N-Nitroso-N-methylaniline | CAS#614-00-6 | Tumor inducer

N-Nitroso-N-methylaniline
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 112025

CAS#: 614-00-6

Description: N-Nitroso-N-methylaniline is an N-nitrosamine. 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. 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.

Chemical Structure

N-Nitroso-N-methylaniline

CAS# 614-00-6

Instruction

Theoretical Analysis

MedKoo Cat#: 112025
Name: N-Nitroso-N-methylaniline
CAS#: 614-00-6
Chemical Formula: C7H8N2O
Exact Mass: 136.06
Molecular Weight: 136.150
Elemental Analysis: C, 61.75; H, 5.92; N, 20.58; O, 11.75

Price and Availability

Size	Price	Availability
25mg	USD 280	2 Weeks
50mg	USD 540	2 Weeks
100mg	USD 840	2 Weeks
250mg	USD 1340	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Synonym: N methyl N Nitrosoaniline; NMA; NSC 137; NSC-137; NSC137

IUPAC/Chemical Name: N-methyl-N-phenylnitrous amide

InChi Key: MAXCWSIJKVASQC-UHFFFAOYSA-N

InChi Code: InChI=1S/C7H8N2O/c1-9(8-10)7-5-3-2-4-6-7/h2-6H,1H3

SMILES Code: O=NN(C1=CC=CC=C1)C

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: To be determined

Shelf Life: >2 years if stored properly

Drug Formulation: To be determined

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 136.15 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Mirvish SS, Ramm MD. Demonstration of in vivo formation of the nitrosamine N-nitroso-N-methylaniline from amyl nitrite. Cancer Lett. 1987 Aug;36(2):125-9. doi: 10.1016/0304-3835(87)90083-8. PMID: 2887279.

2: Kroeger-Koepke MB, Koepke SR, McClusky GA, Magee PN, Michejda CJ. 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. doi: 10.1073/pnas.78.10.6489. PMID: 6947239; PMCID: PMC349065.

3: Koepke SR, Kroeger-Koepke MB, Michejda CJ. Evidence for an unstable DNA adduct from N-nitroso-N-methylaniline. Chem Res Toxicol. 1990 Jan- Feb;3(1):17-20. doi: 10.1021/tx00013a003. PMID: 2131819.

4: Stiborová M, Hansíková H, Frei E. 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. doi: 10.1016/s0304-3835(97)89405-0. PMID: 9018075.

5: Koepke SR, Tondeur Y, Farrelly JG, Stewart ML, Michejda CJ, Kroeger-Koepke MB. Metabolism of 15N-labelled N-nitrosodimethylamine and N-nitroso-N- methylaniline by isolated rat hepatocytes. Biochem Pharmacol. 1984 May 1;33(9):1509-13. doi: 10.1016/0006-2952(84)90420-9. PMID: 6732867.

6: Scheper T, Appel KE, Schunack W, Somogyi A, Hildebrandt AG. Metabolic denitrosation of N-nitroso-N-methylaniline: detection of amine-metabolites. Chem Biol Interact. 1991;77(1):81-96. doi: 10.1016/0009-2797(91)90007-t. PMID: 1983965.

7: Gold B, Farber J, Rogan E. An investigation of the metabolism of N-nitroso-N- methylaniline by phenobarbital- and pyrazole-induced Sprague-Dawley rat liver and esophagus derived S-9. Chem Biol Interact. 1987 Mar;61(3):215-28. doi: 10.1016/0009-2797(87)90002-0. PMID: 3568192.

8: Anderson D, Blowers SD, Craddock VM. The effects of S9 mix from rat oesophagus, salivary gland, and liver on the mutagenicity of the rat oesophageal carcinogen N-nitroso-N-methylaniline in the Salmonella typhimurium assay. Mutat Res. 1985 Jan-Feb;142(1-2):13-8. doi: 10.1016/s0165-7992(85)80005-1. PMID: 3883137.

