B2417

Benzamil hydrochloride hydrate

Name: Benzamil hydrochloride hydrate
Brand: SIGMA

≥98% (HPLC), ENaC and NCX inhibitor, solid

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)

MDL number:

MFCD28147597

UNSPSC Code:

12352200

PubChem Substance ID:

24278262

NACRES:

NA.77

Product Name

Benzamil hydrochloride hydrate, ≥98% (HPLC)

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

assay

≥98% (HPLC)

form

solid

storage condition

desiccated

color

yellow

solubility

methanol: 10 mg/mL
DMSO: >20 mg/mL

storage temp.

2-8°C

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

N_ω-Benzyl derivative of amiloride.

pictograms

GHS07

signalword

Warning

hcodes

H315,H319,H335

pcodes

P261 - P264 - P271 - P280 - P302 + P352 - P305 + P351 + P338

Hazard Classifications

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

target_organs

Respiratory system

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number

0000351697

0000180747

0000129799

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Mechanotransduction current is essential for stability of the transducing stereocilia in mammalian auditory hair cells.

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+

Structure-activity relations of amiloride and its analogues in blocking the mechanosensitive channel in Xenopus oocytes.

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

Modulation of cardiac performance by amiloride and several selected derivatives of amiloride.

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

Involvement of the epithelial sodium channel in initiation of mechanically evoked swallows in anaesthetized rats.

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

Molecular principles of assembly, activation, and inhibition in epithelial sodium channel.

Sigrid Noreng et al.

eLife, 9 (2020-07-31)

The molecular bases of heteromeric assembly and link between Na+ self-inhibition and protease-sensitivity in epithelial sodium channels (ENaCs) are not fully understood. Previously, we demonstrated that ENaC subunits - α, β, and γ - assemble in a counterclockwise configuration when

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