U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C30H60N3O3.3I
Molecular Weight 891.5291
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GALLAMINE TRIETHIODIDE

SMILES

[I-].[I-].[I-].CC[N+](CC)(CC)CCOC1=CC=CC(OCC[N+](CC)(CC)CC)=C1OCC[N+](CC)(CC)CC

InChI

InChIKey=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

HIDE SMILES / InChI
Molecular Formula HI
Molecular Weight 127.9124
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C30H60N3O3
Molecular Weight 510.8157
Charge 3
Count
Stereochemistry MIXED
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Gallamine triethiodide is a synthetic nondepolarizing blocking drug, which is allosteric antagonist of muscarinic M2 acetylcholine receptor and inhibitor of acetylcholinesterase. It was used under brand name flaxedil to stabilize muscle contractions during surgical procedures. However, this usage was discontinued. It was shown, that gallamine caused tachycardia by depressing the vagus nerve and, occasionally, hypertension and increased cardiac output.

CNS Activity

Originator

Approval Year

1951
104
Targets

Targets

Primary TargetPharmacologyConditionPotency
Muscarinic acetylcholine receptor M2
121
Target ID: P08172
Gene ID: 1129.0
Gene Symbol: CHRM2
Target Organism: Homo sapiens (Human)
Antagonist
2778
Acetylcholinesterase
207
Target ID: P22303|||Q53F46
Gene ID: 43.0
Gene Symbol: ACHE
Target Organism: Homo sapiens (Human)
Inhibitor
8297
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
Approved
8429
FLAXEDIL

Approved Use

Unknown
Doses

Doses

DosePopulationAdverse events​
40 mg single, intrathecal
Accidental dose
Dose: 40 mg
Route: intrathecal
Route: single
Dose: 40 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4406747
unhealthy, 33 years
n = 1
Health Status: unhealthy
Age Group: 33 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4406747
Other AEs: Convulsions...
Other AEs:
Convulsions
Sources:
https://pubmed.ncbi.nlm.nih.gov/4406747
6 mg/kg single, intravenous
Highest studied dose
Dose: 6 mg/kg
Route: intravenous
Route: single
Dose: 6 mg/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/7371706
unhealthy
n = 7
Health Status: unhealthy
Sex: M
Population Size: 7
Sources:
https://pubmed.ncbi.nlm.nih.gov/7371706
Sources:
https://pubmed.ncbi.nlm.nih.gov/7371706
100 mg single, intravenous
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13998750
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13998750
Other AEs: Ventricular tachycardia...
Other AEs:
Ventricular tachycardia
Sources:
https://pubmed.ncbi.nlm.nih.gov/13998750
AEs

AEs

AESignificanceDosePopulation
Convulsions
40 mg single, intrathecal
Accidental dose
Dose: 40 mg
Route: intrathecal
Route: single
Dose: 40 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/4406747
unhealthy, 33 years
n = 1
Health Status: unhealthy
Age Group: 33 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/4406747
Ventricular tachycardia
100 mg single, intravenous
Dose: 100 mg
Route: intravenous
Route: single
Dose: 100 mg
Sources:
https://pubmed.ncbi.nlm.nih.gov/13998750
unhealthy
Health Status: unhealthy
Sources:
https://pubmed.ncbi.nlm.nih.gov/13998750
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Kv1.3
17

K+ channels
70
Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
Kv1.3
32
 likely
K+ channels
70
 yes
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY565499
https://www.001chemical.com/chem/65-29-2
1PlusChem LLC
1P00EA4U
ABI Chem
AC1L1FYQ
AK Scientific
X5036
AbovChem LLC
HY-B0416
ApexBio Technology
B1610
AstaTech
C76041
BLD Pharm
BD131802
BOC Sciences
65-29-2
BioSynth
W-104798
Chem Scene
CS-2520
ChemShuttle
151696
Compound Cloud
3450
Compound Cloud
6172
Hairui
HR124463
http://www.hairuichem.com/en/product/65-29-2.html
KeyOrganics
AS-57694
MedChem Express
HY-B0416
MolPort
MolPort-003-666-195
Molcore
MC565499
https://www.molcore.com/product/65-29-2
Molnova
M15481
MuseChem
A000240
NCI Plated 2007
102690
Selleck Chemicals
S2471
Sigma Aldrich
1288000
Sigma Aldrich
1288000|USP
Sigma Aldrich
G0100000
Sigma Aldrich
G0100000|SIAL
Sigma Aldrich
G8134
Smolecule
S545841
http://www.smolecule.com/products/s545841
THE BioTek
bt-286831
https://www.thebiotek.com/product/inhibitors/bt-286831
TargetMol
T0720
TimTec
ST50990471
Toronto Research Chemicals
G188570
Toronto Research Chemicals
H592890
W&J PharmaChem
50C407253
ZINC
ZINC000003830882
http://zinc15.docking.org/substances/ZINC000003830882
eMolecules
538874
eMolecules
72980134
eNovation Chemicals
D766568
mcule
MCULE-9106832696
https://mcule.com/MCULE-9106832696/
PubMed

