Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H38N2.2I |
| Molecular Weight | 512.2953 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[I-].[I-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
InChI
InChIKey=ARMLJSXXXFXSLQ-UHFFFAOYSA-L
InChI=1S/C16H38N2.2HI/c1-17(2,3)15-13-11-9-7-8-10-12-14-16-18(4,5)6;;/h7-16H2,1-6H3;2*1H/q+2;;/p-2
| Molecular Formula | HI |
| Molecular Weight | 127.91241 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C16H38N2 |
| Molecular Weight | 258.4863 |
| Charge | 2 |
| Count |
|
| Stereochemistry | MIXED |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 2 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2362997 |
|||
Target ID: CHEMBL220 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Preventing | SYNCURINE Approved UseSyncurine is a short acting depolarizing muscle relaxant or neuromuscular blocking agent, and is used in anesthesia to induce paralysis. |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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. | 2010-06-16 |
|
| Mucosal sensitization to German cockroach involves protease-activated receptor-2. | 2010-05-24 |
|
| [Application of antiseptic dekasan in urgent abdominal surgery]. | 2010-05-13 |
|
| Drug interaction: focusing on response surface models. | 2010-05 |
|
| Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes. | 2010-05 |
|
| [Dekasan application in treatment of infected pancreatic necrosis and its complications]. | 2010-03 |
|
| Role of phospholipases in fungal fitness, pathogenicity, and drug development - lessons from cryptococcus neoformans. | 2010 |
|
| Divergence of allosteric effects of rapacuronium on binding and function of muscarinic receptors. | 2009-12-28 |
|
| 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. | 2009-06-01 |
|
| Single fiber electromyographic jitter and detection of acute changes in neuromuscular function in young and adult rats. | 2009-04-16 |
|
| Stabilization of Torpedo californica acetylcholinesterase by reversible inhibitors. | 2009-01-27 |
|
| Identification of mechanosensitive genes during embryonic bone formation. | 2008-12 |
|
| Amazing stability of phosphate-quaternary amine interactions. | 2008-08 |
|
| Pharmacological evaluation of contractile activity of the dog heartworm Dirofilaria immitis. | 2008-03 |
|
| Allergen uptake, activation, and IL-23 production by pulmonary myeloid DCs drives airway hyperresponsiveness in asthma-susceptible mice. | 2008 |
|
| Differences in susceptibility to German cockroach frass and its associated proteases in induced allergic inflammation in mice. | 2007-12-08 |
|
| Lymph heart in chick--somitic origin, development and embryonic oedema. | 2007-12 |
|
| Inhibition of choline transport by redox-active cholinomimetic bis-catechol reagents. | 2007-11-15 |
|
| Discovery of a novel nicotinic receptor antagonist for the treatment of nicotine addiction: 1-(3-Picolinium)-12-triethylammonium-dodecane dibromide (TMPD). | 2007-10-15 |
|
| 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. | 2007-09 |
|
| Diverse inhibitory actions of quaternary ammonium cholinesterase inhibitors on Torpedo nicotinic ACh receptors transplanted to Xenopus oocytes. | 2007-08 |
|
| Effect of in ovo immobilization on development of chick hind-limb articular cartilage: an evaluation using micro-MRI measurement of delayed gadolinium uptake. | 2006-12 |
|
| Early effects of embryonic movement: 'a shot out of the dark'. | 2006-04 |
|
| Dequalinium-induced protofibril formation of alpha-synuclein. | 2006-02-10 |
|
| Toxicity of polymyxins: a systematic review of the evidence from old and recent studies. | 2006-02 |
|
| Correlation of antifungal activity with fungal phospholipase inhibition using a series of bisquaternary ammonium salts. | 2006-01-26 |
|
| Receptor protection studies comparing recombinant and native nicotinic receptors: Evidence for a subpopulation of mecamylamine-sensitive native alpha3beta4* nicotinic receptors. | 2006-01-09 |
|
| Quaternary ammonium anticholinesterases have different effects on nicotinic receptors: is there a single binding site? | 2006 |
|
| Muscle relaxants--decamethonium. | 2005-12 |
|
| Structural basis of acetylcholinesterase inhibition by triterpenoidal alkaloids. | 2005-06-17 |
|
| The theaflavin fraction is responsible for the facilitatory effect of black tea at the skeletal myoneural junction. | 2005-05-13 |
|
| Expression of the alpha7 nicotinic acetylcholine receptor in human lung cells. | 2005-04-04 |
|
| Evaluation of mechanisms of azinphos-methyl resistance in the codling moth Cydia pomonella (L.). | 2004-10 |
|
| [Application of the Decasan at the practice of urgent surgery]. | 2004-09 |
|
| Decamethonium bromide-mediated inhibition of embryonic muscle development. | 2004-04 |
|
| Mechanical modulation of cartilage structure and function during embryogenesis in the chick. | 2004-01 |
|
| Long-lasting activation of rhythmic neuronal activity by a novel mechanosensory system in the crustacean stomatogastric nervous system. | 2004-01 |
|
| Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. | 2003-12 |
|
| GABAergic systems modulate nicotinic receptor-mediated seizures in mice. | 2003-09 |
|
| Pharmacological characterization of recombinant bovine alpha3beta4 neuronal nicotinic receptors stably expressed in HEK 293 cells. | 2003-06-12 |
|
| beta-Amyloid aggregation induced by human acetylcholinesterase: inhibition studies. | 2003-02-01 |
|
| Effects of membranotropic agents on mono- and multilayer structures of dipalmitoylphosphatidylcholine. | 2002-12 |
|
| Structure of a complex of the potent and specific inhibitor BW284C51 with Torpedo californica acetylcholinesterase. | 2002-10 |
|
| Short-term rigid and flaccid paralyses diminish growth of embryonic chick limbs and abrogate joint cavity formation but differentially preserve pre-cavitated joints. | 2002-09 |
|
| Characterization of [(125) I]epibatidine binding and nicotinic agonist-mediated (86) Rb(+) efflux in interpeduncular nucleus and inferior colliculus of beta2 null mutant mice. | 2002-06 |
|
| Molecular conformation-activity relationship of decamethonium congeners. | 2002-05 |
|
| [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 ganglion blocking agents on nicotine extensor convulsions and lethality in mice. | 1969-09 |
|
| Sympathetic outflows from cervical spinal cord in the dog. | 1966-04-15 |
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
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.
2. The uptake of labelled decamethonium increased steadily with time and was interpreted in terms of the entry of decamethonium into the fibres. The permeability at 10-100 μm was similar to that of sodium.
3. The uptake of decamethonium at the end-plate region was dependent on the concentration. At low values the uptake in depolarized muscle was uniform along the fibres. Increase in concentration produced a peak at the end-plate region. This was interpreted as a change in permeability such that half the maximum effect was present at a concentration of approximately 5 μm.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 18:48:53 GMT 2025
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on
Mon Mar 31 18:48:53 GMT 2025
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| Record UNII |
TX886PAQ89
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| Record Status |
Validated (UNII)
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| Record Version |
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CHEMBL1190
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74014
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100000087745
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DTXSID90931293
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215-816-4
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1420-40-2
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C033019
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TX886PAQ89
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| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
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ACTIVE MOIETY |