Basic information
- CAS
65-29-2- Standard SMILES
CC[N+](CC)(CC)CCOc1cccc(OCC[N+](CC)(CC)CC)c1OCC[N+](CC)(CC)CC.[I-].[I-].[I-]- InChIKey
REEUVFCVXKWOFE-UHFFFAOYSA-K- Molecular formula
- C30H60I3N3O3
- Average molar mass
- 891.5 g/mol
- Monoisotopic mass
- 891.1769
Overview
A synthetic nondepolarizing blocking drug. The actions of gallamine triethiodide are similar to those of tubocurarine, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. It should be used cautiously in patients at risk from increased heart rate but may be preferred for patients with bradycardia. (From AMA Drug Evaluations Annual, 1992, p198)
Names & identifiers
- Preferred name
- Gallamine Triethiodide
- IUPAC
- 2-[2,3-bis[2-(triethylazaniumyl)ethoxy]phenoxy]ethyl-triethylazanium triiodide
- English name
- Gallamine triethiodide
- Molecular formula
- C30H60I3N3O3
- Molecular weight
- 891.53
Names & synonyms
GALLAMINE TRIETHIODIDE65-29-2FlaxedilBenzcurine iodideRemyolanSyncurarineRelaxanSincurarineRetensinTricuranGallaminii iodidumGallamine-3ETI
Show more names
gallaminef2559rp3697gallaminflacedil
Gallamine triiodoethylateFourneau 2559Gallamine iodideGallamina triodoetilatoGallamini triethiodidumTriethiodure de gallamineGallamin triethiodideGallamone triethiodide
Database identifiers
- CAS
65-29-2- PubChem CID
- 6172
- DTXSID
DTXSID5023089- ChEMBL
CHEMBL1200993- UNII
- Q3254X40X2
- EC Number
- 200-605-1
Properties
Computed structural properties
- Topological polar surface area
- 27.7 Ų
- Hydrogen bond donors
- 0
- Hydrogen bond acceptors
- 6
- Rotatable bonds
- 21
- Heavy atoms
- 39
- Formal charge
- 0
- Complexity
- 489
Experimental & physicochemical properties
OdorODORLESS
Color/Form
WHITE AMORPHOUS POWDER
White crystals from acetone/water
Solubility
Soluble
Freely sol in water, alcohol, dil acetone; sparingly sol in anhyd acetone, ether, benzene, chloroform
Very soluble in water and ethanol; slightly soluble in ethyl ether and acetone.
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
DecompositionWhen heated to decomposition it emits very toxic fumes of ammonia, nitroxides, and iodine.
Melting Point
152-153
147.5 °C
Other Experimental PropertiesHYGROSCOPIC
Physicochemical properties
- Melting point
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationEthanaminium, 2,2',2''-[1,2,3-benzenetriyltris(oxy)]tris[N,N,N-triethyl-, triiodide: Does not have an individual approval but may be used under an appropriate group standard
Other Safety InformationIMAP assessments - Ethanaminium, 2,2',2''-[1,2,3-benzenetriyltris(oxy)]tris[N,N,N-triethyl-, triiodide: Human health tier I assessment
FDA Requirements
Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Safety & protection
Disposal Methods
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Chemistry & industry
Pharmacology
Pharmacodynamics
Gallamine Triethiodide is a nondepolarizing neuromuscular blocking drug (NDMRD) used as an adjunct to anesthesia to induce skeletal muscle relaxation. The actions of gallamine triethiodide are similar to those of tubocurarine, but this agent blocks the cardiac vagus and may cause sinus tachycardia and, occasionally, hypertension and increased cardiac output. Muscle groups differ in their sensitivity to these types of relaxants with ocular muscles (controlling eyelids) being most sensitive, followed by the muscles of the neck, jaw, limbs and then abdomen. The diaphragm is the least sensitive muscle to NDMRDs. Although the nondepolarizing neuromuscular blocking drugs do not have the same adverse effects as succinylcholine, their onset of action is slower. They also have a longer duration of action, making them more suitable for maintaining neuromuscular relaxation during major surgical procedures.
Mechanism of Action
It competes with acetylcholine (ACh) molecules and binds to muscarinic acetylcholine receptors on the post-synaptic membrane of the motor endplate. It acts by combining with the cholinergic receptor sites in muscle and competitively blocking the transmitter action of acetylcholine. It blocks the action of ACh and prevents activation of the muscle contraction process. It can also act on nicotinic presynaptic acetylcholine receptors which inhibits the release of ACh.
GALLAMINE TRIETHIODIDE...PRODUCES SKELETAL MUSCLE RELAXATION BY COMBINING WITH RECEPTOR SITE AT NEUROMUSCULAR JUNCTION & BLOCKING ACTION OF NEUROTRANSMITTER ACETYLCHOLINE.
IN RAT PHRENIC NERVE-DIAPHRAGM GALLAMINE HAD NO SIGNIFICANT EFFECTS ON ELECTROGENIC PROPERTIES OF EXCITABLE MEMBRANES OF MOTOR NERVE TERMINALS & MUSCLE FIBERS; IT DEPRESSED RESPONSE OF POSTSYNAPTIC RECEPTORS TO ACTION OF ACETYLCHOLINE.
AT NEUROMUSCULAR JUNCTIONS IN MICE AND FROGS, FOLLOWING STEP CHANGES OF MEMBRANE POTENTIAL FROM -70 TO -130 MV, GALLAMINE (5 UMOL) IN THE PRESENCE OF ACETYLCHOLINE (3 UMOL) CAUSED AN INITIAL RAPID DECR IN CURRENT FOLLOWED BY OPENING OF CHANNELS AT A SLOWER RATE THAN WITH ACETYLCHOLINE ALONE. WHEN THE INTERNAL POTENTIAL WAS REDUCED TO -70 MV, THERE WAS A RAPID INCR IN CURRENT AT FIRST, FOLLOWED BY THE USUAL DECR WHICH WAS AGAIN SLOWER THAN NORMAL. THUS, GALLAMINE MAY PRODUCE A POTENTIAL-DEPENDENT BLOCK OF OPEN ION CHANNELS.
Biological Half-Life135 minutes /From table/
Related reactions
0 records
No reaction records under the current filter.
Compound notes
Loading…