Definition
Alkaloid from various plant spp. incl. Mentha spp.. Also present in cocoa, black tea and scotch whiskey. Flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents.; Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name 'Assert'.
Description
Quinoline is found in alcoholic beverages. Quinoline is an alkaloid from various plant species including Mentha species. Also present in cocoa, black tea and scotch whiskey. Quinoline is a flavouring ingredient Quinoline is a heterocyclic aromatic organic compound. It has the formula C9H7N and is a colourless hygroscopic liquid with a strong odour. Aged samples, if exposed to light, become yellow and later brown. Quinoline is only slightly soluble in cold water but dissolves readily in hot water and most organic solvents. Quinoline is mainly used as a building block to other specialty chemicals. Approximately 4 tonnes are produced annually according to a report published in 2005.[citation needed] Its principal use is as a precursor to 8-hydroxyquinoline, which is a versatile chelating agent and precursor to pesticides. Its 2- and 4-methyl derivatives are precursors to cyanine dyes. Oxidation of quinoline affords quinolinic acid (pyridine-2,3-dicarboxylic acid), a precursor to the herbicide sold under the name Assert. Quinoline has been shown to exhibit catabolic, anti-microbial, anti-tumor, anti-fungal and anti-cancer functions (A7755, A7756, A7757, A7759, A7760).
Top Gene Interactions
Related Pathways
Quinoline Health Effects
General Information
- Metabolism: PAH metabolism occurs in all tissues, usually by cytochrome P-450 and its associated enzymes. PAHs are metabolized into reactive intermediates, which include epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations. The phenols, quinones, and dihydrodiols can all be conjugated to glucuronides and sulfate esters; the quinones also form glutathione conjugates. (L10)
- Uses/Sources: PAHs are released into the environment via the combustion of fossil fuels, coke oven emissions and vehicle exhausts, as well as naturally from forest fires and vocanic eruptions. PAHs from these sources may contaminate nearly water systems. They are also found in coal tar and charbroiled food. (L10)
- Health Effects: PAHs are carcinogens and have been associated with the increased risk of skin, respiratory tract, bladder, stomach, and kidney cancers. They may also cause reproductive effects and depress the immune system. (L10)
- Symptoms: Acute exposure to PAHs causes irritation and inflammation of the skin and lung tissue. (A10)
- Treatment: There is no know antidote for PAHs. Exposure is usually handled with symptomatic treatment. (L10)
- Route of Exposure: Oral (L10) ; inhalation (L10)
Toxicity
- Carcinogenicity: Not listed by IARC. IARC has evaluated related PAHs (L2154).
- Toxicity: LD50: 331 mg/kg (Oral, Rat) (T14) LD50: 540 mg/kg (Dermal, Rabbit) (T14)
Mechanism of Action
| Target Name | Mechanism of Action | References |
|---|---|---|
|
Cytochrome P450 2D6 Nuclear receptor ROR-beta Proteinase-activated receptor 1 |
8487254 23611293 16380251 |
|
| DNA | The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32) |
17997381 1995 11460716 |
|
Aryl hydrocarbon receptor Glycine N-methyltransferase |
Many PAH's induce the expression of cytochrome P450 enzymes, especially CYP1A1, CYP1A2, and CYP1B1, by binding to the aryl hydrocarbon receptor or glycine N-methyltransferase protein. These enzymes metabolize PAH's into their toxic intermediates. The reactive metabolites of PAHs (epoxide intermediates, dihydrodiols, phenols, quinones, and their various combinations) covalently bind to DNA and other cellular macromolecules, initiating mutagenesis and carcinogenesis. (L10, L23, A27, A32) |
17997381 1995 11460716 |
Quinoline Interacts with Diseases
| Disease | Inference Score | References/Inference Genes |
| Stomach Neoplasms | 44.21 |
|
| Lung Neoplasms | 28.15 |
|
| Prostatic Neoplasms | 23.72 |
|
| Adenocarcinoma | 23.4 |
|
| Liver Cirrhosis, Experimental | 23.34 |
|
| Neoplasm Invasiveness | 22.81 |
|
| Colorectal cancer | 22.47 |
|
| Neoplasm Metastasis | 21.42 |
|
| Breast carcinoma | 19.16 |
|
| Squamous cell carcinoma | 18.98 |
|
| Reperfusion Injury | 18.79 |
|
| Esophageal squamous cell carcinoma | 16.41 |
|
| Hepatocellular carcinoma | 16.4 |
|
| Colonic neoplasm | 16.24 |
|
| Melanoma | 15.65 |
|
| Mesothelioma, Malignant | 15.16 |
|
| Liver Neoplasms | 14.21 |
|
| Carcinoma | 13.72 |
|
| Crohn's disease | 13.71 |
|
| Carcinoma, Non-Small-Cell Lung | 12.93 |
|