Laudanosine
| Laudanosine | ||
|---|---|---|
 | ||
| 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 | ||
| CAS number | 2688-77-9  | |
| PubChem | 73397 | |
| Properties | ||
| Molecular formula | C21H27NO4 | |
| Molar mass | 357.44 g mol−1 | |
| Melting point | 89 °C | |
(verify) (what is: / ?)Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 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
- ↑ 1.0 1.1 Fodale V, Santamaria LB (July 2002). "Laudanosine, an atracurium and cisatracurium metabolite". Eur J Anaesthesiol 19 (7): 466–73. PMID 12113608.
- ↑ Burger A (2005) [1954]. "The Benzylisoquinoline Alkaloids". In Manske RHF, Holmes HL (eds.). The Alkaloids: Chemistry and Physiology 4. New York: Academic Press. p. 48. ISBN 0-12-469504-3. Retrieved September 18, 2008 through Google Book Search.
- ↑ Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M (May 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.
- ↑ Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I (Sep 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.
- ↑ Katz Y, Gavish M (Jan 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.