Methylephedrine

Methylephedrine
Clinical data
Trade namesMetheph, Methy-F, Tybraine
Other namesN-Methylephedrine; N-Methyl-(–)-ephedrine; L-Methylephedrine; N-Methyl-L-ephedrine; (−)-N-Methylephedrine; N,N-Dimethylnorephedrine
Drug classSympathomimetic; Norepinephrine releasing agent; Bronchodilator; Nasal decongestant; Antitussive
Pharmacokinetic data
Metabolites• Methylephedrine N-oxide[1][2]
• Ephedrine[1][2]
• Norephedrine[1][2]
ExcretionUrine[1]
Identifiers
  • (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.008.203 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO
Molar mass179.263 g·mol−1
3D model (JSmol)
  • C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C
  • 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.[3][4][1] It is reported to be used in various over-the-counter cough and cold preparations throughout the world, including Japan.[1]

The drug is an ephedrine-like sympathomimetic and activates α- and β-adrenergic receptors.[5] Chemically, it is a substituted amphetamine and is closely related to ephedrine.[3][4]

Methylephedrine was discovered by 1927.[6] It is mostly no longer marketed as a prescription drug.[4] The drug is also found naturally as an alkaloid in Ephedra species including Ephedra sinica, Ephedra vulgaris, and Ephedra distachya.[3][6]

  1. ^ a b c d e f Cite error: The named reference DrugBank was invoked but never defined (see the help page).
  2. ^ a b c Inoue T, Suzuki S (January 1990). "The metabolism of (+-)-methylephedrine in rat and man". Xenobiotica; the Fate of Foreign Compounds in Biological Systems. 20 (1): 99–106. doi:10.3109/00498259009046816. PMID 2327112.
  3. ^ a b c Cite error: The named reference Elks2014 was invoked but never defined (see the help page).
  4. ^ a b c Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
  5. ^ Cite error: The named reference Docherty2008 was invoked but never defined (see the help page).
  6. ^ a b Smith (1927). "CCLXX. l-Methylephedrine, an alkaloid from Ephedra species". J. Chem. Soc.: 2056–2059. doi:10.1039/jr9270002056.