N-Nitroso-N-methylaniline
(Synonyms: N-甲基-N-亚硝基苯胺) 目录号 : GC49859
An N-nitrosamine
Cas No.:614-00-6
Sample solution is provided at 25 µL, 10mM.
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Quality Control & SDS
- View current batch:
- Purity: >98.00%
- COA (Certificate Of Analysis)
- SDS (Safety Data Sheet)
- Datasheet
N-Nitroso-N-methylaniline is an N-nitrosamine.1 It induces the formation of esophageal, pharyngeal, and tongue tumors in rats when administered at a concentration of 200 mg/L in the drinking water or 15 mg/ml via oral gavage.2 N-Nitroso-N-methylaniline is toxic to rats with LD50 values of 336 and 225 mg/kg for male and female rats, respectively. It reduces survival of hamsters but only induces a low incidence of tumors in this species when administered at a dose of 5 mg/week for a total dose of 1.8 mmol.1
1.Lijinsky, W., and Kovatch, R.M.Comparative carcinogenesis by nitrosomethylalkylamines in Syrian hamstersCancer Res.48(23)6648-6652(1988) 2.Goodall, C.M., Lijinsky, W., Tomatis, L., et al.Toxicity and oncogenicity of nitrosomethylaniline and nitrosomethylcyclohexylamineToxicol. Appl. Pharmacol.17(2)426-432(1970)
| Cas No. | 614-00-6 | SDF | Download SDF |
| 别名 | N-甲基-N-亚硝基苯胺 | ||
| Canonical SMILES | O=NN(C)C1=CC=CC=C1 | ||
| 分子式 | C7H8N2O | 分子量 | 136.2 |
| 溶解度 | Chloroform: soluble,DMSO: soluble,Ethanol: soluble,Methanol: soluble | 储存条件 | -20°C |
| General tips | 请根据产品在不同溶剂中的溶解度选择合适的溶剂配制储备液；一旦配成溶液，请分装保存，避免反复冻融造成的产品失效。 储备液的保存方式和期限：-80°C 储存时，请在 6 个月内使用，-20°C 储存时，请在 1 个月内使用。 为了提高溶解度，请将管子加热至37℃，然后在超声波浴中震荡一段时间。 |
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| Shipping Condition | 评估样品解决方案：配备蓝冰进行发货。所有其他可用尺寸：配备RT，或根据请求配备蓝冰。 | ||
| 制备储备液 | |||
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1 mg | 5 mg | 10 mg |
| 1 mM | 7.3421 mL | 36.7107 mL | 73.4214 mL |
| 5 mM | 1.4684 mL | 7.3421 mL | 14.6843 mL |
| 10 mM | 0.7342 mL | 3.6711 mL | 7.3421 mL |
| 第一步：请输入基本实验信息（考虑到实验过程中的损耗，建议多配一只动物的药量） | ||||||||||
| 给药剂量 | mg/kg |  |
动物平均体重 | g | |
每只动物给药体积 | ul | |
动物数量 | 只 |
| 第二步：请输入动物体内配方组成（配方适用于不溶于水的药物；不同批次药物配方比例不同，请联系GLPBIO为您提供正确的澄清溶液配方） | ||||||||||
| % DMSO % % Tween 80 % saline | ||||||||||
| 计算重置 | ||||||||||
计算结果:
工作液浓度： mg/ml；
DMSO母液配制方法： mg 药物溶于 μL DMSO溶液（母液浓度 mg/mL，
体内配方配制方法：取 μL DMSO母液，加入 μL PEG300，混匀澄清后加入μL Tween 80，混匀澄清后加入 μL saline，混匀澄清。
1. 首先保证母液是澄清的；
2.
一定要按照顺序依次将溶剂加入，进行下一步操作之前必须保证上一步操作得到的是澄清的溶液，可采用涡旋、超声或水浴加热等物理方法助溶。
3. 以上所有助溶剂都可在 GlpBio 网站选购。
Metabolic denitrosation of N-Nitroso-N-methylaniline: detection of amine-metabolites
Chem Biol Interact 1991;77(1):81-96.PMID:1983965DOI:10.1016/0009-2797(91)90007-t.
The enzymatic denitrosation of N-Nitroso-N-methylaniline (NMA) was investigated by measuring the resulting amine metabolites when NMA was incubated with liver microsomes of PB-pretreated mice. Aniline was found to be the main amine metabolite. Small amounts of the secondary amine, N-methylaniline (MA) and its metabolite, p-methylaminophenol (p-MAP), could also be detected. Incubation of MA resulted in the formation of aniline and p-MAP. The velocity of the metabolism of MA was somewhat faster than that of NMA. On the basis of the measured Vmax values the formation of aniline from MA or from NMA proceeded at nearly identical rates. The dissociation constants as a measure of binding affinity to cytochrome (cyt.) P-450 were determined by measuring the binding spectra. NMA has one Ks of 3.1 mM, whereas MA shows two apparent Ks values, 650 microM and 25 mM, respectively. The results are discussed in relation to the enzymatic mechanism of denitrosation of NMA.
