DIETHYLCARBAMAZINE CITRATE

DIETHYLCARBAMAZINE CITRATE Basic information
Product Name:DIETHYLCARBAMAZINE CITRATE
Synonyms:EthylaMinoazine-d3 Citrate;Filaribits-d3;Filazine-d3;Franocide-d3;Franozan-d3;Hetrazan-d3;N,N-Diethyl-4-(Methyl-d3)-1-piperazinecarboxaMide 2-Hydroxy-1,2,3-propanetricarboxylate;N,N-Diethyl-4-(Methyl-d3)-1-piperazinecarboxaMide Citrate Salt
CAS:1642-54-2
MF:C16H29N3O8
MW:391.42
EINECS:216-696-6
Product Categories:HETRAZAN;Miscellaneous Reagents;Antibiotics A to Z;Antibiotics A-F;Heterocyclic Building Blocks;Piperazines;Antiparasitic / Antiprotozoal / Anthelminthic;C16 to C29;Spectrum of Activity;Antibiotics;Building Blocks;Chemical Synthesis
Mol File:1642-54-2.mol
DIETHYLCARBAMAZINE CITRATE Structure
DIETHYLCARBAMAZINE CITRATE Chemical Properties
Melting point 140 °C
Boiling point 516.39°C (rough estimate)
density 1.1718 (rough estimate)
refractive index 1.6500 (estimate)
storage temp. 2-8°C
solubility Very soluble in water, soluble in ethanol (96 per cent), practically insoluble in acetone.
form powder
color White to Almost white
Water Solubility almost transparency
BRN 3836352
BCS Class1
CAS DataBase Reference1642-54-2(CAS DataBase Reference)
EPA Substance Registry SystemDiethylcarbamazine citrate (1642-54-2)
Safety Information
Hazard Codes T+,T
Risk Statements 22-26-23
Safety Statements 22-36/37/39-45
RIDADR UN 2811 6.1/PG 2
WGK Germany 3
RTECS TL1225000
HazardClass 6.1(b)
PackingGroup III
HS Code 2933595960
Hazardous Substances Data1642-54-2(Hazardous Substances Data)
ToxicityLD50 orally in rats: 1.38 g/kg (Harned)
MSDS Information
ProviderLanguage
SigmaAldrich English
DIETHYLCARBAMAZINE CITRATE Usage And Synthesis
Chemical PropertiesWhite or almost white, crystalline powder, slightly hygroscopic.
OriginatorHetrazan,Lederle,US,1949
UsesDiethylcarbamazine Citrate can be used as an anthelmintic. The LD50 in rats is 1.38 g/kg.
DefinitionChEBI: Diethylcarbamazine citrate is a piperazinecarboxamide.
Manufacturing ProcessTo 50 cc of water was added 18 grams of 1-methylpiperazine dihydrochloride and 8.34 grams of sodium hydroxide. When solution had been effected the beaker was cooled to 10°C and with stirring, 4.17 grams of sodium hydroxide dissolved in 15 cc of water and 14 grams of diethyl carbamyl chloride were added simultaneously. When all had been added, the solution was extracted 3 times with ether which was then dried and filtered. The ether solution was saturated with dry hydrogen chloride. A yellow gum appeared which on trituration gave a white, hygroscopic solid which was filtered and dried in a drying pistol. The N,N-diethyl-4-methyl-1-piperazine-carboxamide hydrochloride had a melting point of 150°-155°C.
If the compound itself is desired, the salt is dissolved in water and the solution saturated with a mild alkali such as potassium carbonate. The product is then extracted with chloroform, dried, and after removal of the chloroform, distilled.
Therapeutic FunctionAnthelmintic
General DescriptionCrystalline solid, scored white tablets. Used against filariasis in man and animals.
Health Hazard(Non-Specific -- Drugs, n.o.s.) May be fatal if inhaled, swallowed or absorbed through skin. Contact may cause burns to skin and eyes. Fire may produce irritating or poisonous gases. Runoff from fire control or dilution water may cause pollution. The average adult man tolerates a single dose of 1.5 gm without ill effects.
Fire HazardWhen heated to decomposition, DIETHYLCARBAMAZINE CITRATE emits toxic fumes of nitrogen oxides. Avoid decomposing heat.
Safety ProfilePoison by inhalation and intravenous routes. Moderately toxic by ingestion, subcutaneous, and intraperitoneal routes. An experimental teratogen. When heated to decomposition it emits toxic fumes of NOx.
Veterinary Drugs and TreatmentsOnce the hallmark agent for heartworm disease prophylaxis in dogs, DEC is no longer commercially available in the USA (in oral veterinary dosage forms). DEC is approved for use for the prophylaxis of heartworm disease (D. immitis), and/or the treatment of ascariasis in dogs. The drug is also used in ferrets and zoo animals susceptible to heartworm. DEC is used in dogs at higher dosages as alternative therapy for several other parasites (see Dosage section below). Some products were labeled for use in cats to treat ascarid infections.
In cats, DEC may help alleviate the course (preventing lymphoma development) of FeLV infection.
In the U.K., DEC is used as an injectable product to control parasitic bronchitis (Dictyocaulus viviparous) in sheep and cattle.
In humans, DEC is indicated as a filaricidal for the treatment of Wucheria bancrofti, Brugia malayi, Loa loa, and Onchocerca volvulus.


DIETHYLCARBAMAZINE CITRATE Preparation Products And Raw materials
Raw materialsSodium carbonate-->Diethylcarbamyl chloride-->Sodium hydroxide-->1-Methylpiperazine
1,1,3,3-Tetraethylurea 3-HYDROXY-3-METHYLGLUTARIC ACID PIPERAZINE HEXAHYDRATE piperazine-1-carboxamide Citric acid monohydrate DIETHYLCARBAMAZINE CITRATE PIPERAZINE-1-CARBOXYLIC ACID DIMETHYLAMIDE N-(2-DIMETHYLAMINOETHYL)-N-METHYLFORMAM& 1-FORMYL-4-METHYLPIPERAZINE TRICARBALLYLIC ACID Ammonium citrate tribasic PIPERAZINE DL-MALATE 1-Piperazinecarbaldehyde (R)-(-)-CITRAMALIC ACID DIETHYLCARBAMAZINE (S)-(+)-CITRAMALIC ACID D(+)-Malic acid 2-ETHYL-2-HYDROXYBUTYRIC ACID

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