METICRANE Chemical Properties

Melting point:

236-237°

Boiling point:

549.1±60.0 °C(Predicted)

Density 

1.4366 (rough estimate)

refractive index 

1.6800 (estimate)

storage temp. 

Sealed in dry,2-8°C

solubility 

≥ 12.45mg/mL in DMSO

form 

Solid

pka

9.71±0.20(Predicted)

color 

White to off-white

EPA Substance Registry System

2H-1-Benzothiopyran-7-sulfonamide, 3,4-dihydro-6-methyl-, 1,1-dioxide (1084-65-7)

Safety Information

WGK Germany 

2

RTECS 

XK6360000

Toxicity

mouse,LD50,intraperitoneal,10gm/kg (10000mg/kg),Oyo Yakuri. Pharmacometrics. Vol. 8, Pg. 217, 1974.

MSDS

• Language:English Provider:SigmaAldrich

METICRANE Usage And Synthesis

Originator

Fontilix,Diamant

Uses

diuretic, antihypertensive

Definition

ChEBI: Meticrane is a thiochromane.

Manufacturing Process

64.5 g of 6-methylthiachromane were dissolved in 500 ml of acetic acid and 250 ml of 110-volume hydrogen peroxide were added. The solution was placed on a water bath for 1.5 hour; it was then diluted with iced water, the precipitate obtained was recovered, and this was washed and dried. There were obtained 59.6 g of 6-methylthiachromane-1,1-dioxide (yield: 77.5%; melting point 79°-81°C).
52 g of this product were added to 250 ml of chlorosulfonic acid and the mixture was placed on a water bath at a temperature of 70°-75°C for 2 hours. It was allowed to cool and poured onto crushed ice; the product was extracted by means of chloroform, the extracted solutions were washed and the chloroform was evaporated. There were obtained 67 g of crude 6-methyl- 7-chloro-sulfonyl-thiachromane-1,1-dioxide (yield: 86%; melting point 158°- 161°C).
47 g of this sulfochloride were introduced into 200 ml of liquid ammonia. The mixture was left to stand at ambient temperature until the ammonia evaporated. The residue was taken up in water and the solution was acidified. The precipitate formed was centrifuged, washed with water and dried. There were obtained 30.8 g of 6-methyl-7-sulfamido-thiachromane-1,1-dioxide, recrystallized from 2-methoxy ethanol (yield: 49%; MP: 236°-237°C).

Therapeutic Function

Diuretic

METICRANE(1084-65-7)Related Product Information

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