Benztropine Mesylate

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Cat Number

API0232294

CAS Number

102701-02-0

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CAS Number

102701-02-0

Storage

Store at room temperature

Synonyms

Cogentin mesylate; Benztropine (mesylate); 3-Diphenylmethoxytropane methanesulfonate

Molecular Formula

C22H29NO4S

Molecular Weight

403.5

Smiles

CN1C2CCC1CC(C2)OC(C3=CC=CC=C3)C4=CC=CC=C4.CS(=O)(=O)O

Appearance

White to almost white powder to crystal

Melting Point

139.0-143.0°C

General Description

Benztropine mesylate is a synthetic compound with a tropane ring and a benzohydryl group, structurally related to atropine. Its chemical structure is 3-(diphenylmethoxy)-8-methyl-8-azabicyclo[3.2.1]octane methanesulfonate. Benztropine is a white to off-white crystalline powder, soluble in water. It is a potent anticholinergic agent with both central and peripheral effects.

Mechanism of Action

Benztropine acts as a competitive antagonist at muscarinic acetylcholine receptors, blocking the effects of acetylcholine in the central nervous system and peripheral tissues. It has a higher affinity for central M1 receptors, reducing the cholinergic overactivity in the basal ganglia, which is responsible for the extrapyramidal symptoms. The drug also inhibits the reuptake of dopamine, contributing to its therapeutic effect.

Application

Benztropine is indicated for the treatment of Parkinson's disease, particularly for the management of tremor and rigidity, and for the control of extrapyramidal side effects caused by antipsychotic drugs, such as dystonia and akathisia. It is effective in reducing the symptoms of drug-induced movement disorders.

A cell-based phenotypic screen of 2,546 FDA-approved drugs identified benztropine mesylate as a selective inhibitor of breast cancer stem cells (BCSCs). It potently inhibited sphere formation and self-renewal, reduced ALDH-high and CD44+/CD24- subpopulations, and suppressed tumor-initiating potential in a 4T1 mouse model. Mechanistically, it targets acetylcholine receptors, dopamine transporters/receptors, and/or histamine receptors. This study provides a screening platform for anti-CSC agents and identifies benztropine as a promising candidate.

Fig. 1 Chemical screening for compounds that selectively inhibit the viability of HMLER-shEcad spheres. (Cui J, et al., 2017)

References

Cui J, et al. New use of an old drug: inhibition of breast cancer stem cells by benztropine mesylate. Oncotarget. 2017;8(1):1007-1022.

Photoaffinity labeling of the dopamine transporter with a benztropine analog ([¹²⁵I]GA II 34) identified cross‑linking at Asp79/Leu80 in TM1, with molecular modeling supporting adduction to Leu80 and a binding pose similar to cocaine. However, structural stabilization differences from cocaine may underlie benztropine's distinct neurochemical profile. This provides insight into the binding mechanisms of non‑addictive DAT ligands.

Fig. 2 Computational Docking and Molecular Dynamics Simulations. (Tomlinson MJ, et al., 2019)

References

Tomlinson MJ, et al. Identification of the benztropine analog [125I]GA II 34 binding site on the human dopamine transporter. Neurochem Int. 2019;123:34-45.

Does Benztropine Mesylate 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 Benztropine Mesylate?

Store at controlled room temperature (15–25°C). Avoid excessive heat above 30°C, which can soften the powder and accelerate degradation.

Is Benztropine Mesylate stable in injectable and oral formulations?

Aqueous solutions are stable when protected from light and stored at room temperature.

How is the impurity benztropine N‑oxide (an oxidative degradation product) monitored?

This degradation product is quantified using a stability‑indicating HPLC method, ensuring it remains within pharmacopoeial limits.