- Tubocurarine
- Tubocurarine hydrochloride
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| Name |
Tubocurarine |
EINECS | N/A |
| CAS No. | 57-95-4 | Density | g/cm3 |
| PSA | 80.62000 | LogP | 6.59770 |
| Solubility | N/A | Melting Point |
N/A |
| Formula | C37H41 N2 O6 | Boiling Point | °Cat760mmHg |
| Molecular Weight | 624.84 | Flash Point | °C |
| Transport Information | N/A | Appearance | N/A |
| 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 | N/A |
| Molecular Structure |
|
Hazard Symbols | N/A |
| 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; |
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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