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 15:16:50 UTC |
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Update Date | 2023-02-21 17:18:20 UTC |
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HMDB ID | HMDB0014935 |
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Secondary Accession Numbers | |
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Metabolite Identification |
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Common Name | Tolazoline |
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Description | Tolazoline, also known as priscoline or divascol, belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. Tolazoline is a drug which is used for the treatment of pulmonary artery anomalies. Tolazoline is a very strong basic compound (based on its pKa). It is however most commonly used in veterinary medicine, to reverse xylazine-induced sedation. It is a vasodilator that is used to treat spasms of peripheral blood vessels (as in acrocyanosis). It has also been used (in conjunction with sodium nitroprusside) successfully as an antidote to reverse the severe peripheral vasoconstriction which can occur as a result of overdose with certain 5-HT2A agonist drugs such as 25I-NBOMe, DOB and Bromodragonfly (prolonged severe vasoconstriction can lead to gangrene if untreated). Tolazoline is a non-selective competitive α-adrenergic receptor antagonist. |
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Structure | InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12) |
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Synonyms | Value | Source |
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2-Benzyl-2-imidazoline | ChEBI | 2-Benzyl-4,5-imidazoline | ChEBI | 2-Benzylimidazoline | ChEBI | 4,5-Dihydro-2-(phenylmethyl)-1H-imidazole | ChEBI | Tolazine | Kegg | Divascol | HMDB | Tolazoline hydrochloride | HMDB | Pridazole | HMDB | Tolazoline monohydrochloride | HMDB | Benzalolin | HMDB | Novartis brand OF tolazoline hydrochloride | HMDB | Priscoline | HMDB | Ciba vision brand OF tolazoline hydrochloride | HMDB | Priscol | HMDB |
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Chemical Formula | C10H12N2 |
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Average Molecular Weight | 160.2157 |
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Monoisotopic Molecular Weight | 160.100048394 |
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IUPAC Name | 2-benzyl-4,5-dihydro-1H-imidazole |
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Traditional Name | tolazoline |
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CAS Registry Number | 59-98-3 |
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SMILES | C(C1=NCCN1)C1=CC=CC=C1 |
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InChI Identifier | InChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12) |
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InChI Key | JIVZKJJQOZQXQB-UHFFFAOYSA-N |
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Chemical Taxonomy |
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Description | Belongs to the class of organic compounds known as benzene and substituted derivatives. These are aromatic compounds containing one monocyclic ring system consisting of benzene. |
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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 | Not Available |
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Direct Parent | Benzene and substituted derivatives |
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Alternative Parents | |
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Substituents | - Imidolactam
- Monocyclic benzene moiety
- 2-imidazoline
- Azacycle
- Organoheterocyclic compound
- Organic 1,3-dipolar compound
- Propargyl-type 1,3-dipolar organic compound
- Carboximidamide
- Carboxylic acid amidine
- Amidine
- Organic nitrogen compound
- Organopnictogen compound
- Hydrocarbon derivative
- Organonitrogen compound
- 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 | Solid |
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Experimental Molecular Properties | Property | Value | Reference |
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Melting Point | 174 °C | Not Available | Boiling Point | Not Available | Not Available | Water Solubility | 1.36 g/L | Not Available | LogP | 1.5 | Not Available |
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Experimental Chromatographic Properties | Experimental Collision Cross Sections |
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Predicted Molecular Properties | |
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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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Tolazoline,1TMS,isomer #1 | C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 1731.1 | Semi standard non polar | 33892256 | Tolazoline,1TMS,isomer #1 | C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 1653.9 | Standard non polar | 33892256 | Tolazoline,1TMS,isomer #1 | C[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 2343.5 | Standard polar | 33892256 | Tolazoline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 1952.6 | Semi standard non polar | 33892256 | Tolazoline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 1901.7 | Standard non polar | 33892256 | Tolazoline,1TBDMS,isomer #1 | CC(C)(C)[Si](C)(C)N1CCN=C1CC1=CC=CC=C1 | 2492.4 | Standard polar | 33892256 |
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| GC-MS SpectraSpectrum Type | Description | Splash Key | Deposition Date | Source | View |
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Experimental GC-MS | GC-MS Spectrum - Tolazoline EI-B (Non-derivatized) | splash10-0006-9400000000-7b6f1c4b249d1fba8927 | 2017-09-12 | HMDB team, MONA, MassBank | View Spectrum | Experimental GC-MS | GC-MS Spectrum - Tolazoline EI-B (Non-derivatized) | splash10-0006-9400000000-7b6f1c4b249d1fba8927 | 2018-05-18 | HMDB team, MONA, MassBank | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tolazoline GC-MS (Non-derivatized) - 70eV, Positive | splash10-0006-9300000000-2b6650aa08c5113fe295 | 2017-09-01 | Wishart Lab | View Spectrum | Predicted GC-MS | Predicted GC-MS Spectrum - Tolazoline 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 - Tolazoline LC-ESI-QQ , positive-QTOF | splash10-03di-0900000000-692cb3b89bff443fa65f | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF | splash10-03di-0900000000-03a59847388e2e741709 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF | splash10-03di-4900000000-54d799a1c61663a2e513 | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF | splash10-0006-9100000000-c36b35a2866405756d0a | 2017-09-14 | HMDB team, MONA | View Spectrum | Experimental LC-MS/MS | LC-MS/MS Spectrum - Tolazoline LC-ESI-QQ , positive-QTOF | splash10-0006-9000000000-c543ee9f104cc9558d70 | 2017-09-14 | HMDB team, MONA | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 10V, Positive-QTOF | splash10-03di-0900000000-47a6c1a5a2d279ab4f92 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 20V, Positive-QTOF | splash10-03di-3900000000-aecd123663a1693e3524 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 40V, Positive-QTOF | splash10-0006-9300000000-ebfb2f09103e6beeeb32 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 10V, Negative-QTOF | splash10-0a4i-0900000000-6468e33c9df294b387c9 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 20V, Negative-QTOF | splash10-0a4i-2900000000-770e7f8c4b1e0ae79868 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 40V, Negative-QTOF | splash10-004l-9600000000-6bb3d6dbc9100efc4368 | 2016-08-03 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 10V, Positive-QTOF | splash10-03di-0900000000-ec9dd3a4861a20c6f98c | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 20V, Positive-QTOF | splash10-03xu-3900000000-01b9796933a01ad40ccf | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 40V, Positive-QTOF | splash10-00kf-9300000000-a6d07f8a048c587a6dd5 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 10V, Negative-QTOF | splash10-0a4i-1900000000-1590a4c64e5f2e58a0d3 | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 20V, Negative-QTOF | splash10-0a4i-4900000000-1f5ee5c9b4a25f0e1faa | 2021-10-11 | Wishart Lab | View Spectrum | Predicted LC-MS/MS | Predicted LC-MS/MS Spectrum - Tolazoline 40V, Negative-QTOF | splash10-00mo-9300000000-bbec6eccba8e917e3e29 | 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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