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G8134

Sigma-Aldrich

Gallamine triethiodide

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

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About This Item

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

Quality Level

200

Assay

≥98% (TLC)

form

powder

mp

235 °C (dec.) (lit.)

solubility

H2O: 100 mg/mL
ethanol: soluble

storage temp.

2-8°C

SMILES string

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

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

InChI key

REEUVFCVXKWOFE-UHFFFAOYSA-K

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.

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.

Caution

Hygroscopic

Pictograms

Exclamation mark
GHS07

Signal Word

Warning

Hazard Statements

H302

Precautionary Statements

P264 - P270 - P301 + P312 - P501

Hazard Classifications

Acute Tox. 4 Oral

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

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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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)]
Paul W Elsinghorst et al.
Journal of medicinal chemistry, 50(23), 5685-5695 (2007-10-20)
Gallamine and tacrine are allosteric antagonists at muscarinic M2 acetylcholine receptors and inhibitors of acetylcholinesterase. At both acetylcholine-binding proteins, gallamine and tacrine are known to occupy two different binding sites: in M2 receptors within the allosteric binding area and in
The inhibitory effect of gallamine on muscarinic receptors
Clark AL and Mitchelson F
British Journal of Pharmacology, 58(3), 323-331 (1976)
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
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)
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