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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2D Structure
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Physico-chemical Properties
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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
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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
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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.
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