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Benzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-

HCID 5966
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Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
16505-84-3
Standard SMILES
CN(CCCCCCCCCCN(C)C(=O)Oc1cccc([N+](C)(C)C)c1)C(=O)Oc1cccc([N+](C)(C)C)c1
InChIKey
RWZVPVOZTJJMNU-UHFFFAOYSA-N
Molecular formula
C32H52N4O4+2
Average molar mass
556.8 g/mol
Monoisotopic mass
556.39885615

Overview

Demarcarium is the bis(quaternary ammonium) dication obtained by N,N'-dimethylation of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is a carbamate ester and a quaternary ammonium ion.

Names & identifiers

Preferred name
Benzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-
IUPAC
trimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium
English name
demarcarium
Molecular formula
C32H52N4O4
Molecular weight
556.77968

Names & synonyms

DemecariumDemecarium ionDemecarium cation16505-84-3ILP8XJ8R5KBenzenaminium, 3,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethyl-DTXSID2046965(m-Hydroxyphenyl)trimethylammonium decamethylenebis(methylcarbamate)N,N'-Bis(3-trimethylammoniumphenoxycarbonyl(-N,N'-dimethyldecamethylenediamine3,3'-(1,10-Decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethylbenzenaminium)Benzenaminium, 3,3'-[1,10-decanediylbis[(methylimino)carbonyloxy]]bis[N,N,N-trimethyl-N,N,N-trimethyl-3-((methyl(10-(methyl(3-(trimethylazaniumyl)phenoxycarbonyl)amino)decyl)carbamoyl)oxy)anilinium
Show more names
demarcariumDemecarium Free Basetrimethyl-[3-[methyl-[10-[methyl-[3-(trimethylazaniumyl)phenoxy]carbonylamino]decyl]carbamoyl]oxyphenyl]azanium
N,N,N-trimethyl-3-{[methyl(10-{methyl[3-(trimethylazaniumyl)phenoxycarbonyl]amino}decyl)carbamoyl]oxy}aniliniumRefChem:57372DTXCID5014745263,3'-(1,10-decanediylbis((methylimino)carbonyloxy))bis(N,N,N-trimethylbenzenaminium)-Benzenaminium, 3,3'-(1,10-Decanediylbis((Methylimino)Carbonyloxy))Bis(N,N,N-Trimethyl)-N,N'-Bis(3-Trimethylammoniumphenoxycarbonyl)-N,N'-DimethyldecamethylenediamineDemecarium [VANDF]Demecarium [WHO-DD]

Properties

Computed structural properties

XLogP
6.6
Topological polar surface area
59.1 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
4
Rotatable bonds
17
Heavy atoms
40
Formal charge
2
Complexity
686

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
LogP-1.75
Solubility1.69e-05 g/L
Melting Point164-170
Physical DescriptionSolid

Physicochemical properties

FDA UNII
8 XJ8R5K · ILP8XJ8R5K

Chemistry & industry

Pharmacology

ATC Code · 2 items

S - Sensory organs

QS - Sensory organs

Pharmacodynamics · 1 item

Demecarium is a long-acting cholinesterase inhibitor and potent miotic. Because of its toxicity, it should be reserved for use in patients with open-angle glaucoma or other chronic glaucomas not satisfactorily controlled with the short-acting miotics and other agents. Application of demecarium to the eye produces intense miosis and ciliary muscle contraction due to inhibition of cholinesterase, allowing acetylcholine to accumulate at sites of cholinergic transmission. These effects are accompanied by increased capillary permeability of the ciliary body and iris, increased permeability of the blood-aqueous barrier, and vasodilation. Myopia may be induced or, if present, may be augmented by the increased refractive power of the lens that results from the accommodative effect of the drug.

Mechanism of Action · 1 item

Demecarium is an indirect-acting parasympathomimetic agent, also known as a cholinesterase inhibitor and anticholinesterase. Cholinesterase inhibitors prolong the effect of acetylcholine, which is released at the neuroeffector junction of parasympathetic postganglion nerves, by inactivating the cholinesterases that break it down. Demecarium inactivates both pseudocholinesterase and acetylcholinesterase. In the eye, this causes constriction of the iris sphincter muscle (causing miosis) and the ciliary muscle (affecting the accommodation reflex and causing a spasm of the focus to near vision). The outflow of the aqueous humor is facilitated, which leads to a reduction in intraocular pressure. Of the two actions, the effect on the accommodation reflex is the more transient and generally disappears before termination of the miosis.

MeSH Pharmacological Classification · 1 item

Drugs that inhibit cholinesterases. The neurotransmitter ACETYLCHOLINE is rapidly hydrolyzed, and thereby inactivated, by cholinesterases. When cholinesterases are inhibited, the action of endogenously released acetylcholine at cholinergic synapses is potentiated. Cholinesterase inhibitors are widely used clinically for their potentiation of cholinergic inputs to the gastrointestinal tract and urinary bladder, the eye, and skeletal muscles; they are also used for their effects on the heart and the central nervous system.

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes

Database identifiers

CAS
16505-84-3、56-94-0
PubChem CID
5966
DTXSID
DTXSID2046965
ChEMBL
CHEMBL1201229
ChEBI
CHEBI:59719
UNII
ILP8XJ8R5K
Nikkaji
J82.023G
Cellular LocationsCytoplasm

Suppliers2 total

上海陶术生物科技股份有限公司13564774135 · [email protected]
TargetMol中国(陶术生物)15002134094 · [email protected]

Additional notes

DefinitionChEBI: Demarcarium is the bis(quaternary ammonium) dication obtained by N,N'-dimethylation of the N,N'-bis[3-(dimethylamino)phenyl carbamate] derivative of 2,13-diazatetradecane. It is a quaternary ammonium ion and a carbamate ester.