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W0641

Sigma-Aldrich

W-84 dibromide

≥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

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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K Jepsen et al.
Pharmacology & toxicology, 63(3), 163-168 (1988-09-01)
W84 (hexamethylene-bis-[dimethyl-(3-phthalimidopropyl)-ammonium bromide]) protects overadditively against an organophosphate-intoxication when applied in combination with atropine. Further experimental evidence led to the hypothesis that W84 exerted an allosteric effect on muscarinic acetylcholine receptors. In order to investigate the action of W84 on
A Christopoulos et al.
European journal of pharmacology, 355(1), 103-111 (1998-10-01)
Using the program Microsoft EXCEL, a spreadsheet was developed for constrained, simultaneous analysis of multiple datasets obtained from equilibrium binding experiments, according to an allosteric model of interaction. This approach was used to quantitate the interaction between the modulator (heptane-1,7-bis
Xi-Ping Huang et al.
Molecular pharmacology, 71(3), 759-768 (2006-11-30)
The 2nd outer loop (o2) of muscarinic acetylcholine receptors (mAChRs) contains a highly conserved cysteine residue that is believed to participate in a disulfide bond and is flanked on either side by epitopes that are critical to the binding of
C Tränkle et al.
Molecular pharmacology, 54(1), 139-145 (1998-07-11)
Muscarinic acetylcholine receptors bind allosteric modulators at a site apart from the orthosteric site used by conventional ligands. We tested in cardiac tissue whether modulator binding to ligand-occupied muscarinic M2 receptors is a preferential event that can be detected using
G Bejeuhr et al.
The Journal of pharmacy and pharmacology, 46(2), 108-112 (1994-02-01)
W84 (N,N,N',N'-tetramethyl-N,N'-bis-(3-phthalimidopropyl)-N,N'-hexane- 1,6- diyl-bis-ammonium dibromide) is a potent stabilizer of antagonist binding to muscarinic receptors; however, W84 hydrolyses in aqueous buffered medium. The synthesis of the stable derivative CHIN3/6 is presented containing a 2-phenyl-quinazolinone instead of the labile phthalimide substituent.
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