(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE

(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE Basic information
Product Name:(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE
Synonyms:Tubocurarin-dichloride;Tubocurarine Chloride (250 mg);Tubocurarine hydrochloride pentahydrate;dichloride,pentahydrate,(+)-tubocurarin;TUBOCURARINE CHLORIDE;Tubocurarine hydroehloride;(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE;D-TUBOCURARINE CHLORIDE PENTAHYDRATE
CAS:6989-98-6
MF:C37H44Cl2N2O7
MW:699.67
EINECS:615-023-7
Product Categories:NIZIN;Complex MoleculesEnzyme Inhibitors;Asymmetric Synthesis;Chiral Building Blocks;Enzyme Inhibitors by Type;Other;Alkaloids;Biochemistry;Isoquinoline Alkaloids
Mol File:6989-98-6.mol
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE Structure
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE Chemical Properties
Melting point 275-280 °C (dec.)(lit.)
density 1.2074 (rough estimate)
refractive index 193 ° (C=1, H2O)
storage temp. 2-8°C
solubility H2O: soluble50 mg/ml, with heating as required, clear to slightly hazy, colorless to yellow
form Crystalline powder
color White to Light yellow to Light orange
optical activity[α]20/D +195±5°, c = 0.5% in H2O
Water Solubility Soluble in water to 50mg/ml, with warming as needed. Also soluble in ethanol or methanol
Sensitive Air Sensitive
Merck 14,9807
BRN 3896374
Stability:Hygroscopic
Safety Information
Hazard Codes T
Risk Statements 25
Safety Statements 45-36/37/39-22
RIDADR UN 1544 6.1/PG 3
WGK Germany 3
RTECS YO5100000
10-23
HazardClass 6.1
PackingGroup III
HS Code 29349990
MSDS Information
ProviderLanguage
SigmaAldrich English
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE Usage And Synthesis
DescriptionTubocurarine chloride is the only naturally occurring neuromuscular blocking agent. It is derived from the bark of the South American plant chondrodendron tomentosum, which has been used for centuries by South American Indians as an arrow poison. I t was the first non-depolarising neuromuscular blocking agent to be used in humans. I t has a marked propensity to produce histamine release and thus hypotension, with possibly a compensatory tachycardia. Historically, tubocurarine, alcuronium and gallamine have been used in clinical practice, but they are no longer available in the UK. A lcuronium chloride is a semisynthetic derivative of toxiferin, an alkaloid of calabash curare. Gallamine triethiodide is a trisquaternary amine. It was first used in France in 1948. The only recent use of gallamine in the UK was as a small pretreatment dose (10 mg) before suxamethonium.
Chemical Propertieswhite to slightly yellowish powder
OriginatorMecostrin,Squibb,US,1946
UsesTubocurarine is used mainly in anesthesiology as a myorelaxant, causing prolonged muscle relaxation during an operation. Small doses are successful at causing temporary relaxation of skeletal muscle without any vital change of primary body functions. It is used particularly in endotracheal intubation or orthopedic surgery for repositioning fractures, resetting compound dislocations, and so on. The main synonyms are tubarine and curarine.
Usesmuscle relaxant (skeletal)
Usesantibacterial
Manufacturing ProcessThe initial step involves extraction of the stems and bark of the plant Chondrodendron tomentosum with water as the solvent.
Producing substantially pure d-tubocurarine chloride essentially comprises treating with picric acid the quaternary-base fraction of a crude curare of the curarine type, hydrolyzing the resulting picrate in an emulsion of hydrochloric acid and a water-immiscible organic solvent for picric acid, recovering crystalline d-tubocurarine chloride from the aqueous phase, dissolving the d_x0002_tubocurarine chloride in a minimum of hot water, allowing the solution to stand at room temperature until the bulk of the d-tubocurarine chloride precipitates, adding sufficient concentrated hydrochloric acid to bring the HCl content up to about 6% and refrigerating the solution.
Therapeutic FunctionMuscle relaxant
General DescriptionTubocurarine chloride,( )-tubocurarine chloride hydrochloride pentahydrate, isprepared from crude curare by a process of purification andcrystallization. Tubocurarine chloride occurs as a white oryellowish white to grayish white, odorless, crystalline powderthat is soluble in water. Aqueous solutions of it are stableto heat sterilization.
The structural formula for (+)-tubocurarine was longthought to be that of Ia (see structure diagram). Throughthe work of Everett et al.,the structure is now knownto be that of Ib. The monoquaternary nature of Ib thusrevealed has caused some reassessment of thinking concerningthe theoretical basis for the blocking action, becauseall had previously assumed a diquaternary structure(i.e., Ia). Nevertheless, this does not negate the earlierconclusions that a diquaternary nature of the molecule provides better blocking action than does a monoquaternarynature (e.g., Ib is approximately fourfold lesspotent than dimethyl tubocurarine iodide). Further, (+)-isotubocurarine chloride (Ic) has twice the activity of Ib inthe particular test used.
Biochem/physiol ActionsTubocurarine is a muscle relaxant and a nicotinic acetylcholine receptor antagonist. It can induce neuromuscular blocking.
(+)-TUBOCURARINE CHLORIDE PENTAHYDRATE Preparation Products And Raw materials
Raw materialsHydrochloric acid-->PICRIC ACID
Sinomenine Palmatine D-TUBOCURARINE CHLORIDE CURARE

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