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UNII:6G5ELX5XYN

Names

[ CAS No. ]:
5694-00-8

[ Name ]:
UNII:6G5ELX5XYN

[Synonym ]:
2-Oxiranecarboxamide
Oxirane-2-carboxamide
UNII:6G5ELX5XYN

Biological Activity

[Description]:

Glycidamide is the genotoxic metabolite of Acrylamide. Glycidamide can react with proteins, such as hemoglobin, or with DNA, and induces genotoxic effects[1].

[Related Catalog]:

Research Areas >> Others
Signaling Pathways >> Others >> Others

[References]

[1]. Besaratinia A, et al. Genotoxicity of acrylamide and glycidamide. J Natl Cancer Inst. 2004 Jul 7;96(13):1023-9.  

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
321.9±31.0 °C at 760 mmHg

[ Melting Point ]:
32-34ºC

[ Molecular Formula ]:
C3H5NO2

[ Molecular Weight ]:
87.077

[ Flash Point ]:
240.8±21.2 °C

[ Exact Mass ]:
87.032028

[ PSA ]:
55.62000

[ LogP ]:
-2.21

[ Vapour Pressure ]:
0.0±0.7 mmHg at 25°C

[ Index of Refraction ]:
1.516

[ Storage condition ]:
Hygroscopic, -20°C Freezer, Under Inert Atmosphere

MSDS

Click to get detail MSDS

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
MB3200000
CHEMICAL NAME :
Glycidamide
CAS REGISTRY NUMBER :
5694-00-8
BEILSTEIN REFERENCE NO. :
1280744
LAST UPDATED :
199712
DATA ITEMS CITED :
10
MOLECULAR FORMULA :
C3-H5-N-O2
MOLECULAR WEIGHT :
87.09
WISWESSER LINE NOTATION :
T3OTJ BVZ

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
800 mg/kg/8D-I
TOXIC EFFECTS :
Behavioral - alteration of operant conditioning Nutritional and Gross Metabolic - weight loss or decreased weight gain Biochemical - Enzyme inhibition, induction, or change in blood or tissue levels - dehydrogenases
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
400 mg/kg
SEX/DURATION :
male 8 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetotoxicity (except death, e.g., stunted fetus)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
800 mg/kg
SEX/DURATION :
male 8 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Effects on Newborn - behavioral
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
350 mg/kg
SEX/DURATION :
male 7 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - spermatogenesis (incl. genetic material, sperm morphology, motility, and count) Reproductive - Paternal Effects - testes, epididymis, sperm duct
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
Dominant lethal test

MUTATION DATA

TEST SYSTEM :
Rodent - mouse
DOSE/DURATION :
100 mg/kg
REFERENCE :
MUREAV Mutation Research. (Elsevier Science Pub. B.V., POB 211, 1000 AE Amsterdam, Netherlands) V.1- 1964- Volume(issue)/page/year: 371,175,1996

Safety Information

[ Symbol ]:

GHS07, GHS08

[ Signal Word ]:
Danger

[ Hazard Statements ]:
H302-H315-H317-H319-H335-H350

[ Precautionary Statements ]:
P201-P261-P280-P305 + P351 + P338-P308 + P313

[ Personal Protective Equipment ]:
Eyeshields;Faceshields;full-face particle respirator type N100 (US);Gloves;respirator cartridge type N100 (US);type P1 (EN143) respirator filter;type P3 (EN 143) respirator cartridges

[ Hazard Codes ]:
T

[ Risk Phrases ]:
45-46-22-36/37/38-43

[ Safety Phrases ]:
53-26-36/37-45

[ RIDADR ]:
NONH for all modes of transport

[ RTECS ]:
MB3200000

[ HS Code ]:
2924299090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2924299090

[ Summary ]:
2924299090. other cyclic amides (including cyclic carbamates) and their derivatives; salts thereof. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Mouse spermatocytes express CYP2E1 and respond to acrylamide exposure.

PLoS ONE 9(5) , e94904, (2014)

Metabolism of xenobiotics by cytochrome P450s (encoded by the CYP genes) often leads to bio-activation, producing reactive metabolites that interfere with cellular processes and cause DNA damage. In t...

Excretion of 2,3-dihydroxy-propionamide (OH-PA), the hydrolysis product of glycidamide, in human urine after single oral dose of deuterium-labeled acrylamide.

Arch. Toxicol. 85(6) , 601-6, (2011)

A dose of 0.99 mg d(3)-acrylamide (d(3)-AA) (13.2 μg/kg body weight) was ingested by a healthy male volunteer. Urine samples were collected over a period of 46 h after the intake and analyzed for the ...

Induction of sister chromatid exchange by acrylamide and glycidamide in human lymphocytes: role of polymorphisms in detoxification and DNA-repair genes in the genotoxicity of glycidamide.

Mutat. Res. 752(1-2) , 1-7, (2013)

Acrylamide (AA) is a probable human carcinogen generated in carbohydrate-rich foodstuffs upon heating. Glycidamide (GA), formed via epoxidation, presumably mediated by cytochrome P450 2E1, is consider...


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