Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C16H38N2.2I |
| Molecular Weight | 512.2953 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| 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 | 127.9124 |
| 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 / 0 |
| 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 |
|---|---|---|
| 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
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
Fri Dec 15 17:35:28 GMT 2023
by
admin
on
Fri Dec 15 17:35:28 GMT 2023
|
| Record UNII |
TX886PAQ89
|
| Record Status |
Validated (UNII)
|
| Record Version |
|
-
Download
| Name | Type | Language | ||
|---|---|---|---|---|
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Common Name | English |
| Code System | Code | Type | Description | ||
|---|---|---|---|---|---|
|
CHEMBL1190
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
74014
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
100000087745
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
DTXSID90931293
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
215-816-4
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
1420-40-2
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
C033019
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
SUB01569MIG
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY | |||
|
TX886PAQ89
Created by
admin on Fri Dec 15 17:35:28 GMT 2023 , Edited by admin on Fri Dec 15 17:35:28 GMT 2023
|
PRIMARY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
PARENT -> SALT/SOLVATE |
| Related Record | Type | Details | ||
|---|---|---|---|---|
|
|
ACTIVE MOIETY |