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I117

Sigma-Aldrich

R(+)-IAA-94

≥98% (HPLC), solid

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Synonym(s):
Indanyloxyacetic acid 94, R(+)-Methylindazone, R(+)-[(6,7-Dichloro-2-cyclopentyl-2,3-dihydro-2-methyl-1-oxo-1H-inden-5-yl)-oxy]acetic acid
Empirical Formula (Hill Notation):
C17H18Cl2O4
CAS Number:
54197-31-8
Molecular Weight:
357.23
PubChem Substance ID:
24277844
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

optical activity

[α]22/D +36.4°, c = 0.86 in methanol(lit.)

color

white

solubility

H2O: 0.2 mg/mL
0.1 M NaOH: 2.8 mg/mL
DMSO: >20 mg/mL
ethanol: 20 mg/mL
dilute aqueous acid: insoluble

storage temp.

2-8°C

SMILES string

C[C@@]1(Cc2cc(OCC(O)=O)c(Cl)c(Cl)c2C1=O)C3CCCC3

InChI

1S/C17H18Cl2O4/c1-17(10-4-2-3-5-10)7-9-6-11(23-8-12(20)21)14(18)15(19)13(9)16(17)22/h6,10H,2-5,7-8H2,1H3,(H,20,21)/t17-/m1/s1

InChI key

RNOJGTHBMJBOSP-QGZVFWFLSA-N

Application

R(+)-IAA-94 has been used as a chloride ion channel inhibitor to study its effects on grepafloxacin uptake by human mononuclear (THP-1) cells . It has also been used as a chloride ion channel inhibitor to study its effects on moxifloxacin uptake by human mononuclear (THP-1) cells.

Features and Benefits

This compound is featured on the Chloride Channels page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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Indanyloxyacetic acid-sensitive chloride channels from outer membranes of skeletal muscle.
Weber-Schurholz S, et al.
The Journal of Biological Chemistry, 268(9), 547-551 (1993)
Influence of T-type Ca2+ (mibefradil) and Cl- (indanyloxyacetic acid 94) channel antagonists on ?1-adrenoceptor mediated contractions in rat aorta.
Duggan AJ and Tabrizchi R
Canadian Journal of Physiology and Pharmacology, 78(9), 714-720 (2000)
Federica Barbieri et al.
Frontiers in pharmacology, 9, 899-899 (2018-09-07)
The antidiabetic biguanide metformin exerts antiproliferative effects in different solid tumors. However, during preclinical studies, metformin concentrations required to induce cell growth arrest were invariably within the mM range, thus difficult to translate in a clinical setting. Consequently, the search
Disposition and intracellular levels of moxifloxacin in human THP-1 monocytes in unstimulated and stimulated conditions
Hall I H, et al.
International Journal of Antimicrobial Agents, 22(6), 579-587 (2003)
Michelle Batthish et al.
Cardiovascular research, 55(3), 660-671 (2002-08-06)
We have recently proposed that chloride (Cl(-)) channels contribute to ischemic preconditioning (IPC) in the myocardium. To further evaluate this hypothesis, we investigated the role of Cl(-) channels in pharmacological preconditioning. Isolated rabbit cardiomyocytes and isolated buffer-perfused rabbit hearts were
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