Record Information |
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Version | 5.0 |
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Status | Expected but not Quantified |
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Creation Date | 2012-09-06 15:16:51 UTC |
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Update Date | 2023-02-21 17:18:26 UTC |
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HMDB ID | HMDB0015189 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tocainide |
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Description | Tocainide is only found in individuals that have used or taken this drug. It is an antiarrhythmic agent which exerts a potential- and frequency-dependent block of sodium channels. [PubChem]Tocainide acts on sodium channels on the neuronal cell membrane, limiting the spread of seizure activity and reducing seizure propagation. Tocainide binds preferentially to the inactive state of the sodium channels.The antiarrhythmic actions are mediated through effects on sodium channels in Purkinje fibers. |
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Structure | CC(N)C(=O)NC1=C(C)C=CC=C1C InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14) |
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Synonyms | Value | Source |
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2-Amino-2',6'-propionoxylidide | ChEBI | 2-Amino-N-(2,6-dimethylphenyl)propanamide | ChEBI | 2-Amino-N-(2,6-dimethylphenyl)propionamid | ChEBI | Alanyl-2,6-xylidide | ChEBI | Tocainida | ChEBI | Tocainidum | ChEBI | AstraZeneca brand OF tocainide hydrochloride | HMDB | Tocainide hydrochloride | HMDB | Tocainide monohdyrochloride, (R)-isomer | HMDB | Tocainide monohydrobromide, (R)-isomer | HMDB | Tocainide monohydrochloride | HMDB | Tocainide, (+-)-isomer | HMDB | Tocainide, (R)-isomer | HMDB | Tocainide, (S)-isomer | HMDB | Tonocard | HMDB | Tocainide monohydrochloride, (+-)-isomer | HMDB | Tocainide monohydrochloride, (S)-isomer | HMDB | Xylotocan | HMDB | Hydrochloride, tocainide | HMDB |
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Chemical Formula | C11H16N2O |
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Average Molecular Weight | 192.2575 |
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Monoisotopic Molecular Weight | 192.126263144 |
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IUPAC Name | 2-amino-N-(2,6-dimethylphenyl)propanamide |
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Traditional Name | tocainide |
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CAS Registry Number | 41708-72-9 |
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SMILES | CC(N)C(=O)NC1=C(C)C=CC=C1C |
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InChI Identifier | InChI=1S/C11H16N2O/c1-7-5-4-6-8(2)10(7)13-11(14)9(3)12/h4-6,9H,12H2,1-3H3,(H,13,14) |
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InChI Key | BUJAGSGYPOAWEI-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as m-xylenes. These are aromatic compounds that contain a m-xylene moiety, which is a monocyclic benzene carrying exactly two methyl groups at the 1- and 3-positions. |
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Kingdom | Organic compounds |
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Super Class | Benzenoids |
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Class | Benzene and substituted derivatives |
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Sub Class | Xylenes |
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Direct Parent | m-Xylenes |
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Alternative Parents | |
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Substituents | - M-xylene
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidic acid derivative
- Carboximidic acid
- Organic nitrogen compound
- Organic oxygen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Primary amine
- Organooxygen compound
- Organonitrogen compound
- Primary aliphatic amine
- Amine
- Aromatic homomonocyclic compound
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Molecular Framework | Aromatic homomonocyclic 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 | |
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Role | Not Available |
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Physical Properties |
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State | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 246 - 266 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1.6 g/L | Not Available | LogP | 1.1 | Not Available |
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Experimental Chromatographic Properties | Not Available |
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Predicted Molecular Properties | | Show more...
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Predicted Chromatographic Properties | Predicted Collision Cross SectionsPredicted Kovats Retention IndicesUnderivatizedDerivatizedDerivative Name / Structure | SMILES | Kovats RI Value | Column Type | Reference |
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Tocainide,1TMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C | 1787.5 | Semi standard non polar | 33892256 | Tocainide,1TMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C | 1763.5 | Standard non polar | 33892256 | Tocainide,1TMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C | 2366.1 | Standard polar | 33892256 | Tocainide,1TMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C | 1640.5 | Semi standard non polar | 33892256 | Tocainide,1TMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C | 1762.0 | Standard non polar | 33892256 | Tocainide,1TMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C | 2417.7 | Standard polar | 33892256 | Tocainide,2TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C | 1752.5 | Semi standard non polar | 33892256 | Tocainide,2TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C | 1810.5 | Standard non polar | 33892256 | Tocainide,2TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C)[Si](C)(C)C | 2054.9 | Standard polar | 33892256 | Tocainide,2TMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C | 1945.4 | Semi standard non polar | 33892256 | Tocainide,2TMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C | 1877.4 | Standard non polar | 33892256 | Tocainide,2TMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C | 2324.5 | Standard polar | 33892256 | Tocainide,3TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 1881.4 | Semi standard non polar | 33892256 | Tocainide,3TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 1943.9 | Standard non polar | 33892256 | Tocainide,3TMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C)[Si](C)(C)C)[Si](C)(C)C | 2055.4 | Standard polar | 33892256 | Tocainide,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C | 2044.9 | Semi standard non polar | 33892256 | Tocainide,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C | 1984.4 | Standard non polar | 33892256 | Tocainide,1TBDMS,isomer #1 | CC1=CC=CC(C)=C1NC(=O)C(C)N[Si](C)(C)C(C)(C)C | 2467.2 | Standard polar | 33892256 | Tocainide,1TBDMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C | 1874.4 | Semi standard non polar | 33892256 | Tocainide,1TBDMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C | 1955.5 | Standard non polar | 33892256 | Tocainide,1TBDMS,isomer #2 | CC1=CC=CC(C)=C1N(C(=O)C(C)N)[Si](C)(C)C(C)(C)C | 2503.6 | Standard polar | 33892256 | Tocainide,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2203.0 | Semi standard non polar | 33892256 | Tocainide,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2232.8 | Standard non polar | 33892256 | Tocainide,2TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2325.9 | Standard polar | 33892256 | Tocainide,2TBDMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2406.0 | Semi standard non polar | 33892256 | Tocainide,2TBDMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2277.6 | Standard non polar | 33892256 | Tocainide,2TBDMS,isomer #2 | CC1=CC=CC(C)=C1NC(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2487.9 | Standard polar | 33892256 | Tocainide,3TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2607.6 | Semi standard non polar | 33892256 | Tocainide,3TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2532.5 | Standard non polar | 33892256 | Tocainide,3TBDMS,isomer #1 | CC1=CC=CC(C)=C1N(C(=O)C(C)N([Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C)[Si](C)(C)C(C)(C)C | 2398.7 | Standard polar | 33892256 |
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Spectra |
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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 - Tocainide GC-MS (Non-derivatized) - 70eV, Positive | splash10-006x-9700000000-90d7f8cfadbf5c481615 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tocainide 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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Experimental LC-MS/MS | LC-MS/MS Spectrum - Tocainide LC-ESI-qTof , Positive-QTOF | splash10-004i-0510000090-3faef8c50f47e62f2ac1 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tocainide , positive-QTOF | splash10-00dl-0900000000-e3e09337d1b754b4c59c | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tocainide 35V, Positive-QTOF | splash10-0006-9400000000-578c55abffed08967f95 | 2021-09-20 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 10V, Positive-QTOF | splash10-006x-1900000000-c7d5dc77b594bd4bfb29 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 20V, Positive-QTOF | splash10-00dl-8900000000-54724c25ef578bc89366 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 40V, Positive-QTOF | splash10-006x-9500000000-794c0ef462fb9d8c4369 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 10V, Negative-QTOF | splash10-0006-0900000000-700b3726d7cb4618c003 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 20V, Negative-QTOF | splash10-00dl-2900000000-4e4c7ecdb9ff631f04ea | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 40V, Negative-QTOF | splash10-00xr-3900000000-01c23922110972f5982f | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 10V, Positive-QTOF | splash10-006x-0900000000-32ecf76928a4f2d8612f | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 20V, Positive-QTOF | splash10-0006-9800000000-6806af9483651aae91f1 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 40V, Positive-QTOF | splash10-0006-9100000000-39dc3374e1a4d42414ac | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 10V, Negative-QTOF | splash10-0006-0900000000-4dd4451b1f851e3d0321 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 20V, Negative-QTOF | splash10-0006-1900000000-6ddceb9e7f7ebd980bdd | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tocainide 40V, Negative-QTOF | splash10-014i-4900000000-2d6249a6af4ddf806fba | 2021-10-11 | Wishart Lab | View Spectrum |
IR SpectraSpectrum Type | Description | Deposition Date | Source | View |
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Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+) | 2023-02-03 | FELIX lab | View Spectrum | Predicted IR Spectrum | IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+) | 2023-02-03 | FELIX lab | View Spectrum |
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Biological Properties |
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Cellular Locations | |
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Biospecimen Locations | |
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Tissue Locations | Not Available |
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Pathways | |
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Normal Concentrations |
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Blood | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01056 | | details | Urine | Expected but not Quantified | Not Quantified | Not Available | Not Available | Taking drug identified by DrugBank entry DB01056 | | details |
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Abnormal Concentrations |
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| Not Available |
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Associated Disorders and Diseases |
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Disease References | None |
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Associated OMIM IDs | None |
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External Links |
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DrugBank ID | DB01056 |
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Phenol Explorer Compound ID | Not Available |
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FooDB ID | Not Available |
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KNApSAcK ID | Not Available |
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Chemspider ID | 35632 |
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KEGG Compound ID | C07142 |
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BioCyc ID | Not Available |
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BiGG ID | Not Available |
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Wikipedia Link | Tocainide |
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METLIN ID | Not Available |
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PubChem Compound | 38945 |
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PDB ID | Not Available |
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ChEBI ID | 9611 |
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Food Biomarker Ontology | Not Available |
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VMH ID | Not Available |
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MarkerDB ID | Not Available |
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Good Scents ID | Not Available |
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References |
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Synthesis Reference | Not Available |
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Material Safety Data Sheet (MSDS) | Not Available |
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General References | Not Available |
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