ChemicalBook > CAS DataBase List > 5,7-Diiodo-8-quinolinol

5,7-Diiodo-8-quinolinol

CAS No.83-73-8
Chemical Name:5,7-Diiodo-8-quinolinol
CBNumber:CB2170413
Molecular Formula:C9H5I2NO
Formula Weight:396.95
MOL File:83-73-8.mol

5,7-Diiodo-8-quinolinol Property

Melting point >200 °C (dec.) (lit.)
Boiling point 370.95°C (rough estimate)
Density 2.3013 (estimate)
storage temp. Refrigerator
solubility DMSO (Slightly, Heated), Ethyl Acetate (Slightly, Heated)
form Solid
pka pKa 8.0 (Uncertain)
color Pale Yellow to Light Beige
Water Solubility 1g/L at 26℃
Merck 14,5042
InChIKey UXZFQZANDVDGMM-UHFFFAOYSA-N
LogP 0.602 at 26℃
CAS DataBase Reference 83-73-8(CAS DataBase Reference)
EWG's Food Scores 1
FDA UNII 63W7IE88K8
ATC code G01AC01
NIST Chemistry Reference 5,7-Diiodo-8-hydroxyquinoline(83-73-8)
EPA Substance Registry System 5,7-Diiodo-8-quinolinol (83-73-8)
UNSPSC Code 41116107
NACRES NA.24

Safety

Hazard Codes :Xn
Risk Statements :22-41
Safety Statements :26-36/37/39
RIDADR :3249
WGK Germany :3
RTECS :VC5775000
HazardClass :6.1(b)
PackingGroup :III
HS Code :29334900
Hazardous Substances Data :83-73-8(Hazardous Substances Data)
Toxicity :LD50 intravenous in mouse: 56mg/kg

Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal wordDanger
Hazard statements H302-H318
Precautionary statements P280-P301+P312+P330-P305+P351+P338+P310

5,7-Diiodo-8-quinolinol Price More Price(1)

Brand: Sigma-Aldrich(India)
Product number: D123609
Product name : 5,7-Diiodo-8-hydroxyquinoline
Purity: 95%
Packaging: 100G
Price: ₹7003.78
Updated: 2022/06/14
Buy: Buy

5,7-Diiodo-8-quinolinol Chemical Properties,Usage,Production

Originator Diiodohydroxyquinoline,Adco Co.
Uses It acts as an amoebicidal and so used in the treatment of amoebiasis, balantidiasis (an infection caused by protozoa).
Uses Iodoquinol is an amebocide used against E. histolytica, and it is active against both cysts and trophozoites that are localized in the lumen of the intestine. It is considered the drug of choice for treating asymptomatic or moderate forms of amebiasis. The mechanism of action is unknown. Iodoquinol is used for diseases caused by moderate intestinal amebiasis. Synonyms of this drug are diquinol, iodoxin, diiodoquin, amebaquin, and others.
Definition ChEBI: Iodoquinol is a monohydroxyquinoline that is quinolin-8-ol in which the hydrogens at positions 5 and 7 are replaced by iodine. It is considered the drug of choice for treating asymptomatic or moderate forms of amoebiasis. It has a role as an antiamoebic agent, an antibacterial agent, an antiseptic drug and an antiprotozoal drug. It is a monohydroxyquinoline and an organoiodine compound.
Indications Iodoquinol (diiodohydroxyquin, Yodoxin, Moebiquin) is a halogenated 8-hydroxyquinoline derivative whose precise mechanism of action is not known but is thought to involve an inactivation of essential parasite enzymes. Iodoquinol kills the trophozoite forms of E. histolytica, B. coli, B. hominis, and Dientamoeba fragilis.
Iodoquinol is absorbed from the gastrointestinal tract and is excreted in the urine as glucuronide and sulfate conjugates. Most of an orally administered dose is excreted in the feces. Iodoquinol has a plasma half-life of about 12 hours.
Iodoquinol is the drug of choice in the treatment of asymptomatic amebiasis and D. fragilis infections. It is also used in combination with other drugs in the treatment of other forms of amebiasis and as an alternative to tetracycline in the treatment of balantidiasis.
Adverse reactions are related to the iodine content of the drug; the toxicity is often expressed as skin reactions, thyroid enlargement, and interference with thyroid function studies. Headache and diarrhea also occur. Chronic use of clioquinol, a closely related agent, has been linked to a myelitislike illness and to optic atrophy with permanent loss of vision.
Manufacturing Process 5,7-Diiodo-8-quinolinol widely used as an intestinal antiseptic, especially as an antiamebic agent. It is also used topically in other infections and may cause CNS and eye damage. It is known by very many similar trade names worldwide.
0.01 mol 8-oxychinoline and 0.01 mol salicylic acid were dissolved in 500 ml of water and then 0.05 mol potassium iodide was added. The mixture was heated to temperature 90°-100°C. After that 0.01 mol of KIO3 by little tiles was added. The next tile was added after a disappearence of discharging iodine. Then 10 ml 2 N HCl was added. The solid product was fallen, filtered off, washed with hot water and in 0.25 N NaOH dissolved. The solution was filtered and the clear filtrate precipitated with a very little excess of HCl. The product 5,7-diiodo-8-quinolinol was filtered, washed with hot water and dried. MP: 200°-250°C (with decomposition).
brand name Quinadome (Bayer); Yodoxin (Glenwood).
Therapeutic Function Antibacterial
Flammability and Explosibility Non flammable
Clinical Use 5,7-Diiodo-8-quinolinol, 5,7-diiodo-8-hydroxyquinoline,or diiodohydroxyquin (Yodoxin, Diodoquin, Diquinol) is ayellowish to tan microcrystalline, light-sensitive substancethat is insoluble in water. It is recommended for acute andchronic intestinal amebiasis but is not effective in extraintestinaldisease. Because a relatively high incidence of topicneuropathy has occurred with its use, iodoquinol should notbe used routinely for traveler’s diarrhea.
Safety Profile Poison by ingestion and intravenous routes. Human systemic effects by ingestion: eye effects. Mutation data reported. When heated to decomposition it emits very toxic fumes of Iand Nox
Synthesis Iodoquinol, 5,7-diiodo-8-quinolinol (37.2.2), is made by iodination of 8-oxyquinoline (37.2.1) using a mixture of potassium iodide/potassium iodate. The initial 8-hydroxyquinolin (37.2.1) is made from 2-aminophenol and glycerol in the presence of sulfuric acid and nitrobenzene (Skraup synthesis).
Purification Methods It crystallises from xylene and is dried at 70o in a vacuum. [Beilstein 21 II 58.]