chemistry

Mecamylamine

Mecamylamine 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 Mecamylamine rather than just read about it. In short: Mecamylamine (INN, BAN; or mecamylamine hydrochloride (USAN); brand names Inversine, Vecamyl) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensive drug. In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmace…

Key takeaways

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

Reference excerpt

Mecamylamine (INN, BAN; or mecamylamine hydrochloride (USAN); brand names Inversine, Vecamyl) is a non-selective, non-competitive antagonist of the nicotinic acetylcholine receptors (nAChRs) that was introduced in the 1950s as an antihypertensive drug. In the United States, it was voluntarily withdrawn from the market in 2009 but was brought to market in 2013 as Vecamyl and eventually was marketed by Turing Pharmaceuticals. Chemically, mecamylamine is a secondary aliphatic amine, with a pKaH of 11.2

Medical uses Mecamylamine has been used as an orally-active ganglionic blocker in treating autonomic dysreflexia and hypertension, but, like most ganglionic blockers, it is more often used now as a research tool. Mecamylamine is also sometimes used as an antiaddictive drug to help people stop smoking tobacco, and is now more widely used for this application than it is for lowering blood pressure. This effect is thought to be due to its blocking α3β4 nicotinic receptors in the brain. It has also been reported to bring about sustained relief from tics in Tourette syndrome when a series of more usually used agents had failed. In a recent double-blind, placebo-controlled Phase II trial in Indian patients with major depression, (S)-mecamylamine (TC-5214) appeared to have efficacy as an augmentation therapy. This is the first substantive evidence that shows that compounds where the primary pharmacology is antagonism to neuronal nicotinic receptors will have antidepressant properties. TC-5214 is currently in Phase III of clinical development as an add-on treatment and on stage II as a monotherapy treatment for major depression. The first results reported from the Phase III trials showed that TC-5214 failed to meet the primary goal and the trial did not replicate the effects that had been encouraging in the Phase II trial. Development is funded by Targacept and AstraZeneca. It did not produce meaningful, beneficial results on patients as measured by changes on the Montgomery-Asberg Depression Rating Scale after eight weeks of treatment as compared with placebo.

Overdose The LD50 for the HCl salt in mice: 21 mg/kg (i.v.); 37 mg/kg (i.p.); 96 mg/kg (p.o.).

Pharmacology (S)-(+)-Mecamylamine dissociates more slowly from α4β2 and α3β4 receptors than does the (R)-(−)-enantiomer. A large SAR study of mecamylamine and its analogs was reported by a group from Merck in 1962. Another, more recent SAR study was undertaken by Suchocki et al. A comprehensive review of the pharmacology of mecamylamine was published in 2001.

History Mecamylamine was brought to market by Merck & Co. in the 1950s; in 1996 Merck sold the asset to Layton Bioscience. In 2002, Targacept acquired it from Layton, intending to repurpose it for CNS conditions. Targacept voluntarily withdrew mecamylamine from the market in 2009 for reasons not related to safety or efficacy. Manchester Pharmaceuticals brought the drug back to market in 2013. Retrophin acquired Manchester in 2014 and after Martin Shkreli was forced out of Retrophin, in 2014 his new company, Turing Pharmaceuticals, acquired the rights to mecamylamine from Retrophin.

Illustrations

Worked examples

Example 1 — a first encounter with Mecamylamine

Start with the simplest possible case. Write down what Mecamylamine 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 Mecamylamine 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 Mecamylamine 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 Mecamylamine

In research: Mecamylamine 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 Mecamylamine 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: Mecamylamine is common in secondary-school and first-year university syllabi. It links to neighbouring topics Bicyclic compounds, Nicotinic antagonists, Secondary amines, so understanding it makes those chapters shorter.
In everyday life: Look for Mecamylamine 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 Mecamylamine in 20 minutes

Read the reference excerpt below once, without taking notes.
Close the page and write down what Mecamylamine 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 Mecamylamine out loud to somebody else — or to Teacher Smith in the lgStudy chat.

Frequently asked questions

What is Mecamylamine in simple terms?

Why does Mecamylamine 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 Mecamylamine?

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 Mecamylamine.