Decamethonium bromide

Base Information

• Chemical Name: Decamethonium bromide
• CAS No.: 541-22-0
• Deprecated CAS: 60869-65-0
• Molecular Formula: C16H38 N2 . 2 Br
• Molecular Weight: 418.299
• European Community (EC) Number: 208-772-2
• UNII: 55C6RK944K
• DSSTox Substance ID: DTXSID2022886
• Wikidata: Q27261300
• NCI Thesaurus Code: C65365
• Pharos Ligand ID: D25TCYG3P4F1
• ChEMBL ID: CHEMBL1134
• Mol file: 541-22-0.mol

Synonyms:(DM)Br2;decamethonium;decamethonium bromide;decamethonium dibromide;decamethonium dichloride;decamethonium dihydroxide;decamethonium diiodide;decamethonium dipricrate;decamethonium iodide;decamethylenebis(trimethylammonium)bromide

Chemical Property of Decamethonium bromide

Chemical Property:

• Appearance/Colour: crystalline solid
• Melting Point: 263-267 °C(lit.)
• Boiling Point: °Cat760mmHg
• Flash Point: °C
• PSA: 0.00000
• Density: g/cm³
• LogP: -2.47240
• Storage Temp.: Inert atmosphere,Room Temperature
• Water Solubility.: almost transparency
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 11
• Exact Mass: 418.13812
• Heavy Atom Count: 20
• Complexity: 164

Purity/Quality:

98%,99%, ^*data from raw suppliers

Decamethonium Bromide ^*data from reagent suppliers

Safty Information:

• Pictogram(s): R25:Toxic if swallowed.
• Hazard Codes: T
• Statements: 25-36/37/38
• Safety Statements: 26-45

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C.[Br-].[Br-]
• Description: Decamethonium is a depolarizing neuromuscular blocking agent. It is a partial agonist of muscle-type nicotinic acetylcholine receptors (nAChRs). Decamethonium activates α1β1-containing adult mouse muscle-type nAChRs expressed in X. laevis oocytes with an EC50 value of 40 μM using voltage clamp electrophysiology. It is also a nondepolarizing antagonist of neuronal-type nAChRs, inhibiting mouse α7-, α3β2-, α3β4-, and α4β2-containing receptors with IC50 values of 7.4, 405, 28, and 59 μM, respectively. Decamethonoium is a competitive antagonist of α4β2-containing nAChRs expressed in SH-EP1 cells (IC50 = 52 μM for the human receptor). It also inhibits electric eel acetylcholinesterase (AChE) and blocks electrically-evoked tibialis muscle twitches in anesthetized cats with ED95 values of 35 and 70 μg/kg for cats under chloralose and ether anesthesia, respectively. Formulations containing decamethonium have been used to induce paralysis during anesthesia.
• Uses: antipsychotic
• Biological Functions: Decamethonium was one of the first neuromuscular blocking agents to be synthesized. An SAR study on a series of bis-quaternary ammonium compounds with varying numbers of methylene groups separating the nitrogen atoms demonstrated that maximal neuromuscular blockade occurred with 10 to 12 unsubstituted methylene groups. Activity diminished as the number of carbons was either decreased or increased. The compound with six methylene groups, hexamethonium, is a nicotinic antagonist at autonomic ganglia (ganglionic blocking agent). All the compounds in this series that possessed neuromuscular blocking activity also caused depolarization of the postjunctional membrane.

Technology Process of Decamethonium bromide

There total 3 articles about Decamethonium bromide which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 52.0%

1,10-dibromodecane (4101-68-2) + trimethylamine (75-50-3) → decamethonium bromide (541-22-0)

Guidance literature:

In methanol; at 20 ℃; for 48h;

DOI:10.1016/j.bmc.2010.03.067

Reference yield: 30.0%

trimethylamine hydrochloride (593-81-7) + 1,10-dibromodecane (4101-68-2) → (10-bromodecyl)trimethylammonium Bromide (36707-88-7) + decamethonium bromide (541-22-0)

Guidance literature:

With potassium hydroxide; In ethanol; for 72h;

DOI:10.1039/b418055k

Reference yield:

C36H60O30*C16H38N2(2+)*2Br(1-) → decamethonium bromide (541-22-0) + alpha cyclodextrin (10016-20-3)

Guidance literature:

In water-d2; at 25 ℃; Rate constant; Equilibrium constant; Thermodynamic data; ΔS(excit.), ΔH(excit.);

DOI:10.1139/cjc-76-6-843

upstream raw materials:

1,10-dibromodecane

trimethylamine

trimethylamine hydrochloride

Refernces

• 1、 Maiti, Kajari,Mitra, Debolina,Mitra, Rajendra N.,Panda, Amiya K.,Das, Prasanta K.,Rakshit, Animesh K.,Moulik, Satya P.. "Self-aggregation of synthesized novel bolaforms and their mixtures with sodium dodecyl sulfate (SDS) and cetyltrimethylammonium bromide (CTAB) in aqueous medium". experimental part. p. 7499 - 7508. Retrieved 2010/11/04.
• 2、 Lyon, Angela P.,Banton, Nicola J.,Macartney, Donal H.. "Kinetics of the self-assembly of α-cyclodextrin [2]pseudorotaxanes with polymethylene threads bearing quaternary ammonium and phosphonium end groups". . p. 843 - 850. Retrieved 2007/10/03.