Laudanosine: Difference between revisions

| verifiedrevid = 398754844▼

| IUPACName = (1''S'')-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy- 2-methyl-3,4-dihydro-1''H''-isoquinoline▼

| Section2 = {{Chembox Properties▼

| C=21 |H=27 |N=1 |O=4▼

'''Laudanosine''' or '''''N''-methyltetrahydropapaverine''' is a recognized metabolite<ref name=Fodale>{{cite journal |author=Fodale V, Santamaria LB |title=Laudanosine, an atracurium and cisatracurium metabolite |journal=Eur J Anaesthesiol |volume=19 |issue=7 |pages=466–73 |year=2002 |month=July |pmid=12113608}}</ref> 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.<ref>{{cite book |chapterurl=http://books.google.com/books?id=KxTKLlac60wC&pg=PA55&dq=laudanosine&sig=ACfU3U2OZxmvO0Pl8Jnp8KuGXHzMllcnQA#PPA48,M1 |chapter=The Benzylisoquinoline Alkaloids |author=Burger A |title=The Alkaloids: Chemistry and Physiology |origyear=1954 |year=2005 |volume=4 |editor=Manske RHF, Holmes HL (eds.) |pages=48 |location=New York |publisher=Academic Press |isbn=0-12-469504-3}} Retrieved September 18, 2008 through [[Google Book Search]].</ref> Partial [[Dehydration reaction|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 receptor]]s, [[opioid receptor]]s, and [[nicotinic acetylcholine receptor]]s,<ref name=Fodale/><ref>{{cite journal |author=Katz Y, Weizman A, Pick CG, Pasternak GW, Liu L, Fonia O, Gavish M |title=Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity |journal= Brain Res |volume=646 |issue=2 |pages=235–241 |year=1994 |month=May |pmid=8069669 |doi=10.1016/0006-8993(94)90084-1 }}</ref><ref>{{cite journal |author= Exley R, Iturriaga-Vásquez P, Lukas RJ, Sher E, Cassels BK, Bermudez I |title=Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors |journal= Br J Pharmacol |volume=146 |issue=1 |pages=15–24 |year=2005 |month=Sep|pmid=15980871 |doi= 10.1038/sj.bjp.0706307 |pmc= 1576253 }}</ref> but not benzodiazepinergic or muscarinic receptors which are also involved in epilepsy and other types of seizures.<ref>{{cite journal |author= Katz Y, Gavish M |title= Laudanosine does not displace receptor-specific ligands from the benzodiazepinergic or muscarinic receptors |journal= Anesthesiol |volume=70|issue=1 |pages= 109–111 |year=1989 |month= Jan |pmid= 2536252 |doi= 10.1097/00000542-198901000-00020 }}</ref>▼