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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:50 UTC
Update Date2020-02-26 21:40:37 UTC
HMDB IDHMDB0014935
Secondary Accession Numbers
  • HMDB14935
Metabolite Identification
Common NameTolazoline
DescriptionTolazoline, 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 pulmonary vasodilator indicated used to decrease pulmonary vascular resistance (PVR) in persistent pulmonary hypertension of the newborn (PPHN). Tolazoline is a very strong basic compound (based on its pKa). It is used in treatment of persistent pulmonary hypertension of the newborn. Tolazoline usually reduces pulmonary arterial pressure and vascular resistance. Vasodilation by means of a direct effect on peripheral vascular smooth muscle and indirect effects produced, in part, by release of endogenous histamine; tolazoline has moderate alpha-adrenergic blocking activity and has histamine agonist activity.
Structure
Data?1582753237
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 Weight160.2157
Monoisotopic Molecular Weight160.100048394
IUPAC Name2-benzyl-4,5-dihydro-1H-imidazole
Traditional Nametolazoline
CAS Registry Number59-98-3
SMILES
C(C1=NCCN1)C1=CC=CC=C1
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)
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
Ontology
Disposition

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting Point174 °CNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.36 g/LNot Available
LogP1.5Not 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
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-7b6f1c4b249d1fba8927Spectrum
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0006-9400000000-7b6f1c4b249d1fba8927Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0006-9300000000-2b6650aa08c5113fe295Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-692cb3b89bff443fa65fSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-0900000000-03a59847388e2e741709Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-03di-4900000000-54d799a1c61663a2e513Spectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9100000000-c36b35a2866405756d0aSpectrum
LC-MS/MSLC-MS/MS Spectrum - LC-ESI-QQ , positivesplash10-0006-9000000000-c543ee9f104cc9558d70Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-03di-0900000000-47a6c1a5a2d279ab4f92Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-03di-3900000000-aecd123663a1693e3524Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0006-9300000000-ebfb2f09103e6beeeb32Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-0900000000-6468e33c9df294b387c9Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4i-2900000000-770e7f8c4b1e0ae79868Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-004l-9600000000-6bb3d6dbc9100efc4368Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00797 details
UrineExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00797 details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00797
Phenol Explorer Compound IDNot Available
FooDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID5303
KEGG Compound IDC07147
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkTolazoline
METLIN IDNot Available
PubChem Compound5504
PDB IDNot Available
ChEBI ID28502
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB ID
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General ReferencesNot Available

Enzymes

General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
Alpha-2 adrenergic receptors mediate the catecholamine- induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazoline > clonidine > epinephrine > norepinephrine > phenylephrine > dopamine > p-synephrine > p-tyramine > serotonin = p-octopamine. For antagonists, the rank order is yohimbine > phentolamine = mianserine > chlorpromazine = spiperone = prazosin > propanolol > alprenolol = pindolol
Gene Name:
ADRA2A
Uniprot ID:
P08913
Molecular weight:
48956.3
References
  1. Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
In peripheral tissues, the H1 subclass of histamine receptors mediates the contraction of smooth muscles, increase in capillary permeability due to contraction of terminal venules, and catecholamine release from adrenal medulla, as well as mediating neurotransmission in the central nervous system
Gene Name:
HRH1
Uniprot ID:
P35367
Molecular weight:
55783.6
References
  1. Roll C, Hanssler L: [Interaction of tolazoline and cimetidine in persistent fetal circulation of the newborn infant]. Monatsschr Kinderheilkd. 1993 Apr;141(4):297-9. [PubMed:8487790 ]
General function:
Involved in G-protein coupled receptor protein signaling pathway
Specific function:
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol- calcium second messenger system. Its effect is mediated by G(q) and G(11) proteins
Gene Name:
ADRA1A
Uniprot ID:
P35348
Molecular weight:
51486.0
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Teskin O, Uydes-Dogan BS, Enc Y, Alp FI, Kaleli D, Keser S, Iyigun T, Bilgen F, Dagsali S, Ozdemir O: Comparative effects of tolazoline and nitroprusside on human isolated radial artery. Ann Thorac Surg. 2006 Jan;81(1):125-31. [PubMed:16368348 ]
  4. Song W, Zhang Y, Xia L, Liu G: [Effects of some mexiletine derivatives on alpha 1-adrenoceptors]. Yao Xue Xue Bao. 1998;33(2):102-5. [PubMed:11938943 ]