Product Name

  • Name

    Tubocurarine

  • EINECS
  • CAS No. 57-95-4
  • Density g/cm3
  • Solubility
  • Melting Point
  • Formula C37H41 N2 O6
  • Boiling Point °Cat760mmHg
  • Molecular Weight 624.84
  • Flash Point °C
  • Transport Information
  • Appearance
  • Safety A deadly poison by subcutaneous, intraperitoneal, intramuscular, and intravenous routes. Human toxicity: Large doses and overdoses may cause respiratory paralysis and hypotension. When heated to decomposition it emits toxic fumes of NOx.
  • Risk Codes
  • Molecular Structure Molecular Structure of 57-95-4 (Tubocurarine)
  • Hazard Symbols
  • Synonyms Tubocuraranium,7',12'-dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyl-;Tubocurarine (8CI);(+)-Tubocurarine;13H-4,6:21,24-Dietheno-8,12-metheno-1H-pyrido[3',2':14,15][1,11]dioxacycloeicosino[2,3,4-ij]isoquinolinium,2,3,13a,14,15,16,25,25a-octahydro-9,19-dihydroxy-18,29-dimethoxy-1,14,14-trimethyl-,[13aR-(13aR*,25aS*)]-;Tubocurarin;d-Tubocurarine;
  • PSA 80.62000
  • LogP 6.59770

Tubocurarine Chemical Properties

Product Name: Tubocurarine
The MF of Tubocurarine (CAS NO.57-95-4) is C37H41N2O6.

                   
The MW of Tubocurarine (CAS NO.57-95-4) is 609.7307.
Synonyms of Tubocurarine (CAS NO.57-95-4): (+)-7',12'-Dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraran-2'-ium ; 7',12'-Dihydroxy-6,6'-dimethoxy-2,2',2'-trimethyltubocuraran-2'-ium

Tubocurarine History

It is one of the chemicals that can be obtained from curare, itself an extract of Chondrodendron tomentosum, a plant found in South American jungles which is used as a source of arrow poison. Native Indians hunting animals with this poison were able to eat the animal's contaminated flesh without being affected by the toxin because tubocurarine cannot easily cross mucous membranes and is thus inactive orally.
Medically, first used in 1912. Introduced in anaesthesia in 1942. The correct chemical structure was only elucidated circa 1970, even though the plant had been known since the Spanish Conquest.
The word curare comes from the South American Indian name for the arrow poison: "ourare". Presumably the initial syllable was pronounced with a heavy glottal stroke. Tubocurarine is so called because the plant samples containing it were first shipped to Europe in tubes.
Today, tubocurarine has fallen into disuse in western medicine, as safer synthetic alternatives such as atracurium are available.

 

Tubocurarine Uses

  Tubocurarine (CAS NO.57-95-4) is an antagonist of nicotinic neuromuscular acetylcholine receptors that is used to paralyse patients undergoing.

Tubocurarine Production

 Tubocurarine biosynthesis involves a radical coupling of two enantiomeric tetrahydrobenzylisoquinolines, more specifically, the two enantiomers of N-methyl-coclaurine. (R) and (S)-N-methyl-coclaurine come from a Mannich-like reaction between dopamine and 4-hydroxyphenyl-acetaldehyde, facilitated by norcoclaurine synthase (NCS). Both dopamine and 4-hydroxyphenylacetyladehyde originate from L-tyrosine. The biosynthetic pathway is described in more detail in the figures. Methylation of the amine and hydroxyl substituents are facilitated by S-adenosyl methionine (SAM).

Tubocurarine Toxicity Data With Reference

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
chicken LD50 intravenous 700ug/kg (0.7mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 122, Pg. 152, 1959.
dog LD50 intravenous 500ug/kg (0.5mg/kg)   Archives Internationales de Pharmacodynamie et de Therapie. Vol. 80, Pg. 172, 1949.
dog LDLo intramuscular 250ug/kg (0.25mg/kg)   Journal of Pharmacy and Pharmacology. Vol. 10, Pg. 638, 1958.
mouse LD50 intraperitoneal 410ug/kg (0.41mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Archives Internationales de Pharmacodynamie et de Therapie. Vol. 153, Pg. 308, 1965.
mouse LD50 intravenous 130ug/kg (0.13mg/kg) PERIPHERAL NERVE AND SENSATION: FLACCID PARALYSIS WITHOUT ANESTHESIA (USUALLY NEUROMUSCULAR BLOCKAGE) Arzneimittel-Forschung. Drug Research. Vol. 15, Pg. 130, 1965.
mouse LD50 subcutaneous 525ug/kg (0.525mg/kg)   Proceedings of the Society for Experimental Biology and Medicine. Vol. 85, Pg. 603, 1954.
mouse LD50 unreported 450ug/kg (0.45mg/kg) AUTONOMIC NERVOUS SYSTEM: "SMOOTH MUSCLE RELAXANT (MECHANISM UNDEFINED, SPASMOLYTIC)" Pharmaceutical Chemistry Journal Vol. 2, Pg. 117, 1968.
rabbit LD50 intravenous 20ug/kg (0.02mg/kg)   Rendiconti Istituto Superiore di Sanita Vol. 13, Pg. 339, 1950.
rabbit LD50 subcutaneous 500ug/kg (0.5mg/kg)   "Structure et Activite Pharmacodyanmique des Medicaments du Systeme Nerveux Vegetatif," Bovet, D., and F. Bovet-Nitti, New York, S. Karger, 1948Vol. -, Pg. 631, 1948.
rat LD50 intraperitoneal 220ug/kg (0.22mg/kg) BEHAVIORAL: ATAXIA

LUNGS, THORAX, OR RESPIRATION: OTHER CHANGES

CARDIAC: OTHER CHANGES
Journal of Pharmacology and Experimental Therapeutics. Vol. 92, Pg. 454, 1948.
rat LDLo intramuscular 500ug/kg (0.5mg/kg) LUNGS, THORAX, OR RESPIRATION: RESPIRATORY DEPRESSION Journal of Pharmacy and Pharmacology. Vol. 10, Pg. 638, 1958.

Tubocurarine Safety Profile

A deadly poison by subcutaneous, intraperitoneal, intramuscular, and intravenous routes. Human toxicity: Large doses and overdoses may cause respiratory paralysis and hypotension. When heated to decomposition it emits toxic fumes of NOx.

Tubocurarine Specification

Tubocurarine chloride is an alkaloid of the benzylisoquinoline type.

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