ChemicalBook > CAS DataBase List > Amodiaquine

Amodiaquine

Product Name
Amodiaquine
CAS No.
86-42-0
Chemical Name
Amodiaquine
Synonyms
CAM-AQI;CAM-AQ1;Miaquin;Camoquin;Camochin;Camoquine;SN 10,751;NSC 13453;Camoquinal;Flavoquine
CBNumber
CB8344720
Molecular Formula
C20H22ClN3O
Formula Weight
355.86
MOL File
86-42-0.mol
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Amodiaquine Property

Melting point:
208°C
Boiling point:
478.0±45.0 °C(Predicted)
Density 
1.258
storage temp. 
-20°C Freezer
solubility 
DMSO (Slightly, Sonicated), Methanol (Slightly)
form 
Solid
pka
9.43±0.50(Predicted)
color 
Pale Yellow to Light Yellow
CAS DataBase Reference
86-42-0(CAS DataBase Reference)
NIST Chemistry Reference
Amodiaquine(86-42-0)
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Safety

Hazardous Substances Data
86-42-0(Hazardous Substances Data)
Toxicity
LD50 oral in mouse: 550mg/kg
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

Precautionary statements

P264Wash hands thoroughly after handling.

P264Wash skin thouroughly after handling.

P270Do not eat, drink or smoke when using this product.

P301+P312IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.

P330Rinse mouth.

P501Dispose of contents/container to..…

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N-Bromosuccinimide Price

Cayman Chemical
Product number
15954
Product name
Amodiaquine
Purity
≥95%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
15954
Product name
Amodiaquine
Purity
≥95%
Packaging
5mg
Price
$134
Updated
2024/03/01
Cayman Chemical
Product number
15954
Product name
Amodiaquine
Purity
≥95%
Packaging
10mg
Price
$236
Updated
2024/03/01
Cayman Chemical
Product number
15954
Product name
Amodiaquine
Purity
≥95%
Packaging
50mg
Price
$723
Updated
2024/03/01
TRC
Product number
A634200
Product name
Amodiaquine
Packaging
100mg
Price
$520
Updated
2021/12/16
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Amodiaquine Chemical Properties,Usage,Production

Description

Amodiaquine is a prodrug form of the antimalarial compound N-desethyl amodiaquine . It is active against several strains of P. falciparum in vitro (EC50s = 0.23-0.52 nM) and exhibits a synergistic effect when used in combination with N-desethyl amodiaquine. Amodiaquine dose-dependently inhibits development of parasitemia in a mouse model of P. berghei infection.

Chemical Properties

Cyrstalline Solid

Originator

Camoquin HCl,Parke Davis,US,1950

Uses

An antimalarial

Definition

ChEBI: A quinoline having a chloro group at the 7-position and an aryl amino group at the 4-position.

Indications

Amodiaquine (Camoquin) is another 4-aminoquinoline derivative whose antimalarial spectrum and adverse reactions are similar to those of chloroquine, although chloroquine-resistant parasites may not be amodiaquine- resistant to the same degree. Prolonged treatment with amodiaquine may result in pigmentation of the palate, nail beds, and skin. There is a 1:2000 risk of agranulocytosis and hepatocellular dysfunction when the drug is used prophylactically.

Manufacturing Process

72.8 g (0.5 mol) of p-aminophenol hydrochloride is dissolved in 500 cc of water and added to 99 g (0.5 mol) of 4,7-dichloroquinoline. After a few minutes of warming in a steam bath, 4-(4'-hydroxyanilino)-7-chloroquinoline hydrochloride, of sufficient purity for use in further experiments, precipitates as a yellow crystalline solid. Recrystallized from methanol, the MP is over 300°C.
A mixture consisting of 13.5 g of 4-(4'-hydroxyanilino)-7-chloroquinoline hydrochloride dissolved in absolute ethanol is treated with a solution of 4.38 g of diethylamine and 1.8 g of paraformaldehyde in 20 cc of absolute ethanol. The reaction mixture is heated under reflux for 16 hours, evaporated to onehalf volume and the warm solution treated with an excess of hydrogen chloride dissolved in absolute ethanol. Acetone is added to the warm solution until it becomes turbid and then the solution is cooled. The crude dihydrochloride which separates is collected and purified by recrystallization from methanol; MP 240-242°C.
By using an equivalent amount of 4-(4'-hydroxyanilino)-7-bromoquinoline in the above procedure, 4-(3'-diethylaminomethyl-4'-hydroxyanilino)-7- bromoquinoline dihydrochloride is obtained; MP (base) 206-208°C dec.

brand name

Camoquin (Parke-Davis);Amodoquin tablets;Basoquin;Caniquin.

