Tolazoline (CED0008238)

Record Information
Version1.0
Creation Date2016-05-25 18:23:02 UTC
Update Date2026-08-17 23:28:47 UTC
Accession NumberCHEM022186
Identification
Common NameTolazoline
ClassSmall Molecule
Description
Tolazoline is an organic compound with the formula C10H12N2 and an average molecular weight of 160.22 g/mol. Tolazoline belongs to the benzene and substituted derivatives, a class of benzenoids within the organic compounds. The compound has been identified in 22 recorded sources. Within the category of healthcare, pharmaceuticals, and veterinary products, it is used in peripheral vasodilators and topical products for joint and muscular pain. It is also found in food, food processing, and cookware, specifically in food preservation and the preparation of malt and vinegar. In household cleaning and consumer products, it appears in soap detergents, perfumes within detergents and soaps, tobacco smoke filters, and non-electric simulated smoking devices. Additionally, it is released from electrical and electronic equipment, including amplifiers, antennas, electric switches, cores yokes or armatures, and conductors or conductive bodies characterised by the conductive materials. The recorded exposure route for tolazoline is intravenous. Regarding its biological activity, there are 7 recorded protein targets. It acts as an agonist, antagonist, or binder of the Alpha-1A adrenergic receptor (ADRA1A), the Alpha-2A adrenergic receptor (ADRA2A), the Histamine H1 receptor (HRH1), and the Histamine H2 receptor (HRH2), as well as 3 other proteins.
Contaminant TypeNot Available
Chemical Structure
Synonyms
ValueSource
2-Benzyl-2-imidazolineChEBI
2-Benzyl-4,5-imidazolineChEBI
2-BenzylimidazolineChEBI
4,5-Dihydro-2-(phenylmethyl)-1H-imidazoleChEBI
TolazineKegg
DivascolHMDB
Tolazoline hydrochlorideHMDB
PridazoleHMDB
Tolazoline monohydrochlorideHMDB
BenzalolinHMDB
Novartis brand OF tolazoline hydrochlorideHMDB
PriscolineHMDB
Ciba vision brand OF tolazoline hydrochlorideHMDB
PriscolHMDB
Chemical FormulaC10H12N2
Average Molecular Mass160.216 g/mol
Monoisotopic Mass160.100 g/mol
CAS Registry Number59-98-3
IUPAC Name2-benzyl-4,5-dihydro-1H-imidazole
Traditional Nametolazoline
SMILESC(C1=NCCN1)C1=CC=CC=C1
InChI IdentifierInChI=1S/C10H12N2/c1-2-4-9(5-3-1)8-10-11-6-7-12-10/h1-5H,6-8H2,(H,11,12)
InChI KeyJIVZKJJQOZQXQB-UHFFFAOYSA-N
Chemical Taxonomy
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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassNot Available
Direct ParentBenzene and substituted derivatives
Alternative Parents
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
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginNot Available
Cellular LocationsNot Available
Biofluid LocationsNot Available
Tissue LocationsNot Available
ApplicationsNot Available
Biological RolesNot Available
Chemical RolesNot Available
Organoleptic EffectsNot Available
Physical Properties
StateNot Available
AppearanceNot Available
Experimental Properties
PropertyValue
Melting PointNot Available
Boiling PointNot Available
SolubilityNot Available
Predicted Properties
PropertyValueSource
Water Solubility1.36 g/LALOGPS
logP2.05ALOGPS
logP1.2ChemAxon
logS-2.1ALOGPS
pKa (Strongest Basic)10.25ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area24.39 ŲChemAxon
Rotatable Bond Count2ChemAxon
Refractivity49.07 m³·mol⁻¹ChemAxon
Polarizability17.94 ųChemAxon
Number of Rings2ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyDeposition DateView
GC-MSGC-MS Spectrumsplash10-0006-9400000000-7b6f1c4b249d1fba8927Not AvailableView Spectrum
GC-MSGC-MS Spectrumsplash10-0006-9400000000-7b6f1c4b249d1fba8927Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS Spectrumsplash10-0006-9300000000-2b6650aa08c5113fe295Not AvailableView Spectrum
Predicted GC-MSPredicted GC-MS SpectrumNot AvailableNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-692cb3b89bff443fa65fNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-0900000000-03a59847388e2e741709Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-03di-4900000000-54d799a1c61663a2e513Not AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9100000000-c36b35a2866405756d0aNot AvailableView Spectrum
