N,N'-Dinitrosopiperazine

Modify Date: 2024-01-02 11:59:25

N,N'-Dinitrosopiperazine Structure
N,N'-Dinitrosopiperazine structure
 Common Name N,N'-Dinitrosopiperazine
CAS Number 140-79-4 Molecular Weight 144.132
Density 1.5±0.1 g/cm3 Boiling Point 406.1±38.0 °C at 760 mmHg
Molecular Formula C4H8N4O2 Melting Point N/A
MSDS N/A Flash Point 199.4±26.8 °C

 Use of N,N'-Dinitrosopiperazine


N,N'-Dinitrosopiperazine (1,4-Dinitrosopiperazine; DNP) is a carcinogen with specificity for nasopharyngeal epithelium and facilitates NPC metastasis. N,N'-Dinitrosopiperazine regulates multiple signaling pathways through protein phosphorylation, including LYRIC at serine 568[1].

 Names

Name 1,4-Dinitrosopiperazine
Synonym More Synonyms

 N,N'-Dinitrosopiperazine Biological Activity

Description N,N'-Dinitrosopiperazine (1,4-Dinitrosopiperazine; DNP) is a carcinogen with specificity for nasopharyngeal epithelium and facilitates NPC metastasis. N,N'-Dinitrosopiperazine regulates multiple signaling pathways through protein phosphorylation, including LYRIC at serine 568[1].
Related Catalog
In Vitro N,N'-Dinitrosopiperazine (0.5-100 μM; 48 hours) has no inhibitory effects on the labeled 6-10B cells, and LDH activity is not significantly altered by DNP treatment in the 0.5-8 μM concentration range. However, it is cytotoxic from the concentration 10 μM[1]. N,N'-Dinitrosopiperazine (2-8 μM; 24 hours) induces 6-10B cell invasion and motility in a dose-dependent manner. At 6 μM, when compares to the control group, DNP increases cell invasion at 421.7% and cell motility is increased by 328.2%[1]. N,N'-Dinitrosopiperazine (6 μM; 24 hours) increases the expression of phospho-LYRIC s568 and LYRIC expression in CNE1 cells[1]. Cell Viability Assay[1] Cell Line: The labeled 6-10B cells Concentration: 0.5, 1, 2, 4, 6, 8, 10, 20, 40, 80, or 100 μM Incubation Time: 48 hours Result: Had no inhibitory effects at the concentration 0-8 μM. Western Blot Analysis[1] Cell Line: The NPC cell line CNE1 Concentration: 6 μM Incubation Time: 24 hours Result: Increased phospho-LYRIC s568 and LYRIC expression.
In Vivo N,N'-Dinitrosopiperazine (injected into the tail veins; 40 mg/kg; 30 days) inhibits cell motility and invasion, and facilitates NPC metastasis in vivo. From a IHC result, Phospho-LYRIC expression is higher in the metastatic tumors of DNP-treated mice than in those of the untreated control mice[1]. Animal Model: BABL/c nude mice injected with labeled 6-10B cell suspensions (1 × 104 cells) with or without DNP(40 mg/kg)[1] Dosage: 40 mg/kg Administration: Injected into the tail veins; 30 days Result: Induced LYRIC phosphorylation at serine 568 associated with NPC metastasis in vivo.
References

[1]. Damao Huang, et al. Identification of Novel Signaling Components in N,N'-dinitrosopiperazine-mediated Metastasis of Nasopharyngeal Carcinoma by Quantitative Phosphoproteomics. BMC Cancer. 2014 Apr 5;14:243.

 Chemical & Physical Properties

Density 1.5±0.1 g/cm3
Boiling Point 406.1±38.0 °C at 760 mmHg
Molecular Formula C4H8N4O2
Molecular Weight 144.132
Flash Point 199.4±26.8 °C
Exact Mass 144.064728
PSA 65.34000
LogP -0.88
Vapour Pressure 0.0±0.9 mmHg at 25°C
Index of Refraction 1.648

 Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
TL6300000
CHEMICAL NAME :
Piperazine, 1,4-dinitroso-
CAS REGISTRY NUMBER :
140-79-4
BEILSTEIN REFERENCE NO. :
0135106
LAST UPDATED :
199701
DATA ITEMS CITED :
38
MOLECULAR FORMULA :
C4-H8-N4-O2
MOLECULAR WEIGHT :
144.16
WISWESSER LINE NOTATION :
T6N DNTJ ANO DNO

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
160 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
100 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 :
1040 mg/kg/1Y-I
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Gastrointestinal - tumors Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1070 mg/kg/53W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors Liver - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
140 mg/kg female 15-21 day(s) after conception
TOXIC EFFECTS :
Tumorigenic - Carcinogenic by RTECS criteria Reproductive - Tumorigenic effects - transplacental tumorigenesis Blood - leukemia
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
1568 mg/kg/28W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
720 mg/kg/72W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1800 mg/kg/64W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1100 mg/kg/110W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
2250 mg/kg/50W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
7300 mg/kg/52W-C
TOXIC EFFECTS :
Tumorigenic - neoplastic by RTECS criteria Lungs, Thorax, or Respiration - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
560 mg/kg/10W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
300 mg/kg
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Skin and Appendages - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1086 mg/kg/69W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Brain and Coverings - tumors Gastrointestinal - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
5280 mg/kg/44W-I
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Lungs, Thorax, or Respiration - tumors Liver - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1120 mg/kg/20W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors
TYPE OF TEST :
TD - Toxic dose (other than lowest)
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
1680 mg/kg/30W-C
TOXIC EFFECTS :
Tumorigenic - equivocal tumorigenic agent by RTECS criteria Sense Organs and Special Senses (Olfaction) - tumors
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
140 mg/kg
SEX/DURATION :
female 15-21 day(s) after conception
TOXIC EFFECTS :
Reproductive - Effects on Newborn - live birth index (measured after birth)
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
DOSE :
400 mg/kg
SEX/DURATION :
lactating female 20 day(s) post-birth
TOXIC EFFECTS :
Reproductive - Effects on Newborn - weaning or lactation index (e.g., # alive at weaning per # alive at day 4)
TYPE OF TEST :
Specific locus test
TYPE OF TEST :
DNA damage
TYPE OF TEST :
Unscheduled DNA synthesis
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
DNA inhibition
TYPE OF TEST :
Cytogenetic analysis

MUTATION DATA

TYPE OF TEST :
Host-mediated assay
TEST SYSTEM :
Rodent - mouse Bacteria - Salmonella typhimurium
DOSE/DURATION :
10 mg/kg
REFERENCE :
CNREA8 Cancer Research. (Public Ledger Building, Suit 816, 6th & Chestnut Sts., Philadelphia, PA 19106) V.1- 1941- Volume(issue)/page/year: 37,4572,1977

 Safety Information

HS Code 2933599090

 Synthetic Route

 Customs

HS Code 2933599090
Summary 2933599090. other compounds containing a pyrimidine ring (whether or not hydrogenated) or piperazine ring in the structure. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:20.0%

 Synonyms

EINECS 205-434-6
NN'-Dinitrosopiperazine
Piperazine, 1,4-dinitroso-
1,4-Dinitrosopiperazine
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