864071-82-9 Usage
Description
N'-Nitrosonornicotine-N-b-D-glucuronide, with the chemical abstracts service number 864071-82-9, is a specialized compound that plays a significant role in the field of organic synthesis. This molecule is characterized by its unique structure, which incorporates a nitroso group attached to a nicotine derivative linked to a b-D-glucuronide moiety. The presence of these functional groups endows N'-Nitrosonornicotine-N-b-D-glucuronide with specific chemical properties that make it valuable for various applications in organic chemistry.
Uses
Used in Organic Synthesis:
N'-Nitrosonornicotine-N-b-D-glucuronide is utilized as a key intermediate in organic synthesis for the preparation of a variety of complex organic molecules. Its unique structure allows it to serve as a building block or a precursor in the synthesis of pharmaceuticals, agrochemicals, and other specialty chemicals. The nitroso and glucuronide functionalities within the molecule can be strategically manipulated to form a wide array of products, making it a versatile component in the synthesis of target compounds.
Used in Pharmaceutical Development:
In the pharmaceutical industry, N'-Nitrosonornicotine-N-b-D-glucuronide is employed as a starting material for the development of new drugs. Its structural features can be exploited to design and synthesize novel therapeutic agents with potential applications in treating various diseases and medical conditions. N'-Nitrosonornicotine-N-b-D-glucuronide's ability to be modified and functionalized makes it an attractive candidate for drug discovery and optimization processes.
Used in Research and Development:
N'-Nitrosonornicotine-N-b-D-glucuronide also finds use in academic and industrial research settings, where it can be employed to study the reactivity and properties of nitroso and glucuronide groups. Researchers can use this compound to investigate new reaction pathways, develop innovative synthetic methods, and explore the potential of this unique molecular framework in various chemical transformations.
Check Digit Verification of cas no
The CAS Registry Mumber 864071-82-9 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 8,6,4,0,7 and 1 respectively; the second part has 2 digits, 8 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 864071-82:
(8*8)+(7*6)+(6*4)+(5*0)+(4*7)+(3*1)+(2*8)+(1*2)=179
179 % 10 = 9
So 864071-82-9 is a valid CAS Registry Number.
864071-82-9Relevant articles and documents
Preparation of pyridine-N-glucuronides of tobacco-specific nitrosamines
Upadhyaya, Pramod,McIntee, Edward J.,Hecht, Stephen S.
, p. 555 - 561 (2001)
Nicotine and cotinine are metabolized to pyridine-N-glucuronides in humans. This suggests that the analogous metabolites of the carcinogenic nicotine-related nitrosamines N′-nitrosonornicotine (NNN), 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanone (NNK), and 4-(methylnitrosamino)-1-(3-pyridyl)-1-butanol (NNAL) should also be formed in people exposed to these compounds via tobacco products. We describe the synthesis of the appropriate pyridine-N-glucuronides: pyridyl-N-β-D-glucopyranuronosyl-N′-nitrosonornicotinium inner salt (NNN-N-Gluc, 8), 4-(methylnitrosamino)-1-(3-pyridyl-N-β-D-glucopyranuronosyl)-1 -butanonium inner salt (NNK-N-Gluc, 9), and 4-(methylnitrosamino)-1-(3-pyridyl-N-β-D-glucopyranuronosyl)-1 -butanolonium inner salt (NNAL-N-Gluc, 10). The starting material, methyl 2,3,4-tri-O-acetyl-1-bromo-1-deoxy-α-D-glucopyranuronate (1), is prepared in two steps from glucuronolactone. Reactions of 1 with racemic NNN (2), NNK (3), or racemic NNAL (4) are carried out with no solvent and the crude products are deprotected by treatment with base, giving the desired N-glucuronides 8-10 in 5-7% overall yield after HPLC purification. The N-glucuronides were characterized by 1H NMR, including COSY and NOESY spectra, and by MS and MS/MS. NNN-N-Gluc exists as a 52:48 ratio of (E)- and (Z)-rotamers, which were partially separated by HPLC. This ratio was surprisingly similar to the (E):(Z) ratio for NNN itself suggesting hydrogen bonding of the (Z)-nitroso oxygen atom to the 2″-hydroxyl group of the glucuronide moiety. Partial HPLC separations of the (E)- and (Z)-rotamers of NNK-N-Gluc and the (E)- and (Z)-rotamers as well as the (R)- and (S)-diastereomers of NNAL-N-Gluc were also achieved. The standards prepared in this study as well as the HPLC conditions developed for their separation will be important for analysis of these compounds in human urine.