Therapeutic Function

Antimalarial

World Health Organization (WHO)

Amodiaquine, an antimalarial agent related to chloroquine, was introduced over 40 years ago for the treatment and prophylaxis of malaria. The drug was voluntarily withdrawn in the United Kingdom in 1975 for commercial reasons but was subsequently reintroduced in 1985 to meet the medical demand for an antimalarial drug to deal with the rapid spread of chloroquine-resistant falciparum malaria in Asia and Africa. By 1986 a significant number of cases of agranulocytosis associated with prophylactic use, some of which were fatal, had been reported there and it has been estimated that the frequency of this risk is of the order of 1:2,000. Although most cases occurred when amodiaquine had been used in combination with other antimalarials, the major manufacturer decided to withdraw the prophylactic indication worldwide following discussions with experts. Preparations remain available for the treatment of acute attacks of malaria which involves only a short period of exposure to the drug. (Reference: (WHODI) WHO Drug Information, 1, 5, 1987)

Pharmaceutical Applications

A mono-Mannich-base 4-aminoquinoline, formulated as the dihydrochloride dihydrate or free base for oral administration. It is active against P. falciparum and P. vivax and is more active than chloroquine for the treatment of uncomplicated P. falciparum malaria. Chloroquine-resistant strains may remain susceptible, but resistance to amodiaquine is also spreading in some regions of Africa. The pharmacological properties are similar to those of chloroquine. The terminal elimination halflife is 1–3 weeks. It is rapidly and extensively metabolized to the desethyl derivative which has reduced antiplasmodial activity. Prophylactic use has been abandoned because of agranulocytosis and hepatotoxicity due to formation of a quinoneimine metabolite. A fixed dose combination with artesunate and derivatives (for example, isoquine) with altered metabolism and reduced toxicity is in development.

Clinical Use

Treatment of falciparum malaria

Clinical Use

Mechanistically, it is very similar to chloroquine and does nothave any advantages over the other 4-aminoquinoline drugs.When used for prophylaxis of malaria, it had a higher incidenceof hepatitis and agranulocytosis than that was chloroquine.There is evidence that the hydroquinone (phenol)amine system readily oxidizes to a quinone imine either autoxidatively and/or metabolically, and this productmay contribute to amodiaquine’s toxicity.

Synthesis

Amodiaquin, 4-[(7-chloro-4-quinilyl)amino]-|á-diethylmaino-o-cresol (37.1.1.21), is made by reacting 4,7-dichloroquineoline (37.1.1.1) with 4-aminophenol to make 7-chloro-4-(4-hydroxyphenylamino)-quiniline (37.1.1.20), which then undergoes an aminomethylation reaction using formaldehyde and diethylamine, giving amodiaquin.

Purification Methods

Amodiaquin crystallises from 2-ethoxyethanol or EtOH. [Burckhalter et al. J Am Chem Soc 70 1363 1948, Beilstein 22 III/IV 4647.]

Amodiaquine Preparation Products And Raw materials

Raw materials

Preparation Products

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Amodiaquine Suppliers

Chengdu Saint - Kay Biotechnology Co., Ltd.
Tel
028-85157043 15882256948
Email
676046971@qq.com
Country
China
ProdList
4396
Advantage
58
J & K SCIENTIFIC LTD.
Tel
010-82848833 400-666-7788
Fax
86-10-82849933
Email
jkinfo@jkchemical.com
Country
China
ProdList
96815
Advantage
76
Chemsky(shanghai)International Co.,Ltd.
Tel
021-50135380
Email
shchemsky@sina.com
Country
China
ProdList
32321
Advantage
50
Hangzhou Yuhao Chemical Technology Co., Ltd
Tel
0571-82693216
Fax
+86-571-82880190
Email
info@yuhaochemical.com
Country
China
ProdList
9387
Advantage
52
BOC Sciences
Tel
1-631-485-4226; 16314854226
Email
info@bocsci.com
Country
United States
ProdList
14055
Advantage
65
Beijing HuaMeiHuLiBiological Chemical
Tel
010-56205725
Fax
010-65763397
Email
waley188@sohu.com
Country
China
ProdList
12335
Advantage
58
Nanjing Norris-Pharm Technology Co., Ltd
Tel
13901585132
Fax
+86-25-52131256
Email
799750417@qq.com
Country
China
ProdList
8878
Advantage
55
ChemStrong Scientific Co.,Ltd
Tel
0755-0755-66853366 13670046396
Fax
0755-28363542
Email
sales@chem-strong.com
Country
China
ProdList
18070
Advantage
56
Shanghai EFE Biological Technology Co., Ltd.
Tel
021-65675885 18964387627
Fax
021-65675885
Email
info@efebio.com
Country
China
ProdList
9806
Advantage
58
Raw material medicin reagent co.,Ltd
Tel
Email
sales@njromanme.com
Country
China
ProdList
4529
Advantage
58
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View Lastest Price from Amodiaquine manufacturers

Career Henan Chemical Co
Product
Amodiaquine 86-42-0
Price
US $1.00/KG
Min. Order
1KG
Purity
Min98% HPLC
Supply Ability
g/kg/ton
Release date
2020-02-05

86-42-0, AmodiaquineRelated Search:


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