| Identification | More | [Name]
2-AMINO-BETA-NAPHTHOTHIAZOLE | [CAS]
40172-65-4 | [Synonyms]
SKA 31
-2-amine
AKOS BBS-00006561
IFLAB-BB F1386-0401
naphtho[1,2-d]thiazoL
LABOTEST-BB LT00154570
2-Amino-β-naphthothiazole
2-AMINONAPHTHO-1,2-THIAZOLE
2-AMINO-BETA-NAPHTHOTHIAZOLE
naphtho[1,2-d]thiazol-2-amine
2-AMINO-NAPHTHO[1,2-D]THIAZOLE
NAPHTHO[1,2-D]THIAZOL-2-YLAMINE
Naphtho[1,2-d]thiazol-2(1H)-imine
benzo[e][1,3]benzothiazol-2-amine
NAPHTHO[1,2-D][1,3]THIAZOL-2-AMINE
Naphtho[1,2-d]thiazol-2-amine (9CI)
2-(2-amino-5,6-dihydro-4H-pyrimidin-1-yl)acetic acid | [EINECS(EC#)]
254-822-1 | [Molecular Formula]
C11H8N2S | [MDL Number]
MFCD00051329 | [Molecular Weight]
200.26 | [MOL File]
40172-65-4.mol |
| Chemical Properties | Back Directory | [Melting point ]
184-188°C | [Boiling point ]
417.1±28.0 °C(Predicted) | [density ]
1.403±0.06 g/cm3(Predicted) | [storage temp. ]
Keep in dark place,Sealed in dry,2-8°C | [solubility ]
DMSO: ≥30mg/mL | [form ]
solid | [pka]
3.50±0.30(Predicted) | [color ]
Off-white | [Stability:]
Stable for 1 year as supplied. Solutions in DMSO may be stored at -20°C for up to 2 months. | [InChI]
1S/C11H8N2S/c12-11-13-10-8-4-2-1-3-7(8)5-6-9(10)14-11/h1-6H,(H2,12,13) | [InChIKey]
FECQXVPRUCCUIL-UHFFFAOYSA-N | [SMILES]
Nc1nc2c(ccc3ccccc23)s1 | [CAS DataBase Reference]
40172-65-4(CAS DataBase Reference) | [EPA Substance Registry System]
Naphtho[1,2-d]thiazol-2-amine (40172-65-4) |
| Safety Data | Back Directory | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin . | [Safety Statements ]
S22:Do not breathe dust .
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection . | [WGK Germany ]
WGK 3 | [TSCA ]
TSCA listed | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Oral
Eye Irrit. 2 |
| Hazard Information | Back Directory | [Description]
SKA-31 (40172-65-4) is a KCa3.1 and KCa2 potassium channel activator (EC50 =260, 2900, 2900 nM for KCa3.1, KCa2.1 and KCa2.2 respectively). Enhanced acetylcholine-induced EDHF dilator response in mouse carotid arteries and lowers blood pressure in mouse models at 30 mg/Kg.1,2 Evokes robust vasodilation in rat mesenteric arteries.3 | [Uses]
SKA-31 is a potent potassium channel activator with EC50s of 260 nM, 1.9 μM, 2.9 μM, and 2.9 μM for KCa3.1, KCa2.2, KCa2.1 and KCa2.3, respectively. SKA-31 potentiates endothelium-derived hyperpolarizing factor response and lowers blood pressure[1]. | [Biological Activity]
Activator of K Ca 3.1 and K Ca 2 channels (EC 50 values are 260, 2900, 2900 nM for K Ca 3.1, K Ca 2.1 and K Ca 2.2 respectively). Potentiates acetylcholine-induced EDHF-type dilations of mouse carotid arteries and lowers blood pressure in normotensive and hypertensive mice. | [in vivo]
SKA-31 is not acutely toxic and has good pharmacokinetic properties[1].
SKA-31 potentiates native KCa3.1 and KCa2.3 in murine carotid endothelium with EC50 values of 225 nM and 1.6 μM for KCa3.1 and KCa2.3, respectively[1].
SKA-31 stimulates KCa3.1 and KCa2.3 in vascular endothelial cells and increases acetylcholine-induced endothelium-derived hyperpolarizing factor (EDHF) -mediated vasodilation[1].
SKA-31 potentiates EDHF-type vasodilations and lowers blood pressure in mice. Injections of SKA-31 (1-30 mg/kg; i.p.) lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-)[1].
| Animal Model: | 16-25 weeks mice[1] | | Dosage: | 1 mg/kg, 10 mg/kg, and 30 mg/kg | | Administration: | Intraperitoneal injection | | Result: | Lower MAP over 24 hours in normotensive wild-type mice but not in KCa3.1(-/-) mice (-/-). |
| [storage]
+4°C | [References]
Sankaranaravanan et al. (2009), Naphtho[1,2-d]thiazol-2-ylamine (SKA-31), a new activator of KCa2 and KCa3.1 potassium channels, potentiates the endothelium-derived hyperpolarizing factor response and lowers blood pressure; Mol. Pharmacol., 75 281
Brahler et al. (2009), Genetic deficit of SK3 and IK1 channels disrupts the endothelium-derived hyperpolarizing factor vasodilator and causes hypertension ; Circulation, 119 2323
Khaddaj-Mallat al. (2018), SKA-31, an activator of endothelial Ca2+-activated K+ channels evokes robust vasodilation in rat mesenteric arteries; Eur. J. Pharmacol., 831 60 |
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