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Methantheline

HCID 4097
NotesReactions
Basic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
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Basic information

CAS
5818-17-7
Standard SMILES
CC[N+](C)(CC)CCOC(=O)C1c2ccccc2Oc2ccccc21
InChIKey
GZHFODJQISUKAY-UHFFFAOYSA-N
Molecular formula
C21H26NO3+
Average molar mass
340.4 g/mol
Monoisotopic mass
340.19126869

Overview

Methantheline is a member of xanthenes.

Names & identifiers

Preferred name
Methantheline
IUPAC
diethyl-methyl-[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium
English name
methantheline
Molecular formula
C21H26NO3+
Molecular weight
340.44

Names & synonyms

methanthelineMethantheliniumMethanthelinum5818-17-7Methantheline ionMethantheline cation36EI79TX7IDTXSID7046964Ethanaminium, N,N-diethyl-N-methyl-2-((9H-xanthen-9-ylcarbonyl)oxy)-diethyl(methyl)(2-((9H-xanthen-9-yl)carbonyloxy)ethyl)azaniumdiethyl(methyl){2-[(9H-xanthen-9-yl)carbonyloxy]ethyl}azaniumRefChem:156972
Show more names
β-Methylethylammonioethyl-9-xanthen carboxylate2-(9H-Xanthene-9-ylcarbonyloxy)ethyldiethylmethylaminiumEthanaminium,N,N-diethyl-N-methyl-2-[(9H-xanthen-9-ylcarbonyl)oxy]-
DTXCID5026964Banthine bromideMethanthine bromideN,N-Diethyl-N-methyl-2-[(9H-xanthen-9-ylcarbonyl)oxy]ethanaminiumCAS-53-46-3NCGC00016239-01UNII-36EI79TX7Idiethyl-methyl-[2-(9H-xanthene-9-carbonyloxy)ethyl]azanium

Database identifiers

CAS
5818-17-7
PubChem CID
4097
DTXSID

Properties

Computed structural properties

XLogP
3.3
Topological polar surface area
35.5 Ų
Hydrogen bond donors
0
Hydrogen bond acceptors
3
Rotatable bonds
7
Heavy atoms
25
Formal charge
1
Complexity
426

Experimental & physicochemical properties

DrugsPharmaceuticals -> Listed in ZINC15
Solubility1.32e-04 g/L
Human DrugsPharmaceuticals
Physical DescriptionSolid

Physicochemical properties

FDA UNII
36 EI79TX7I · 36EI79TX7I

Chemistry & industry

Pharmacology

ATC Code · 2 items

A - Alimentary tract and metabolism

QA - Alimentary tract and metabolism

Pharmacodynamics · 1 item

Methantheline is a synthetic quarternary ammonium antimuscarinic used to relieve cramps or spasms of the stomach, intestines, and bladder. It can be used together with antacids or other medicines, such as H2-receptor antagonists, in the treatment of peptic ulcer. Methantheline inhibits muscarinic actions at postganglionic parasympathetic neuroeffector sites.

Mechanism of Action · 1 item

Methantheline inhibits the muscarinic actions of acetylcholine on structures innervated by postganglionic cholinergic nerves as well as on smooth muscles that respond to acetylcholine but lack cholinergic innervation. These postganglionic receptor sites are present in the autonomic effector cells of the smooth muscle, cardiac muscle, sinoatrial and atrioventricular nodes, and exocrine glands. Depending on the dose, anticholinergics may reduce the motility and secretory activity of the gastrointestinal system, and the tone of the ureter and urinary bladder and may have a slight relaxant action on the bile ducts and gallbladder.

Metabolism/MetabolitesHepatic, by enzymatic hydrolysis.
MeSH Pharmacological Classification · 1 item

Drugs that bind to but do not activate MUSCARINIC RECEPTORS, thereby blocking the actions of endogenous ACETYLCHOLINE or exogenous agonists. Muscarinic antagonists have widespread effects including actions on the iris and ciliary muscle of the eye, the heart and blood vessels, secretions of the respiratory tract, GI system, and salivary glands, GI motility, urinary bladder tone, and the central nervous system.

Absorption, Distribution and ExcretionRapidly absorbed.
Cellular LocationsMembrane

Related reactions

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Compound notes

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On this pageBasic informationOverviewNames & identifiersPropertiesChemistry & industryRelated reactionsCompound notes
DTXSID7046964
ChEMBL
CHEMBL1201264
ChEBI
CHEBI:6817
UNII
36EI79TX7I
Nikkaji
J8.071C

Uses & manufacturing

Use ClassificationPharmaceuticals

Suppliers3 total

北京华美互利生物化工010-56205725 · [email protected]
赛纳斯特化学(欢迎点击联系)021-60343070
Shaanxi Didu New Materials Co. Ltd+86-86-17392712779 +86-13289823923 · [email protected]

Additional notes

DefinitionChEBI: Methantheline is a member of xanthenes.