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616-91-1

616-91-1 structure
616-91-1 structure
Name N-acetyl-L-cysteine
Synonyms AC-ASP-GLU
2-(acetylamino)-3-sulfanylpropanoic acid
N-acetyl-L-aspartyl-L-glutamate
Acetylcysteine
(R)-2-Acetamido-3-mercaptopropanoic acid
AC-ASP-GLU H2O
MFCD00004880
N-Acetylcysteine
EINECS 210-498-3
N-acetyl-aspartatylglutamate
NAAGA
SPAGLUMIC ACID
N-acetylcycteine
N-ACETYL-3-MERCAPTOALANINE
AC-ASP-GLU-OH
L-N-acetyl-cysteine
Isospaglumic acid
(2R)-2-acetylamino-2-carboxyethanethiol
N-acetyl-L-aspartyl-L-glutamic acid
Cysteine, N-acetyl-
N-acetyl-(R)-cysteine
Naaxia
ACETYL-D-E
N-Acetyl-L-Cysteine
NAAG
N-Acetyl-cysteine
Description Acetylcysteine is a mucolytic agent which reduces the thickness of the mucus.
Related Catalog
Target

Human Endogenous Metabolite

In Vitro N-acetylcysteine prevents apoptotic DNA fragmentation and maintains long-term survival in the absence of other trophic support in serum-deprived PC12 cells. N-acetylcysteine also prevents death of PC12 cells and sympathetic neurons[2]. N-acetylcysteine causes dose-dependent reductions in viability in rat and human aortic smooth muscle cells[3]. N-acetylcysteine activates the Ras-extracellular signal-regulated kinase (ERK) pathway in PC12 cells. N-acetylcysteine protects neuronal cells from death evoked by withdrawal of trophic support. N-acetylcysteine increases nitric oxide (NO) release from protein-bound stores in vascular tissue. N-acetylcysteine pretreatment of PC12 cells interferes with NGF-dependent signaling and neurite outgrowth, and it is suggested that N-acetylcysteine interferes with redox-sensitive steps in the NGF mechanism[4].
In Vivo N-acetylcysteine (150, 300 mg/kg) treatment significantly reduces liver transaminases in all groups of treatment, mostly in group N-acetylcysteine 300. Lung glutathione peroxidase is significantly increases in group N-acetylcysteine 300 (P=0.04), while the other oxidation biomarkers show no significant differences[1]. N-acetylcysteine improves cognition of 12-month-old SAMP8 mice in both the T-maze footshock avoidance paradigm and the lever press appetitive task without inducing non-specific effects on motor activity, motivation to avoid shock, or body weight[5].
Cell Assay For survival experiments, washed cells are resuspended in RPM1 1640 medium and plated in 0.5 mL at a density of 8-10×105 per well in 24 well plastic culture dishes coated with rat tail collagen. To feed, but to avoid loss of floating cells, fresh medium (0.2 mL) is added to the cultures on days 1, 5, and 10. For experiments involving "primed" PC12 cells, cultures are pretreated for l-2 weeks with NGF in RPM1 1640 medium supplemented with 1% heat-iN-acetylcysteinetivated horse serum. The cells are then washed and passaged into serum-free RPM1 1640 medium.
Animal Admin Rats: Rats are randomLy allocated into five groups: sham group (n=5), control group with IIR (n=8) and three groups with IIR who are given N-acetylcysteine in different dosages: 150 mg/kg intraperitoneally 5 min before ischemia (n=8, group N-acetylcysteine 150), 300 mg/kg i.p 5 min before ischemia (n=7, group N-acetylcysteine 300), and 150 mg/kg i.p 5 min before ischemia plus 150 mg/kg 5 min before reperfusion (n=7, group N-acetylcysteine 150 + 150). After 4 h of reperfusion, the animals are euthanized by exsanguination from the abdominal aorta.
References

[1]. Kalimeris K, et al. N-acetylcysteine ameliorates liver injury in a rat model of intestinal ischemia reperfusion. J Surg Res. 2016 Dec;206(2):263-272

[2]. Ferrari G, et al. N-acetylcysteine (D- and L-stereoisomers) prevents apoptotic death of neuronal cells. J Neurosci. 1995 Apr;15(4):2857-66.

[3]. Tsai JC, et al. Induction of apoptosis by pyrrolidinedithiocarbamate and N-acetylcysteine in vascular smooth muscle cells. J Biol Chem. 1996 Feb 16;271(7):3667-70.

[4]. Yan CY, et al. Prevention of PC12 cell death by N-acetylcysteine requires activation of the Ras pathway. J Neurosci. 1998 Jun 1;18(11):4042-9.

