Gepirone Hydrochloride

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Cat Number

API0232162

CAS Number

83928-66-9

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Product Detail Description Customer Q&A

CAS Number

83928-66-9

Storage

Store at room temperature

Synonyms

Gepirone HCl; Travivo; Exxua; Gepirone ER; BMY 13805-1; Org 33062

Molecular Formula

C19H30ClN5O2

Molecular Weight

395.9

Smiles

CC1(CC(=O)N(C(=O)C1)CCCCN2CCN(CC2)C3=NC=CC=N3)C.Cl

Appearance

White to off-white crystalline powder

Melting Point

106-108°C

Boiling Point

562.3±60.0°C at 760 mmHg (Predicted)

Relative Density

1.142±0.06

General Description

Gepirone hydrochloride is an azapirone derivative structurally related to buspirone, acting as a selective serotonin 5-HT1A receptor partial agonist. Its chemical structure contains a pyrimidinylpiperazine and a bicyclic imide moiety. Unlike buspirone, gepirone has no significant affinity for dopamine D2 receptors. The hydrochloride salt enhances solubility. Gepirone is a selective serotonin modulator with minimal benzodiazepine-like or sedative properties.

Mechanism of Action

Gepirone acts as a partial agonist at presynaptic and postsynaptic 5-HT1A receptors. At presynaptic (somatodendritic) autoreceptors in the raphe nuclei, it reduces serotonergic firing (acute effect). After chronic administration, these autoreceptors desensitize, leading to increased postsynaptic 5-HT1A activation and enhanced serotonergic transmission in forebrain regions. This delayed onset of increased serotonin activity is thought to produce antidepressant effects without the sexual side effects of SSRIs.

Application

Gepirone is indicated for the treatment of major depressive disorder (MDD) in adults. It has been investigated for generalized anxiety disorder (GAD) as well. Unlike SSRIs, gepirone does not commonly cause sexual dysfunction, weight gain, or sleep disturbances. The drug is metabolized primarily by CYP3A4, and its absorption is markedly increased by food, requiring consistent administration with meals.

Does Gepirone Hydrochloride require protection from moisture during storage?

Yes, it is hygroscopic and readily absorbs moisture, leading to caking and potential hydrolysis. Store in tightly sealed, moisture-proof containers with desiccant.

What is the recommended storage temperature for Gepirone Hydrochloride?

Store at controlled room temperature (15-25°C). Avoid excessive heat above 30°C, which can accelerate oxidative degradation of the pyrimidine ring.

Is Gepirone Hydrochloride stable in extended-release tablet formulations?

Yes, when formulated with moisture-protective coatings and packaged in blisters.

How is the impurity gepirone 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.