| Identification | More | [Name]
Tilorone dihydrochloride | [CAS]
27591-69-1 | [Synonyms]
2,7-BIS[2-(DIETHYLAMINO)ETHOXY]-9-FLUORENONE DIHYDROCHLORIDE
TILORONE DIHYDROCHLORIDE
TILORONE HYDROCHLORIDE
2,7-bis(2-(diethylamino)ethoxy)-9h-fluoren-9-ondihydrochloride
2,7-bis(2-(diethylamino)ethoxy)-fluoren-9-ondihydrochloride
2,7-bis(2-(diethylamino)ethoxy)-fluoren-9-onedihydrochloride
bis-deae-fluorenonehydrochloride
nsc-143969
TILORONE 2HCL | [Molecular Formula]
C25H36Cl2N2O3 | [MDL Number]
MFCD00134071 | [Molecular Weight]
483.47 | [MOL File]
27591-69-1.mol |
| Chemical Properties | Back Directory | [Melting point ]
230-233 °C(lit.)
| [storage temp. ]
Sealed in dry,Room Temperature | [solubility ]
Methanol (Slightly) | [form ]
Solid | [color ]
Orange | [Merck ]
13,9517 | [InChI]
InChI=1S/C25H34N2O3.2ClH/c1-5-26(6-2)13-15-29-19-9-11-21-22-12-10-20(30-16-14-27(7-3)8-4)18-24(22)25(28)23(21)17-19;;/h9-12,17-18H,5-8,13-16H2,1-4H3;2*1H | [InChIKey]
BSVYJQAWONIOOU-UHFFFAOYSA-N | [SMILES]
C12C=CC(OCCN(CC)CC)=CC=1C(=O)C1C=C(OCCN(CC)CC)C=CC2=1.Cl.Cl | [CAS DataBase Reference]
27591-69-1(CAS DataBase Reference) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS07,GHS08 | [Signal word ]
Warning | [Hazard statements ]
H302+H312+H332-H315-H319-H335-H351 | [Precautionary statements ]
P280-P301+P312-P302+P352+P312-P304+P340+P312-P305+P351+P338-P308+P313 | [Hazard Codes ]
Xn | [Risk Statements ]
R20/21/22:Harmful by inhalation, in contact with skin and if swallowed .
R36/37/38:Irritating to eyes, respiratory system and skin .
R40:Limited evidence of a carcinogenic effect. | [Safety Statements ]
S7:Keep container tightly closed .
S22:Do not breathe dust .
S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S37/39:Wear suitable gloves and eye/face protection . | [WGK Germany ]
3
| [RTECS ]
LL9000000
| [HS Code ]
2922.39.4500 | [Storage Class]
11 - Combustible Solids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Carc. 2
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3 | [Toxicity]
LD50 in mice, rats (single dose): 959, 852 mg/kg orally; 145, 244 mg/kg i.p. (Krueger, Mayer) |
| Hazard Information | Back Directory | [Description]
Tilorone is an orally active, antiviral compound that induces interferon production and is reported to have antitumor, anti-inflammatory, and neuroprotective actions.1,2,3 With chronic administration, tilorone induces lysosomal glycosaminoglycan storage, rendering glycosaminoglycans resistant to enzymatic degradation.4 | [Chemical Properties]
Orange-yellow crystalline powder | [Uses]
antiviral | [Definition]
ChEBI: Tilorone dihydrochloride is the dihydrochloride salt of tilorone. It is used as an antiviral drug to treat influenza, herpes infection, viral hepatitis, acute respiratory viral infections and SARS. It has a role as an anti-inflammatory agent, an antineoplastic agent, an interferon inducer, a nicotinic acetylcholine receptor agonist and an antiviral drug. It contains a tilorone(2+). | [Brand name]
Tilorone is INN. | [General Description]
Effect of tilorone dihydrochloride on the changes of transmembrane potential of mitochondrial membranes of the isolated rat hepatocytes has been investigated. Tilorone dihydrochloride is an orally active, interferon-inducing antiviral agent. | [Synthesis]
2 (100 g, 0.47 mol) was mixed with 2-diethylaminoethyl chloride hydrochloride (300 g, 1.74 mol), KOH (225 g, 4.01 mol), water (320 mL), and toluene (1.5 L), and the reaction was carried out at reflux for 24 hours. After completion of the reaction, the emulsion was cooled to room temperature and the organic layer was separated. The organic layer was washed with 3 mol/L aqueous KOH (500 mL) and subsequently concentrated to dryness under vacuum. The residue was dissolved in anhydrous ethanol (420 g) and the pH was adjusted to 3.0 by passing gaseous HCl. The orange product was recrystallized by ethanol, and after filtration and drying, 200 g of tilolone hydrochloride (Compound 1) was obtained in 93% yield. The melting point of the product was 231-233°C (literature value 235-236°C [22]).IR (KBr) spectrum showed characteristic absorption peaks: 2943.3, 2596.5 (CH), 1708.9 (C=O) cm?1. ESI-MS (m/z): 411.0 [M+H]? , molecular formula C??H??N?O? (molecular weight 410.3).1H-NMR (400 MHz, D?O) chemical shift δ (ppm): 7.12 (d, J=6.5Hz, 2H), 6.99 (dd, J=6.5,1.6Hz, 2H), 6.89 (d, J=1.6Hz, 2H), 4.39 (t, J=3.6Hz , 4H), 3.68 (t, J=3.6Hz, 4H), 3.42 (q, J=5.6Hz, 8H), 1.44 (t, J=5.8Hz, 12H). | [References]
[1] Crystal Growth and Design, 2012, vol. 12, # 12, p. 6118 - 6125
[2] Molecules, 2015, vol. 20, # 12, p. 21458 - 21463 |
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Mascot I.E. Co., Ltd Gold
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Energy Chemical
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