Laudanosine

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Laudanosine
File:Laudanosine.svg
style="background: #F8EABA; text-align: center;" colspan="2" | Identifiers
CAS number 2688-77-9
PubChem 73397
style="background: #F8EABA; text-align: center;" colspan="2" | Properties
Molecular formula C21H27NO4
Molar mass 357.44 g mol−1
Melting point

89 °C

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
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.

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, opioid receptors, and nicotinic acetylcholine receptors,[1][3][4] but not benzodiazepinergic 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 RHF, Holmes HL (eds.). The Alkaloids: Chemistry and Physiology. 4. New York: Academic Press. pp. p. 48. ISBN 0124695043.  Retrieved September 18, 2008 through Google Book Search.
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