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G8134

Sigma-Aldrich

Gallamine triethiodide

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

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About This Item

Formule empirique (notation de Hill):
C30H60I3N3O3
Numéro CAS:
65-29-2
Poids moléculaire :
891.53
Numéro CE :
200-605-1
Numéro MDL:
MFCD00011832
Code UNSPSC :
12352116
ID de substance PubChem :
24277837
Nomenclature NACRES :
NA.77

Pureté

≥98% (TLC)

Forme

powder

Pf

235 °C (dec.) (lit.)

Solubilité

H2O: 100 mg/mL
ethanol: soluble

Température de stockage

2-8°C

Chaîne SMILES 

[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

Clé InChI

REEUVFCVXKWOFE-UHFFFAOYSA-K

Informations sur le gène

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

Actions biochimiques/physiologiques

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.

Caractéristiques et avantages

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.

Attention

Hygroscopic

Pictogrammes

Exclamation mark
GHS07

Mention d'avertissement

Warning

Mentions de danger

H302

Classification des risques

Acute Tox. 4 Oral

Code de la classe de stockage

11 - Combustible Solids

Classe de danger pour l'eau (WGK)

WGK 3

Équipement de protection individuelle

dust mask type N95 (US), Eyeshields, Gloves

Certificats d'analyse (COA)

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Consulter la Bibliothèque de documents

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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