56-94-0 Usage
Description
Demecarium bromide, also known as (m-hydroxyphenyl)trimethylammonium bromide decamethylenebis[methylcarbamate], is a long-acting miotic agent that belongs to the class of anticholinesterase inhibitors. It is a slightly hygroscopic powder, freely soluble in water or alcohol, and has a pH range of 5 to 7.5 in ophthalmic solutions. Its efficacy and toxicity are comparable to other potent anticholinesterase inhibitor drugs.
Uses
Used in Veterinary Medicine:
Demecarium bromide is used as a veterinary medicine for treating elevated intraocular pressure associated with primary glaucoma. It helps in reducing intraocular pressure by causing constriction of the iris sphincter muscle and the ciliary muscle, which facilitates the outflow of aqueous humor.
Used in Anticancer Applications:
Demecarium bromide is used as an anticancer agent for pancreatic islet cells. It modulates various oncological signaling pathways, exerting inhibitory effects on tumor growth and progression.
Used in Ophthalmology:
Demecarium bromide is used as a long-acting miotic agent for treating wide-angle glaucoma and accommodative esotropia. Its maximal effect occurs hours after administration, and the effect may persist for days.
Chemical Properties:
Demecarium bromide is a white solid with the brand name Humorsol (Merck). It is an inhibitor of acetylcholinesterase and pseudocholinesterase, with a long duration of action.
Originator
Humorsol ,MSD ,US,1959
Manufacturing Process
N,N,N,N'-tetramethyldecamethylene diamine is reacted with phosgene in
toluene under agitation. The phosgene which escapes through an ascending
cooling tube together with the evolved methyl chloride is condensed in a cold
trap. As soon as immixture has been completed, the temperature is raised to
100°C and the phosgene recovered in the trap is vaporized and bubbled
through the solution again, the escaping gas being recondensed and returned
once more. The repeated passage through the reagents of the phosgene that
has not yet reacted is continued for 7 hours. When the solution is cool it is
passed through a filter, the remaining phosgene is removed from the clear
solution by distillation and the remainder distilled in vacuo.A solution of 11.9 parts of m-dimethylaminophenol in 90 parts of xylene
(isomer mixture) is added to a solution of sodium methylate consisting of 2.0
parts of sodium and 25 parts of methanol. The methanol is then completely
removed by distillation and the temperature raised until the boiling point of
the xylene is reached. The decamethylene-bis-(N-methyl carbamic chloride) is
added to the remainder which contains the sodium salt of m dimethylaminophenol in the form of solid crystals. The reagent mixture is
heated and maintained at a temperature of 100°C and continuously agitated.
After having been cooled it is washed three times in water, three times in a
5% solution of caustic soda, and another three times in water. The xylene is
then evaporated in vacuo and the oily residue freed of any remaining traces of
xylene by allowing it to stand in air when the product crystallized completely.
In this manner 15.6 parts of decamethylene-bis-(N-methyl carbamic acid mdimethylaminophenylester) are obtained, This is in turn reacted with methyl
bromide to give the desired product. The decamethylene-bis-(N-methyl
carbamic acid m-dimethylaminophenylesterbromomethylate) appears after
precipitation from a solution in acetic acid with methyl ethyl ketone in the
form of a finely crystalline powder with a micro melting point between 164°
and 170°C.
Veterinary Drugs and Treatments
Demecarium is a potent carbamate inhibitor that may reduce intraocular
pressures for up to 48 hours in canines. Demecarium
reversibly inhibits anticholinesterase thereby causing miosis.
Demecarium is generally used in preventive management of the
contralateral eye in canine patients after the diagnosis of an acute
congestive crisis of primary glaucoma in the other eye. It is not used
in secondary glaucoma. Demecarium has the advantage of once or
twice daily dosing.
Check Digit Verification of cas no
The CAS Registry Mumber 56-94-0 includes 5 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 2 digits, 5 and 6 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 56-94:
(4*5)+(3*6)+(2*9)+(1*4)=60
60 % 10 = 0
So 56-94-0 is a valid CAS Registry Number.
InChI:InChI=1/C32H52N4O4.2BrH/c1-33(31(37)39-29-21-17-19-27(25-29)35(3,4)5)23-15-13-11-9-10-12-14-16-24-34(2)32(38)40-30-22-18-20-28(26-30)36(6,7)8;;/h17-22,25-26H,9-16,23-24H2,1-8H3;2*1H/q+2;;/p-2
