Laudanosine

Structural formula
General
Surname	Laudanosine
other names	(1 S ) -1 - [(3,4-dimethoxyphenyl) methyl] -6,7-dimethoxy-2-methyl-3,4-dihydro-1 H -isoquinoline N -methyltetrahydropapaverine
Molecular formula	C 21 H 27 NO 4
External identifiers / databases
CAS number 2688-77-9 EC number 220-253-2 ECHA InfoCard 100.018.412 PubChem 73397 ChemSpider 66114 Wikidata Q408074
properties
Molar mass	357.44 g mol −1
Physical state	firmly
Melting point	89 ° C
solubility	soluble in ethanol , chloroform and diethyl ether
safety instructions
GHS labeling of hazardous substances danger H and P phrases H: 301-311-331 P: 261-280-301 + 310-311
As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Laudanosine is a toxic benzylisoquinoline - alkaloid , which in small amounts in the opium poppy occurs and structurally related to papaverine is related ( N -methyl-tetrahydropapaverine).

Opium poppy, Papaver somniferum , from whose milk laudanosine - among other alkaloids - can be isolated.

It is also a potentially toxic breakdown product of the muscle relaxants atracurium and (to a lesser extent) cisatracurium .

Laudanosine penetrates the blood-brain barrier and has an epileptogenic effect through interactions with GABA , opioid and nicotinic acetylcholine receptors . H. cerebrally exciting. It can lead to a drop in blood pressure ( hypotension ) and a slow heartbeat ( bradycardia ) in the cardiovascular system . In practice, however, the effects of laudanosine usually do not play a role in the usual doses of muscle relaxants. It also increases the MAC value of the volatile narcotics used during anesthesia . Laudanosine is excreted renally .

Individual evidence

1. ↑ ^{a b c} Entry on laudanosine. In: Römpp Online . Georg Thieme Verlag, accessed on June 13, 2014.
2. ↑ ^{a b} Data sheet DL-Laudanosine from Sigma-Aldrich , accessed on April 7, 2011 ( PDF ).
3. ↑ ^{a b} Fodale V, Santamaria LB: Laudanosine, an atracurium and cisatracurium metabolite . In: European Journal of Anaesthesiology . 19, No. 7, July 2002, pp. 466-473. PMID 12113608 .