Tetryzoline Property

Melting point:

117-119 °C(Solv: heptane (142-82-5); ethanol (64-17-5))

Boiling point:

393.5±21.0 °C(Predicted)

Density 

1.20±0.1 g/cm3(Predicted)

solubility 

Chloroform (Slightly), DMSO (Slightly)

form 

Solid

pka

pKa 10.51 (Uncertain)

color 

Off-White to Pale Yellow

NIST Chemistry Reference

1H-Imidazole, 4,5-dihydro-2-(1,2,3,4-tetrahydro-1-naphthalenyl)-(84-22-0)

Safety

Hazardous Substances Data

84-22-0(Hazardous Substances Data)

Hazard and Precautionary Statements (GHS)

Symbol(GHS)

Signal word

Warning

Hazard statements

H302Harmful if swallowed

Precautionary statements

P280Wear protective gloves/protective clothing/eye protection/face protection.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

Tetryzoline Chemical Properties,Usage,Production

Originator

Tyzine,Pfizer,US,1954

Uses

Tetrahydrozoline is generally used in the form of eye drops for constriction of blood vessels as well as locally for minor inflammations and bites.

Definition

ChEBI: Tetryzoline is a member of imidazolines and a carboxamidine. It has a role as a sympathomimetic agent and a nasal decongestant. It is a conjugate base of a tetryzoline(1+).

Manufacturing Process

A mixture of 540 grams (9.0 mols) of ethylenediamine, 270 grams (1.53 mols) of 1,2,3,4tetrahydro-α-naphthoic acid, and 360 ml (4.32 mols) of concentrated hydrochloric acid was introduced into a two-liter, three-necked flask fitted with a thermometer, stirrer, and distillation takeoff. The mixture was distilled under a pressure of about 20 mm of mercury absolute until the temperature rose to 210°C. Thereafter, heating was continued under atmospheric pressure and when the temperature reached about 260°C, an exothermic reaction was initiated. The heat was then adjusted to maintain a reaction temperature of 275° to 280°C for 45 minutes and the mixture thereafter cooled to room temperature.
900 ml of 4 N hydrochloric acid was added and the aqueous layer stirred with warming until a clear, brown solution resulted. This brown solution was made strongly alkaline with sodium hydroxide. The oil that separated solidified and was collected on a filter leaving filtrate A. The solid was dissolved in 370 ml of alcohol with warming, and the solution was treated with 130 ml of concentrated hydrochloric acid with stirring and cooling. This acidified mixture was diluted with 300 ml of ether and chilled. The solid salt was collected and dried and the filtrate concentrated to approximately 300 ml, diluted with 300 ml of ether and the salt which separated collected and dried.
Filtrate A was extracted with ether, dried, acidified with alcoholic hydrogen chloride, and the salt which separated was collected and dried. There was thus obtained, when all the salt had been combined, 250 grams (69.3% of the theoretical yield) of 2-(1,2,3,4-tetrahydro-1-naphthyl)imidazoline hydrochloride, melting at 256° to 257°C.

Therapeutic Function

Nasal decongestant, Pharmaceutic aid

Synthesis

Tetrahydrozoline, 2-(1,2,3,4-tetrahydro-1-naphthalenyl)-2-imidazoline (11.1.41), is synthesized in one step by the heterocyclization of 1-cyanotetraline with ethylenediamine [45].