Tilorone dihydrochloride Chemical Properties

Melting point:

230-233 °C(lit.)

storage temp. 

Sealed in dry,Room Temperature

solubility 

Methanol (Slightly)

form 

Solid

color 

Orange

Merck 

14,9440

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 Information

Hazard Codes 

Xn

Risk Statements 

20/21/22-36/37/38-40

Safety Statements 

7-22-26-37/39

WGK Germany 

3

RTECS 

LL9000000

HS Code 

2922.39.4500

Toxicity

LD50 in mice, rats (single dose): 959, 852 mg/kg orally; 145, 244 mg/kg i.p. (Krueger, Mayer)

MSDS

• Language:English Provider:SigmaAldrich

Tilorone dihydrochloride Usage And Synthesis

Description

Tilorone is an orally active, antiviral compound that induces interferon production and is reported to have antitumor, anti-inflammatory, and neuroprotective actions. With chronic administration, tilorone induces lysosomal glycosaminoglycan storage, rendering glycosaminoglycans resistant to enzymatic degradation.

Chemical Properties

Orange-yellow crystalline powder

Uses

Tilorone dihydrochloride is an orally active, interferon-inducing antiviral agent.

Uses

Tilorone dihydrochloride was used to study the interaction of drugs with synthetic self-complementary DNA by SPR (Surface Plasmon Resonance).

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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