Metabolism of 15N-labelled N-nitrosodimethylamine and N-Nitroso-N-methylaniline by isolated rat hepatocytes
Biochem Pharmacol 1984 May 1;33(9):1509-13.PMID:6732867DOI:10.1016/0006-2952(84)90420-9.
The N-demethylation of 15N-labeled N-nitrosodimethylamine (DMN) and N-Nitroso-N-methylaniline (NMA) by isolated rat hepatic cells has been investigated. The values obtained in this system for molecular nitrogen formed during metabolism, compared with substrate consumed, were DMN 47%, NMA 23%, and N-nitroso-N-methylurea (NMU) 105%. The results for DMN are roughly halfway between those previously determined with rat liver S-9 fraction in vitro (33%) and in vivo (67%). For NMA, the hepatocyte data are closer to those obtained from S-9 in vitro (19%), rather than the in vivo (52%). No mixed nitrogen ( 15N14N ) or labeled nitrogen oxides were found.
Demonstration of in vivo formation of the nitrosamine N-Nitroso-N-methylaniline from amyl nitrite
Cancer Lett 1987 Aug;36(2):125-9.PMID:2887279DOI:10.1016/0304-3835(87)90083-8.
Kaposi's sarcoma is associated with Acquired Immune Deficiency Syndrome (AIDS) in U.S. homosexuals. A possible explanation is that butyl nitrite, inhaled as a drug of abuse, initiates the tumor via the in vivo formation of N-nitroso compounds. To demonstrate that such a process can occur, we injected mice i.p. with the amine N-methylaniline (250 mg/kg), gavaged them 30 min later with amyl nitrite (AmNO2, 40 mg/kg), killed the mice after another 30 or 60 min, and analyzed the carcasses for N-Nitroso-N-methylaniline (NMA). We obtained 480 +/- 130 (mean +/- S.E. for 6 mice killed after 30 min) and 380 +/- 40 (for 6 mice killed after 60 min) nmol NMA/mouse. Much lower yields were obtained when AmNO2 was injected i.p. and methylaniline was gavaged. Hence, relatively large amounts of at least one nitrosamine can be produced in vivo from simple nitrite esters.
Metabolism of carcinogenic N-Nitroso-N-methylaniline by purified cytochromes P450 2B1 and P450 2B2
Cancer Lett 1996 Dec 20;110(1-2):11-7.PMID:9018075DOI:10.1016/s0304-3835(97)89405-0.
N-Nitroso-N-methylaniline (NMA) is an esophageal carcinogen in the rat. The in vitro enzymatic metabolism of NMA was investigated using cytochromes P450 2B1 and P450 2B2, isolated from liver microsomes of rats pretreated with phenobarbital (PB), reconstituted with NADPH-cytochrome P450 reductase and dilauroylphosphatidylcholine. Formaldehyde is produced by both cytochromes P450 (P450). NMA is a better substrate for P450 2B1 than for P450 2B2. The maximal velocity (Vmax) values are 3.3 and 1.6 nmol HCHO/min per nmol P450 for P450 2B1 and P450 2B2, respectively. Beside formation of formaldehyde, aniline and p-aminophenol (p-AP) are found to be metabolites formed from NMA by both P450 isoenzymes. P450 2B1 also affords phenol, while none was found with the P450 2B2 isoenzyme. Phenol formation presumably arose from direct alpha-C-hydroxylation of NMA via a benzenediazonium ion (BDI) intermediate. The results suggest strongly that P450 2B1 catalyzes both alpha-C-hydroxylation and denitrosation of NMA while P450 2B2 catalyzes only denitrosation. Therefore, the P450 2B1 isoenzyme participates in the activation of NMA to the ultimate carcinogenic BDI.
alpha-Hydroxylation pathway in the in vitro metabolism of carcinogenic nitrosamines: N-nitrosodimethylamine and N-Nitroso-N-methylaniline
Proc Natl Acad Sci U S A 1981 Oct;78(10):6489-93.PMID:6947239DOI:10.1073/pnas.78.10.6489.
Evolution of 15N2-labeled molecular nitrogen was used to gauge the extent of alpha-hydroxylation during rat liver homogenate metabolism of doubly 15N-labeled N-nitrosodimethylamine (DMN) and N-nitrosomethylaniline (NMA). These measurements were correlated with the extent of total metabolism as measured by the disappearance of the nitrosamines and by the formation of formaldehyde. The results indicate that approximately 34% of DMN and 19% of NMA were metabolized by the alpha-hydroxylation pathway. Positive controls utilizing doubly 15N-labeled N-nitroso-N-methylurea yielded 96% of labeled nitrogen. These results are in variance with previously published data which claimed that either less than 5% or about 100% of DMN is metabolized by that route in vitro. Formaldehyde formation was shown to be a poor measure of the extent of metabolism. Semicarbazide gave rise to both formaldehyde and nitrogen, which makes it an undesirable component of the in vitro metabolism mixtures, particularly when those two substances are being measured.