| Width: | 200px |
| Tradename: | Metheph, Methy-F, Tybraine |
| Class: | Sympathomimetic |
| Metabolites: | • Methylephedrine N-oxide[1] • Ephedrine • Norephedrine |
| Excretion: | Urine |
| Cas Number: | 552-79-4 |
| Pubchem: | 64782 |
| Drugbank: | DB11278 |
| Chemspiderid: | 58315 |
| Unii: | SHS9PGQ2LS |
| Kegg: | D08206 |
| Chebi: | 113556 |
| Chembl: | 445001 |
| Synonyms: | N-Methylephedrine; N-Methyl-(–)-ephedrine; L-Methylephedrine; N-Methyl-L-ephedrine; (−)-N-Methylephedrine; N,N-Dimethylnorephedrine |
| Iupac Name: | (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol |
| C: | 11 |
| H: | 17 |
| N: | 1 |
| O: | 1 |
| Smiles: | C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C |
| Stdinchi: | 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 |
| Stdinchikey: | 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.[2]
Rarely, heart failure and stroke in association with use of methylephedrine have been reported.[3] [4] [5]
Methylephedrine shows reinforcing effects, a measure of addiction and misuse potential, in monkeys.
Methylephedrine is a sympathomimetic and ephedrine-like agent. Ephedrine and related agents act as norepinephrine releasing agents and hence as indirectly acting sympathomimetics. In relation to this, methylephedrine stimulates α- and β-adrenergic receptors. The drug has bronchodilator and nasal decongestant effects.
The occupancy of the dopamine transporter (DAT) by racemic methylephedrine has been studied.[6]
Methylephedrine is metabolized into ephedrine and norephedrine. It is excreted in urine 33 to 40% unchanged, 15% as methylephedrine N-oxide, and 8% as ephedrine after 24hours.
Methylephedrine, also known as (1R,2S)-β-hydroxy-N,N-dimethyl-α-methyl-β-phenethylamine and as (1R,2S)-β-hydroxy-N,N-dimethylamphetamine, is a substituted phenethylamine and amphetamine derivative. It is the N-methylated derivative of ephedrine ((1R,2S)-β-hydroxy-N-methylamphetamine).
A closely related compound and stereoisomer of methylephedrine is N-methylpseudoephedrine. Another related analogue is dimethylamphetamine (N,N-dimethylamphetamine), which is said to be a prodrug of methamphetamine and/or amphetamine.[7] Other analogues include etafedrine (N-ethylephedrine) and cinnamedrine (N-cinnamylephedrine).
The experimental log P of methylephedrine is 2.47 and its predicted log P ranges from 1.7 to 1.74.[8] [9] [10]
In organic chemistry, N-methylephedrine is used as a resolving agent and as a precursor to chiral supporting electrolytes, phase-transfer catalysts, and reducing agents.[11]
Methylephedrine was discovered via isolation from Ephedra by 1927.
Methylephedrine is the generic name of the drug and its .[12] [13] [14] In the case of the hydrochloride salt, its generic name is methylephedrine hydrochloride and this is its . Brand names of methylephedrine include Metheph, Methy-F, and Tybraine, among others.
Similarly to ephedrine, methylephedrine may have misuse potential. The drug shows reinforcing effects in monkeys.[15] It is one of the four constituents of BRON, a Japanese over-the-counter cough medicine with reports of misuse.[16] However, addiction liability of BRON was attributed primarily to the codeine component. A case report of addiction to methylephedrine exists.
Methylephedrine is on the World Anti-Doping Agency's prohibited list.[17]