Laudanosine

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Laudanosine
Laudanosine.svg
Names
IUPAC name
(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy- 2-methyl-3,4-dihydro-1H-isoquinoline
Other names
N-Methyl-1,2,3,4-tetrahydropapaverine
Identifiers
2688-77-9 YesY
ChemSpider 66114 N
EC Number 220-253-2
Jmol 3D model Interactive image
PubChem 73397
Properties
C21H27NO4
Molar mass 357.45 g·mol−1
Melting point 89 °C (192 °F; 362 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
Infobox references

Laudanosine or N-methyltetrahydropapaverine is a recognized metabolite[1] of atracurium and cisatracurium. Laudanosine decreases the seizure threshold, and thus it can induce seizures if present at sufficient threshold concentrations; however such concentrations are unlikely to be produced consequent to chemodegradable metabolism of clinically administered doses of cisatracurium or atracurium.

File:Slaapbol R0017601.JPG
Capsule of Papaver somniferum showing latex (opium) exuding from incision. Laudanosine occurs naturally in small amounts (0.1%) in opium.

Laudanosine also occurs naturally in minute amounts (0.1%) in opium, from which it was first isolated in 1871.[2] Partial dehydrogenation of laudanosine will lead to papaverine, the alkaloid found in the opium poppy plant (Papaver somniferum).

Laudanosine is a benzyltetrahydroisoquinoline alkaloid. It has been shown to interact with GABA receptors, glycine receptors, opioid receptors, and nicotinic acetylcholine receptors,[1][3][4] but not benzodiazepine or muscarinic receptors which are also involved in epilepsy and other types of seizures.[5]

References

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  2. Burger A (2005) [1954]. "The Benzylisoquinoline Alkaloids". In Manske RH, Holmes HL. The Alkaloids: Chemistry and Physiology. 4. New York: Academic Press. p. 48. ISBN 0-12-469504-3.<templatestyles src="Module:Citation/CS1/styles.css"></templatestyles> Retrieved September 18, 2008 through Google Book Search.
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