Synonym
Nitrosocimetidine; CCRIS 1952; CCRIS-1952; CCRIS1952
IUPAC/Chemical Name
Guanidine, 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)-1-nitroso-
InChi Key
LFTUYYPQNCJQGN-UHFFFAOYSA-N
InChi Code
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)
SMILES Code
O=NN(C)/C(NCCSCC1=C(C)NC=N1)=N\C#N
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
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
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
Preparing Stock Solutions
The following data is based on the
product
molecular weight
281.34
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 |
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.
