Methylscopolamine bromide

Pharmaceutical drug

A03BB03 (WHO) S01FA03 (WHO)

Pharmacokinetic dataElimination half-life3–4 hrsIdentifiers

IUPAC name

(1R,2S,4R,5S,7R)-{[(2R)-3-hydroxy-2-phenylpropanoyl]oxy}-9,9-dimethyl-3-oxa-9-azoniatricyclo[3.3.1.0^2,4]nonane

CAS Number

155-41-9

PubChem CID

441342

DrugBank

DB00462^Y

ChemSpider

21106347^Y

UNII

RTN51LK7WL

ChEMBL

ChEMBL376897^Y

PDB ligand

3C0 (PDBe, RCSB PDB)

CompTox Dashboard (EPA)

DTXSID2040608

ECHA InfoCard100.005.314

Chemical and physical dataFormulaC₁₈H₂₄NO₄Molar mass318.388 g/mol (398.297 g/mol with bromide) g·mol⁻¹3D model (JSmol)

Interactive image

SMILES

OC[C@H](c1ccccc1)C(=O)O[C@H]2C[C@@H]3[N+](C)(C)[C@H](C2)[C@H]4O[C@@H]34

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^Y
Key:LZCOQTDXKCNBEE-IKIFYQGPSA-N^Y

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Methylscopolamine or methscopolamine, usually provided as the bromide or nitrate salt, is an oral medication used along with other medications to treat peptic ulcers by reducing stomach acid secretion.^[1] Proton pump inhibitors and antihistamine medications have made this use obsolete. It can also be used for stomach or intestinal spasms, to reduce salivation, and to treat motion sickness. Methscopolamine is also commonly used as a drying agent, to dry up post-nasal drip, in cold, irritable bowel syndrome and allergy medications^[2]

Methscopolamine, a methylated derivative of scopolamine, is a muscarinic antagonist structurally similar to the neurotransmitter acetylcholine. Its mechanism of action involves blocking the muscarinic acetylcholine receptors.

It was patented in 1902 and approved for medical use in 1947.^[3] Methscopolamine is an FDA-approved analog to hyoscine butylbromide.

Brand names

Brand names include Extendryl, AlleRx, Rescon, Pamine.

References

^ Drugs.com: Methscopolamine
^ Gennaro AR. The Science and Practice of Pharmacy. Remington. pp. 402–403, 1025. ISBN 0912734043.
^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 446. ISBN 9783527607495.

Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional
bowel
disorders

Antimuscarinics

Tertiary amino group	Oxyphencyclimine Camylofin Mebeverine Trimebutine Rociverine Dicycloverine Dihexyverine Difemerine Piperidolate
Quaternary ammonium compounds	Benzilone Mepenzolate Pipenzolate Glycopyrronium Oxyphenonium Penthienate Methantheline Propantheline Otilonium Tridihexethyl Isopropamide Hexocyclium Poldine Bevonium Diphemanil Tiemonium Prifinium Timepidium Fenpiverinium