Record Information |
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Version | 5.0 |
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Status | Detected but not Quantified |
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Creation Date | 2021-09-11 13:52:53 UTC |
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Update Date | 2022-11-23 22:29:16 UTC |
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HMDB ID | HMDB0254524 |
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Secondary Accession Numbers | None |
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Metabolite Identification |
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Common Name | Methapyrilene |
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Description | Methapyrilene, also known as lullamin or restryl, belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. Methapyrilene is a very strong basic compound (based on its pKa). In humans, methapyrilene is involved in methapyrilene h1-antihistamine action. It has relatively strong sedative effects, to the extent that its primary use was as a medication for insomnia rather than for its antihistamine action. All of these products were reformulated in the late 1970s when methapyrilene was demonstrated to cause liver cancer in rats when given chronically. Together with scopolamine, it was the main ingredient in Sominex, Nytol, and Sleep-Eze. It was sold under the trade names Co-Pyronil and Histadyl EC. Methapyrilene is an antihistamine and anticholinergic of the pyridine chemical class which was developed in the early 1950s. The thionyl halides should not be confused with "thionylan" and include thionyl fluoride, thionyl chloride, and thionyl bromide. "Thionylan" redirects here. It also provided the sedative component of Excedrin PM. This compound has been identified in human blood as reported by (PMID: 31557052 ). Methapyrilene is not a naturally occurring metabolite and is only found in those individuals exposed to this compound or its derivatives. Technically Methapyrilene is part of the human exposome. The exposome can be defined as the collection of all the exposures of an individual in a lifetime and how those exposures relate to health. An individual's exposure begins before birth and includes insults from environmental and occupational sources. |
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Structure | CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1 InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3 |
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Synonyms | Value | Source |
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2-[[2-(Dimethylamino)ethyl]-2-thenylamino]pyridine | ChEBI | Histadyl | ChEBI | Lullamin | ChEBI | Methypyrilene | ChEBI | N,N-Dimethyl-n'-pyrid-2-yl-n'-2-thenylethylenediamine | ChEBI | N,N-Dimethyl-n'-pyridin-2-yl-n'-(2-thienylmethyl)ethane-1,2-diamine | ChEBI | N-(alpha-Pyridyl)-N-(alpha-thenyl)-n',n'-dimethylethylenediamine | ChEBI | Paradormalene | ChEBI | Pyrathyn | ChEBI | Pyrinistab | ChEBI | Pyrinistol | ChEBI | Rest-ON | ChEBI | Restryl | ChEBI | Semikon | ChEBI | Sleepwell | ChEBI | Thenylene | ChEBI | Thenylpyramine | ChEBI | Thionylan | ChEBI | N-(a-Pyridyl)-N-(a-thenyl)-n',n'-dimethylethylenediamine | Generator | N-(Α-pyridyl)-N-(α-thenyl)-n',n'-dimethylethylenediamine | Generator | Tenalin | MeSH | N,N-Dimethyl-n'-2-pyridinyl-n'-(2-thienylmethyl)-1,2-ethanediamine | MeSH | Methapyrilene | MeSH |
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Chemical Formula | C14H19N3S |
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Average Molecular Weight | 261.39 |
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Monoisotopic Molecular Weight | 261.129968798 |
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IUPAC Name | N-[2-(dimethylamino)ethyl]-N-[(thiophen-2-yl)methyl]pyridin-2-amine |
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Traditional Name | rest-on |
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CAS Registry Number | Not Available |
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SMILES | CN(C)CCN(CC1=CC=CS1)C1=CC=CC=N1 |
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InChI Identifier | InChI=1S/C14H19N3S/c1-16(2)9-10-17(12-13-6-5-11-18-13)14-7-3-4-8-15-14/h3-8,11H,9-10,12H2,1-2H3 |
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InChI Key | HNJJXZKZRAWDPF-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as dialkylarylamines. These are aliphatic aromatic amines in which the amino group is linked to two aliphatic chains and one aromatic group. |
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Kingdom | Organic compounds |
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Super Class | Organic nitrogen compounds |
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Class | Organonitrogen compounds |
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Sub Class | Amines |
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Direct Parent | Dialkylarylamines |
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Alternative Parents | |
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Substituents | - Dialkylarylamine
- Aminopyridine
- Imidolactam
- Pyridine
- Heteroaromatic compound
- Thiophene
- Tertiary aliphatic amine
- Azacycle
- Organoheterocyclic compound
- Organopnictogen compound
- Hydrocarbon derivative
- Aromatic heteromonocyclic compound
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Molecular Framework | Aromatic heteromonocyclic compounds |
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External Descriptors | |
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Ontology |
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Physiological effect | Not Available |
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Disposition | |
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Process | Not Available |
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Role | Not Available |
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Physical Properties |
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State | Not Available |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | Not Available | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | Not Available | Not Available | LogP | Not Available | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | |
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatized |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted GC-MS | Predicted GC-MS Spectrum - Methapyrilene GC-MS (Non-derivatized) - 70eV, Positive | splash10-0a4j-9110000000-4181872f47d3a02dd809 | 2021-09-23 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Methapyrilene GC-MS (Non-derivatized) - 70eV, Positive | Not Available | 2021-10-12 | Wishart Lab | View Spectrum |
MS/MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Positive-QTOF | splash10-03di-2090000000-6a82f3fa59dfcb3d5cbb | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Positive-QTOF | splash10-00xr-9580000000-66df093facc7da7ba9a4 | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Positive-QTOF | splash10-05fr-7900000000-187b0a5cc21b2289ac2c | 2016-08-01 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Negative-QTOF | splash10-03di-1190000000-3839376e1dbdc67717b4 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Negative-QTOF | splash10-03dr-2790000000-8d6a8b1bba5b77d67199 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Negative-QTOF | splash10-0a4i-9300000000-8fb70107ed819654b063 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Positive-QTOF | splash10-03di-0090000000-459dc8d4959d8ddcb7af | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Positive-QTOF | splash10-03xs-4090000000-00c2ba1773b22af75a4f | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Positive-QTOF | splash10-0592-9400000000-3b73e8d3f5c2ab2ffa05 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 10V, Negative-QTOF | splash10-03di-0090000000-76de687c6f5596a5f70c | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 20V, Negative-QTOF | splash10-0bu9-5930000000-d00db17d32d33f7ae619 | 2021-10-12 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Methapyrilene 40V, Negative-QTOF | splash10-001i-8900000000-32c1bdff1e8fd5d287f1 | 2021-10-12 | Wishart Lab | View Spectrum |
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