Methylatropine

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;
	(what is this?) (verify)

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]

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]

References

^ 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.
^ Smith RD, Grzelak ME, Coffin VL (April 1994). "Methylatropine blocks the central effects of cholinergic antagonists". Behavioural Pharmacology. 5 (2): 167–175. doi:10.1097/00008877-199404000-00008. PMID 11224265.
^ "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.

This article incorporates public domain material from Methylatropine Bromide. National Institutes of Health.

[Elks2014-1] 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.

[2] Smith RD, Grzelak ME, Coffin VL (April 1994). "Methylatropine blocks the central effects of cholinergic antagonists". Behavioural Pharmacology. 5 (2): 167–175. doi:10.1097/00008877-199404000-00008. PMID 11224265.

[drugsandcats-3] "Methylatropine Bromide". Inxight: Drugs. National Center for Advancing Translational Sciences (NCATS), National Institutes of Health, U.S. Department of Health and Human Services.

[4] 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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See also

References