepatocytes in the liver from NAPQI toxicity.
Mucolytic therapy
?Inhaled acetylcysteine is indicated for mucolytic (""mucusdissolving"") therapy as an adjuvant in respiratory conditions with excessive and / or thick mucus production. Such conditions include emphysema, bronchitis, tuberculosis, bronchiectasis, amyloidosis, pneumonia, cystic fibrosis, chronic obstructive pulmonary disease, and pulmonary fibrosis. It is also used post-operatively, as a diagnostic aid, and in tracheotomy care. It may be considered ineffective in cystic fibrosis.For this indication, acetylcysteine acts to reduce mucus viscosity by splitting disulfide bonds linking proteins present in the mucus (mucoproteins).
Nephroprotective agent
Oral acetylcysteine is used for the prevention of radiocontrastinduced nephropathy (a form of acute renal failure). Some studies show that prior administration of acetylcysteine markedly decreases radiocontrast nephropathy, whereas others appear to cast doubt on its efficacy.
Treatment of cyclo phosphamide - induced hemorrhagic cystitis
Acetylcysteine has been used for cyclophosphamide-induced hemorrhagic cystitis, although mesna is generally preferred due to the ability of acetylcysteine to diminish the effectiveness of cyclophosphamide.
Microbiological use
Acetylcysteine can be used in Petroff's method i.e. liquefaction and decontamination of sputum, in preparation for diagnosis of tuberculosis.
Interstitial lung disease
Acetylcysteine is used in the treatment of interstitial lung disease to prevent disease progression.
Psychiatry
Acetylcysteine has been shown to reduce the symptoms of both schizophrenia and bipolar disorder in two placebo controlled trials conducted at Melbourne University. It is thought to act via modulation of NMDA glutamate receptors or by increasing glutathione.
Poly cystic ovary syndrome
In a small prospective trial comparing acetylcysteine to metformin (which is the standard drug treatment for PCOS), both treatments resulted in a significant decrease in body mass index, hirsutism score, fasting insulin, HOMA index, free testosterone and menstrual irregularity compared with baseline values, and both treatments had equal efficacy.

9.8 Uses: A metabolite of Methyl Isocyanate.
N-Acetyl cysteine (NAC), by itself a poor scavenger of oxidants, is converted inside cells to yield sulfane sulfur species, which are very potent scavengers of oxidants.

9.9 Uses: An antioxidant mucolytic acetylated amino acid.
N-acetyl-l-cysteine (NAC) is a derivative of the dietary amino acid l-cysteine. NAC has a high affinity for lung tissue, which it supports through mucolytic and antioxidant action. NAC also enhances glutathione production and plays a role in heavy metal detoxification.

9.10 Uses: n-acetyl-l-cysteine is a skin conditioner. It may also be used as an anti-aging ingredient given a demonstrated ability to regulate skin atrophy and reduce the appearance of fine lines and wrinkles.

9.11 Definition: ChEBI: An N-acetyl-L-amino acid that is the N-acetylated derivative of the natural amino acid L-cysteine.

9.12 Manufacturing Process: To a suspension of 35.2 grams (0.2 mol) of L-cysteine hydrochloride monohydrate stirred in a reaction vessel containing 87 ml of 91% aqueous tetrahydrofuran under a nitrogen atmosphere there is added 54.4 grams (0.4 mol) of sodium acetate trihydrate. The mixture is stirred for 20 minutes at room temperature to insure neutralization of the hydrochloride salt resulting in the formation of a suspension of equimolar amounts of cysteine and sodium acetate.
The mixture is then chilled to 3-6°C by external cooling and 20 ml (20.8 grams, 0.21 mol) of acetic anhydride is added thereto in dropwise fashion with cooling in the above range. The resulting mobile suspension is stirred for 6 hours at room temperature, allowed to stand overnight, and finally heated at reflux (72°C) for 4 hours. The resulting suspension of sodium N-acetyl-Lcysteinate is then neutralized by treatment at 5-10°C with 8 grams of hydrogen chloride. Resulting sodium chloride is removed by filtration and the product is isolated by distilling the solvent from the filtrate in vacuum and crystallizing the residue from 35 ml of water, yield 26.3 grams (80.6%) of Nacetylcysteine as a white solid, MP 109-110°C.

9.13 Brand name: Acetadote (Cumberland); Mucomyst (Apothecon); Mucosil (Dey).

9.14 Therapeutic Function: Expectorant

9.15 General Description: Formulation: Solution in Tris-HCl (pH 8), NaCl, Glycerol

9.16 Usage: A mucolytic agent for isolation of mycobacteria from sputum.N-Acetyl-L-cysteine is used in the liquefaction and decontamination of sputum during the preparation for recovery of mycobacterium, which is called as Petroff's method. It shows antiviral activity against the influenza A viruses. It is used in the treatment of interstitial lung disease to prevent disease progression. It is an antioxidant, dietary supplement and protects liver. Further, it forms complexes with palladium, thereby it dissolves in water and remove palladium from drugs. Further, it is used in the treatment of paracetamol overdose. In addition to this, it is involved in the treatment of autism, Alzheimer's disease, bipolar disorder, major depressive disorder, obsessive-compulsive disorder, schizophrenia, and specific drug addictions like cocaine and cannabis.

10. Computational chemical data

Molecular Weight: 163.19500g/mol
Molecular Formula: C₅H₉NO₃S
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 163.03031432
Monoisotopic Mass: 163.03031432
Complexity: 148
Rotatable Bond Count: 3
Hydrogen Bond Donor Count: 3
Hydrogen Bond Acceptor Count: 4
Topological Polar Surface Area: 67.4
Heavy Atom Count: 10
Defined Atom Stereocenter Count: 1
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 1
CACTVS Substructure Key Fingerprint: AAADccBiMABAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAHgQQCAAACCjFwASCCALAAgQIAAGQGAAAAAAAAAAAAIGIAAACAAAAACAAQAAAFgCQAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAAA==

11. Question & Answer

Top 9 Benefits of NAC (N-Acetyl Cysteine) Feb 24 2021
Cysteine is a semi-essential amino acid. It’s considered semi-essential because your body can produce it from other amino acids, namely methionine and serine. It becomes essential only when the dietary intake of methionine and serine is low. Cysteine is found in most high-protein foods, such ...
Various Uses of N-Acetyl Cysteine Feb 24 2021
N-acetyl cysteine (NAC), as a nutritional supplement, is a greatly applied antioxidant in vivo and in vitro. N-Acetyl Cysteine is a precursor of L-cysteine that results in glutathione elevation biosynthesis. It acts directly as a scavenger of free radicals, especially oxygen radicals. N-Acetyl Cyst...

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