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SML2160

Sigma-Aldrich

R-568 hydrochloride

≥95% (HPLC)

Synonym(s):

2-chloro-N-[(1R)-1-(3-methoxyphenyl)ethyl]-benzenepropanamine hydrochloride (1:1), KRN 568 hydrochloride, NPS-R 568 hydrochloride, Norcalcin hydrochloride, R 568 hydrochloride, Tecalcet hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C18H22ClNO · HCl
CAS Number:
177172-49-5
Molecular Weight:
340.29
MDL number:
MFCD16038895
UNSPSC Code:
12352200
NACRES:
NA.77

Key Documents

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assay

≥95% (HPLC)

form

powder

optical activity

[α]/D +35 to +40°, c = 0.5 in chloroform-d

storage condition

desiccated

color

white to beige

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

SMILES string

C[C@@H](NCCCC1=C(C=CC=C1)Cl)C2=CC=CC(OC)=C2.Cl

InChI

1S/C18H22ClNO.ClH/c1-14(16-8-5-10-17(13-16)21-2)20-12-6-9-15-7-3-4-11-18(15)19;/h3-5,7-8,10-11,13-14,20H,6,9,12H2,1-2H3;1H/t14-;/m1./s1

InChI key

YJXUXANREVNZLH-PFEQFJNWSA-N

Biochem/physiol Actions

Calcium-sensing receptor (CaSR) allosteric agonist; calcimimetic
R-568 is a positive allosteric modulator of the calcium-sensing receptor (CaSR), increasing the sensitivity to activation by extracellular Ca2+. In rats, orally administered R-568 decreases plasma levels of PTH and Ca2+ and, at higher doses, increases plasma levels of calcitonin.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

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Jenny Ying Lin Lu et al.
The Journal of pharmacology and experimental therapeutics, 331(3), 775-786 (2009-09-18)
Over 257 mutations in the human calcium-sensing receptor (hCaSR) gene have been reported. Heterozygous inactivating mutations can result in familial hypocalciuric hypercalcemia (FHH), whereas homozygous inactivating mutations can cause life-threatening neonatal severe hyperparathyroidism (NSHPT). Activating mutations in the hCaSR can
Fanny Bery et al.
Cancers, 12(4) (2020-04-08)
The mechanisms underlying neuroendocrine (NE) differentiation in prostate cancer (PCa) remain mostly uncharacterized. Since a deregulated calcium homeostasis has been reported in neuroendocrine prostate cancer (NEPC), we explored herein the link between NE differentiation and the calcium-sensing receptor (CaSR). CaSR
Asuka Masumoto et al.
Journal of atherosclerosis and thrombosis, 24(7), 716-724 (2016-11-15)
Vascular calcification (VC) is a risk factor of cardiovascular and all-cause mortality in patients with chronic kidney disease (CKD). CKD-mineral and bone metabolism disorder is an important problem in patients with renal failure. Abnormal levels of serum phosphate and calcium
Abhishek Aggarwal et al.
Biochimica et biophysica acta, 1853(9), 2158-2167 (2015-02-24)
The inverse correlation between dietary calcium intake and the risk of colorectal cancer (CRC) is well known, but poorly understood. Expression of the calcium-sensing receptor (CaSR), a calcium-binding G protein-coupled receptor is downregulated in CRC leading us to hypothesize that

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