Ipsapirone | CAS#95847-70-4 | 5HT1A agonist

Ipsapirone
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WARNING: This product is for research use only, not for human or veterinary use.

MedKoo CAT#: 562321

CAS#: 95847-70-4 (free base)

Description: Ipsapirone, also known as BAY q 7821, is a new pyrimidinylpiperazine ligand potent and specific for 5-HT1A receptors. Ipsapirone hydrochloride has potential therapeutic use in affective disorders.

Chemical Structure

Ipsapirone

CAS# 95847-70-4 (free base)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 562321
Name: Ipsapirone
CAS#: 95847-70-4 (free base)
Chemical Formula: C19H23N5O3S
Exact Mass: 401.15
Molecular Weight: 401.485
Elemental Analysis: C, 56.84; H, 5.77; N, 17.44; O, 11.95; S, 7.99

Price and Availability

Size	Price	Availability
25mg	USD 250	2 Weeks
50mg	USD 450	2 Weeks
100mg	USD 750	2 Weeks
200mg	USD 1250	2 Weeks
500mg	USD 2650	2 Weeks
1g	USD 4250	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 92589-98-5 (HCl) 95847-70-4 (free base)

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

Appearance: Solid powder

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

More Info:

Product Data:

Product Data

Instruction:

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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/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMF	10.0	24.91
	DMSO	12.0	29.90
	DMSO:PBS (pH 7.2) (1:40)	0.0	0.06

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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