A calcimimetic and CaSR agonist
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Small Molecule Modulators
Receptor Pharmacology
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Research Area

Calindol (hydrochloride)

Item No. 17575

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
N-[(1R)-1-(1-naphthalenyl)ethyl]-1H-indole-2-methanamine, monohydrochloride
CAS Number
729610-18-8
Molecular Formula
C21H20N2 • HCl
Formula Weight
336.9
Purity
≥98%
Formulation
A crystalline solid
Solubility(Learn about Variance in Solubility)
DMF: 50 mg/mlDMSO: 50 mg/mlDMSO:PBS (pH 7.2) (1:2): 0.3 mg/mlEthanol: 15 mg/ml
λmax
224, 272, 282 nm
SMILES
C[C@H](C1=C(C=CC=C2)C2=CC=C1)NCC3=CC4=CC=CC=C4N3.Cl
InChi Code
InChI=1S/C21H20N2.ClH/c1-15(19-11-6-9-16-7-2-4-10-20(16)19)22-14-18-13-17-8-3-5-12-21(17)23-18;/h2-13,15,22-23H,14H2,1H3;1H/t15-;/m1./s1
InChi Key
KFILKQPBQZIRST-XFULWGLBSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    1 mg

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    Product Description

    Calindol is a phenylalkylamine calcimimetic that facilitates the activation of the calcium-sensing receptor (CaSR), a G protein-coupled receptor that triggers phosphatidylinositol (PI)-intracellular calcium signaling and, in some cell types, cell proliferation.1 It potently stimulates PI hydrolysis and proliferation through human CaSR (pEC50 values are 6.9 and 7.4, respectively) in the presence of calcium.2 Calindol directly interacts with CaSR in transmembrane domains and triggers PI hydrolysis less effectively in the absence of calcium, indicating that it is an allosteric modulator that cooperates with calcium to activate the CaSR.2,3,4 Calindol is used to study the properties and distribution of CaSR in different types of cells and tissues.4,5

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Kessler, A., Faure, H., Petrel, C., et al. N2-benzyl-N1-(1-(1-naphthyl)ethyl)-3-phenylpropane-1,2-diamines and conformationally restrained indole analogues: Development of calindol as a new calcimimetic acting at the calcium sensing receptor. Bioorg. Med. Chem. Lett. 14(12), 3345-3349 (2004).

    2. Ma, J.N., Owens, M., Gustafsson, M., et al. Characterization of highly efficacious allosteric agonists of the human calcium-sensing receptor. J. Pharmacol. Exp. Ther. 337(1), 275-284 (2011).

    3. Petrel, C., Kessler, A., Dauban, P., et al. Positive and negative allosteric modulators of the Ca2+-sensing receptor interact within overlapping but not identical binding sites in the transmembrane domain. The Journal of Biological Chemisty 279(18), 18990-18997 (2004).

    4. Ray, K., Tisdale, J., Dodd, R.H., et al. Calindol, a positive allosteric modulator of the human Ca2+ receptor, activates an extracellular ligand-binding domain-deleted rhodopsin-like seven-transmembrane structure in the absence of Ca2+. The Journal of Biological Chemisty 280(44), 37013-37020 (2005).

    5. Weston, A.H., Absi, M., Ward, D.T., et al. Evidence in favor of a calcium-sensing receptor in arterial endothelial cells: Studies with calindol and Calhex 231. Circ. Res. 97(4), 391-398 (2005).