Laudanosine

Laudanosine

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
ChemSpider	66114 N
EC Number	220-253-2
Jmol 3D model	Interactive image
PubChem	73397
InChI InChI=1S/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1 N Key: KGPAYJZAMGEDIQ-KRWDZBQOSA-N N InChI=1/C21H27NO4/c1-22-9-8-15-12-20(25-4)21(26-5)13-16(15)17(22)10-14-6-7-18(23-2)19(11-14)24-3/h6-7,11-13,17H,8-10H2,1-5H3/t17-/m0/s1 Key: KGPAYJZAMGEDIQ-KRWDZBQOBO
SMILES CN1CCc2cc(c(cc2[C@@H]1Cc3ccc(c(c3)OC)OC)OC)OC
Properties
Chemical formula	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 YN ?)
Infobox references

Laudanosine or N-methyltetrahydropapaverine is a recognized metabolite 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. 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, but not benzodiazepine or muscarinic receptors which are also involved in epilepsy and other types of seizures.