Carbamazepine

Base Information

• Chemical Name: Carbamazepine
• CAS No.: 298-46-4
• Molecular Formula: C15H12N2O
• Molecular Weight: 236.273
• Hs Code.: 29339900
• European Community (EC) Number: 206-062-7
• NSC Number: 755920,169864
• UNII: 33CM23913M
• DSSTox Substance ID: DTXSID4022731
• Nikkaji Number: J8.590A
• Wikipedia: Carbamazepine
• Wikidata: Q410412
• NCI Thesaurus Code: C341
• RXCUI: 2002
• Pharos Ligand ID: 7U7WXCCPXPYL
• Metabolomics Workbench ID: 42899
• ChEMBL ID: CHEMBL108
• Mol file: 298-46-4.mol

Synonyms:Amizepine;Carbamazepine;Carbamazepine Acetate;Carbamazepine Anhydrous;Carbamazepine Dihydrate;Carbamazepine Hydrochloride;Carbamazepine L-Tartrate (4:1);Carbamazepine Phosphate;Carbamazepine Sulfate (2:1);Carbazepin;Epitol;Finlepsin;Neurotol;Tegretol

Chemical Property of Carbamazepine

Chemical Property:

• Appearance/Colour: white solid
• Vapor Pressure: 5.78E-07mmHg at 25°C
• Melting Point: 189-192 °C
• Refractive Index: 1.669
• Boiling Point: 410.984 °C at 760 mmHg
• PKA: 13.94±0.20(Predicted)
• Flash Point: 202.356 °C
• PSA: 46.33000
• Density: 1.266 g/cm³
• LogP: 4.15250
• Storage Temp.: 2-8°C
• Solubility.: 45% (w/v) aq 2-hydroxypropyl-β-cyclodextrin: soluble29mg/mL
• Water Solubility.: pract. insoluble
• XLogP3: 2.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 0
• Exact Mass: 236.094963011
• Heavy Atom Count: 18
• Complexity: 326

Purity/Quality:

99% ^*data from raw suppliers

Carbamazepine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn,T,F
• Statements: 42/43-22-20/21/22-39/23/24/25-23/24/25-11
• Safety Statements: 37-24-22-36/37/39-36-45-36/37-16

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Anticonvulsants
• Canonical SMILES: C1=CC=C2C(=C1)C=CC3=CC=CC=C3N2C(=O)N
• Recent ClinicalTrials: A Study of the Effects of Itraconazole or Carbamazepine on LY3537982 in Healthy Participants
• Recent EU Clinical Trials: Randomised factorial design controlled trial comparing carbamazepine, levetiracetam or active monitoring combined with or without sleep behaviour intervention in treatment naive children with rolandic epilepsy
• Chemical Structure and History: Carbamazepine (CBZ) is a tricyclic iminostilbene derivative synthesized in 1957 and introduced in 1963 in Europe as an antiepileptic drug.
• Medical Uses: Carbamazepine (CBZ) is a common anticonvulsant primarily used to treat epilepsy and nerve pain by reducing the spread of seizure activity in the brain. It is also used for generalized tonic-clonic seizures and complex partial seizures.
• Administration: CBZ can be administered orally or rectally in similar doses, particularly for patients unable to take it orally, such as perioperatively.
• Degradation Studies: Carbamazepine is frequently detected in water and wastewater effluents, being one of the most commonly found active pharmaceutical ingredients (APIs) in river catchments worldwide. Advanced oxidation processes (AOPs) have been extensively studied for carbamazepine degradation, involving various types of radicals and activation methods.
• Toxicity and Side Effects: CBZ toxicity can manifest in various ways, including disturbances of eye movements, resulting in dizziness, blurred vision, diplopia, or ataxia. It induces microsomal enzymes, accelerating its own metabolism, leading to variations in elimination half-lives depending on the length of treatment.
• Pregnancy Considerations: Biotransformation of CBZ during pregnancy changes only slightly, which may result in lower CBZ plasma concentrations.

Technology Process of Carbamazepine

There total 63 articles about Carbamazepine 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: 98.8%

dibenzoazepine (256-96-2) + sodium isocyanate (917-61-3) → carbamazepin (298-46-4)

Guidance literature:

In water; acetic acid; at 15 - 60 ℃; for 4h; Product distribution / selectivity;

Reference yield: 93.2%

potassium cyanate (590-28-3) + dibenzoazepine (256-96-2) → carbamazepin (298-46-4)

Guidance literature:

In water; acetic acid; at 20 - 80 ℃; for 2 - 5.5h; Product distribution / selectivity;

Reference yield: 92.0%

trans-10,11-dibromo-10,11-dihydro-5H-dibenzazepine-5-carboxamide (59690-99-2,141701-26-0,143667-56-5) → carbamazepin (298-46-4)

Guidance literature:

With tetraethylammonium perchlorate; In water; N,N-dimethyl-formamide; cathode: Hg, working potential: -0.5 V, charge: 1.9-2.1 F/mol, 3-4 h;

upstream raw materials:

10-Brom-5-carbamoyl-5H-dibenzazepin

5-cyanodibenzazepine

5H-dibenz[b,f]azepine-5-carbonylchloride

trans-10,11-dibromo-10,11-dihydro-5H-dibenzazepine-5-carboxamide

Downstream raw materials:

5-cyanodibenzazepine

3-Hydroxycarbamazepine

10,11-dihydro-10-hydroxy-5H-dibenz[b,f]azepine-5-carboxamide

(10S)-10-[(2R)-(acetyloxy)(phenyl)ethanoate]-10,11-dihydro-5H-dibenzo[b,f]azepine-5-carboxamide

Refernces

• 1、 Shamshin, V. P.,Voronin, V. G.,Borisov, M. M.,Mufazalova, T. P.. "SYNTHESIS OF CARBAMAZEPINE AND ITS ANTIALCOHOL ACTIVITY". . p. 443 - 448. Retrieved 1987.
• 2、 -. "Clean and efficient preparation method of carbamazepine". Paragraph 0036-0053. . Retrieved 2021/06/21.
• 3、 -. "Intermediate compound, carbamazepine and derivative thereof as well as preparation method of oxcarbazepine and derivative thereof". . . Retrieved 2019/12/25.