9: Koepke SR, Kroeger-Koepke MB, Michejda CJ. N-nitroso-N-methylaniline: possible mode of DNA modification. IARC Sci Publ. 1987;(84):68-70. PMID: 3679445.

10: Aleksandrov VA. Vliianie N-nitrozo-N-metilanilina i N-nitrozo-N-étilanilina na émbriony krys [The effect of N-nitroso-N-methylaniline and N-nitroso-N- ethylaniline on the rat embryo]. Vopr Onkol. 1968;14(3):37-8. Russian. PMID: 5653598.

11: Quan Z, Khan S, O'Brien PJ. Role of cytochrome P-450IIE1 in N-nitroso-N- methylaniline induced hepatocyte cytotoxicity. Chem Biol Interact. 1992 Aug 28;83(3):221-33. doi: 10.1016/0009-2797(92)90099-7. PMID: 1516150.

12: Koepke SR, Kroeger-Koepke MB, Michejda CJ. Mechanism of DNA binding by the oesophageal carcinogen N-nitroso-N-methylaniline. IARC Sci Publ. 1991;(105):346-50. PMID: 1855878.

13: Pylypiw HM Jr, Harrington GW. Determination of N-nitroso-N-methylaniline in whole blood, serum, and urine. Anal Chem. 1981 Dec;53(14):2365-7. doi: 10.1021/ac00237a059. PMID: 7316215.

14: Stiborová M, Schmeiser HH, Wiessler M, Frei E. Direct evidence for the formation of deoxyribonucleotide adducts from carcinogenic N-nitroso-N- methylaniline revealed by the 32P-postlabeling technique. Cancer Lett. 1999 Apr 26;138(1-2):61-6. doi: 10.1016/s0304-3835(98)00369-3. PMID: 10378774.

15: Miura M, Inami K, Yoshida M, Yamaguchi K, Mashino T, Mochizuki M. Isolation and structural identification of a direct-acting mutagen derived from N-nitroso- N-methylpentylamine and Fenton's reagent with copper ion. Bioorg Med Chem. 2011 Sep 15;19(18):5693-7. doi: 10.1016/j.bmc.2011.07.012. Epub 2011 Jul 23. PMID: 21873073.

16: Deng S, Bai X, Li Y, Wang B, Kong B, Liu Q, Xia X. Changes in moisture, colour, residual nitrites and N-nitrosamine accumulation of bacon induced by nitrite levels and dry-frying temperatures. Meat Sci. 2021 Nov;181:108604. doi: 10.1016/j.meatsci.2021.108604. Epub 2021 Jun 12. PMID: 34144342.

17: Oliveira MS, Ghogare AA, Abramova I, Greer EM, Prado FM, Di Mascio P, Greer A. Mechanism of Photochemical O-Atom Exchange in Nitrosamines with Molecular Oxygen. J Org Chem. 2015 Jun 19;80(12):6119-27. doi: 10.1021/acs.joc.5b00633. Epub 2015 Jun 5. PMID: 26000876.

18: Loeppky RN, Elomari S. N-Alkyl-N-cyclopropylanilines as mechanistic probes in the nitrosation of N,N-dialkyl aromatic amines. J Org Chem. 2000 Jan 14;65(1):96-103. doi: 10.1021/jo991104z. PMID: 10813901.

19: Kroeger-Koepke MB, Reuber MD, Iype PT, Lijinsky W, Michejda CJ. The effect of substituents in the aromatic ring on carcinogenicity of N-nitrosomethylaniline in F344 rats. Carcinogenesis. 1983;4(2):157-60. doi: 10.1093/carcin/4.2.157. PMID: 6402317.

20: Lorr NA, Tu YY, Yang CS. The nature of nitrosamine denitrosation by rat liver microsomes. Carcinogenesis. 1982;3(9):1039-43. doi: 10.1093/carcin/3.9.1039. PMID: 7139859.

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