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B2417

Sigma-Aldrich

Benzamil hydrochloride hydrate

≥98% (HPLC)

Synonym(s):

N-(Benzylamidino)-3,5-diamino-6-chloropyrazinecarboxamide hydrochloride hydrate

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About This Item

Empirical Formula (Hill Notation):
C13H14ClN7O · HCl · xH2O
CAS Number:
161804-20-2
Molecular Weight:
356.21 (anhydrous basis)
UNSPSC Code:
12352200
PubChem Substance ID:
24278262
NACRES:
NA.77

Quality Level

100

Assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

yellow

solubility

methanol: 10 mg/mL
DMSO: >20 mg/mL

storage temp.

2-8°C

SMILES string

O.Cl.Nc1nc(N)c(nc1Cl)C(=O)NC(=N)NCc2ccccc2

InChI

1S/C13H14ClN7O.ClH.H2O/c14-9-11(16)20-10(15)8(19-9)12(22)21-13(17)18-6-7-4-2-1-3-5-7;;/h1-5H,6H2,(H4,15,16,20)(H3,17,18,21,22);1H;1H2

InChI key

YAJQRPFIYXRNKS-UHFFFAOYSA-N

Gene Information

human ... SCNN1A(6337) , SCNN1B(6338) , SCNN1D(6339) , SCNN1G(6340)
mouse ... Scnn1a(20276) , Scnn1b(20277) , Scnn1d(140501) , Scnn1g(20278)
rat ... Scnn1a(25122) , Scnn1b(24767) , Scnn1g(24768)

Biochem/physiol Actions

Selective and potent blocker of Na+/H+ and Na+/Ca2+ channels

Features and Benefits

This compound is featured on the Acid-Sensing (Proton-gated) Ion Channels (ASICs) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Other Notes

Nω-Benzyl derivative of amiloride.

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H315 - H319 - H335

Hazard Classifications

Eye Irrit. 2 - Skin Irrit. 2 - STOT SE 3

Target Organs

Respiratory system

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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J W Lane et al.
British journal of pharmacology, 106(2), 283-286 (1992-06-11)
1. Patch clamp recording techniques have been used to compare the block caused by amiloride and some of its structural analogues of the mechanosensitive (MS) cation selective channel in frog (Xenopus laevis) oocytes. 2. Like amiloride, the amiloride analogues dimethylamiloride
A Catalina Vélez-Ortega et al.
eLife, 6 (2017-03-30)
Mechanotransducer channels at the tips of sensory stereocilia of inner ear hair cells are gated by the tension of 'tip links' interconnecting stereocilia. To ensure maximal sensitivity, tip links are tensioned at rest, resulting in a continuous influx of Ca2+
G N Pierce et al.
The Journal of pharmacology and experimental therapeutics, 265(3), 1280-1291 (1993-06-01)
Amiloride and its derivatives (benzamil, dichlorobenzamil, 5-(N,N-dimethyl)-amiloride, 5-(N-ethyl-N-isopropyl)-amiloride, (N,N-hexamethylene)- amiloride and 5-(N-methyl-N-isobutyl)-amiloride) are commonly used as selective blockers of Na+/Ca++ exchange or Na+/H+ exchange. Very little information is currently available regarding their effects on cardiac performance. It was observed that
Takanori Tsujimura et al.
The Journal of physiology, 597(11), 2949-2963 (2019-04-30)
Afferents carried by the superior laryngeal nerve play a primary role in the initiation of laryngeal mechanically evoked swallows in anaesthetized rats. Amiloride and its analogues inhibit swallowing evoked by mechanical stimulation, but not swallowing evoked by chemical and electrical
Angela Ballesteros et al.
eLife, 7 (2018-08-01)
The hair cell mechanotransduction (MET) channel complex is essential for hearing, yet it's molecular identity and structure remain elusive. The transmembrane channel-like 1 (TMC1) protein localizes to the site of the MET channel, interacts with the tip-link responsible for mechanical
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