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Nornicotine

$144

  • Brand : BIOFRON

  • Catalogue Number : BN-O1353

  • Specification : 98%(HPLC)

  • CAS number : 494-97-3

  • Formula : C9H12N2

  • Molecular Weight : 148.2

  • PUBCHEM ID : 91462

  • Volume : 5mg

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Catalogue Number

BN-O1353

Analysis Method

Specification

98%(HPLC)

Storage

2-8°C

Molecular Weight

148.2

Appearance

Botanical Source

Structure Type

Category

SMILES

C1CC(NC1)C2=CN=CC=C2

Synonyms

(S)-3-(Pyrrolidin-2-yl)pyridine/3-(2-Pyrrolidinyl)pyridine/3-(2S)-2-pyrrolidinylpyridine/(S)-Nornicotine/3-[(2S)-pyrrolidin-2-yl]pyridine

IUPAC Name

3-[(2S)-pyrrolidin-2-yl]pyridine

Density

1.043g/cm3

Solubility

Soluble in Chloroform,Dichloromethane,Ethyl Acetate,DMSO,Acetone,etc.

Flash Point

111.291ºC

Boiling Point

269.999ºC at 760 mmHg

Melting Point

InChl

InChl Key

MYKUKUCHPMASKF-VIFPVBQESA-N

WGK Germany

RID/ADR

HS Code Reference

Personal Projective Equipment

Correct Usage

For Reference Standard and R&D, Not for Human Use Directly.

Meta Tag

provides coniferyl ferulate(CAS#:494-97-3) MSDS, density, melting point, boiling point, structure, formula, molecular weight etc. Articles of coniferyl ferulate are included as well.>> amp version: coniferyl ferulate

No Technical Documents Available For This Product.

PMID

27568381

Abstract

Nornicotine is a natural alkaloid produced by plants in the genus Nicotiana and is structurally related to nicotine. Importantly, nornicotine is the direct precursor of tobacco-specific nitrosamine N’-nitrosonornicotine, which is a highly potent human carcinogen. Microbial detoxification and degradation of nicotine have been well characterized; however, until now, there has been no information on the molecular mechanism of nornicotine degradation. In this study, we demonstrate the transformation of nornicotine by the nicotine-degrading strain Shinella sp. HZN7. Three transformation products were identified as 6-hydroxy-nornicotine, 6-hydroxy-myosmine, and 6-hydroxy-pseudooxy-nornicotine by UV spectroscopy, high-resolution mass spectrometry, nuclear magnetic resonance, and Fourier transform-infrared spectroscopy analyses. The two-component nicotine dehydrogenase genes nctA1 and nctA2 were cloned, and their product, NctA, was confirmed to be responsible for the conversion of nornicotine into 6-hydroxy-nornicotine as well as nicotine into 6-hydroxy-nicotine. The 6-hydroxy-nicotine oxidase, NctB, catalyzed the oxidation of 6-hydroxy-nornicotine to 6-hydroxy-myosmine, and it spontaneously hydrolyzed into 6-hydroxy-pseudooxy-nornicotine. However, 6-hydroxy-pseudooxy-nornicotine could not be further degraded by strain HZN7. This study demonstrated that nornicotine is partially transformed by strain HZN7 via nicotine degradation pathway.

KEYWORDS

6-Hydroxy-myosmine; 6-Hydroxy-nicotine oxidase; 6-Hydroxy-nornicotine; 6-Hydroxy-pseudooxy-nornicotine; Nicotine dehydrogenase; Nornicotine; Shinella sp. HZN7

Title

Conversion of nornicotine to 6-hydroxy-nornicotine and 6-hydroxy-myosmine by Shinella sp. strain HZN7.

Author

Qiu J1, Li N1, Lu Z2, Yang Y1, Ma Y3, Niu L4, He J5, Liu W4.

Publish date

2016 Dec

PMID

28960905

Abstract

Nornicotine, an alkaloid constituent of tobacco, is a precursor to the carcinogen N-nitrosonornicotine that is produced during the curing and processing of tobacco. Accumulating evidence reveals that nornicotine enantiomers have different neurochemical and behavioral effects. In the present study, an accurate and rapid method was developed for the enantioseparation of (R)-(+)-nornicotine and (S)-(-)-nornicotine enantiomers in tobacco by ultra-performance convergence chromatography with tandem mass spectrometry. Chromatographic conditions were investigated to achieve the optimal resolution of two enantiomers. Results indicated that (R)-(+)-nornicotine and (S)-(-)-nornicotine could be separated within 5 min when ammonium hydroxide was added into the cosolvent, and the best resolution (Rs = 4.76) was achieved on a immobilized cellulose tris-(3,5-dichlorophenylcarbamate) chiral stationary phase. The proposed method was validated and was finally applied to analyze the compositions of (R)-(+)-nornicotine and (S)-(-)-nornicotine in three typical types of tobaccos (flue-cured, burley, and oriental). It was found that, enantiomer fraction of nornicotine (the proportion of (S)-(-)-nornicotine in the nornicotine pool) in burley tobacco samples was relatively high and constant compared with flue-cured and oriental tobaccos. The effective and rapid enantioseparation of nornicotine may help the understanding of alkaloid metabolites in different tobacco varieties and may also benefit pharmacological studies of alkaloid enantiomers.

© 2017 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.

KEYWORDS

enantioseparation; nornicotine; tandem mass spectrometry; tobacco; ultraperformance convergence chromatography

Title

Enantioseparation of nornicotine in tobacco by ultraperformance convergence chromatography with tandem mass spectrometry.

Author

Deng H1, Wang Y1, Bian Z1, Liu S1, Fan Z1, Li Z1, Yang F1, Tang G1.

Publish date

2017 Dec

PMID

26536586

Abstract

PURPOSE:
The purpose of the current study was to evaluate the influences of nornicotine and nicotine (NT) in cigarette smoke on the expression of vascular endothelial growth factor (VEGF) and pigment epithelium-derived factor (PEDF) in retinal pigment epithelium cells and human umbilical vein endothelial cells (HUVECs). Furthermore, the angiogenic behaviors of endothelial cells under nornicotine and NT treatment were assessed by using in vitro methods.

METHODS:
ARPE-19 cells and HUVECs were treated with different concentrations of either nornicotine or NT for different periods of time. The cell proliferative effect was investigated by using the method of MTT analysis. HUVEC migration and tube formation were assessed by using the scratch assay and Matrigel models. The expressions of VEGF and PEDF gene and protein in both types of cells were examined by real-time RT-PCR and Western blot.

RESULTS:
There was no proliferation of ARPE-19 cells following treatment with various concentrations of nornicotine or NT. In contrast, nornicotine or NT significantly stimulated HUVEC proliferation, migration and tube formation. Nornicotine and NT upregulated the expression of VEGF but suppressed the expression of PEDF at both mRNA and protein levels in a dose- and time-dependent manner in ARPE-19 cells and HUVECs.

CONCLUSIONS:
Our results demonstrate that nornicotine and NT promoted endothelial cellular proliferation, migration and tube formation of HUVECs in vitro. These effects might be partly due to simultaneous modulation of VEGF/PEDF signaling in ARPE-19 cells and HUVECs.

© 2015 S. Karger AG, Basel.

Title

Nornicotine and Nicotine Induced Neovascularization via Increased VEGF/PEDF Ratio.

Author

Zhang Y1, Ma A, Wang L, Zhao B.

Publish date

2015


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