Basic information
- CAS
59-98-3- Standard SMILES
c1ccc(CC2=NCCN2)cc1- InChIKey
JIVZKJJQOZQXQB-UHFFFAOYSA-N- Molecular formula
- C10H12N2
- Average molar mass
- 160.22 g/mol
- Monoisotopic mass
- 160.10004839
Overview
Tolazoline is a member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group. It has a role as a vasodilator agent, an antihypertensive agent and an alpha-adrenergic antagonist.
Names & identifiers
- Preferred name
- Tolazoline
- IUPAC
- 2-benzyl-4,5-dihydro-1H-imidazole
- English name
- Tolazoline
- Molecular formula
- C10H12N2
- Molecular weight
- 160.22
Names & synonyms
tolazoline59-98-32-Benzylimidazoline2-Benzyl-4,5-dihydro-1H-imidazoleBenzazoline2-Benzyl-2-imidazoline2-Benzyl-4,5-imidazolineTolazolinaTolazineTolazolinum4,5-Dihydro-2-(phenylmethyl)-1H-imidazole1H-Imidazole, 4,5-dihydro-2-(phenylmethyl)-
Show more names
PriscolineVasodilVasimidArtonilKasimidLambrilPriscolBenzolinciba3259
CHH9H12AQ3NSC-35110BenzalolinDTXSID3023683CHEBI:28502RefChem:56141DTXCID103683C04AB02
Database identifiers
- CAS
59-98-3- PubChem CID
- 5504
- DTXSID
DTXSID3023683- ChEMBL
CHEMBL770- ChEBI
CHEBI:28502- UNII
- CHH9H12AQ3
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 24.4 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 2
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 169
Experimental & physicochemical properties
DrugsPharmaceuticals -> Listed in ZINC15
LogP1.5
Solubility1.36e+00 g/L
Melting Point174 °C
Physical DescriptionSolid
Dissociation Constants10.3
Collision Cross Section133.41 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]
Physicochemical properties
- Melting point
- 66 · 66-69 °C(lit.)
- Boiling point
- 188 °C/20mmHg · 188°C/20mmHg(lit.)
- Density
- 1.0849 · 1.0849 (rough estimate)
- refractive index
- 1.6392 · 1.6392 (estimate)
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302+H312+H332 (44.1%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationTolazoline: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Other Safety InformationIMAP assessments - 1H-Imidazole, 4,5-dihydro-2-(phenylmethyl)-: Human health tier I assessment
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety data
- PPE
- dust mask type N95 (US), Eyeshields, Faceshields, Gloves
- wgk
- 3
- rtecs
- NJ1925000
- hs_code
- 2933299090
- Toxicity
- cyt-ham:lng 62,500 mg/L GMCRDC 27,95,81
- risk_code
- 20/21/22-36/37/38
- Signal word
- Warning
- Symbol(GHS)
- GHS07
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
M - Musculo-skeletal system
QC - Cardiovascular system
QV - Various
QM - Musculo-skeletal system
PharmacodynamicsTolazoline is a pulmonary vasodilator indicated used to decrease pulmonary vascular resistance (PVR) in persistent pulmonary hypertension of the newborn (PPHN).
Mechanism of Action
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. Tolazoline usually reduces pulmonary arterial pressure and vascular resistance.
MeSH Pharmacological Classification
Drugs that bind to but do not activate alpha-adrenergic receptors thereby blocking the actions of endogenous or exogenous adrenergic agonists. Adrenergic alpha-antagonists are used in the treatment of hypertension, vasospasm, peripheral vascular disease, shock, and pheochromocytoma.
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Drugs used to cause dilation of the blood vessels.
Cellular LocationsMembrane
Applications
UsesTolazoline is used for treating stable forms of pulmonary hypertension in newborns, and in cases where systemic arterial oxygenation cannot be achieved in the usual manner under careful observation of professionals.
UsesReactant for synthesis of imidazoline-containing drug
Related reactions
5 records
Compound notes
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