| Identification | Back Directory | [Name]
NS8593 HYDROCHLORIDE | [CAS]
875755-24-1 | [Synonyms]
NS8593
NS8593 HCl
NS8593 HYDROCHLORIDE
N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-benzimidazol-2-amine
: N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]-1H-Benzimidazol-2-amine hydrochloride | [Molecular Formula]
C17H17N3.ClH | [MDL Number]
MFCD11045298 | [MOL File]
875755-24-1.mol | [Molecular Weight]
299.803 |
| Chemical Properties | Back Directory | [storage temp. ]
2-8°C | [solubility ]
DMSO: >10mg/mL | [form ]
powder | [color ]
White to off-white | [Optical Rotation]
[α]/D +54 to +62°, c =0.5 in methanol | [InChI]
1S/C17H17N3.ClH/c1-2-8-13-12(6-1)7-5-11-14(13)18-17-19-15-9-3-4-10-16(15)20-17;/h1-4,6,8-10,14H,5,7,11H2,(H2,18,19,20);1H/t14-;/m1./s1 | [InChIKey]
VWEKCDTXUUPBNA-PFEQFJNWSA-N | [SMILES]
Cl[H].C1C[C@@H](Nc2nc3ccccc3[nH]2)c4ccccc4C1 |
| Hazard Information | Back Directory | [Description]
NS 8593 is an inhibitory gating modifier of small-conductance calcium-activated potassium (KCa2/SK) channels (Kds = 0.42, 0.6, and 0.73 μM for KCa2.1/SK1, KCa2.2/SK2, and KCa2.3/SK3, respectively, in the presence of calcium) that decreases the calcium sensitivity of SK channels.1 It is selective for KCa2/SK channels over intermediate- (KCa3.1/IKCa1) and large-conductance (BK) potassium channels at 10 μM. NS 8593 induces relaxation of potassium- or acetylcholine chloride-precontracted isolated tracheal rings from wild-type mice (IC50s = 8.9 and 39.8 μM, respectively) or from mice in an ovalbumin-induced model of allergic asthma (IC50s = 16.4 and 32.2 μM, respectively).2 It inhibits aerosolized acetylcholine chloride-induced increases in respiratory system resistance in mice when administered as an aerosol at a dose of 500 μM. NS 8593 (5 mg/kg) decreases the duration of burst-pacing-induced atrial fibrillation in normotensive and spontaneously hypertensive rats.3 | [Uses]
NS8593 hydrochloride has been used to study its effect on the growth of MDA-MB-231 cells (M.D. Anderson and metastasis breast cancer cells). | [Biochem/physiol Actions]
The compound (R)-N-(benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphtylamine (NS8593) reversibly inhibited recombinant SK3-mediated currents (human and rat SK3) with potencies around 100 nM. NS8593 did not inhibit 125I-apamin binding. NS8593 decreased the calcium sensitivity by shifting the activation curve for Ca2+ to the right, only slightly affecting the maximal Ca2+-activated SK current. NS8593 inhibited all the SK1-3 subtypes Ca2+-dependently (Kd = 0.42, 0.60, and 0.73 μM, respectively, at 0.5 μM Ca2+. NS8593 did not affect the calcium-activated potassium channels of intermediate and large conductance (hIK and hBK channels, respectively). NS8593-mediated inhibition was prevented in the presence of a high concentration of the positive modulator NS309. | [in vivo]
NS8593 (compound 14) (3 and 10 mg/kg intravenously) is able to affect firing rate and firing pattern of dopaminergic neurons in vivo in C57Bl/6 mice[1]. | [storage]
Store at +4°C | [References]
[1] DORTE STR?BAEK. Inhibitory gating modulation of small conductance Ca2+-activated K+ channels by the synthetic compound (R)-N-(benzimidazol-2-yl)-1,2,3,4-tetrahydro-1-naphtylamine (NS8593) reduces afterhyperpolarizing current in hippocampal CA1 neurons.[J]. Molecular Pharmacology, 2006, 70 5: 1771-1782. DOI: 10.1124/mol.106.027110
[2] BEI-BEI LIU . NS8593 inhibits Ca2+ permeant channels reversing mouse airway smooth muscle contraction[J]. Life sciences, 2019, 238: Article 116953. DOI: 10.1016/j.lfs.2019.116953
[3] JONAS G DINESS. Effects on atrial fibrillation in aged hypertensive rats by Ca(2+)-activated K(+) channel inhibition.[J]. Hypertension, 2011, 57 6: 1129-1135. DOI: 10.1161/hypertensionaha.111.170613 |
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