N-methyl scopolamine   Click here for help

GtoPdb Ligand ID: 316

Abbreviated name: NMS
Synonyms: methylscopolamine | methylscopolamine bromide | N-methylscopolamine | Pamine®
Approved drug
N-methyl scopolamine is an approved drug (FDA (1953))
Compound class: Synthetic organic
Comment: The approved drug methylscopolamine bromide consists of N-methyl scopolamine and bromide ions. There is some ambiguity in the literature and in other databases surrounding the exact stereochemistry of N-methyl scopolamine. Alternative representations include CHEMBL3140030 and CHEMBL376897.
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Ligand Activity Visualisation Charts

These are box plot that provide a unique visualisation, summarising all the activity data for a ligand taken from ChEMBL and GtoPdb across multiple targets and species. Click on a plot to see the median, interquartile range, low and high data points. A value of zero indicates that no data are available. A separate chart is created for each target, and where possible the algorithm tries to merge ChEMBL and GtoPdb targets by matching them on name and UniProt accession, for each available species. However, please note that inconsistency in naming of targets may lead to data for the same target being reported across multiple charts.

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View interactive charts of activity data across species
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 4
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 59.06
Molecular weight 318.17
XLogP 0.59
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES OCC(c1ccccc1)C(=O)OC1CC2C3C(C(C1)[N+]2(C)C)O3
Isomeric SMILES OC[C@H](c1ccccc1)C(=O)OC1C[C@@H]2[C@@H]3[C@H]([C@H](C1)[N+]2(C)C)O3
InChI InChI=1S/C18H24NO4/c1-19(2)14-8-12(9-15(19)17-16(14)23-17)22-18(21)13(10-20)11-6-4-3-5-7-11/h3-7,12-17,20H,8-10H2,1-2H3/q+1/t12?,13-,14-,15+,16-,17+/m1/s1
InChI Key LZCOQTDXKCNBEE-XJMZPCNVSA-N
No information available.
Summary of Clinical Use Click here for help
Used as an adjunctive therapy in the treatment of peptic ulcers, and to treat nausea and vomiting caused by motion sickness. The 1953 US FDA approval was for a formulation containing methscopolamine bromide. There is no EU-wide EMA approval for use of this drug. Individual national approval agencies may have granted marketing authorisation.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Muscarinic receptor antagonist in the vomiting centre, part of the parasympathetic nervous system.
External links Click here for help
For extended ADME data see the following:

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