144980-29-0
144980-29-0 structure
- Name: Repinotan (BAYx3702)
- Chemical Name: 2-[4-[[(2R)-3,4-dihydro-2H-chromen-2-yl]methylamino]butyl]-1,1-dioxo-1,2-benzothiazol-3-one
- CAS Number: 144980-29-0
- Molecular Formula: C21H24N2O4S
- Molecular Weight: 400.49100
- Catalog: Signaling Pathways GPCR/G Protein 5-HT Receptor
- Create Date: 2016-07-01 18:17:40
- Modify Date: 2025-08-25 18:00:59
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Repinotan (BAY x 3702 free base) is a potent, selective, brain-penetrant and orally active 5-HT1A receptor agonist, with Ki values of 0.19 nM (calf hippocampus), 0.25 nM (rat and human cortex), and 0.59 nM (rat hippocampus). Repinotan has a weak affinity for other related receptors. Repinotan has pronounced neuroprotective effects[1].
| Name | 2-[4-[[(2R)-3,4-dihydro-2H-chromen-2-yl]methylamino]butyl]-1,1-dioxo-1,2-benzothiazol-3-one |
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| Synonyms |
Repinotan [INN]
Repinotan Bay x3702 UNII-05PB82Z52L |
| Description | Repinotan (BAY x 3702 free base) is a potent, selective, brain-penetrant and orally active 5-HT1A receptor agonist, with Ki values of 0.19 nM (calf hippocampus), 0.25 nM (rat and human cortex), and 0.59 nM (rat hippocampus). Repinotan has a weak affinity for other related receptors. Repinotan has pronounced neuroprotective effects[1]. |
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| Related Catalog | |
| Target |
5-HT1A Receptor:0.19 nM (Ki, In calf hippocampus) 5-HT1A Receptor:0.25 nM (Ki, In rat and human cortex) 5-HT1A Receptor:0.59 nM (Ki, In rat hippocampus) 5-HT7 Receptor:6 nM (Ki) |
| In Vitro | Repinotan binds with lower affinity to 5-HT7 (Ki = 6 nM), α1- and α2 adrenergic (Ki = 6 nM and 7 nM, respectively), 5-HT1D (36 nM), dopamine D2 and D4 (48 nM and 91 nM, respectively), σ sites (176 nM) and 5-HT2C (310 nM) receptors[1]. Exposure to repinotan protects rat cortical and hippocampal neurons in cultures from apoptosis induced by 25 nM Staurosporine. After Staurosporine-induced apoptosis, Repinotan, at 50 pM to 1 μM, reduces the release of lactate dehydrogenase, DNA fragmentation, and apoptotic body formation in a concentration-dependent manner[1]. |
| In Vivo | Repinotan (1-100 μg/kg) causes strong, dose-dependent infarct reductions in permanent middle cerebral artery occlusion, transient middle cerebral artery occlusion, and traumatic brain injury paradigms[1]. The half-life of Repinotan in plasma is relatively short (t1/2 = 0.6 h in rat; 0.4 h in rhesus monkeys), and Repinotan is extensively metabolized[1]. |
| References |
| Density | 1.284g/cm3 |
|---|---|
| Boiling Point | 599.5ºC at 760 mmHg |
| Molecular Formula | C21H24N2O4S |
| Molecular Weight | 400.49100 |
| Flash Point | 316.4ºC |
| Exact Mass | 400.14600 |
| PSA | 84.09000 |
| LogP | 4.00430 |
| Vapour Pressure | 2.49E-14mmHg at 25°C |
| Index of Refraction | 1.603 |