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Details

Stereochemistry ACHIRAL
Molecular Formula C16H38N2
Molecular Weight 258.4869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 2

SHOW SMILES / InChI
Structure of DECAMETHONIUM

SMILES

C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C

InChI

InChIKey=MTCUAOILFDZKCO-UHFFFAOYSA-N
InChI=1S/C16H38N2/c1-17(2,3)15-13-11-9-7-8-10-12-14-16-18(4,5)6/h7-16H2,1-6H3/q+2

HIDE SMILES / InChI
Decamethylene disquaternary salts, with a ten-carbon (C10) chain between the quaternary groups, had the most potent curariform action in the series of polymethylene bisquaternaries. Decamethonium was used clinically as a neuromuscular blocking drug for a short time. Decamethonium was different from d-tubocurarine and that it produced a transient augmentation of contraction. C10 produces neuromuscular block by initiating some active response in the endplate or muscle fibre. Unlike d-tubocurare, decamethonium was not reversed by anticholinesterase agents.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Preventing
SYNCURINE

Approved Use

Syncurine is a short acting depolarizing muscle relaxant or neuromuscular blocking agent, and is used in anesthesia to induce paralysis.
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Sympathetic outflows from cervical spinal cord in the dog.
1966 Apr 15
Effects of ganglion blocking agents on nicotine extensor convulsions and lethality in mice.
1969 Sep
[Microbiological validation of the composition of "decaceol", an antiseptic prolonged-release drug].
2002
Mechanistic investigation of the interaction between bisquaternary antimicrobial agents and phospholipids by liquid secondary ion mass spectrometry and differential scanning calorimetry.
2002
Effects of membranotropic agents on mono- and multilayer structures of dipalmitoylphosphatidylcholine.
2002 Dec
Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice.
2002 Jun
Molecular conformation-activity relationship of decamethonium congeners.
2002 May
Structure of a complex of the potent and specific inhibitor BW284C51 with Torpedo californica acetylcholinesterase.
2002 Oct
Short-term rigid and flaccid paralyses diminish growth of embryonic chick limbs and abrogate joint cavity formation but differentially preserve pre-cavitated joints.
2002 Sep
Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.
2003 Dec
beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies.
2003 Feb 1
Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells.
2003 Jun 12
GABAergic systems modulate nicotinic receptor-mediated seizures in mice.
2003 Sep
Decamethonium bromide-mediated inhibition of embryonic muscle development.
2004 Apr
Mechanical modulation of cartilage structure and function during embryogenesis in the chick.
2004 Jan
Long-lasting activation of rhythmic neuronal activity by a novel mechanosensory system in the crustacean stomatogastric nervous system.
2004 Jan
Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.).
2004 Oct
[Application of the Decasan at the practice of urgent surgery].
2004 Sep
Expression of the alpha7 nicotinic acetylcholine receptor in human lung cells.
2005 Apr 4
Muscle relaxants--decamethonium.
2005 Dec
Structural basis of acetylcholinesterase inhibition by triterpenoidal alkaloids.
2005 Jun 17
The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction.
2005 May 13
Quaternary ammonium anticholinesterases have different effects on nicotinic receptors: is there a single binding site?
2006
Early effects of embryonic movement: 'a shot out of the dark'.
2006 Apr
Effect of in ovo immobilization on development of chick hind-limb articular cartilage: an evaluation using micro-MRI measurement of delayed gadolinium uptake.
2006 Dec
Toxicity of polymyxins: a systematic review of the evidence from old and recent studies.
2006 Feb
Dequalinium-induced protofibril formation of alpha-synuclein.
2006 Feb 10
Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts.
2006 Jan 26
Receptor protection studies comparing recombinant and native nicotinic receptors: Evidence for a subpopulation of mecamylamine-sensitive native alpha3beta4* nicotinic receptors.
2006 Jan 9
Diverse inhibitory actions of quaternary ammonium cholinesterase inhibitors on Torpedo nicotinic ACh receptors transplanted to Xenopus oocytes.
2007 Aug
Lymph heart in chick--somitic origin, development and embryonic oedema.
2007 Dec
Differences in susceptibility to German cockroach frass and its associated proteases in induced allergic inflammation in mice.
2007 Dec 8
Inhibition of choline transport by redox-active cholinomimetic bis-catechol reagents.
2007 Nov 15
Discovery of a novel nicotinic receptor antagonist for the treatment of nicotine addiction: 1-(3-Picolinium)-12-triethylammonium-dodecane dibromide (TMPD).
2007 Oct 15
The effect of some curarizing drugs in unanaesthetized man. I. d-Tubocurarine chloride, gallamonium iodide, decamethonium iodide, succinylcholine iodide and its bis-monoethyl-substituted derivative in single or repeated doses. Acta Anaesth. Scandinav. 1957, 1, 15-39.
2007 Sep
Allergen uptake, activation, and IL-23 production by pulmonary myeloid DCs drives airway hyperresponsiveness in asthma-susceptible mice.
2008
Amazing stability of phosphate-quaternary amine interactions.
2008 Aug
Identification of mechanosensitive genes during embryonic bone formation.
2008 Dec
Pharmacological evaluation of contractile activity of the dog heartworm Dirofilaria immitis.
2008 Mar
Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors.
2009 Dec 28
Stabilization of Torpedo californica acetylcholinesterase by reversible inhibitors.
2009 Jan 27
Bone marrow cell derived arginase I is the major source of allergen-induced lung arginase but is not required for airway hyperresponsiveness, remodeling and lung inflammatory responses in mice.
2009 Jun 1
Single fiber electromyographic jitter and detection of acute changes in neuromuscular function in young and adult rats.
2009 Mar-Apr
[Application of antiseptic dekasan in urgent abdominal surgery].
2009 Nov-Dec
Role of phospholipases in fungal fitness, pathogenicity, and drug development - lessons from cryptococcus neoformans.
2010
In silico modeling of the specific inhibitory potential of thiophene-2,3-dihydro-1,5-benzothiazepine against BChE in the formation of beta-amyloid plaques associated with Alzheimer's disease.
2010 Jun 16
[Dekasan application in treatment of infected pancreatic necrosis and its complications].
2010 Mar
Drug interaction: focusing on response surface models.
2010 May
Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes.
2010 May
Mucosal sensitization to German cockroach involves protease-activated receptor-2.
2010 May 24
Patents

