Mecamylamine Hydrochloride

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Cat Number

API0232188

CAS Number

826-39-1

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Product Detail Description Scientific Support Customer Q&A

CAS Number

826-39-1

EINECS

212-555-8

Storage

Store at room temperature

Synonyms

Inversine; Mevasin; Mekamin hydrochloride; Vecamyl; Mecamine hydrochloride; Mecamylamine HCl

Molecular Formula

C11H22ClN

Molecular Weight

203.75

Smiles

CC1(C2CCC(C2)C1(C)NC)C.Cl

Appearance

White, odorless, crystalline powder

Melting Point

>240°C (dec.)

Boiling Point

189.3°C at 760 mmHg

Relative Density

1.07

General Description

Mecamylamine hydrochloride is a secondary amine with a bicyclic (bridgehead) structure, a ganglionic blocker that acts as a nicotinic acetylcholine receptor antagonist. Its structure contains a 2,3,3-trimethyl-2-azabicyclo[2.2.1]heptane core, forming a white crystalline powder with a molecular weight of 203.8 Da.

Mechanism of Action

Mecamylamine binds directly to the nicotinic receptor at the postsynaptic membrane of autonomic ganglia, blocking the depolarizing action of acetylcholine. This inhibits sympathetic and parasympathetic transmission at the ganglionic level, leading to vasodilation, decreased cardiac output, and reduced gastrointestinal motility. The drug also has central nervous system effects due to its ability to cross the blood-brain barrier.

Application

Mecamylamine is indicated for the treatment of moderate to severe hypertension, particularly in patients resistant to other antihypertensive agents. It is also used off-label for the management of Tourette syndrome and for smoking cessation, as it blocks the reinforcing effects of nicotine.

Mecamylamine, a nicotinic acetylcholine receptor antagonist that crosses the blood-brain barrier, has been evaluated for CNS disorders including addiction, mood disorders, cognitive impairment, and ADHD. Its stereoisomers S(+)- and R(−)-mecamylamine have differential effects. Importantly, therapeutic CNS effects occur at doses 3-fold lower than those used for hypertension, reducing peripheral side effects. Mecamylamine remains a promising candidate for CNS indications, particularly addiction.

Fig. 1 Schild analysis of mecamylamine inhibition of nicotine-evoked [3H]DA overflow from superfused rat striatal slices. (Nickell JR, et al., 2013)

References

Nickell JR, et al. Potential therapeutic uses of mecamylamine and its stereoisomers. Pharmacol Biochem Behav. 2013;108:28-43.

Does Mecamylamine Hydrochloride require protection from light during long-term storage?

Yes, it is photosensitive. UV exposure can cause photodegradation and discoloration. Store in light-resistant containers, preferably amber glass.

What is the recommended storage temperature for Mecamylamine Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidation of the secondary amine group.

Is Mecamylamine Hydrochloride hygroscopic, and how is this managed?

It is slightly hygroscopic. Under high humidity (>70% RH), it may absorb moisture and clump. Storage in tightly sealed containers with desiccant is recommended.

How is the impurity mecamylamine N-oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability-indicating HPLC method, ensuring it remains within ICH qualification thresholds.