Methylatropine

Chemical compound

Pharmaceutical compound

Methylatropine
Clinical data

Trade names	Eumydrin
Other names	Methylatropinium; Methyl atropine; Methyl atropine nitrate; Methylatropine nitrate; Atropine methyl nitrate
ATC code	A03BB02 (WHO )
Identifiers
IUPAC name (1R,5R)-3-[(3-hydroxy-2-phenylpropanoyl)oxy]-8,8-dimethyl-8-azoniabicyclo[3.2.1]octane
CAS Number	31610-87-4
PubChem CID	1550101
DrugBank	DB13833
ChemSpider	5652
UNII	80719I460H
ChEMBL	ChEMBL1179176
CompTox Dashboard (EPA)	DTXSID50858977 Edit this at Wikidata
Chemical and physical data
Formula	C₁₈H₂₆NO₃
Molar mass	304.410 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[N+]1(C2CCC1CC(C2)OC(=O)C(CO)C3=CC=CC=C3)C
InChI InChI=1S/C18H26NO3/c1-19(2)14-8-9-15(19)11-16(10-14)22-18(21)17(12-20)13-6-4-3-5-7-13/h3-7,14-17,20H,8-12H2,1-2H3/q+1/t14-,15+,16?,17-/m0/s1 Key:PIPAJLPNWZMYQA-WFVVYAPDSA-N
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Methylatropine, sold under the brand name Eumydrin, is a belladonna derivative.^[1]

In 1902, the Bayer Company introduced methylatropine, a quaternary ammonium salt of atropine, as a mydriatic for dilation of the pupil during ophthalmic examination under the brand name of Eumydrin. Because of its highly polar nature it penetrated less readily into the central nervous system than did atropine; hence it was introduced for relieving pyloric spasm in infants.^[2]

The blocking potency of methylatropine is approximately 10-20 times higher than that of atropine at neuromuscular and ganglionic synapses.^[3]

References

[edit ]

^ Elks, J. (2014). The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies. Springer US. p. 1258. ISBN 978-1-4757-2085-3 . Retrieved 28 January 2025.
^ "Methylatropine Bromide". Inxight: Drugs. National Center for Advancing Translational Sciences (NCATS), National Institutes of Health, U.S. Department of Health and Human Services.
^ Gyermek L (1998). "Semisynthetic Derivatives of Tropane Alkaloids and of other Tropane Esters". Pharmacology of Antimuscarinic Agents. Boca Raton: CRC Press. p. 162. ISBN 978-0-8493-8559-9.

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Drugs for functional gastrointestinal disorders (A03)

Drugs for
functional
bowel
disorders

Antimuscarinics

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