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W0641

W-84 dibromide

Name: W-84 dibromide
Brand: SIGMA

≥98% (HPLC), solid

Synonym(s):

Hexamethylene-bis-[dimethyl-(3-phthalimidopropyl)ammonium]dibromide

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About This Item

Empirical Formula (Hill Notation):

C₃₂H₄₄Br₂N₄O₄

CAS Number:

21093-51-6

Molecular Weight:

708.52

MDL number:

MFCD00209827

UNSPSC Code:

12352202

PubChem Substance ID:

24724665

NACRES:

NA.77

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Assay

≥98% (HPLC)

form

solid

color

white

solubility

DMSO: ~11 mg/mL
H₂O: insoluble

storage temp.

−20°C

SMILES string

[Br-].[Br-].C[N+](C)(CCCCCC[N+](C)(C)CCCN1C(=O)c2ccccc2C1=O)CCCN3C(=O)c4ccccc4C3=O

InChI

1S/C32H44N4O4.2BrH/c1-35(2,23-13-19-33-29(37)25-15-7-8-16-26(25)30(33)38)21-11-5-6-12-22-36(3,4)24-14-20-34-31(39)27-17-9-10-18-28(27)32(34)40;;/h7-10,15-18H,5-6,11-14,19-24H2,1-4H3;2*1H/q+2;;/p-2

InChI key

DZRJZDQAGMZGGA-UHFFFAOYSA-L

Biochem/physiol Actions

Potent allosteric modulator of M₂ muscarinic acetylcholine receptors.

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

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Certificates of Analysis (COA)

Lot/Batch Number

035K4610

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Allosteric effects of the alkane-bis-ammonium compound W84 and of tacrine on [3H]pirenzepine binding at M1-receptors in rat cerebral cortex.

K Mohr et al.

Pharmacology & toxicology, 75(6), 391-394 (1994-12-01)

The bis-quaternary W84, hexamethylene-bis-[dimethyl-(3-phthalimidopropyl)-ammonium bromide], is a potent allosteric modulator of M2-cholinoceptors. In this study we aimed at quantifying its allosteric effect on the dissociation of [3H]pirenzepine from M1-cholinoceptors in rat cerebral cortex and to measure the effects on association

Comparison of structurally different allosteric modulators of muscarinic receptors by self-organizing neural networks.

U Holzgrabe et al.

Journal of molecular graphics, 14(4), 185-193 (1996-08-01)

Similarities in the molecular structure and surface properties of the allosteric modulators of muscarinic receptors, alcuronium, gallamine, tubocurarine, and the hexamethonium compound W84, a well-known pharmacological tool, are explored. The analysis of the molecular electrostatic potential (MEP) as well as

Interaction of Mg2+ with the allosteric site of muscarinic M2 receptors.

U Burgmer et al.

Naunyn-Schmiedeberg's archives of pharmacology, 357(4), 363-370 (1998-05-30)

Mg2+-ions have been suspected to attenuate the inhibitory effect of allosteric modulators on the dissociation of orthosteric ligands from muscarinic M2 receptors. It was aimed to gain more insight into the molecular events underlying the effect of Mg2+. The interaction

Allosteric site in M2 acetylcholine receptors: evidence for a major conformational change upon binding of an orthosteric agonist instead of an antagonist.

Maren Grossmüller et al.

Naunyn-Schmiedeberg's archives of pharmacology, 372(4), 267-276 (2005-12-20)

Muscarinic acetylcholine receptors contain two distinct ligand binding sites, i.e. the orthosteric site for acetylcholine and other conventional ligands, and an allosteric site located at the entrance of the ligand binding pocket. We used a set of allosteric agents to

Development of a new type of allosteric modulator of muscarinic receptors: hybrids of the antagonist AF-DX 384 and the hexamethonio derivative W84.

Marion Mohr et al.

Journal of medicinal chemistry, 47(12), 3324-3327 (2004-05-28)

Various fragments of the hexamethonio-type allosteric agent W84 were linked to the secondary amino group of the muscarinic M(2) acetylcholine receptor-preferring antagonist AF-DX 384 to increase the area of attachment with the allosteric site. Addition of only the phthalimido moiety

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