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Merck

G8134

Gallamine triethiodide

≥98% (TLC), allosteric muscarinic receptor antagonist, powder

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About This Item

Empirical Formula (Hill Notation):
C30H60I3N3O3
CAS Number:
65-29-2
Molecular Weight:
891.53
NACRES:
NA.77
PubChem Substance ID:
24277837
UNSPSC Code:
12352116
EC Number:
200-605-1
MDL number:
MFCD00011832

Product Name

Gallamine triethiodide, ≥98% (TLC), powder, muscarinic receptor antagonist

Quality Level

200

InChI key

REEUVFCVXKWOFE-UHFFFAOYSA-K

InChI

1S/C30H60N3O3.3HI/c1-10-31(11-2,12-3)22-25-34-28-20-19-21-29(35-26-23-32(13-4,14-5)15-6)30(28)36-27-24-33(16-7,17-8)18-9;;;/h19-21H,10-18,22-27H2,1-9H3;3*1H/q+3;;;/p-3

SMILES string

[I-].[I-].[I-].CC[N+](CC)(CC)CCOc1cccc(OCC[N+](CC)(CC)CC)c1OCC[N+](CC)(CC)CC

assay

≥98% (TLC)

form

powder

mp

235 °C (dec.) (lit.)

solubility

H2O: 100 mg/mL
ethanol: soluble

storage temp.

2-8°C

Gene Information

human ... CHRM1(1128), CHRM2(1129), CHRM3(1131), CHRM4(1132), CHRM5(1133), CHRNA1(1134), CHRNB1(1140), CHRND(1144), CHRNE(1145), CHRNG(1146)

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Application

Gallamine triethiodide has been used:
  • as a relaxant for measuring spinal trigeminal nucleus recordings from single neurons.
  • as an antagonist in neuroblastoma cells as M2 receptor
  • to reduce eye movement during retinal surgery in rat

Biochem/physiol Actions

Gallamine triethiodide has anti-muscarinic effect. It is a competitive antagonist for the muscarinic receptor. Gallamine is regarded as neuromuscular blocking agent.
Muscle relaxant; allosteric muscarinic receptor antagonist with an order of potency of M2 > M1 = M4 > M3 = M5. Ligand for the peripheral anionic binding site of acetylcholinesterase.

Disclaimer

Hygroscopic

Features and Benefits

This compound is a featured product for Neuroscience research. Click here to discover more featured Neuroscience products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Acetylcholine Receptors (Muscarinic) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

hcodes

H302

Hazard Classifications

Acute Tox. 4 Oral

Storage Class

11 - Combustible Solids

wgk

WGK 3

ppe

dust mask type N95 (US), Eyeshields, Gloves

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Certificates of Analysis (COA)

Lot/Batch Number
MKCL6737
MKCL2118
MKBX4561V
SLBH0969V
SLBD3707V

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Dar'ya S Redka et al.
Molecular pharmacology, 74(3), 834-843 (2008-06-17)
The M(2) muscarinic receptor has two topographically distinct sites: the orthosteric site and an allosteric site recognized by compounds such as gallamine. It also can exhibit cooperative effects in the binding of orthosteric ligands, presumably to the orthosteric sites within
Sandrine B Daval et al.
Molecular pharmacology, 84(1), 71-85 (2013-04-23)
Bitopic binding properties apply to a variety of muscarinic compounds that span and simultaneously bind to both the orthosteric and allosteric receptor sites. We provide evidence that fluorescent pirenzepine derivatives, with the M1 antagonist fused to the boron-dipyrromethene [Bodipy (558/568)]
Transcriptional response to muscarinic acetylcholine receptor stimulation: regulation of Egr-1 biosynthesis by ERK, Elk-1, MKP-1, and calcineurin in carbachol-stimulated human neuroblastoma cells
Rossler O, et al.
Archives of Biochemistry and Biophysics, 470(1), 93-102 (2008)
Neuromuscular blocking drugs: discovery and development
Raghavendra T
Journal of the Royal Society of Medicine, 95(7), 363-367 (2002)
J Eichler et al.
Molecular pharmacology, 45(2), 335-340 (1994-02-01)
Comparison of the effect of three 'peripheral' site ligands, propidium, d-tubocurarine, and gallamine, on acetylcholinesterase (acetylcholine hydrolase; EC 3.1.1.7) of Torpedo and chicken shows that all three are substantially more effective inhibitors of the Torpedo enzyme than of the chicken
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