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Laudanosine









Laudanosine


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Laudanosine

Skeletal formula

Space-filling model
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

CAS Number

  • 2688-77-9 ☑Y

3D model (JSmol)
  • Interactive image

ChemSpider

  • 66114 ☒N

ECHA InfoCard
100.018.412

EC Number
 220-253-2


PubChem CID
  • 73397




Properties

Chemical formula
C21H27NO4

Molar mass
 357.45 g·mol−1

Melting point
 89 °C (192 °F; 362 K)

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).


☒N verify (what is ☑Y☒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. ^ ab 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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  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. 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". Anesthesiology. 70 (1): 109–111. doi:10.1097/00000542-198901000-00020. PMID 2536252.















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