Diethylcarbamazine

Base Information

• Chemical Name: Diethylcarbamazine
• CAS No.: 90-89-1
• Deprecated CAS: 12672-34-3,8028-18-0,8028-18-0
• Molecular Formula: C10H21 N3 O
• Molecular Weight: 199.296
• Hs Code.: 2933599590
• European Community (EC) Number: 202-023-3
• UNII: V867Q8X3ZD
• DSSTox Substance ID: DTXSID1022928
• Nikkaji Number: J4.329J
• Wikipedia: Diethylcarbamazine
• Wikidata: Q409267
• NCI Thesaurus Code: C65378
• Metabolomics Workbench ID: 43019
• ChEMBL ID: CHEMBL684
• Mol file: 90-89-1.mol

Synonyms:Carbamazine;Citrate, Diethylcarbamazine;Diethylcarbamazine;Diethylcarbamazine Citrate;Diethylcarbamazine Citrate (1:1);Diethylcarbamazine Citrate (1:2);Diethylcarbamazine L-Tartrate (1:1);Diethylcarbamazine Maleate;Diethylcarbamazine Monohydrochloride;Diethylcarbamazine Phosphate (1:1);Hetrazan;Loxuran;Maleate, Diethylcarbamazine;Monohydrochloride, Diethylcarbamazine;Notezine

Chemical Property of Diethylcarbamazine

Chemical Property:

• Appearance/Colour: off-white crystalline powder
• Vapor Pressure: 0.00136mmHg at 25°C
• Melting Point: 137 - 140 C
• Refractive Index: 1.4930 (estimate)
• Boiling Point: 127-129℃ (10 Torr)
• PKA: pKa 7.7 (Uncertain)
• Flash Point: 98 C
• PSA: 26.79000
• Density: 1.013g/cm³
• LogP: 0.57140
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 0.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 2
• Exact Mass: 199.168462302
• Heavy Atom Count: 14
• Complexity: 184

Purity/Quality:

99.9% ^*data from raw suppliers

N,N-Diethyl-4-methyl-1-piperazinecarboxamide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): UN NO.
• Hazard Codes: UN NO.

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCN(CC)C(=O)N1CCN(CC1)C
• Recent ClinicalTrials: Host Response to Infection and Treatment in Filarial Diseases
• Indications: DEC is used for the treatment of individual cases infected by Wuchereria bancrofti, Brugia malayi, B. timori andLoa loa. It may also be used for large scale chemotherapeutic control of filariasis. DEC is also used in Acanthocheilonema streptocerca infestations and in tropical eosinophilia. In onchocerciasis, DEC should only be used when ivermectin is not available. Diethylcarbamazine citrate (Hetrazan) is active against several microfilaria and adult filarial worms. It interferes with the metabolism of arachidonic acid and blocks the production of prostaglandins, resulting in capillary vasoconstriction and impairment of the passage of the microfilaria. Diethylcarbamazine also increases the adherence of microfilariae to the vascular wall, platelets, and granulocytes. Diethylcarbamazine is absorbed from the gastrointestinal tract, and peak blood levels are obtained in 4 hours; the drug disappears from the blood within 48 hours. The intact drug and its metabolites are excreted in the urine. Diethylcarbamazine is the drug of choice for certain filarial infections, such as Wuchereria bancrofti, Brugia malayi and Loa loa. Since diethylcarbamazine is not universally active against filarial infections, a specific diagnosis based on blood smears, biopsy samples, and a geographic history is important. Dosage should be adjusted in patients with renal impairment. Caution is necessary when using this agent, particularly when treating onchocerciasis.The sudden death of the microfilariae can produce mild to severe reactions within hours of drug administration. These are manifested by fever, lymphadenopathy, cutaneous swelling, leukocytosis, and intensification of any preexisting eosinophilia, edema, rashes, tachycardia, and headache. If microfilariae are present in the eye, further ocular damage may result. Other side effects are relatively mild and range from malaise, headache, and arthralgias to gastrointestinal symptoms.
• Description: Discovered in the 1940s, diethylcarbamazine (DEC) has proven to be especially effective as a filaricidal agent. The incidence of filariasis among American troops during World War II necessitated a search for drugs with an antifalarial spectrum of activity. The once-popular piperazine also was discovered during these initial screenings. Although chemically similar, the activity again helminths is quite different. Piperazine is active against nematodes, whereas DEC is active against falaria and microfalaria.
• Clinical Use: Filariasis It has also been used for visceral larva migrans, but experience is limited and there is little evidence of its efficacy.

Technology Process of Diethylcarbamazine

There total 8 articles about Diethylcarbamazine which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

N,N-diethylcarbamyl chloride (88-10-8) → diethylcarbamazine (90-89-1)

Guidance literature:

Multi-step reaction with 2 steps

1: ethanol

2: formic acid

With formic acid; ethanol;

DOI:10.1021/jo01159a019

Reference yield:

1-methyl-piperazine (109-01-3) + N,N-diethylcarbamyl chloride (88-10-8) → diethylcarbamazine (90-89-1)

Guidance literature:

With chloroform;

DOI:10.1021/jo01159a019

Reference yield:

formaldehyd (50-00-0,30525-89-4,61233-19-0) + N,N-diethylpiperazine-1-carboxamide (119-54-0) → diethylcarbamazine (90-89-1)

Guidance literature:

With formic acid;

DOI:10.1021/jo01159a019

upstream raw materials:

1-methyl-piperazine

O-phenyl N,N-diethylcarbamate

N,N-diethylcarbamyl chloride

4-methyl-piperazine-1-carbonyl chloride

Downstream raw materials:

4-diethylcarbamoyl-1-methyl-1-tetradecyl-piperazinium; bromide

Refernces