2-Amino-beta-naphthothiazole

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2-Amino-beta-naphthothiazole manufacturers

  • SKA-31
  • SKA-31 pictures
  • $30.00
  • 2026-08-08
  • CAS:40172-65-4
  • Purity: 99.38%
  • Supply Ability: 10g
2-Amino-beta-naphthothiazole Basic information
Product Name:2-Amino-beta-naphthothiazole
Synonyms:NAPHTHO[1,2-D][1,3]THIAZOL-2-AMINE;NAPHTHO[1,2-D]THIAZOL-2-YLAMINE;2-AMINO-NAPHTHO[1,2-D]THIAZOLE;2-AMINONAPHTHO-1,2-THIAZOLE;AKOS BBS-00006561;IFLAB-BB F1386-0401;LABOTEST-BB LT00154570;naphtho[1,2-d]thiazol-2-amine
CAS:40172-65-4
MF:C11H8N2S
MW:200.26
EINECS:254-822-1
Product Categories:BENZOTHIAZOLE
Mol File:40172-65-4.mol
2-Amino-beta-naphthothiazole Structure
2-Amino-beta-naphthothiazole Chemical Properties
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
pka3.50±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.
InChI1S/C11H8N2S/c12-11-13-10-8-4-2-1-3-7(8)5-6-9(10)14-11/h1-6H,(H2,12,13)
InChIKeyFECQXVPRUCCUIL-UHFFFAOYSA-N
SMILESNc1nc2c(ccc3ccccc23)s1
CAS DataBase Reference40172-65-4(CAS DataBase Reference)
EPA Substance Registry SystemNaphtho[1,2-d]thiazol-2-amine (40172-65-4)
Safety Information
Hazard Codes Xn
Risk Statements 20/21/22-36/37/38-36-22
Safety Statements 22-36/37/39-26
WGK Germany WGK 3
TSCA TSCA listed
Storage Class11 - Combustible Solids
Hazard ClassificationsAcute Tox. 4 Oral
Eye Irrit. 2
MSDS Information
2-Amino-beta-naphthothiazole Usage And Synthesis
DescriptionSKA-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
UsesSKA-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 ActivityActivator 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[1] ANANTHAKRISHNAN SANKARANARAYANAN. 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.[J]. Molecular Pharmacology, 2009, 75 2: 281-295. DOI:10.1124/mol.108.051425
[2] SEBASTIAN BRÄHLER. Genetic deficit of SK3 and IK1 channels disrupts the endothelium-derived hyperpolarizing factor vasodilator pathway and causes hypertension.[J]. Circulation, 2009, 119 17: 2323-2332. DOI:10.1161/circulationaha.108.846634
[3] RAYAN KHADDAJ-MALLAT  Andrew P B  Cini Mathew John. SKA-31, an activator of endothelial Ca2+-activated K+ channels evokes robust vasodilation in rat mesenteric arteries[J]. European journal of pharmacology, 2018, 831: Pages 60-67. DOI:10.1016/j.ejphar.2018.05.006
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