Tolazoline
Synonym(s):2-Benzyl-2-imidazoline;2-Benzyl-4,5-dihydro-1H-imidazole;Benzidazol;Phenylmethylimidazoline;Tolazoline
- CAS NO.:59-98-3
- Empirical Formula: C10H12N2
- Molecular Weight: 160.22
- MDL number: MFCD00005182
- EINECS: 200-448-9
- SAFETY DATA SHEET (SDS)
- Update Date: 2024-11-19 20:33:22
What is Tolazoline?
Originator
Priscoline,Ciba,US,1948
The Uses of Tolazoline
Tolazoline 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.
The Uses of Tolazoline
Reactant for synthesis of imidazoline-containing drug
Background
A vasodilator that apparently has direct actions on blood vessels and also increases cardiac output. Tolazoline can interact to some degree with histamine, adrenergic, and cholinergic receptors, but the mechanisms of its therapeutic effects are not clear. It is used in treatment of persistent pulmonary hypertension of the newborn.
Indications
For the treatment of pulmonary artery anomalies
Definition
ChEBI: A member of the class of imidazoles that is 4,5-dihydro-1H-imidazole substituted by a benzyl group.
Manufacturing Process
The phenyl-acetiminoether hydrochloride of the formula from 12 parts of benzylcyanide and ethanol and HCl is mixed with 8 parts of ethylenediamine hydrate which has been diluted with little alcohol, whereby the crystals go into solution. The whole is then heated on the water-bath until the ammonia odor has disappeared, cooled, concentrated caustic potash solution added, and the separated oil extracted with ether. The solution is dried with potassium carbonate and potassium hydroxide. After evaporation a pale oil is left which distills at 147°C under a pressure of 9 mm and which solidifies in the condenser to a white crystalline mass. The yield amounts to 90% of the theory. The hydrochloride melts at 168° to 170°C.
Therapeutic Function
Vasodilator
General Description
2-Benzylimidazoline is an active vasodilator.
Pharmacokinetics
Tolazoline is a pulmonary vasodilator indicated used to decrease pulmonary vascular resistance (PVR) in persistent pulmonary hypertension of the newborn (PPHN).
Pharmacology
Tolazoline is a weak, reversible α-adrenoblocker that lowers resistance of peripheral blood vessels and elevates venous capacity. However, it also exhibits β-adrenomimetic activity, which consists of the stimulation of cardiac work and is manifest as tachycardia, cholinergic activity, which consists of stimulation of the gastrointestinal tract, and histamine-like activity, which consists of stimulation of gastric secretion.
Safety Profile
Poison by ingestion,intraperitoneal, and intravenous routes. Mutation data reported. When heated to decomposition it emits toxicfumes of NOx.
Synthesis
Tolazoline, 2-benzyl-2-imidazoline (12.2.7), is synthesized by the heterocyclation of the ethyl ester of iminophenzylacetic acid with ethylendiamine (12.2.6), which forms the desired product (12.2.7) [32¨C35]. The structure of tolazoline is strikingly similar to |á-adrenergic agonists, which are antiedema sympathomimetics.
Metabolism
Not Available
Properties of Tolazoline
Melting point: | 66-69 °C(lit.) |
Boiling point: | 188°C/20mmHg(lit.) |
Density | 1.0849 (rough estimate) |
refractive index | 1.6392 (estimate) |
storage temp. | 2-8°C |
solubility | alcohol: freely soluble |
form | Solid |
pka | pKa 10.3(H2O
t undefined
I = 0.1) (Uncertain) |
color | Crystals from pet ether |
Merck | 14,9506 |
CAS DataBase Reference | 59-98-3(CAS DataBase Reference) |
NIST Chemistry Reference | 1H-Imidazole, 4,5-dihydro-2-(phenylmethyl)-(59-98-3) |
EPA Substance Registry System | 1H-Imidazole, 4,5-dihydro-2-(phenylmethyl)- (59-98-3) |
Safety information for Tolazoline
Signal word | Warning |
Pictogram(s) |
Exclamation Mark Irritant GHS07 |
GHS Hazard Statements |
H315:Skin corrosion/irritation H319:Serious eye damage/eye irritation H335:Specific target organ toxicity, single exposure;Respiratory tract irritation |
Precautionary Statement Codes |
P261:Avoid breathing dust/fume/gas/mist/vapours/spray. P280:Wear protective gloves/protective clothing/eye protection/face protection. P301+P312:IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. P305+P351+P338:IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing. |
Computed Descriptors for Tolazoline
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