Basic information Safety Supplier Related

Benzamidine hydrochloride

Basic information Safety Supplier Related

Benzamidine hydrochloride Basic information

Product Name:
Benzamidine hydrochloride
Synonyms:
  • amidinobenzenehydrochloride
  • benzamidiniumchloride
  • 2-hydroxybenzene-1-carboxiMidaMide hydrochloride
  • Additive Screening Solution 37/Fluka kit no 78374
  • Benzamidine hydrochloride solution
  • Benzamidine hydrochl
  • BenziMidaMide hydrochloride
  • BenzaMidine Hydrochloride , 96.0%(T)
CAS:
1670-14-0
MF:
C7H9ClN2
MW:
156.61
EINECS:
216-795-4
Product Categories:
  • Phenyls & Phenyl-Het
  • Core Bioreagents
  • Enzyme InhibitorsEnzyme Inhibitors by Enzyme
  • R to
  • Research Essentials
  • Trypsin Inhibitors
  • Pharmaceutical Intermediates
  • Anilines, Aromatic Amines and Nitro Compounds
  • Phenyls & Phenyl-Het
Mol File:
1670-14-0.mol
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Benzamidine hydrochloride Chemical Properties

Melting point:
86-88 °C(lit.)
storage temp. 
2-8°C
solubility 
DMF: 25 mg/ml
DMSO: 25 mg/ml
Ethanol: 10 mg/ml
PBS (pH 7.2): 3 mg/ml
form 
Powder
color 
White to off-white
PH
4.0 to 6.5(50g/L, 25 ℃)
Water Solubility 
soluble
BRN 
3594959
Stability:
Stable for 2 years from date of purchase as supplied. Solutions are not stable and must be prepared fresh daily
InChIKey
LZCZIHQBSCVGRD-UHFFFAOYSA-N
CAS DataBase Reference
1670-14-0(CAS DataBase Reference)
EPA Substance Registry System
Benzenecarboximidamide, monohydrochloride (1670-14-0)
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Safety Information

Hazard Codes 
Xi
Risk Statements 
36/37/38
Safety Statements 
26-37/39-36
WGK Germany 
3
RTECS 
CV6260000
3-21
HS Code 
29252900

MSDS

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Benzamidine hydrochloride Usage And Synthesis

Description

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.

Chemical Properties

white to off-white powder

Uses

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.

Preparation

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.

Biological Activity

Benzamidine hydrochloride is an reversible competitive inhibitor of trypsin-like serine proteases, with Kis of 97 μM, 21 μM, 20 μM and 110 μM for uPA, trypsin, tryptase and factor Xa, respectively.

Safety Profile

Moderately toxic byintraperitoneal route. When heated to decomposition itemits toxic vapors of NOx, HCl, and Cl-.

in vitro

Benzamidine hydrochloride has weak inhibition for tPA and thrombin, with Kis of 750 μM and 320 μM, respectively.

References

1) Markwardt?et al. (1968)?Comparative studies on the inhibition of trypsin, plasmin, and thrombin by derivatives of benzylamine and benzamide; Eur. J. Biochem.,?6?502 2) Deutscher?et al.?(1990),?Maintaining protein stability; Methods Enzymol.,?182?83 3) Jaswinski?et al.?(1990),?Preparations of extracts from yeast; Methods Enzymol.,?182?154 4) Ensinck?et al.?(1972),?Use of Benzamidine as a proteolytic inhibitor in the radioimmunoassay of glucagon in plasma; J. Clin. Endocrinol. Metab.,?35?463 5) Jeffcoate?et al. (1974),?Use of benzamidine to prevent the destruction of thyrotropin-releasing hormone (TRH) by blood; Endocrinol. Metab,?38?155

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