N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-1,3-benzodiazol-2-amine hydrochloride

• ChemBase ID: 153962
• Molecular Formular: C17H18ClN3
• Molecular Mass: 299.79792
• Monoisotopic Mass: 299.11892527
• SMILES: c1ccc2c(c1)CCC[C@H]2Nc1[nH]c2ccccc2n1.Cl
• Canonical SMILES: c1ccc2c(c1)[C@@H](CCC2)Nc1nc2c([nH]1)cccc2.Cl
• InChI: 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

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-1,3-benzodiazol-2-amine hydrochloride
• IUPAC Traditional name: N-[(1R)-1,2,3,4-tetrahydronaphthalen-1-yl]-1H-1,3-benzodiazol-2-amine hydrochloride
• Synonyms: : N-[(1R)-1,2,3,4-tetrahydro-1-naphthalenyl]-1H-Benzimidazol-2-amine hydrochloride; N-[(1R)-1,2,3,4-Tetrahydro-1-naphthalenyl]-1H-Benzimidazol-2-amine hydrochloride; NS8593 hydrochloride; NS8593 盐酸盐

Database IDs

• CAS Number: 875755-24-1
• PubChem SID: 162248101
• PubChem CID: 71311765

CALCULATED PROPERTIES

• H Donor: 2
• LogD (pH = 5.5): 2.9868622
• LogD (pH = 7.4): 4.009615
• Log P: 4.129798
• Molar Refractivity: 81.43 cm^3
• Polarizability: 32.001534 Å^3
• Polar Surface Area: 40.71 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true
• Acid pKa: 12.3818655
• H Acceptors: 2

PROPERTIES

Physical Property

• Solubility: DMSO: >10 mg/mL; H2O: insoluble
• Apperance: powder

Safety Information

• German water hazard class: 3
• GHS Hazard statements: H413
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC)
• Empirical Formula (Hill Notation): C17H17N3 · HCl

DETAILS

Sigma Aldrich - N2538

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.