A partial agonist of serotonin 5-HT1A receptors
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Active Metabolite(s)
340912-(1-Piperazinyl)pyrimidine
Alternative(s)
39918Ipsapirone
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Ipsapirone (hydrochloride)

Item No. 22075

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-[4-[4-(2-pyrimidinyl)-1-piperazinyl]butyl]-1,2-benzisothiazol-3(2H)-one, 1,1-dioxide, monohydrochloride
CAS Number
92589-98-5
Synonyms
  • TVXQ 7821
Molecular Formula
C19H23N5O3S • HCl
Formula Weight
437.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 10 mg/mlDMSO: 20 mg/mlDMSO:PBS (pH 7.2) (1:40): 0.025 mg/mlEthanol: Slightly soluble
λmax
236, 284 nm
SMILES
O=S1(N(CCCCN2CCN(C3=NC=CC=N3)CC2)C(C4=C1C=CC=C4)=O)=O.Cl
InChi Code
InChI=1S/C19H23N5O3S.ClH/c25-18-16-6-1-2-7-17(16)28(26,27)24(18)11-4-3-10-22-12-14-23(15-13-22)19-20-8-5-9-21-19;/h1-2,5-9H,3-4,10-15H2;1H
InChi Key
USDUGJXCPKBJTN-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    5 mg

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    25 mg

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    Product Description

    Ipsapirone is a partial agonist of the serotonin (5-HT) receptor 5-HT1A (Ki = 10 nM in hippocampal membranes).1 It reduces 5-HT release in rat ventral hippocampus in vivo.2 Low doses of ipsapirone decrease, while high doses increase, extracellular dopamine release in murine nucleus accumbens.3 Extracellular dopamine levels in murine striatum increase following administration of ipsapirone at concentrations >0.1 mg/kg. Ipsapirone has anxiolytic effects in vivo, inhibiting foot shock-induced aggression and passive avoidance behavior in rats (ED50s = 2.2 and 0.5 mg/kg, respectively).4 Formulations containing ipsapirone have been used to treat depression and borderline personality disorder.5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Glaser, T., and Traber, J. Binding of the putative anxiolytic TVX Q 7821 to hippocampal 5-hydroxytryptamine (5-HT) recognition sites. Naunyn Schmiedebergs Arch. Pharmacol. 329(3), 211-215 (1985).

    2. Sharp, T., Bramwell, S.R., and Grahame-Smith, D.G. 5-HT1 agonists reduce 5-hydroxytryptamine release in rat hippocampus in vivo as determined by brain microdialysis. Br. J. Pharmacol. 96(2), 283-290 (1989).

    3. Ichikawa, J., and Meltzer, H.Y. The effect of ipsapirone and S(−)-pindolol on dopamine release in rat striatum and nucleus accumbens. Brain Res. 842(2), 445-451 (1999).

    4. Traber, J., Davies, M.A., Dompert, W.U., et al. Brain serotonin receptors as a target for the putative anxiolytic TVX Q 7821. Brain Res. Bull. 12(6), 741-744 (1984).

    5. Rausch, J.L., Johnson, M.E., Kasik, K.E., et al. Temperature regulation in depression: Functional 5HT1A receptor adaptation differentiates antidepressant response. Neuropsychopharmacology 31(10), 2274-2280 (2006).