LC-MS/MSLC-MS/MS Spectrumsplash10-0006-9000000000-c543ee9f104cc9558d70Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-47a6c1a5a2d279ab4f92Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-3900000000-aecd123663a1693e3524Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0006-9300000000-ebfb2f09103e6beeeb32Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-0900000000-6468e33c9df294b387c9Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-2900000000-770e7f8c4b1e0ae79868Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-004l-9600000000-6bb3d6dbc9100efc4368Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03di-0900000000-ec9dd3a4861a20c6f98cNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-03xu-3900000000-01b9796933a01ad40ccfNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00kf-9300000000-a6d07f8a048c587a6dd5Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-1900000000-1590a4c64e5f2e58a0d3Not AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-0a4i-4900000000-1f5ee5c9b4a25f0e1faaNot AvailableView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrumsplash10-00mo-9300000000-bbec6eccba8e917e3e29Not AvailableView Spectrum
Toxicity Profile
Mechanism of ToxicityNot Available
Carcinogenicity (IARC Classification)Not Available
Minimum Risk LevelNot Available
SymptomsNot Available
TreatmentNot Available
Toxicity Values
Toxicity ValueUnitValue RangeOrganismDose DescriptorRoute of ExposurePredicted or ExperimentalReference
650.0Log mg/kg[370:1200]RatLD50oralpredictedNot Available
Health Effects
Health EffectRelationshipDirectionReference
Exposure Sources
Source IDSourceSectorReference
10InsecticidesAgriculture & land managementNot Available
291Peripheral vasodilatorsHealthcare, pharmaceuticals & veterinary productsNot Available
364Topical products for joint and muscular painHealthcare, pharmaceuticals & veterinary productsNot Available
505AmplifiersElectrical & Electronic EquipmentNot Available
506AntennasElectrical & Electronic EquipmentNot Available
511Conductors Or Conductive Bodies Characterised By The Conductive MaterialsElectrical & Electronic EquipmentNot Available
513Cores Yokes Or ArmaturesElectrical & Electronic EquipmentNot Available
517Electric SwitchesElectrical & Electronic EquipmentNot Available
518Electrically Stimulated Smoking DevicesElectrical & Electronic EquipmentNot Available
519ElectrodesElectrical & Electronic EquipmentNot Available
521Fixed Capacitors And Their ManufactureElectrical & Electronic EquipmentNot Available
524Hybrid CapacitorsElectrical & Electronic EquipmentNot Available
525Line Transmission SystemsElectrical & Electronic EquipmentNot Available
531RelaysElectrical & Electronic EquipmentNot Available
537Television SystemsElectrical & Electronic EquipmentNot Available
539Video GamesElectrical & Electronic EquipmentNot Available
545Food PreservationFood, food processing & cookwareNot Available
547Preparation Of MaltFood, food processing & cookwareNot Available
548Preparation Of VinegarFood, food processing & cookwareNot Available
559Non Electric Simulated Smoking DevicesHousehold cleaning & consumer productsNot Available
561Perfumes Within Detergents And SoapsHousehold cleaning & consumer productsNot Available
563Soap DetergentsHousehold cleaning & consumer productsNot Available
569Tobacco Smoke FiltersHousehold cleaning & consumer productsNot Available
578Making CigarsIndustrial manufacturing & chemical processingNot Available
579Manufacture Of Iron Or SteelIndustrial manufacturing & chemical processingNot Available
580Manufacture Preparation Of Tobacco ProductsIndustrial manufacturing & chemical processingNot Available
583Anchoring EquipmentMarine, shipping & aquacultureNot Available
596AcaricidesAgriculture & land managementNot Available
598Fertiliser DistributorsAgriculture & land managementNot Available
600Herbicides And AlgicidesAgriculture & land managementNot Available
601Lawn MowersAgriculture & land managementNot Available
602MolluscicidesAgriculture & land managementNot Available
603NematocidesAgriculture & land managementNot Available
605Pest RepellantsAgriculture & land managementNot Available
606Plant Growth RegulatorsAgriculture & land managementNot Available
609AftershavePersonal care & cosmeticsNot Available
610Aftersun ProductsPersonal care & cosmeticsNot Available
611Anti Perspirants Or Body DeoderantsPersonal care & cosmeticsNot Available
