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 images Image
PubChem 73397
Properties
C21H27NO4
Molar mass 357.44 g·mol−1
Melting point 89 °C (192 °F; 362 K)
Except where noted otherwise, data is given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
 N verify (what isYesY/N?)
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.

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[edit]

  1. ^ a b Fodale V, Santamaria LB (July 2002). "Laudanosine, an atracurium and cisatracurium metabolite". Eur J Anaesthesiol 19 (7): 466–73. doi:10.1017/s0265021502000777. PMID 12113608. 
  2. ^ 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.
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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.