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73785-40-7-Nitrosocimetidine Nitrosocimetidine

Nitrosocimetidine

For research use only. Not for therapeutic Use.

  • CAT Number: I033362
  • CAS Number: 73785-40-7
  • Molecular Formula: C10H15N7OS
  • Molecular Weight: 281.338
  • Purity: 98%
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Related Small Molecules: Eteplirsen     Sograzepide     Afloqualone    

Nitrosocimetidine is a possible metabolite of cimetidine, and a genotoxic agent.


Catalog Number I033362
CAS Number 73785-40-7
Synonyms

Nitrosocimetidine; CCRIS 1952; CCRIS-1952; CCRIS1952

Molecular Formula C10H15N7OS
Purity 98%
Solubility Soluble in DMSO
Appearance Solid powder
Storage Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
IUPAC Name Guanidine, 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)-1-nitroso-
InChI InChI=1S/C10H15N7OS/c1-8-9(15-7-14-8)5-19-4-3-12-10(13-6-11)17(2)16-18/h7H,3-5H2,1-2H3,(H,12,13)(H,14,15)
InChIKey LFTUYYPQNCJQGN-UHFFFAOYSA-N
SMILES O=NN(C)/C(NCCSCC1=C(C)NC=N1)=NC#N
Reference

1: Habs M, Eisenbrand G, Habs H, Schmähl D. No evidence of carcinogenicity of N-nitrosocimetidine in rats. Hepatogastroenterology. 1982 Dec;29(6):265-6. PMID: 7152460.
2: Ogiu T, Hard GC, Magee PN, Jensen DE. Comparison of the acute toxicity of N-nitrosocimetidine with three structurally related carcinogens in the rat. Toxicol Pathol. 1986;14(4):395-403. doi: 10.1177/019262338601400402. PMID: 3809892.
3: Anderson LM, Giner-Sorolla A, Haller IM, Budinger JM. Effects of cimetidine, nitrite, cimetidine plus nitrite, and nitrosocimetidine on tumors in mice following transplacental plus chronic lifetime exposure. Cancer Res. 1985 Aug;45(8):3561-6. PMID: 4016736.
4: Frank N, Tsuda M, Ohgaki H, Frei E, Kato T, Sato S. Detoxifying potential of thioproline against N-nitroso compounds, N-nitrosodimethylamine and N-nitrosocimetidine. Cancer Lett. 1990 Apr 30;50(3):167-72. doi: 10.1016/0304-3835(90)90260-5. PMID: 2322930.
5: Alldrick AJ, Rowland IR, Gangolli SD. Exposure of E. coli to nitrosocimetidine induces the adaptive response to alkylating agents. Mutat Res. 1984 Mar;139(3):111-4. doi: 10.1016/0165-7992(84)90003-4. PMID: 6366536.
6: Romert L, Swedmark S, Jenssen D. Thiol-enhanced decomposition of MNNG, ENNG, and nitrosocimetidine: relationship to mutagenicity in V79 Chinese hamster cells. Carcinogenesis. 1991 May;12(5):847-53. doi: 10.1093/carcin/12.5.847. PMID: 2029748.
7: Henderson EE, Basilio M, Davis RM. Cellular DNA damage by nitrosocimetidine: a comparison with N-methyl-N’-nitroso-nitrosoguanidine and x-irradiation. Chem Biol Interact. 1981 Dec;38(1):87-98. doi: 10.1016/0009-2797(81)90155-1. PMID: 7326809.
8: Inoue K, Shibata T, Kosaka H, Uozumi M, Tsuda S, Abe T. Induction of sister- chromatid exchanges by N-nitrosocimetidine in cultured human lymphocytes and its inhibition by chemical compounds. Mutat Res. 1985 Apr-May;156(1-2):117-21. doi: 10.1016/0165-1218(85)90014-x. PMID: 4000174.
9: Foster AB, Jarman M, Manson D, Schulten HR. Structure and reactivity of nitrosocimetidine. Cancer Lett. 1980 Mar;9(1):47-52. doi: 10.1016/0304-3835(80)90139-1. PMID: 7370975.
10: Frank N, Sato S, Tsuda M. pH-dependent degradation of nitrosocimetidine and its mechanisms. Jpn J Cancer Res. 1988 Oct;79(10):1083-8. doi: 10.1111/j.1349-7006.1988.tb01530.x. PMID: 3143696; PMCID: PMC5917633.

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