PubMed

TitleDatePubMed
The inhibitory effect of gallamine on muscarinic receptors.
1976 Nov
Detection, quantitation, and verification of allosteric interactions of agents with labeled and unlabeled ligands at G protein-coupled receptors: interactions of strychnine and acetylcholine at muscarinic receptors.
1995 Aug
Pharmacological comparison of the cloned human and rat M2 muscarinic receptor genes expressed in the murine fibroblast (B82) cell line.
1998 Feb
Interactions of orthosteric and allosteric ligands with [3H]dimethyl-W84 at the common allosteric site of muscarinic M2 receptors.
2003 Jul
Patents

Patents

20080275003
2
7947854
2

Sample Use Guides

In Vivo Use Guide
Single 4 and 6 mg/kg i.v. doses
Route of Administration: Intravenous
In Vitro Use Guide
The mechanisms of action of gallamine on nerve terminals, cholinergic receptors, and the threshold for propagation of end-plate potentials to the muscle fiber were investigated in rat phrenic nerve-diaphragm preparations. Intracellular studies were made with glass microelectrodes to determine changes in end-plate potentials and miniature end-plate potentials produced by gallamine at concentrations between 10(-7) M to 10(-4) M. Gallamine excited and then depressed the release of transmitter from nerve terminals.
Substance Class Chemical
Created
by admin
on Sat Dec 16 18:02:26 UTC 2023
Edited
by admin
on Sat Dec 16 18:02:26 UTC 2023
Record UNII
Q3254X40X2
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GALLAMINE TRIETHIODIDE
HSDB   INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
BENZCURINE IODIDE
Common Name English
GALLAMINE TRIETHIODIDE [MI]
Common Name English
SYNCURARINE
Common Name English
REMYOLAN
Common Name English
GALLAMINE TRIETHIODIDE [ORANGE BOOK]
Common Name English
GALLAMINE TRIETHIODIDE [HSDB]
Common Name English
GALLAMINE TRIETHIODIDE [WHO-IP]
Common Name English
GALLAMINE TRIETHIODIDE [MART.]
Common Name English
GALLAMINE TRIETHIODIDE [USP IMPURITY]
Common Name English
NSC-102690
Code English
GALLAMINI TRIETHIODIDUM [WHO-IP LATIN]
Common Name English
GALLAMINE TRIETHIODIDE [VANDF]
Common Name English
FLAXEDIL
Brand Name English
gallamine triethiodide [INN]
Common Name English
ETHANAMINIUM, 2,2',2''-(BENZENE-1,2,3-TRIYLTRIS(OXY))TRIS(N,N,N-TRIETHYL-, TRIIODIDE
Systematic Name English
Gallamine triethiodide [WHO-DD]
Common Name English
[v-Phenenyltris(oxyethylene)]tris[triethylammonium] triiodide
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
NCI_THESAURUS C66886
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
Code System Code Type Description
MESH
D005703
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
INN
1928
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
RXCUI
4639
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY RxNorm
HSDB
3229
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
CAS
65-29-2
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
PUBCHEM
6172
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
SMS_ID
100000084492
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
EVMPD
SUB07872MIG
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
MERCK INDEX
m5643
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
200-605-1
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
ChEMBL
CHEMBL360055
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
NCI_THESAURUS
C65798
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
DRUG BANK
DB00483
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
WIKIPEDIA
GALLAMINE TRIETHIODIDE
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
FDA UNII
Q3254X40X2
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
NSC
102690
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
GALLAMINE TRIETHIODIDE
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY Description: A white or almost white powder; odourless. Solubility: Very soluble in water; sparingly soluble in ethanol (~750 g/l) TS; practically insoluble in ether R. Category: Muscle relaxant. Storage: Gallamine triethiodide should be kept in a tightly closed container, protected from light. Additional information: Gallamine triethiodide is hygroscopic. Definition: Gallamine triethiodide contains not less than 98.0% and not more than 101.0% of C30H60I3N3O3, calculated withreference to the dried substance.
EPA CompTox
DTXSID5023089
Created by admin on Sat Dec 16 18:02:26 UTC 2023 , Edited by admin on Sat Dec 16 18:02:26 UTC 2023
PRIMARY
Related Record Type Details
Structure of TRIETHYLGALLAMINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966