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Procyclidine Hydrochloride: Chemical Structure, Mechanism of Action, SAR, Synthesis, Uses & Side Effects

Chemical Structure:

  • C19H29NO · HCl

Chemical Structure
Chemical Structure

Mechanism of Action:

  • Procyclidine is an anticholinergic agent which works by relaxing smooth muscle, which stops muscle spasms.

Structure-Activity Relationship (SAR) of Procyclidine Hydrochloride:

1.Tertiary Amine:

  • Procyclidine contains a tertiary amine, a common feature in many anticholinergic drugs, contributing to its ability to cross the blood-brain barrier and exert central effects.

2.Cyclic Structure:

  • The bicyclic structure of procyclidine is crucial for its activity. Alterations in this structure can significantly affect the drug's affinity for muscarinic receptors and its overall efficacy.

3.Aromatic Ring:

  • The presence of an aromatic ring is important for the molecule's pharmacological activity, contributing to its binding affinity and overall efficacy.

4.Alkyl Side Chain:

  • The length and structure of the alkyl side chain attached to the nitrogen atom can influence the selectivity and potency of the drug.

Synthesis of Procyclidine Hydrochloride (Chemical Reaction):

The synthesis of Procyclidine Hydrochloride typically involves the following steps:

1.Formation of the Bicyclic Structure:

  • Starting compounds (e.g., cyclohexanone derivatives) → Bicyclic Intermediate

2.Introduction of the Tertiary Amine:

  • Bicyclic Intermediate + Amine source → Procyclidine Base

3.Formation of Hydrochloride Salt:

  • Procyclidine Base + Hydrochloric Acid → Procyclidine Hydrochloride

  • In this synthesis, the key steps involve forming the bicyclic structure integral to procyclidine's activity, followed by the introduction of the tertiary amine to complete the active molecule's structure.

  • Finally, the hydrochloride salt is formed to improve the drug's stability and solubility.

Uses:

  • Ø  It is used to treat the stiffness, tremors, spasms, and poor muscle control of Parkinson's disease.

Side Effects:

  • Side effects include dry mouth, blurred vision, constipation, dizziness, and confusion.

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