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Demecarium bromide

Product Name
Demecarium bromide
CAS No.
56-94-0
Chemical Name
Demecarium bromide
Synonyms
2br;bc48;e)(2:1);tonilen;humorsol;tosmicil;tosmilen;tosmilene;visumatic;frumtosnil
CBNumber
CB6501408
Molecular Formula
C32H52Br2N4O4
Formula Weight
716.59
MOL File
56-94-0.mol
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Demecarium bromide Property

Melting point:
162-167 °C (decomp)
storage temp. 
Store at -20°C
solubility 
DMSO:160.0(Max Conc. mg/mL);223.28(Max Conc. mM)
form 
Solid
color 
White
InChIKey
YHKBUDZECQDYBR-UHFFFAOYSA-L
SMILES
C1(=CC=CC([N+](C)(C)C)=C1)OC(=O)N(C)CCCCCCCCCCN(C)C(=O)OC1=CC=CC([N+](C)(C)C)=C1.[Br-].[Br-]
CAS DataBase Reference
56-94-0(CAS DataBase Reference)
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Safety

HS Code 
2924296000
Hazardous Substances Data
56-94-0(Hazardous Substances Data)
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

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

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N-Bromosuccinimide Price

TRC
Product number
D230720
Product name
DemecariumBromide
Packaging
1g
Price
$1940
Updated
2021/12/16
AK Scientific
Product number
C745
Product name
Demecariumbromide
Packaging
10mg
Price
$48
Updated
2021/12/16
ChemScene
Product number
CS-0030928
Product name
DemecariumBromide
Packaging
5mg
Price
$60
Updated
2021/12/16
Biosynth Carbosynth
Product number
FD38039
Product name
Demecarium bromide
Packaging
5mg
Price
$80
Updated
2021/12/16
ChemScene
Product number
CS-0030928
Product name
DemecariumBromide
Packaging
10mg
Price
$90
Updated
2021/12/16
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Demecarium bromide Chemical Properties,Usage,Production

Chemical Properties

White Solid

Originator

Humorsol ,MSD ,US,1959

Uses

Demecarium is a disymmetrical compound that contains two ammonium and two carbamate groups. It is a reversible cholinesterase inhibitor that is longer lasting than the others. It is used to constrict pupils, elevate intraocular pressure in treating glaucoma, and also for alleviating atropine mydriasis.

Uses

anticancer agent for pancreatic islet cells

Uses

Demecarium Bromide is an acetylcholinesterase inhibitor and veterinary medicine used to treat elevated intraocular pressure associated with primary glaucoma.

Definition

ChEBI: The methobromide salt of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is an inhibitor of acetylcholinesterase and pseudocholinesterase, with a long duration of action. It is u ed in the treatment of chronic open-angle glaucoma: in the eye, it causes constriction of the iris sphincter muscle and the ciliary muscle, facilitating the outflow of the aqueous humor and so reducing intraocular pressure.

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.

brand name

Humorsol (Merck).

Therapeutic Function

Cholinergic (ophthalmic)

General Description

Demecarium bromide,(m-hydroxyphenyl)trimethylammonium bromide, decamethylenebis[methylcarbamate] (Humorsol), is the diester of(m-hydroxyphenyl)trimethylammonium bromide with decamethylene-bis-(methylcarbamic acid) and thus is comparableto a bis-prostigmine molecule.
It occurs as a slightly hygroscopic powder that is freelysoluble in water or alcohol. Ophthalmic solutions of the drughave a pH of 5 to 7.5. Aqueous solutions are stable and maybe sterilized by heat. Its efficacy and toxicity are comparableto those of other potent anticholinesterase inhibitor drugs. Itis a long-acting miotic used to treat wide-angle glaucomaand accommodative esotropia. Maximal effect occurs hoursafter administration, and the effect may persist for days.

Synthesis

Demecarium, N,N??-decamethylene-bis-[meta-(N-methylcarbamoyloxy)- phenyl-trimethylammonium] hydroxide (13.2.18), is made by reacting two moles of phosgene with 1,10-bis-(methylamino)-decano(N,N??-dimethyldecamethylen-1,10-diamine, giving the bis-carbamoylchloride (13.2.16), which is transformed into bis-carbamoylester (13.2.17) by reaction with two moles of the 3-dimethylaminophenol sodium salt. Reacting this with methylbromide gives demecarium (13.2.18) [49].

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.