612Body Washing Or Cleaning ImplementsPersonal care & cosmeticsNot Available
613DepilatoriesPersonal care & cosmeticsNot Available
614Essential Oils Or PerfumesPersonal care & cosmeticsNot Available
615Eye Makeup ProductsPersonal care & cosmeticsNot Available
617Lip Care ProductsPersonal care & cosmeticsNot Available
618Lip Makeup ProductsPersonal care & cosmeticsNot Available
632ApparelTextiles, leather & furnishingsNot Available
642FootwearTextiles, leather & furnishingsNot Available
643HeadwearTextiles, leather & furnishingsNot Available
652RopesTextiles, leather & furnishingsNot Available
662Yarns Or ThreadsTextiles, leather & furnishingsNot Available
Pathways
2 pathways
Targets
StructureProteinUniProt IDOrganismRelationshipDetails
Click to view 3D structureNischarinQ4G017Rattus norvegicusPredicted (SEA)0.778492
Nischarin structureClick to view 3D structureNischarinQ9Y2I1HumansPredicted (SEA)0.622794
Alpha-1A adrenergic receptor structureClick to view 3D structureAlpha-1A adrenergic receptorP35348HumansPredicted (SEA)23.2769
Alpha-2C adrenergic receptor structureClick to view 3D structureAlpha-2C adrenergic receptorP18825HumansPredicted (SEA)12.6894
Click to view 3D structureAlpha-1D adrenergic receptorP25100HumansPredicted (SEA)14.0129
Alpha-2B adrenergic receptor structureClick to view 3D structureAlpha-2B adrenergic receptorP18089HumansPredicted (SEA)16.5819
Click to view 3D structureAlpha-1B adrenergic receptorP35368HumansPredicted (SEA)25.2231
Alpha-2A adrenergic receptor structureClick to view 3D structureAlpha-2A adrenergic receptorP08913HumansPredicted (SEA)37.5233
5-hydroxytryptamine receptor 1D structureClick to view 3D structure5-hydroxytryptamine receptor 1DP28221HumansPredicted (SEA)35.7328
Click to view 3D structureAlpha-2A adrenergic receptorQ28838Bos taurusPredicted (SEA)3.03612
5-hydroxytryptamine receptor 1A structureClick to view 3D structure5-hydroxytryptamine receptor 1AP08908HumansPredicted (SEA)198.749
5-hydroxytryptamine receptor 1B structureClick to view 3D structure5-hydroxytryptamine receptor 1BP28222HumansPredicted (SEA)65.4712
Trace amine-associated receptor 1 structureClick to view 3D structureTrace amine-associated receptor 1Q96RJ0HumansPredicted (SEA)9.809
5-hydroxytryptamine receptor 2C structureClick to view 3D structure5-hydroxytryptamine receptor 2CP28335HumansPredicted (SEA)223.972
5-hydroxytryptamine receptor 2A structureClick to view 3D structure5-hydroxytryptamine receptor 2AP28223HumansPredicted (SEA)304.079
Click to view 3D structureAlpha-1A adrenergic receptorP18130Bos taurusPredicted (SEA)33.1638
5-hydroxytryptamine receptor 2B structureClick to view 3D structure5-hydroxytryptamine receptor 2BP41595HumansPredicted (SEA)195.557
Cytochrome P450 2D6 structureClick to view 3D structureCytochrome P450 2D6P10635HumansPredicted (SEA)412.679
Click to view 3D structureAlpha-1A adrenergic receptorP43140Rattus norvegicusPredicted (SEA)112.181
5-hydroxytryptamine receptor 6 structureClick to view 3D structure5-hydroxytryptamine receptor 6P50406HumansPredicted (SEA)237.752
Click to view 3D structureAmine oxidase [flavin-containing] BP19643Rattus norvegicusPredicted (SEA)42.2721
Muscarinic acetylcholine receptor M4 structureClick to view 3D structureMuscarinic acetylcholine receptor M4P08173HumansPredicted (SEA)153.519
Click to view 3D structure5-hydroxytryptamine receptor 1AP19327Rattus norvegicusPredicted (SEA)393.061
Sigma non-opioid intracellular receptor 1 structureClick to view 3D structureSigma non-opioid intracellular receptor 1Q99720HumansPredicted (SEA)486.947
5-hydroxytryptamine receptor 7 structureClick to view 3D structure5-hydroxytryptamine receptor 7P34969HumansPredicted (SEA)385.899
Concentrations
Not Available
External Links
DrugBank IDDB00797
HMDB IDHMDB0014935
FooDB IDNot Available
Phenol Explorer IDNot Available
KNApSAcK IDNot Available
BiGG IDNot Available
BioCyc IDNot Available
METLIN IDNot Available
PDB IDNot Available
Wikipedia LinkTolazoline
Chemspider ID5303
ChEBI ID28502
PubChem Compound ID5504
Kegg Compound IDC07147
YMDB IDNot Available
ECMDB IDNot Available
References
Synthesis ReferenceNot Available
MSDSNot Available
General References
1. https://www.ncbi.nlm.nih.gov/pubmed/?term=14366198
2. https://www.ncbi.nlm.nih.gov/pubmed/?term=23321455
3. https://www.ncbi.nlm.nih.gov/pubmed/?term=23438114