Structure via PubChem · Public domain (PubChem)
laudanosine
Sign in to saveLaudanosine or '''N-methyltetrahydropapaverine''' is a metabolite of the pharmaceutical drugs 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.
Chemical data
- Formula
- C21H27NO4
- Molecular weight
- 357.4 g/mol
- IUPAC name
- (1S)-1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
- SMILES
- CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC
- InChIKey
- KGPAYJZAMGEDIQ-KRWDZBQOSA-N
- XLogP
- 3.7
- Polar surface area
- 40.2 Ų
- H-bond donors
- 0
- H-bond acceptors
- 5
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
202 papers- Laudanosine, an atracurium and cisatracurium metabolite.European journal of anaesthesiology · 2002
- Pharmacology of laudanosine in dogs.Anesthesiology · 1986
- Atracurium and laudanosine pharmacokinetics in acute renal failure.Intensive care medicine · 1993
- Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion.Critical care medicine · 1998
- [Cisatracurium].Revista espanola de anestesiologia y reanimacion · 1998
via PubMed
Wikidata facts
- Subclass of
- isoquinoline alkaloid
- Mass
- 357.194
Show 5 more facts
- found in taxon
- Papaver somniferum
- chemical formula
- C₂₁H₂₇NO₄
- canonical SMILES
- CN1CCC2=CC(=C(C=C2C1CC3=CC(=C(C=C3)OC)OC)OC)OC
- isomeric SMILES
- CN1CCC2=CC(=C(C=C2[C@@H]1CC3=CC(=C(C=C3)OC)OC)OC)OC
- Commons category
- Laudanosine
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
1 sectionsContents
- References
Laudanosine or '''N-methyltetrahydropapaverine' is a metabolite of the pharmaceutical drugs 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.
thumb|left|Capsule of Papaver somniferum showing latex (opium) exuding from incision. Laudanosine occurs naturally in small amounts (0.1%) in opium.
Excerpted from Wikipedia’s “laudanosine” article, available under the CC BY-SA 4.0 licence.