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.
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| Names | |
|---|---|
| IUPAC name
(1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy- 2-methyl-3,4-dihydro-1H-isoquinoline
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| Other names
N-Methyl-1,2,3,4-tetrahydropapaverine
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| Identifiers | |
| ECHA InfoCard | 100.018.412 |
PubChem CID
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CompTox Dashboard (EPA)
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| Properties | |
| C21H27NO4 | |
| Molar mass | 357.450 g·mol−1 |
| Melting point | 89 °C |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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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
- ^ a b Fodale V, Santamaria LB (2002). "Laudanosine, an atracurium and cisatracurium metabolite". Eur J Anaesthesiol. 19 (7): 466–73. PMID 12113608.
{{cite journal}}: Unknown parameter|month=ignored (help) - ^ Burger A (2005) [1954]. "The Benzylisoquinoline Alkaloids". In Manske RHF, Holmes HL (eds.) (ed.). The Alkaloids: Chemistry and Physiology. Vol. 4. New York: Academic Press. p. 48. ISBN 0-12-469504-3.
{{cite book}}:|editor=has generic name (help); External link in|chapterurl=|chapterurl=ignored (|chapter-url=suggested) (help) Retrieved September 18, 2008 through Google Book Search. - ^ Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M (1994). "Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity". Brain Res. 646 (2): 235–241. doi:10.1016/0006-8993(94)90084-1. PMID 8069669.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I (2005). "Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors". Br J Pharmacol. 146 (1): 15–24. doi:10.1038/sj.bjp.0706307. PMC 1576253. PMID 15980871.
{{cite journal}}: Unknown parameter|month=ignored (help)CS1 maint: multiple names: authors list (link) - ^ Katz Y, Gavish M (1989). "Laudanosine does not displace receptor-specific ligands from the benzodiazepinergic or muscarinic receptors". Anesthesiol. 70 (1): 109–111. doi:10.1097/00000542-198901000-00020. PMID 2536252.
{{cite journal}}: Unknown parameter|month=ignored (help)
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