chemistry

Methylephedrine

Methylephedrine is a chemistry topic covered in the lgStudy science library. This page brings together a partial reference excerpt, illustrations, worked examples, real-world applications and a short study plan, so you can understand Methylephedrine rather than just read about it. In short: 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.

Key takeaways

Methylephedrine belongs to chemistry; place it in that map before memorising details.
Learn the definition first, then one example that makes the definition concrete.
Connect Methylephedrine to a quantity you can measure, compute or draw — that is where exam questions come from.
Reproduce the core statement of Methylephedrine from memory before moving on to harder problems.

Reference excerpt

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.

Side effects Rarely, heart failure and stroke in association with use of methylephedrine have been reported. Methylephedrine shows reinforcing effects, a measure of addiction and misuse potential, in monkeys.

Pharmacology

Pharmacodynamics 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.

Pharmacokinetics 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 24 hours.

Chemistry 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. 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. 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.

History Methylephedrine was discovered via isolation from Ephedra by 1927.

Society and culture

Names Methylephedrine is the generic name of the drug and its BANTooltip British Approved Name. In the case of the hydrochloride salt, its generic name is methylephedrine hydrochloride and this is its BANMTooltip British Approved Name. Brand names of methylephedrine include Metheph, Methy-F, and Tybraine, among others.

Recreational use Similarly to ephedrine, methylephedrine may have misuse potential. The drug shows reinforcing effects in monkeys. It is one of the four constituents of BRON, a Japanese over-the-counter cough medicine with reports of misuse. However, addiction liability of BRON was attributed primarily to the codeine component. A case report of addiction to methylephedrine exists.

Use in sports and exercise Methylephedrine is on the World Anti-Doping Agency's prohibited list.

References

Illustrations

Worked examples

Example 1 — a first encounter with Methylephedrine

Start with the simplest possible case. Write down what Methylephedrine claims or describes in one sentence, then invent the smallest concrete situation in which that sentence is true. In chemistry, the smallest case is usually a single object, a single equation or a single measurement. Check that every symbol or term in your sentence has a meaning in that case.

Example 2 — changing one variable

Take the situation from Example 1 and change exactly one quantity: double it, halve it, or set it to zero. Predict what should happen to Methylephedrine before you calculate. Comparing your prediction with the result is the fastest way to find out whether you understand the idea or only the words.

Example 3 — an exam-style question

Typical questions about Methylephedrine ask you to (a) state it precisely, (b) apply it to given data, and (c) explain a limitation. Practise writing all three answers in under five minutes; the third part is what separates a full-mark answer from an average one.

Applications of Methylephedrine

In research: Methylephedrine appears in chemistry research whenever the underlying quantities have to be modelled precisely. Papers usually cite it as a starting assumption and then explore where it breaks down.
In technology and industry: Engineering practice reuses Methylephedrine in design rules, simulations and safety margins. Knowing the idea lets you read a specification sheet and understand why the numbers look the way they do.
In the classroom: Methylephedrine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Amphetamine alkaloids, Beta-Hydroxyamphetamines, Bronchodilators, so understanding it makes those chapters shorter.
In everyday life: Look for Methylephedrine outside the textbook — in sport, cooking, traffic, electronics or the sky above you. An example you found yourself is remembered far longer than one you were given.

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How to study Methylephedrine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Methylephedrine means in your own words.
Compare your version with the excerpt and mark what you missed.
Work through the three examples above with pen and paper.
Explain Methylephedrine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Methylephedrine in simple terms?

Why does Methylephedrine matter?

Because it connects several chemistry ideas at once: it gives you a definition you can apply, a quantity you can calculate, and a way to check whether a result is plausible.

How should I study Methylephedrine?

Read the excerpt, restate it from memory, then work through the examples and applications listed on this page. The five-step study plan above takes about twenty minutes.

What does this page cover?

It gives you a compact reference excerpt plus original lgStudy explanations, examples, applications and study material on Methylephedrine.