Synonym
BAY q 7821; BAY q-7821; BAY q7821; Ipsapirone
IUPAC/Chemical Name
1,1-Dioxo-2-[4-(4-pyrimidin-2-ylpiperazin-1-yl)butyl]-1,2-benzothiazol-3-one
InChi Key
TZJUVVIWVWFLCD-UHFFFAOYSA-N
InChi Code
InChI=1S/C19H23N5O3S/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
SMILES Code
O=C(C1=CC=CC=C12)N(CCCCN3CCN(C4=NC=CC=N4)CC3)S2(=O)=O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
Biological target:
Ipsapirone (TVX Q 7821) is an anxiolytic compound and a 5-HT1A receptor partial agonist. Ipsapirone (TVX Q 7821) also exhibits 5-HT1A receptor antagonistic effect, and only at high doses it can also produce an inhibitory effect on 5-HT2 and the α1-adrenergic function.
In vitro activity:
Perfusion with ipsapirone (100 nM, 10 min) inhibited the firing rate of DRN 5-HT cells (maximal change in the firing rate: 94.49 ± 3.34%, n = 13) (Figures 2C,E).
Reference: Front Pharmacol. 2022 Sep 6;13:956886. https://pubmed.ncbi.nlm.nih.gov/36147343/
In vivo activity:
The effects of ipsapirone, a ligand of the 5-HT1A receptors and a new potential anxiolytic, on sleep/wakefulness regulation were examined in the rat. The effects of ipsapirone (3 mg kg-1) persisted after infusion of the neurotoxin 5,7-dihydroxytryptamine into the dorsal raphe nucleus which induced the sub-total destruction of the serotoninergic system.
Reference: J Sleep Res. 1993 Jun;2(2):103-109. https://pubmed.ncbi.nlm.nih.gov/10607079/
|
Solvent |
mg/mL |
mM |
| Solubility |
| DMF |
10.0 |
24.91 |
| DMSO |
12.0 |
29.90 |
| DMSO:PBS (pH 7.2) (1:40) |
0.0 |
0.06 |
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
401.49
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Mendiguren A, Aostri E, Alberdi E, Pérez-Samartín A, Pineda J. Functional characterization of cannabidiol effect on the serotonergic neurons of the dorsal raphe nucleus in rat brain slices. Front Pharmacol. 2022 Sep 6;13:956886. doi: 10.3389/fphar.2022.956886. PMID: 36147343; PMCID: PMC9485894.
2. Borroto-Escuela DO, Li X, Tarakanov AO, Savelli D, Narváez M, Shumilov K, Andrade-Talavera Y, Jimenez-Beristain A, Pomierny B, Díaz-Cabiale Z, Cuppini R, Ambrogini P, Lindskog M, Fuxe K. Existence of Brain 5-HT1A-5-HT2A Isoreceptor Complexes with Antagonistic Allosteric Receptor-Receptor Interactions Regulating 5-HT1A Receptor Recognition. ACS Omega. 2017 Aug 31;2(8):4779-4789. doi: 10.1021/acsomega.7b00629. Epub 2017 Aug 22. PMID: 28920103; PMCID: PMC5597955.
3. Tissier MH, Lainey E, Fattaccini CM, Hamon M, Adrien J. Effects of ipsapirone, a 5-HT1A agonist, on sleep/wakefulness cycles: probable post-synaptic action. J Sleep Res. 1993 Jun;2(2):103-109. doi: 10.1111/j.1365-2869.1993.tb00070.x. PMID: 10607079.
4. Korte SM, Bouws GA, Koolhaas JM, Bohus B. Neuroendocrine and behavioral responses during conditioned active and passive behavior in the defensive burying/probe avoidance paradigm: effects of ipsapirone. Physiol Behav. 1992 Aug;52(2):355-61. doi: 10.1016/0031-9384(92)90284-9. PMID: 1355919.
In vitro protocol:
1. Mendiguren A, Aostri E, Alberdi E, Pérez-Samartín A, Pineda J. Functional characterization of cannabidiol effect on the serotonergic neurons of the dorsal raphe nucleus in rat brain slices. Front Pharmacol. 2022 Sep 6;13:956886. doi: 10.3389/fphar.2022.956886. PMID: 36147343; PMCID: PMC9485894.
2. Borroto-Escuela DO, Li X, Tarakanov AO, Savelli D, Narváez M, Shumilov K, Andrade-Talavera Y, Jimenez-Beristain A, Pomierny B, Díaz-Cabiale Z, Cuppini R, Ambrogini P, Lindskog M, Fuxe K. Existence of Brain 5-HT1A-5-HT2A Isoreceptor Complexes with Antagonistic Allosteric Receptor-Receptor Interactions Regulating 5-HT1A Receptor Recognition. ACS Omega. 2017 Aug 31;2(8):4779-4789. doi: 10.1021/acsomega.7b00629. Epub 2017 Aug 22. PMID: 28920103; PMCID: PMC5597955.
In vivo protocol:
1. Tissier MH, Lainey E, Fattaccini CM, Hamon M, Adrien J. Effects of ipsapirone, a 5-HT1A agonist, on sleep/wakefulness cycles: probable post-synaptic action. J Sleep Res. 1993 Jun;2(2):103-109. doi: 10.1111/j.1365-2869.1993.tb00070.x. PMID: 10607079.
2. Korte SM, Bouws GA, Koolhaas JM, Bohus B. Neuroendocrine and behavioral responses during conditioned active and passive behavior in the defensive burying/probe avoidance paradigm: effects of ipsapirone. Physiol Behav. 1992 Aug;52(2):355-61. doi: 10.1016/0031-9384(92)90284-9. PMID: 1355919.
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