Record Information |
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Version | 2.0 |
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Creation Date | 2009-07-30 17:58:35 UTC |
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Update Date | 2014-12-24 20:26:06 UTC |
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Accession Number | T3D3474 |
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Identification |
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Common Name | 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine |
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Class | Small Molecule |
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Description | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxin that causes permanent symptoms of Parkinson's disease by killing certain neurons in the substantia nigra of the brain. While MPTP itself does not have opioid effects, it is related to MPPP, a synthetic opioid drug with effects similar to those of heroin and morphine. MPTP can be accidentally produced during the illicit manufacture of MPPP, and that is how its Parkinson-inducing effects were first discovered. MPTP is used to recreate and study the Parkinson's disease in experimental animal models. (2) |
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Compound Type | - Amine
- Industrial Precursor/Intermediate
- Industrial/Workplace Toxin
- Organic Compound
- Synthetic Compound
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Chemical Structure | |
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Synonyms | Synonym | 1,2,3,6-Tetrahydro-1-methyl-4-phenylpyridine | MPTP | N-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine |
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Chemical Formula | C12H15N |
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Average Molecular Mass | 173.254 g/mol |
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Monoisotopic Mass | 173.120 g/mol |
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CAS Registry Number | 28289-54-5 |
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IUPAC Name | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine |
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Traditional Name | MPTP |
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SMILES | CN1CCC(=CC1)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C12H15N/c1-13-9-7-12(8-10-13)11-5-3-2-4-6-11/h2-7H,8-10H2,1H3 |
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InChI Key | InChIKey=PLRACCBDVIHHLZ-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | belongs to the class of organic compounds known as hydropyridines. Hydropyridines are compounds containing a hydrogenated pyridine ring (i.e. containing less than the maximum number of double bonds.). |
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Kingdom | Organic compounds |
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Super Class | Organoheterocyclic compounds |
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Class | Pyridines and derivatives |
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Sub Class | Hydropyridines |
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Direct Parent | Hydropyridines |
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Alternative Parents | |
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Substituents | - Benzenoid
- Hydropyridine
- Monocyclic benzene moiety
- Tertiary aliphatic amine
- Tertiary amine
- Azacycle
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- Amine
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Biological Properties |
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Status | Detected and Not Quantified |
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Origin | Exogenous |
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Cellular Locations | |
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Biofluid Locations | Not Available |
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Tissue Locations | Not Available |
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Pathways | Not Available |
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Applications | Not Available |
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Biological Roles | |
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Chemical Roles | Not Available |
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Physical Properties |
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State | Solid |
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Appearance | White powder. |
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Experimental Properties | Property | Value |
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Melting Point | 40-42°C | Boiling Point | 85-90 °C (at 0.8 mm Hg) | Solubility | Not Available | LogP | Not Available |
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Predicted Properties | |
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Spectra |
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Spectra | Spectrum Type | Description | Splash Key | Deposition Date | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | splash10-0lk9-1900000000-36d037be627c16feb3bd | 2021-09-23 | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-e201fc2a2d42013379aa | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-2900000000-99d91f9b67fcd6f34a76 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-0gb9-8900000000-099735f9e4fb38becc8f | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-d4230bc243608beca34f | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-f32b038842a79e5b2695 | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-05dl-5900000000-3b4830d260c28b17374c | 2016-08-03 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Positive | splash10-00di-0900000000-56283bf2270bbd4df094 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Positive | splash10-00di-0900000000-cbb4be820600db09287e | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Positive | splash10-014i-2900000000-a1f874d4dde6dfbe3b2c | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 10V, Negative | splash10-00di-0900000000-7883e6701106e8531b78 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 20V, Negative | splash10-00di-0900000000-7ffdbc080be1d9a7b5b6 | 2021-10-12 | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - 40V, Negative | splash10-00di-0900000000-396c4310a7b5ec601e1a | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 100 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 1000 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 200 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 300 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 400 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 500 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 600 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 700 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 800 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 13C NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum | 1D NMR | 1H NMR Spectrum (1D, 900 MHz, D2O, predicted) | Not Available | 2021-10-12 | View Spectrum |
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Toxicity Profile |
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Route of Exposure | Not Available |
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Mechanism of Toxicity | MPTP itself is not toxic, and as a lipophilic compound can cross the blood-brain barrier. Once inside the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. MPP+ primarily kills dopamine-producing neurons in a part of the brain called the pars compacta of the substantia nigra. MPP+ interferes with complex I of the electron transport chain, a component of mitochondrial metabolism, which leads to cell death and causes the buildup of free radicals, toxic molecules that contribute further to cell destruction. (2) |
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Metabolism | In the brain, MPTP is metabolized into the toxic cation 1-methyl-4-phenylpyridinium (MPP+) by the enzyme MAO-B of glial cells. (2) |
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Toxicity Values | LD50: 54 mg/kg (Subcutaneous, Mouse) (1) |
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Lethal Dose | Not Available |
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Carcinogenicity (IARC Classification) | No indication of carcinogenicity to humans (not listed by IARC). |
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Uses/Sources | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) is a neurotoxin that causes permanent symptoms of Parkinson's disease by killing certain neurons in the substantia nigra of the brain. MPTP can be accidentally produced during the illicit manufacture of MPPP, and that is how its Parkinson-inducing effects were first discovered. MPTP is used to recreate and study the Parkinson's disease in experimental animal models. |
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Minimum Risk Level | Not Available |
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Health Effects | Not Available |
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Symptoms | Not Available |
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Treatment | Because MPTP itself is not directly harmful, toxic effects of acute MPTP poisoning can be mitigated by the administration of monoamine oxidase inhibitors (MAOIs) such as selegiline. MAOIs prevent the metabolism of MPTP to MPP+ by inhibiting the action of MAO-B, minimizing toxicity and preventing neural death. (2) |
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Normal Concentrations |
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Abnormal Concentrations |
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External Links |
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DrugBank ID | Not Available |
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HMDB ID | Not Available |
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PubChem Compound ID | 1388 |
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ChEMBL ID | CHEMBL24172 |
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ChemSpider ID | 1346 |
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KEGG ID | C04599 |
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UniProt ID | Not Available |
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OMIM ID | |
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ChEBI ID | 17963 |
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BioCyc ID | Not Available |
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CTD ID | Not Available |
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Stitch ID | 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine |
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PDB ID | Not Available |
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ACToR ID | Not Available |
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Wikipedia Link | 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine |
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References |
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Synthesis Reference | Not Available |
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MSDS | T3D3474.pdf |
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General References | - Fuller RW, Hemrick-Luecke SK: Tissue concentrations of MPTP and MPP+ after administration of lethal and sublethal doses of MPTP to mice. Toxicol Lett. 1990 Dec;54(2-3):253-62. [2124381 ]
- Wikipedia. 1-Methyl-4-phenyl-1,2,3,6-tetrahydropyridine. Last Updated 18 July 2009. [Link]
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Gene Regulation |
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Up-Regulated Genes | Gene | Gene Symbol | Gene ID | Interaction | Chromosome | Details |
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Down-Regulated Genes | Not Available |
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