Benzamidiniumchlorid
BenziMidaMide hydrochloride · BENZAMIDINE HCL · BENZENECARBOXIMIDAMIDE HYDROCHLORIDE · benzamidine hydroxychloride · s-dimethylester · BENZAMIDE HCL H2O · Benzamidine hydrochl · benzamidiniumchloride
Identifikatoren & physikalische Daten
| CAS No. | 1670-14-0 |
|---|---|
| Summenformel | C7H8N2.ClH |
| Durchschnittliche Molmasse | 156,61 g/mol |
| Monoisotopische Masse | 156,04542597 g/mol |
| SMILES | Cl.N=C(N)c1ccccc1 |
| InChIKey | LZCZIHQBSCVGRD-UHFFFAOYSA-N |
| PubChem CID | 80289 |
| ChEMBL | CHEMBL537204 |
| EC No. | 216-795-4 |
| DTXSID | DTXSID9044401 |
| Lokaler Name | Benzamidiniumchlorid |
Chemische & physikalische Eigenschaften
| Polarare Oberfläche (TPSA) | 49,9 |
|---|---|
| H-Brücken-Donoren | 3 |
| H-Brücken-Akzeptoren | 1 |
| Frei drehbare Bindungen | 1 |
| Schwere Atome | 10 |
| Formalladung | 0 |
| Komplexität | 103 |
| Stoffklassen | Nitrogen Compounds -> Other Aromatics (Nitrogen) |
| Dampfdruck | 0.02 [mmHg] |
| Physical Description | Beige crystalline solid[Sigma-Aldrich MSDS] |
| Schmelzpunkt | 86-88 °C(lit.) |
| Lagerbedingungen | 2-8°C |
| Löslichkeit | DMF: 25 mg/mlDMSO: 25 mg/mlEthanol: 10 mg/mlPBS (pH 7.2): 3 mg/mlsoluble |
| Aggregatzustand | Powder |
| Farbe | White to off-white |
| pH | 4.0 to 6.5(50g/L, 25 ℃) |
| BRN | 3594959 |
| Stabilität | Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily |
| InChI | InChI=1S/C7H8N2.ClH/c8-7(9)6-4-2-1-3-5-6/h1-5H,(H3,8,9)1H |
| InChIKey | LZCZIHQBSCVGRD-UHFFFAOYSA-N |
| SMILES | C1(C(=N)N)=CC=CC=C1.Cl |
| CAS Datenbank | 1670-14-0(CAS DataBase Reference) |
| EPA chemische Informationen | Benzenecarboximidamide, monohydrochloride (1670-14-0) |
Sicherheit & Vorschriften
| GHS-Einstufung | WarningH315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)Aggregated GHS information provided per 166 reports by companies from 12 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies. |
|---|---|
| Regulatorische Informationen | Chemical: Benzenecarboximidamide, monohydrochlorideStatus: Active Update: 24-06-2021 https://echa.europa.eu/registration-dossier/-/registered-dossier/24030Benzenecarboximidamide, monohydrochloride: Does not have an individual approval but may be used under an appropriate group standard |
| Gefahrenübersicht | Causes somnolence and lung changes in intraperitoneal lethal-dose studies of mice (LD50 = 580 mg/kg)[RTECS] A skin and strong eye irritant[Sigma-Aldrich MSDS] See Pentamidine isethionate. |
| Hazard Classes and Categories | Skin Irrit. 2 (100%) |
| F | 3-21 |
| Wassergefährdungsklasse (WGK) | 3 |
| TSCA-Inventar-Status | TSCA listed |
| Zollcode | 29252900 |
| RTECS-Nr. | CV6260000 |
| R-Sätze (R) | 36/37/38 |
| Gefahrensymbole | Xi |
| Sicherheitshinweise (S) | 26-37/39-36 |
| Lagerklasse | 11 - Combustible Solids |
Anwendungen & Verwendung
Beschreibung
Benzamidine hydrochloride is a reversible inhibitor of trypsin, trypsin-like enzymes, and serine proteases. A concentration of approximately 1 mM is used for general protease inhibition. To inhibit proteases from yeast, a range of 0.5 to 4.0 mM is used and it is for the most part interchangeable with pepstatin A.In addition to being a strong competitive inhibitor of trypsin, benzamidine HCl has been also shown to be a strong competitive inhibitor of thrombin and plasmin. It was also found to be as effective as aprotinin in the prevention of glucagon degradation in human plasma.
Verwenden
Benzamidine is a reversible inhibitor of serine proteases, including trypsin, plasmin, and thrombin (Kis = 35, 350, and 220 μM, respectively). In addition to its use as a general serine protease inhibitor, benzamidine is used, when immobilized, to purify novel proteases.
Herstellung & Synthese
synthetische
To a stainless steel rocking autoclave equipped with a stirrer is added 103.0 gm (1.0 mole) of benzonitrile, 214.0 gm (4.0 mole) of ammonium chloride, and 306.0 gm (18.0 mole) of ammonia is introduced by means of a transfer bomb. The reaction mixture is heated at 150°C for 18 hr (pressure: 1300-6500 psig), cooled, and, with appropriate precautions for the safe control of the excess ammonia, is vented to atmospheric pressure. The reaction mixture is extracted with ether to remove approximately 5% unreacted benzonitrile, and then extracted with hot acetonitrile or ethanol to separate the amidine hydrochloride from the unreacted ammonium chloride. Concentration of the latter affords 120.5 gm (77%) of benzamidine hydrochloride, m.p. 161-163°C.