[5]. Farr SA, et al. The antioxidants alpha-lipoic acid and N-acetylcysteine reverse memory impairment and brain oxidative stress in aged SAMP8 mice. J Neurochem. 2003 Mar;84(5):1173-83.
Density 1.3±0.1 g/cm3
Boiling Point 407.7±40.0 °C at 760 mmHg
Melting Point 106-108 °C(lit.)
Molecular Formula C5H9NO3S
Molecular Weight 163.195
Flash Point 200.4±27.3 °C
Exact Mass 163.030319
PSA 105.20000
LogP -0.15
Vapour Pressure 0.0±2.0 mmHg at 25°C
Index of Refraction 1.519

CHEMICAL IDENTIFICATION

RTECS NUMBER :
HA1660000
CHEMICAL NAME :
Cysteine, N-acetyl-, L-
CAS REGISTRY NUMBER :
616-91-1
LAST UPDATED :
199701
DATA ITEMS CITED :
16
MOLECULAR FORMULA :
C5-H9-N-O3-S
MOLECULAR WEIGHT :
163.21
WISWESSER LINE NOTATION :
SH1YVQMV1 -L

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Multiple routes
SPECIES OBSERVED :
Human - child
DOSE/DURATION :
8480 mg/kg/3D-I
TOXIC EFFECTS :
Liver - liver function tests impaired
REFERENCE :
PEDIAU Pediatrics. (American Academy of Pediatrics, P.O. Box 1034, Evanston, IL 60204) V.1- 1948- Volume(issue)/page/year: 79,281,1987
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
5050 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
TXAPA9 Toxicology and Applied Pharmacology. (Academic Press, Inc., 1 E. First St., Duluth, MN 55802) V.1- 1959- Volume(issue)/page/year: 18,185,1971
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1140 mg/kg
TOXIC EFFECTS :
Gastrointestinal - other changes
REFERENCE :
EJRDD2 European Journal of Respiratory Diseases. (Munksgaard International Pub., c/o Pub. Expediting Inc., 200 Meacham Ave., Elmont, NY 11003) V.61- 1980- Volume(issue)/page/year: 61(Suppl 111),45,1980
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
4400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
EPXXDW European Patent Application. (U.S. Patent and Trademark Office, Foreign Patents, Washington, DC 20231) Volume(issue)/page/year: #0192191
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
400 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NTIS** National Technical Information Service. (Springfield, VA 22161) Formerly U.S. Clearinghouse for Scientific & Technical Information. Volume(issue)/page/year: AD691-490
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
3800 mg/kg
TOXIC EFFECTS :
Brain and Coverings - recordings from specific areas of CNS Behavioral - somnolence (general depressed activity) Lungs, Thorax, or Respiration - other changes
REFERENCE :
JMCMAR Journal of Medicinal Chemistry. (American Chemical Soc., Distribution Office Dept. 223, POB POB 57136, West End Stn., Washington, DC 20037) V.6- 1963- Volume(issue)/page/year: 10,1172,1967
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
>1 gm/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,479,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,479,1979
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
700 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,479,1979 *** REVIEWS *** TOXICOLOGY REVIEW CTOXAO Clinical Toxicology. (New York, NY) V.1-18, 1968-81. For publisher information, see JTCTDW. Volume(issue)/page/year: 12,601,1978 TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,479,1979 TOXICOLOGY REVIEW EJRDD2 European Journal of Respiratory Diseases. (Munksgaard International Pub., c/o Pub. Expediting Inc., 200 Meacham Ave., Elmont, NY 11003) V.61- 1980- Volume(issue)/page/year: 61(Suppl 111),45,1980 TOXICOLOGY REVIEW PBPSDY Pharmacological and Biochemical Properties of Drug Substances. (American Pharmaceutical Assoc., 2215 Constitution Ave., NW, Washington, DC 20037) V.1- 1977- Volume(issue)/page/year: 2,479,1979 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 81688 No. of Facilities: 616 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 4525 (estimated) NOES - National Occupational Exposure Survey (1983) NOES Hazard Code - 81688 No. of Facilities: 1677 (estimated) No. of Industries: 1 No. of Occupations: 14 No. of Employees: 31203 (estimated) No. of Female Employees: 21201 (estimated)
Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Risk Phrases R36/37/38
Safety Phrases S22-S24/25
RIDADR NONH for all modes of transport
WGK Germany 3
RTECS HA1660000
HS Code 2930909090
1222442-92-3 structure

1222442-92-3

~%

616-91-1 structure

616-91-1

16048-89-8 structure

16048-89-8

Literature: Journal of Antibiotics, , vol. 63, # 2 p. 95 - 96
56-89-3 structure

56-89-3

108-24-7 structure

108-24-7

~%

616-91-1 structure

616-91-1

Literature: Biochemical Journal, , vol. 25, p. 619 Biochemical Journal, , vol. 27, p. 1716
108-22-5 structure

108-22-5

52-90-4 structure

52-90-4

~%

616-91-1 structure

616-91-1

Literature: Journal of medicinal chemistry, , vol. 11, # 6 p. 1176 - 1182
463-51-4 structure

463-51-4

56-89-3 structure

56-89-3

~%

616-91-1 structure

616-91-1

Literature: Biochemical Journal, , vol. 25, p. 619 Biochemical Journal, , vol. 27, p. 1716
86124-83-6 structure

86124-83-6

~%

616-91-1 structure

616-91-1

5535-48-8 structure

5535-48-8

Literature: Liebigs Annalen der Chemie, , # 1 p. 22 - 33
HS Code 2930909090
Summary 2930909090. other organo-sulphur compounds. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

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