Methylephedrine

Methylephedrine
Clinical data
Trade names	Metheph, Methy-F, Tybraine
Other names	N-Methylephedrine; N-Methyl-(–)-ephedrine; L-Methylephedrine; N-Methyl-L-ephedrine; (−)-N-Methylephedrine; N,N-Dimethylnorephedrine
Drug class	Sympathomimetic; Norepinephrine releasing agent; Bronchodilator; Nasal decongestant; Antitussive
Pharmacokinetic data
Metabolites	• Methylephedrine N-oxide; • Ephedrine; • Norephedrine
Excretion	Urine
Identifiers
	IUPAC name (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol;
CAS Number	552-79-4;
PubChem CID	64782;
DrugBank	DB11278;
ChemSpider	58315;
UNII	SHS9PGQ2LS;
KEGG	D08206;
ChEBI	CHEBI:113556;
ChEMBL	ChEMBL445001;
CompTox Dashboard (EPA)	DTXSID7045992 ;
ECHA InfoCard	100.008.203
Chemical and physical data
Formula	C11H17NO
Molar mass	179.263 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C;
	InChI InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1; Key:FMCGSUUBYTWNDP-ONGXEEELSA-N;

Methylephedrine, sold under the brand name Metheph among others, is a sympathomimetic medication described as an antiasthmatic agent and used to treat coughing and nasal congestion. It is reported to be used in various over-the-counter cough and cold preparations throughout the world, including Japan.

The drug is an ephedrine-like sympathomimetic and activates α- and β-adrenergic receptors. Chemically, it is a substituted amphetamine and is closely related to ephedrine.

Methylephedrine was discovered by 1927. It is mostly no longer marketed as a prescription drug. The drug is also found naturally as an alkaloid in Ephedra species including Ephedra sinica, Ephedra vulgaris, and Ephedra distachya.