CAS 131119-04-5

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide

Description:

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide, with the CAS number 131119-04-5, is a chemical compound that is a metabolite of the tobacco-specific nitrosamine NNK (4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone). This compound is characterized by its complex structure, which includes a pyridine ring and a glucuronide moiety, indicating that it is a conjugate formed through the process of glucuronidation, a common phase II metabolic reaction that enhances the solubility of lipophilic substances for excretion. The presence of the nitrosamine group suggests potential biological activity, particularly in relation to carcinogenicity, as nitrosamines are known to be potent carcinogens. The glucuronide form typically indicates that the compound is more water-soluble, facilitating its elimination from the body. This compound is of interest in toxicology and cancer research, particularly in studies related to tobacco exposure and its associated health risks. Its analysis can provide insights into the metabolic pathways of tobacco carcinogens and their effects on human health.

Formula: C₁₆H₂₃N₃O₈

InChI: InChI=1/C16H23N3O8/c1-19(18-25)7-3-5-10(9-4-2-6-17-8-9)26-16-13(22)11(20)12(21)14(27-16)15(23)24/h2,4,6,8,10-14,16,20-22H,3,5,7H2,1H3,(H,23,24)/t10?,11-,12-,13+,14-,16+/m0/s1

InChI key: InChIKey=KNPUXTWHFSLCDT-BBYIEOQPSA-N

SMILES: O(C(CCCN(N=O)C)C=1C=CC=NC1)[C@@H]2O[C@H](C(O)=O)[C@@H](O)[C@H](O)[C@H]2O

Synonyms:

• 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol glucuronide
• 4-(Methylnitrosoamino)-1-(3-pyridinyl)butyl β-<span class="text-smallcaps">D</span>-glucopyranosiduronic acid
• 4-[methyl(nitroso)amino]-1-(pyridin-3-yl)butyl beta-D-glucopyranosiduronic acid
• NNAL-glucuronide
• [4-(Methylnitrosamino)-1-(3-pyridyl)but-1-yl] β-O-<span class="text-smallcaps">D</span>-glucosiduronic acid
• beta-D-Glucopyranosiduronic acid, 4-(methylnitrosoamino)-1-(3-pyridinyl)butyl
• β-<span class="text-smallcaps">D</span>-Glucopyranosiduronic acid, 4-(methylnitrosoamino)-1-(3-pyridinyl)butyl
• [4-(Methylnitrosamino)-1-(3-pyridyl)but-1-yl] β-O-D-glucosiduronic acid
• β-D-Glucopyranosiduronic acid, 4-(methylnitrosoamino)-1-(3-pyridinyl)butyl
• 4-(Methylnitrosoamino)-1-(3-pyridinyl)butyl β-D-glucopyranosiduronic acid
• NNAL-β-O-glucuronide
• 4-(MethylnitrosoaMino)-1-(3-pyridinyl)butyl
• 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol O-β-D-glucuronide (mixture of diastereoisomers)
• 4-(MethylnitrosaMino)-1-(3-pyridyl)-1-butanol O-β-D-Glucuronide SodiuM Salt
• 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol O-β-D-Glucuronide (Mixture of Diastereomers)
• 4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol O-β-D-Glucuronide
• 4-(METHYLNITROSAMINO)-1-(3-PYRIDYL)-1-BUTANYL ALPHA-D-GLUCURONIDE
• 4-(MethylnitrosaMino)-1-(3-pyridyl)-1-butanol O-β-D-Glucuronide SodiuM Salt (Mixture of DiastereoMers)
• 4-(MethylnitrosaMino)-1-(3-pyridyl)-1-butanol-d5 O-β-D-Glucuronide (Major)

β-D-Glucopyranosiduronic acid, 4-(methylnitrosoamino)-1-(3-pyridinyl)butyl

CAS: 131119-04-5

Formula: C₁₆H₂₃N₃O₈

Color and Shape: Solid

Molecular weight: 385.3691

Ref: IN-DA000VJ9

4-(Methyl-D3-nitrosamino)-1-(3-pyridyl)-1-butanol-N-b-D-glucuronide

CAS: 131119-04-5

Ref: 7W-GC9222

NNAL-β-O-glucuronide

CAS: 131119-04-5

Formula: C₁₆H₂₃N₃O₈

Molecular weight: 385.37

Ref: 4Z-N-102003

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol O-b-D-Glucuronide Sodium Salt(Mixture of Diastereomers) (>90%)

Controlled Product

CAS: 131119-04-5

Formula: C₁₆H₂₂N₃O₉·Na

Purity: >90%

Color and Shape: White To Dark Orange

Molecular weight: 423.35

Ref: TR-M325720

4-(Methyl-D3-nitrosamino)-1-(3-pyridyl)-1-butanol-N-b-D-glucuronide

CAS: 131119-04-5

4-(Methyl-D3-nitrosamino)-1-(3-pyridyl)-1-butanol-N-b-D-glucuronide is a metabolite of the antihypertensive drug methyldopa. It is excreted in urine and its concentration in urine has been found to be higher in women than in men. This difference has been attributed to an increased uptake by the kidneys, which may be due to sex hormones such as estrogen. Studies have shown that 4-(methyl-D3-nitrosamino)-1-(3pyridyl)-1-butanol-NbDglucuronide can be used as a predictive marker for urothelial carcinoma. The compound is also a metabolite of the plant extract nasturtium officinale, which has been found to have anticancer activity against human bladder cancer cells.

Formula: C₁₆H₂₁D₃N₃O₈

Purity: Min. 95%

Molecular weight: 389.39 g/mol

Ref: 3D-MM04552

4-(Methylnitrosamino)-1-(3-pyridyl)-1-butanol-d5 O-b-D-Glucuronide (Major)(Mixture of Diastereomers)

Controlled Product

CAS: 131119-04-5

Formula: C₁₆H₁₈D₅N₃O₈

Color and Shape: White Solid

Molecular weight: 390.4

Ref: TR-M325722