Patents

Sample Use Guides

The mean (SEM) dose of decamethonium producing 80% twitch tension depression (ED80) when administered alone was 37 (4.0) micrograms/kg.
Route of Administration: Parenteral
In Vitro Use Guide
1. In rat diaphragms immersed in solution containing 5 mm potassium the maximum uptake of labelled decamethonium was found at the end-plate region. In muscles depolarized in solution containing potassium methyl sulphate the uptake was reduced but a peak concentration at the end-plate region was still demonstrated.
Name Type Language
DECAMETHONIUM
HSDB   WHO-DD  
Common Name English
DECAMETHONIUM [WHO-DD]
Common Name English
DECAMETHONIUM ION
Common Name English
DECAMETHONIUM [HSDB]
Common Name English
N,N,N,N',N',N'-HEXAMETHYLDECANE-1,10-DIAMINIUM
Systematic Name English
1,10-DECANEDIAMINIUM, N,N,N,N',N',N'-HEXAMETHYL-
Systematic Name English
DECAMETHONIUM CATION
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29696
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
Code System Code Type Description
EPA CompTox
156-74-1
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
PUBCHEM
2968
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
FDA UNII
C1CG1S3T2W
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
DRUG BANK
DB01245
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
CAS
156-74-1
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
DRUG CENTRAL
789
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
NCI_THESAURUS
C77363
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
WIKIPEDIA
DECAMETHONIUM
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
MESH
C033019
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
EVMPD
SUB01568MIG
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY
HSDB
3221
Created by admin on Sat Jun 26 07:53:19 UTC 2021 , Edited by admin on Sat Jun 26 07:53:19 UTC 2021
PRIMARY