Methylatropine

Methylatropine, also known as methylatropinium or N-methylatropinium, is a quaternary ammonium derivative of atropine sold under the brand name Eumydrin. It is, first and foremost, a potent muscarinic cholinergic antagonist.^[1][2]

Trade namesEumydrin

Other namesMethylatropinium; Methyl atropine; Methyl atropine nitrate; Methylatropine nitrate; Atropine methyl nitrate

ATC code

• A03BB02 (WHO)

CAS Number

• 31610-87-4

Quick facts Clinical data, Trade names ...

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
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
NY (what is this?)  (verify)

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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.^[3]

The blocking potency of methylatropine is approximately 10-20 times higher than that of atropine at neuromuscular and ganglionic synapses.^[4]