| Identification | Back Directory | [Name]
Gepirone | [CAS]
83928-76-1 | [Synonyms]
GEPIRONE
Gepirona
Gepironum
Gepirone er
Gepirone HCl
Gepirone [inn]
Gepironum [latin]
Gepirona [spanish]
ORG-13011(Gepirone)
Gepirone(ORG-13011)
83928-66-9 (Mono-hydrochloride)
4,4-Dimethyl-1-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-2,6-piperidinedione
4,4-Dimethyl-1-(4-(4-(pyrimidin-2-yl)piperazin-1-yl)butyl)piperidine-2,6-dione
2,6-Piperidinedione, 4,4-dimethyl-1-(4-(4-(2-pyrimidinyl)-1-piperazinyl)butyl)- | [Molecular Formula]
C19H29N5O2 | [MDL Number]
MFCD00868196 | [MOL File]
83928-76-1.mol | [Molecular Weight]
359.47 |
| Chemical Properties | Back Directory | [Melting point ]
106-108°C | [Boiling point ]
562.3±60.0 °C(Predicted) | [density ]
1.142±0.06 g/cm3 (20 ºC 760 Torr) | [storage temp. ]
under inert gas (nitrogen or Argon) at 2-8°C | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
7.72±0.10(Predicted) | [color ]
Off-White to Pale Yellow | [InChI]
InChI=1S/C19H29N5O2/c1-19(2)14-16(25)24(17(26)15-19)9-4-3-8-22-10-12-23(13-11-22)18-20-6-5-7-21-18/h5-7H,3-4,8-15H2,1-2H3 | [InChIKey]
QOIGKGMMAGJZNZ-UHFFFAOYSA-N | [SMILES]
N1(CCCCN2CCN(C3=NC=CC=N3)CC2)C(=O)CC(C)(C)CC1=O |
| Hazard Information | Back Directory | [Description]
Gepirone is a chemical analogue of buspirone and also acts as a partial agonist at 5-HT1A receptors. It is active in animal models predictive of anxiolytic action and also shows antidepressant activity in preclinical studies. With long-term administration, gepirone downregulates 5-HT2 receptors, which is a property common to nearly all antidepressant drugs (Stahl 1994). This dual action, suggesting both anxiolytic and antidepressant effects, is typical of many compounds acting at 5-HT1A receptors and may indicate that such compounds may be useful in the treatment of mixed anxiety and depression (Stahl, in press).
Preliminary phase II clinical data have shown that gepirone is an effective anxiolytic that significantly reduces both psychic and somatic symptoms of generalized anxiety disorder. Like buspirone, gepirone does not impair memory, verbal fluency, or psychomotor performance (Harto and Branconnier 1988). | [Uses]
Gepirone is an antidepressant and anxiolytic of the azapirone class. It acts as a selective partial agonist of the 5-HT1A receptor. | [Definition]
ChEBI: Gepirone is a N-arylpiperazine. | [in vivo]
Gepirone (0-3 mg/kg for intraperitoneal injection) interacts with progesterone at 5-HT1A receptors to reduce lordosis behavior in female rats treated with estradiol benzoate and progesterone[1].
Gepirone (10, 15 mg/kg for subcutaneous injection, 2, 7, or 14 days) activates the normosensitive postsynaptic 5-HT1A receptor in Male Sprague-Dawley rats[2].
| Animal Model: | Sprague-Dawley rats[1] | | Dosage: | 0, 0.1, 0.3, 1 and 3 mg/kg | | Administration: | Intraperitoneal injection (i.p.) | | Result: | Increases in lordotic activity at lower doses.
Inhibited lordosis by the 0.3 and 1.0 mg/kg doses and further inhibition was produced by the 3.0 mg/kg dose.
|
| Animal Model: | Male Sprague-Dawley rats[2] | | Dosage: | 10, 15 mg/kg | | Administration: | Subcutaneous injection (s.c.) | | Result: | Decreased the number of spontaneously active 5-HT neurons and firing rate.
Not modified with long-term treatment with ED50 value of 10.1±0.5 μg/kg in controls and 9.7 ±1.9 μg/kg
in treated rats.
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| [IC 50]
5-HT1A Receptor |
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