Azoxymethane

Modify Date: 2024-01-02 13:19:06

Azoxymethane Structure
Azoxymethane structure
Common Name Azoxymethane
CAS Number 25843-45-2 Molecular Weight 74.08180
Density 0.98g/cm3 Boiling Point 92ºC at 760mmHg
Molecular Formula C2H6N2O Melting Point N/A
MSDS Chinese USA Flash Point 9.4ºC
Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger

 Use of Azoxymethane


Azoxymethane is a colon carcinogen which leads to the formation of DNA adducts.

 Names

Name Azoxymethane
Synonym More Synonyms

 Azoxymethane Biological Activity

Description Azoxymethane is a colon carcinogen which leads to the formation of DNA adducts.
Related Catalog
In Vitro Azoxymethane is a colon carcinogen which leads to the formation of DNA adducts. On an equal protein basis, hepatic microsomes are much more active than SI and colon microsomes in NADPH-dependent Azoxymethane bioactivation and N7-mG adduct formation. Hepatic microsomes show the highest activity in the hydroxylation of Azoxymethane, followed by SI and colon microsomes[1].
In Vivo Regardless of the strain, the amounts of O6-mG and N7-mG produced by Azoxymethane are highest in the liver, followed by proximal and distal colons, which have similar levels, and then by duodenum, jejunum and ileum. Results indicate that the Azoxymethane-induced DNA adduct formation in the SI and colon does not depend on bioactivation by hepatic P450 enzymes. Irrespective of the mouse strain, no aberrant crypt foci (ACF) is detected in the colons of saline-treated mice; in contrast, colonic ACF is detected in all three strains of Azoxymethane-treated mice[1]. The Azoxymethane-treated athymic mice have approximately an 11-fold lower tumor incidence than similarly treated WT animals[2].
Kinase Assay The assay for Azoxymethane-induced in vitro DNA adduct formation is performed. Briefly, microsomes (0.5 to 2.0 mg/mL) are incubated with calf thymus DNA (1 mg/mL) and Azoxymethane (200 μM) in a total volume of 1.0 mL. The assay buffer consists of 0.1 M Tris-HCl (pH 7.4), 1 mM EDTA, 20 mM MgCl2, 0.3 M KCl, and 1.5 mM NADPH. Incubations are carried out at 37°C for 60 min in a shaking water bath. An additional 30 nM of NADPH is added after the first 30 min. The reaction is stopped by the addition of 0.5 mL of ice-cold 7.5 M ammonium acetate. DNA is then extracted for tissue homogenates. Control incubations are performed without NADPH[1].
Animal Admin Male, 8 to 10 week old, WT-A/J, IECN-A/J, and LCN-A/J mice (8 per group) are treated with either saline or Azoxymethane (7.5 mg/kg BW, s.c.), once weekly for 3 weeks. Mice are sacrificed 6 weeks post-treatment for aberrant crypt foci (ACF) detection. The entire colon is excised. A longitudinal incision is made along the entire length of the colon, which is further cut into two equal-length segments, representing proximal and distal portions of the colon. The segments are dipped in PBS to remove fecal pellets and then kept flat between filter papers in 10% buffered formalin for at least 24 h. Subsequently, the colons are immersed in freshly prepared 0.1% methylene blue for 10 min and rinsed briefly in deionized H2O to remove excess dye. The colon is mounted carefully on a microscope slide with the mucosal surface side up and viewed under a light microscope. The ACF in the entire mucosal surface of the colon are counted blindly and independently by two investigators and recorded[1].
References

[1]. Megaraj V, et al. Role of hepatic and intestinal p450 enzymes in the metabolic activation of the colon carcinogen azoxymethane in mice. Chem Res Toxicol. 2014 Apr 21;27(4):656-62.

[2]. Whetstone RD, et al. Colon carcinogenesis in wild type and immune compromised mice after treatment with azoxymethane, and azoxymethane with dextran sodium sulfate. Mol Carcinog. 2016 Jul;55(7):1187-95.

 Chemical & Physical Properties

Density 0.98g/cm3
Boiling Point 92ºC at 760mmHg
Molecular Formula C2H6N2O
Molecular Weight 74.08180
Flash Point 9.4ºC
Exact Mass 74.04800
PSA 41.11000
LogP 0.73170
Vapour Pressure 59.7mmHg at 25°C
Index of Refraction 1.427

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
PA2975000
CHEMICAL NAME :
Methane, azoxy-
CAS REGISTRY NUMBER :
25843-45-2
LAST UPDATED :
199503
DATA ITEMS CITED :
37
MOLECULAR FORMULA :
C2-H6-N2-O
MOLECULAR WEIGHT :
74.10
WISWESSER LINE NOTATION :
ON1&UN1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
27 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20 mg/kg/(22D
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Peripheral Nerve and Sensation - peripheral nerve tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - colon tumors Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
3200 ug/kg
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20 mg/kg female 22 day(s) after conception
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Kidney, Ureter, Bladder - Kidney tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intramuscular
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
22 mg/kg/11W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
200 mg/kg/20W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
96 mg/kg/13W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Rectal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
104 mg/kg/33W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - hamster
DOSE/DURATION :
60 mg/kg/20W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
312 mg/kg/39W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
80 mg/kg/10W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - colon tumors Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
20 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - colon tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
64 mg/kg/8W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
12 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - colon tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
45 mg/kg/3W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - colon tumors Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
208 mg/kg/26W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
192 mg/kg/24W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Lungs, Thorax, or Respiration - tumors Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
80 mg/kg/10W-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
37 mg/kg/10W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors Gastrointestinal - colon tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
DOSE :
30 mg/kg
SEX/DURATION :
female 14 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intravenous
DOSE :
30 mg/kg
SEX/DURATION :
female 15 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Embryo or Fetus - fetal death
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Sex chromosome loss and nondisjunction
TYPE OF TEST :
Morphological transformation
TYPE OF TEST :
DNA damage
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Unscheduled DNA synthesis

MUTATION DATA

TYPE OF TEST :
Host-mediated assay
TEST SYSTEM :
Rodent - mouse Bacteria - Salmonella typhimurium
DOSE/DURATION :
250 umol/kg
REFERENCE :
JJIND8 JNCI, Journal of the National Cancer Institute. (Washington, DC) V.61-79, 1978-87. For publisher information, see JNCIEQ. Volume(issue)/page/year: 63,977,1979

 Safety Information

Symbol GHS02 GHS06 GHS08
GHS02, GHS06, GHS08
Signal Word Danger
Hazard Statements H226-H300-H315-H319-H350
Precautionary Statements P201-P210-P280-P301 + P310 + P330-P308 + P313-P337 + P313
Hazard Codes T: Toxic;
Risk Phrases 45-46-10-25-34
Safety Phrases S26;S45;S53;S36/S37/S39
RIDADR UN 1992 3/PG 3
RTECS PA2975000
HS Code 2927000090

 Synthetic Route

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Azoxymethane Structure

Azoxymethane

CAS#:25843-45-2

Literature: Canadian Journal of Chemistry, , vol. 59, p. 264 - 268

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Azoxymethane Structure

Azoxymethane

CAS#:25843-45-2

Literature: Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, , vol. 23, # 8 p. 758

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Azoxymethane Structure

Azoxymethane

CAS#:25843-45-2

Literature: Indian Journal of Chemistry, Section B: Organic Chemistry Including Medicinal Chemistry, , vol. 23, # 8 p. 758

 Customs

HS Code 2927000090
Summary 2927000090 other diazo-, azo- or azoxy-compounds。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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 Synonyms

methyl-methylimino-oxidoazanium
MFCD00126912
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