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Name	Cinacalcet	EINECS	682-701-7
CAS No.	226256-56-0	Density	1.154 g/cm³
PSA	12.03000	LogP	6.53290
Solubility	N/A	Melting Point	N/A
Formula	C₂₂H₂₂F₃N	Boiling Point	440.9 °C at 760 mmHg
Molecular Weight	357.419	Flash Point	220.5 °C
Transport Information	N/A	Appearance	yellow oil
Safety		Risk Codes	N/A
Molecular Structure		Hazard Symbols	N/A
Synonyms	AMG073;Cinacalcet;	Article Data	61

Cinacalcet Synthetic route

: 1073144-62-3
(1R)-1-(naphthalen-1-yl)ethanamine (R)-mandelate

: 21172-43-0
methylsulfonyl-3-(3-trifluoromethylphenyl)propyl ester

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With potassium carbonate In water at 60 - 65℃; for 20h;	100%

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 78573-45-2
3-[3-(trifluoromethyl)phenyl]propan-1-ol

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; D-sorbitol; choline chloride at 60℃; for 12h;	98%
Stage #1: 3-[3-(trifluoromethyl)phenyl]propan-1-ol With 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; [bis(acetoxy)iodo]benzene In dichloromethane at 20℃; for 2h; Stage #2: (R)-1-(1-Naphthyl)ethylamine With sodium tris(acetoxy)borohydride In dichloromethane optical yield given as %ee;	84%
With bis[dichloro(pentamethylcyclopentadienyl)iridium(III)]; sodium hydrogencarbonate In toluene at 110℃; for 17h; Inert atmosphere; Sealed tube;	75%
With C19H22MnN3O3P(1+); potassium hydride In 1,2-dimethoxyethane at 100℃; for 48h; Glovebox; Sealed tube; Inert atmosphere;	50%

: 364782-34-3
cinacalcet hydrochloride

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium carbonate In dichloromethane; water	96%
With water; sodium carbonate In di-isopropyl ether at 25℃; for 2.25h; pH=9.5;

: (R)-cinacalcet (-)-di-para-D-toluoyl tartrate

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With sodium hydroxide In dichloromethane; water for 0.5h; pH=9 - 10;	96%

: 98-08-8
α,α,α-trifluorotoluene

: (R)-3-bromo-N-(1-(naphthalen-1-yl)ethyl)propan-1-amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With aluminum (III) chloride In dichloromethane at 0℃; for 2h;	95.6%

: (R)-α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl-2-ene]-1-naphthalenemethaneamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In ethanol under 1520.1 Torr; for 2h; Pressure;	95%
With hydrogen; palladium on activated carbon In methanol for 14h; Product distribution / selectivity;	90%
With hydrogen; 5%-palladium/activated carbon In toluene at 10 - 30℃; under 152.01 - 1140.08 Torr; Industry scale;	79.4%

: 1201910-95-3
(R)-N-[3-[3-(trifluoromethyl)phenyl]-2-propenylimino]-N-[1-(1-naphthyl)ethylamine]

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogen In ethanol at 80℃; under 7500.75 Torr; for 3h; High pressure;	95%

: 566938-58-7
1-(3-iodopropyl)-3-(trifluoromethyl)benzene

: 3886-70-2
(R)-1-(1-Naphthyl)ethylamine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With potassium carbonate In acetonitrile at 70℃; for 12h;	95%

: (R)-3-(1-(naphthalen-1-yl)ethylamino)-1-(3-(trifluoromethyl)phenyl)propan-1-one

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With hydrogenchloride; zinc In water at 20℃; pH=< 1;	94.1%
With hydrazine hydrate; potassium hydroxide In ethanol at 90 - 180℃; for 2h; Solvent;	83.5%

: 941-98-0
1'-naphthacetophenone

: 104774-87-0
3‐[3‐(trifluoromethyl)phenyl]propan‐1‐amine

: 226256-56-0
cinacalcet

Conditions

Conditions	Yield
With titanium(IV) isopropylate; hydrogen; 1,8-diazabicyclo<5.4.0>undec-7-ene hidrochloride In acetic acid methyl ester at 50℃; under 38002.6 Torr; for 20h; Reagent/catalyst; Solvent; stereoselective reaction;	94%

Cinacalcet Chemical Properties

IUPAC Name: N-[(1R)-1-naphthalen-1-ylethyl]-3-[3-(trifluoromethyl)phenyl]propan-1-amine
Molecular Formula: C₂₂H₂₂F₃N
Molecular Weight: 357.41 g/mol
Canonical SMILES: CC(C1=CC=CC2=CC=CC=C21)NCCCC3=CC(=CC=C3)C(F)(F)F
InChI: InChI=1S/C22H22F3N/c1-16(20-13-5-10-18-9-2-3-12-21(18)20)26-14-6-8-17-7-4-11-19(15-17)22(23,24)25/h2-5,7,9-13,15-16,26H,6,8,14H2,1H3/t16-/m1/s1
Classification Code: Calcimimetic; Treatment of hyperparathyroidism and related disorders, such as hypercalcemia; Treatment of hyperthyroidism
Product Categories: Chiral Reagents;Intermediates & Fine Chemicals; Pharmaceuticals
XLogP3-AA: 6.1
H-Bond Donor: 1
H-Bond Acceptor: 4
Rotatable Bond Count: 6
Exact Mass: 357.170434
MonoIsotopic Mass: 357.170434
Topological Polar Surface Area: 12
Heavy Atom Count: 26
Complexity: 422
Molar Volume: 309.6 cm³
Polarizability: 39.88 10-24 cm³
Surface Tension: 36.8 dyne/cm
Density: 1.154 g/cm³
Flash Point: 220.5 °C
Enthalpy of Vaporization: 69.81 kJ/mol
Boiling Point: 440.9 °C at 760 mmHg
Vapour Pressure of Cinacalcet (CAS NO.226256-56-0): 5.67E-08 mmHg at 25 °C

Cinacalcet Uses

Cinacalcet (CAS NO.226256-56-0) is the first calcimimetic drug approved by the United States Food and Drug Administration for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease. Cinacalcet is indicated for the treatment of secondary hyperparathyroidism in patients with chronic kidney disease on dialysis and hypercalcemia in patients with parathyroid carcinoma.

Cinacalcet Specification

Cinacalcet (CAS NO.226256-56-0), its Synonyms are 1-Naphthalenemethanamine, alpha-methyl-N-(3-(3-(trifluoromethyl)phenyl)propyl)-, (alphaR)- ; N-((1R)-1-(1-Naphthyl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine ; N-((1R)-1-(Naphthalen-1-yl)ethyl)-3-(3-(trifluoromethyl)phenyl)propan-1-amine ; Mimpara . It is yellow oil.

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