Triprolidine hydrochloride

Structure (Triprolidine hydrochloride)

• Triprolidine hydrochloride features a piperidine ring substituted with a dimethylamino group and a propyl chain linked to a benzene ring.

• The hydrochloride salt enhances solubility.

• Chemical Formula: C₁₄H₂₀ClN₃·HCl

Structure Triprolidine hydrochloride

Mode of Action

• Acts as an H₁-receptor antagonist with anticholinergic and sedative properties.

• It inhibits histamine-mediated allergic responses.

Uses

• Allergic rhinitis

• Urticaria

• Cold symptoms

• Cough suppression

Structure-Activity Relationship (SAR)

1. Aromatic Rings: Facilitate binding to H₁ receptors through hydrophobic interactions.

2. Dimethylamino Group: Enhances affinity for H₁ receptors and contributes to CNS effects.

3. Propyl Chain: Increases lipophilicity, aiding in receptor binding.

4. Piperidine Ring: Provides structural rigidity necessary for receptor interaction.

Synthesis

• Triprolidine can be synthesized by alkylating a piperidine derivative with an appropriate benzyl chloride.

Synthetic Route:

Triprolidine can be synthesized through the following steps:

1. Starting Material: Piperidine is reacted with an aromatic aldehyde in a condensation reaction to form a Schiff base.

2. Reduction: The Schiff base is reduced using a suitable reducing agent (e.g., hydrogenation) to yield the corresponding amine.

3. Alkylation: The amine is alkylated with a propyl halide to introduce the propyl chain.

4. Salt Formation: The free base is converted to its hydrochloride salt by reaction with hydrochloric acid.