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Tubocurarine
Systematic (IUPAC) name
6,6'-dimethoxy-2,2,2',2'-tetramethyltubocuraran-2,2'-diium-7',12'-diol
Identifiers
CAS number 57-95-4 (chloride hydrochloride) 6989-98-6 (chloride hydrochloride pentahydrate)
ATC code M03AA02
PubChem 6000
DrugBank APRD00176
ChemSpider 5778
Chemical data
Formula C 37H42Cl2N2O6  
Mol. mass 624.765 g/mol
SMILES eMolecules & PubChem
Synonyms (1S,16R)-9,21-dihydroxy-10,25-dimethoxy-15,15,30-trimethyl-7,23-dioxa-15,30-diazaheptacyclo[22.6.2.2 3,6.18,12.118,22.027,31.0 16,34]hexatriaconta-3,5,8(34),9,11,18(33),19,21,24,26,31,35-dodecaene-15,30-diium
Pharmacokinetic data
Bioavailability  ?
Protein binding 50%
Metabolism  ?
Half life 1-2 Hours
Excretion  ?
Therapeutic considerations
Pregnancy cat.  ?
Legal status banned
Routes I.V.
 Yes check.svgY(what is this?)  (verify)

Tubocurarine is an alkaloid of the benzylisoquinoline type. It is an antagonist of nicotinic neuromuscular acetylcholine receptors[1] that is used to paralyse patients undergoing anaesthesia.

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.

Biosynthesis

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). [2]

References

  1. ^ Wenningmann I, Dilger JP (October 2001). "The kinetics of inhibition of nicotinic acetylcholine receptors by (+)-tubocurarine and pancuronium". Molecular pharmacology 60 (4): 790–6. PMID 11562442. http://molpharm.aspetjournals.org/cgi/pmidlookup?view=long&pmid=11562442.  
  2. ^ Dewick, P. M. Medicinal Natural Products; a Biosynthetic Approach. 3rd ed.; John Wiley and Sons Ltd.: 2009.
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