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 model Interactive image
PubChem 73397
Properties
C21H27NO4
Molar mass 357.45 g·mol−1
Melting point 89 °C (192 °F; 362 K)
Vapor pressure {{{value}}}
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N verify (what is YesYN ?)
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.

File:Slaapbol R0017601.JPG
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

  1. 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. doi:10.1017/s0265021502000777. 
  2. Burger A (2005) [1954]. "The Benzylisoquinoline Alkaloids". In Manske RH, Holmes HL. 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. PMID 8069669. doi:10.1016/0006-8993(94)90084-1. 
  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. PMC 1576253Freely accessible. PMID 15980871. doi:10.1038/sj.bjp.0706307. 
  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. PMID 2536252. doi:10.1097/00000542-198901000-00020.