Demecarium bromide Preparation Products And Raw materials

Raw materials

Preparation Products

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Demecarium bromide Suppliers

Tianjin Keluo Pharmaceutical Technology Co. LTD
Tel
022-23869539 18920052327
Fax
022-83711180
Email
281258989@qq.com
Country
China
ProdList
61
Advantage
58
GUANGZHOU TOPWORK CHEMISTRY CO.,LTD.
Tel
020-87317062 13048089691
Email
852378519@qq.com
Country
China
ProdList
155
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
94657
Advantage
76
ZHIWE CHEMTECH CO LTD
Tel
021-20221225 13917446399
Fax
QQ:115820162
Email
sales@zhiwe.net
Country
China
ProdList
606
Advantage
61
LGM Pharma
Tel
1-(800)-881-8210
Fax
615-250-9817
Email
inquiries@lgmpharma.com
Country
United States
ProdList
2123
Advantage
70
Shanghai Longsheng chemical Co.,Ltd.
Tel
021-58099652-8005 13585536065
Fax
021-58099609
Email
bin.wu@shlschem.com
Country
China
ProdList
9809
Advantage
59
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
AN PharmaTech Co Ltd
Tel
86(21)68097365
Fax
86(21)33321566
Email
sales@anpharma.net
Country
China
ProdList
4891
Advantage
55
Wuhan Senwayer Century Chemical Co.,Ltd
Tel
027-86652399 13627115097;
Fax
86-27-59707018
Email
sales@senwayer.com
Country
China
ProdList
267
Advantage
55
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View Lastest Price from Demecarium bromide manufacturers

S&Y Biochem Co.,Ltd
Product
Demecarium bromide 56-94-0
Price
US $1.00/kg
Min. Order
1kg
Purity
99
Supply Ability
100
Release date
2024-09-20
Dideu Industries Group Limited
Product
Demecarium bromide 56-94-0
Price
US $1.10/g
Min. Order
1g
Purity
99.9%
Supply Ability
100 Tons min
Release date
2021-07-27
Career Henan Chemical Co
Product
Demecarium bromide 56-94-0
Price
US $1.00/g
Min. Order
1g
Purity
99%
Supply Ability
1000KGS
Release date
2019-12-20

56-94-0, Demecarium bromideRelated Search:


  • 2br
  • ammonium,(m-hydroxyphenyl)trimethyl-,bromide,decamethylenebis(methylcarbamat
  • bc48
  • benzenaminium,3,3’-(1,10-decanediylbis((methylimino)carbonyloxy))bis(n,n,n-t
  • benzenaminium,3,3’-(1,10-decanediylbis((methylimino)carbonyloxy))bis(n,n,n-tri
  • decamethylenebis(m-dimethylaminophenyl-n-methylcarbamate)dimethobromide
  • decamethylenebis(n-methylcarbamicacidm-dimethylaminophenylester)bromomethyl
  • demekariumbromide
  • demekastigminebromide
  • e)(2:1)
  • frumtosnil
  • humorsol
  • n,n’-bis(3-trimethylammoniumphenoxycarbonyl)-n,n’-dimethyldecamethylenediamine
  • tonilen
  • tosmicil
  • tosmilen
  • tosmilene
  • visumatic
  • DeMecariuM BroMide USP
  • DEMECARIUM BROMIDE (250 MG)
  • 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(n,n,n-trimethyl-benzenaminium)) dibromide
  • N,N-decamethylenebis(N,N,N-trimethyl-3-methylcarbamoyloxyanilinium) dibromide
  • Demecarium
  • Trimethyl-[3-[methyl-[10-[methyl-(3-trimethylazaniumylphenoxy)carbonylamino]decyl]carbamoyl]oxyphenyl]azanium dibromide
  • 3,3'-[1,10-Decanediylbis[(methylimino)carbonyloxy]]bis[N,N,N-trimethylbenzenaminium]
  • trimethyl-[3-[methyl-[10-[methyl-[3-(trimethylammonio)phenoxy]carbonyl-amino]decyl]carbamoyl]oxyphenyl]ammonium dibromide
  • demecarium bromide
  • (m-hydroxyphenyl)trimethylammoniumbromidedecamethylenebis(methylcarbamate)
  • Demecarium bromide USP/EP/BP
  • 3,3'-(((Decane-1,10-diylbis(methylazanediyl))bis(carbonyl))bis(oxy))bis(N,N,N-trimethylbenzenaminium) bromide
  • Demecarium Bromide (1169001)
  • Demecarium Bromide (100 mg)
  • 56-94-0
  • C32H52N4O42Br
  • C32H52Br2N4O4
  • Other APIs