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541-22-0

541-22-0 Structure

541-22-0 Structure
IdentificationMore
[Name]

DECAMETHONIUM BROMIDE
[CAS]

541-22-0
[Synonyms]

DECAMETHONIUM BROMIDE
DECAMETHYLENEBIS[TRIMETHYL-AMMONIUM BROMIDE]
DECANE-1,10-BIS(TRIMETHYLAMMONIUM BROMIDE)
1,10-Decanediaminium,N,N,N,N’,N’,N’-hexamethyl-,dibromide
10-decanediaminium,n,n,n,n’,n’,n’-hexamethyl-dibromide
decacuran
decamethoniumdibromide
decamethylene-1,10-bistrimethylammoniumdibromide
decamethylenebis(trimethyl-ammoniudibromide
dekamethoniumbromid
syncurine
DECAMETHONIUM BROMIDE, FOR ION PAIR CHRO MATOGRAPHY
Decamethylene bis(trimethylammonium bromide), Decane-1,10-bis(trimethylammonium bromide)
[EINECS(EC#)]

208-772-2
[Molecular Formula]

C16H38Br2N2
[MDL Number]

MFCD00011779
[Molecular Weight]

418.29
[MOL File]

541-22-0.mol
Chemical PropertiesBack Directory
[Appearance]

crystalline solid
[Melting point ]

263-267 °C(lit.)
[storage temp. ]

Inert atmosphere,Room Temperature
[solubility ]

DMF: 2 mg/ml; DMSO: 16 mg/ml; Ethanol: 33 mg/ml; PBS (pH 7.2): 5 mg/ml
[form ]

crystalline
[color ]

off-white
[Stability:]

Stable. Incompatible with strong oxidizing agents.
[Water Solubility ]

almost transparency
[λmax]

λ: 240 nm Amax: 0.04
λ: 250 nm Amax: 0.03
λ: 260 nm Amax: 0.02
λ: 500 nm Amax: 0.02
[Merck ]

2847
[BRN ]

3728288
[InChI]

1S/C16H38N2.2BrH/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
[InChIKey]

HLXQFVXURMXRPU-UHFFFAOYSA-L
[SMILES]

[Br-].[Br-].C[N+](C)(C)CCCCCCCCCC[N+](C)(C)C
[CAS DataBase Reference]

541-22-0(CAS DataBase Reference)
[Storage Precautions]

Moisture sensitive
[EPA Substance Registry System]

Decamethonium dibromide (541-22-0)
Safety DataBack Directory
[Symbol(GHS) ]

Skull and Crossbones (GHS06)
GHS06
[Signal word ]

Danger
[Hazard statements ]

H301-H315-H319-H335
[Precautionary statements ]

P261-P301+P310-P305+P351+P338
[Hazard Codes ]

T
[Risk Statements ]

R25:Toxic if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin .
[Safety Statements ]

S26:In case of contact with eyes, rinse immediately with plenty of water and seek medical advice .
S45:In case of accident or if you feel unwell, seek medical advice immediately (show label where possible) .
[RIDADR ]

UN 2811 6.1/PG 3
[WGK Germany ]

3
[RTECS ]

BP5950000
[F ]

3-10
[TSCA ]

TSCA listed
[HS Code ]

2923.90.0100
[HazardClass ]

6.1(b)
[PackingGroup ]

III
[Storage Class]

6.1C - Combustible acute toxic Cat.3
toxic compounds or compounds which causing chronic effects
[Hazard Classifications]

Acute Tox. 3 Oral
Eye Irrit. 2
Skin Irrit. 2
STOT SE 3
[Toxicity]

LD50 oral in mouse: 190mg/kg
Hazard InformationBack Directory
[General Description]

Crystals derived from methanol and acetone.
[Air & Water Reactions]

Water soluble.
[Health Hazard]

ACUTE/CHRONIC HAZARDS: When heated to decomposition this compound emits very toxic fumes.
[Fire Hazard]

Flash point data for this chemical are not available. DECAMETHONIUM DIBROMIDE is probably combustible.
[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.
[Chemical Properties]

crystalline solid
[Uses]

antipsychotic
[Brand name]

Syncurine (GlaxoSmithKline).
[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.
[References]

[1] W. D. M. PATON  Eleanor J Z. The action of d-tubocurarine and of decamethonium on respiratory and other muscles in the cat[J]. Journal of Physiology-London, 1951, 112 3-4: 311-331. DOI: 10.1113/jphysiol.1951.sp004531
[2] ROGER L PAPKE J A S Lynn Wecker. Activation and inhibition of mouse muscle and neuronal nicotinic acetylcholine receptors expressed in Xenopus oocytes.[J]. Journal of Pharmacology and Experimental Therapeutics, 2010, 333 2: 501-518. DOI: 10.1124/jpet.109.164566
[3] J BREK EATON. Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells.[J]. Molecular Pharmacology, 2003, 64 6: 1283-1294. DOI: 10.1124/mol.64.6.1283
[4] B ROBAIRE  G K. Effects of edrophonium, eserine, decamethonium, d-tubocurarine, and gallamine on the kinetics of membrane-bound and solubilized eel acetylcholinesterase.[J]. Molecular Pharmacology, 1975, 11 6: 722-734.
Spectrum DetailBack Directory
[Spectrum Detail]

DECAMETHONIUM BROMIDE(541-22-0)1HNMR
DECAMETHONIUM BROMIDE(541-22-0)13CNMR
DECAMETHONIUM BROMIDE(541-22-0)IR1
DECAMETHONIUM BROMIDE(541-22-0)IR2
DECAMETHONIUM BROMIDE(541-22-0)Raman
Well-known Reagent Company Product InformationBack Directory
[Alfa Aesar]

Decamethonium bromide, 98%(541-22-0)
[Sigma Aldrich]

541-22-0(sigmaaldrich)
[TCI AMERICA]

Decamethonium Bromide,>98.0%(T)(541-22-0)
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