laudanosine
Identification
| Name | laudanosine |
| IUPAC | 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline |
| CAS Number | 1699-51-0 |
| EINECS | 216-923-9 |
| FDA UNII | Search |
| Molecular Formula | C21 H27 N O4 |
| Molecular Weight | 357.44999000 |
| Nikkaji Number | J10.989D |
Regulatory
Physical Properties
| Assay | 95.00 to 100.00 |
| Food Chemicals Codex Listed | No |
| Boiling Point | 468.10 °C. @ 760.00 mm Hg (est) |
| Flash Point | 268.00 °F. TCC ( 131.20 °C. ) (est) |
| logP (o/w) | 3.630 (est) |
| Soluble in | water, 74.73 mg/L @ 25 °C (est) |
Cosmetic Information
| CosIng | cosmetic data |
| Cosmetic Uses | skin conditioning |
No sensory data available
Safety Information
| Oral/Parenteral Toxicity | Not determined |
| Dermal Toxicity | subcutaneous-mouse LDLo 47 mg/kg |
| Inhalation Toxicity | Not determined |
GHS Classification
['GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)', 'GHS Label elements, including precautionary statements', 'BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)\n\nBEHAVIORAL: ATAXIA\n\nBEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD']
Safety in Use
| Category | cosmetic ingredient for skin conditioning |
| Recommendation for laudanosine usage levels up to | not for fragrance use. |
| Recommendation for laudanosine flavor usage levels up to | not for flavor use. |
No supplier data available
Potential Uses
Natural Occurrence
Synonyms
(1)-1-((3,4-
dimethoxyphenyl)methyl)-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methylisoquinoline
1-[(3,4-
dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
(±)-
laudanosine
iso
quinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (+-)-
1,2,3,4-
tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
PubMed:
[Determination of atracurium and laudanosine in dog plasma during cardiopulmonary bypass by high performance liquid chromatography with fluorometric detection].
PubMed:
Synthesis of 1-substituted tetrahydroisoquinolines by lithiation and electrophilic quenching guided by in situ IR and NMR spectroscopy and application to the synthesis of salsolidine, carnegine and laudanosine.
PubMed:
Synthesis of alkaloids by Stevens rearrangement of nitrile-stabilized ammonium ylides: (±)-laudanosine, (±)-laudanidine, (±)-armepavine, (±)-7-methoxycryptopleurine, and (±)-xylopinine.
PubMed:
Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats.
PubMed:
Methyl-laudanosine: a new pharmacological tool to investigate the function of small-conductance Ca(2+)-activated K(+) channels.
PubMed:
Modulation of rat brain synaptosomal plasma membrane achieved by atracurium and its metabolite laudanosine.
PubMed:
Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion.
PubMed:
Mechanism of the cardiovascular activity of laudanosine: comparison with papaverine and other benzylisoquinolines.
PubMed:
Interactions between laudanosine, GABA, and opioid subtype receptors: implication for laudanosine seizure activity.
PubMed:
Convulsive effects and pharmacokinetics of laudanosine in the rat.
PubMed:
Pharmacology of laudanosine in dogs.
PubMed:
Laudanosine (a metabolite of atracurium) increases the minimum alveolar concentration of halothane in rabbits.
PubMed:
Suicide with cisatracurium and thiopental: forensic and analytical aspects.
PubMed:
Pharmacokinetic modelling of a parent drug and its metabolite. Atracurium and laudanosine.
PubMed:
Atracurium decay and the formation of laudanosine in humans.
PubMed:
Cardiovascular and neurological effects of laudanosine. Studies in mice and rats, and in conscious and anaesthetized dogs.
PubMed:
Electrophysiological characterization of the SK channel blockers methyl-laudanosine and methyl-noscapine in cell lines and rat brain slices.
PubMed:
Effect of atracurium and laudanosine on the release of 3H-noradrenaline.
PubMed:
[Effect of laudanosine on catecholamine release in dogs].
PubMed:
Cardiovascular and electroencephalographic effects of laudanosine in "nephrectomized" cats.
PubMed:
Cerebrospinal fluid concentrations of atracurium, laudanosine and vecuronium following clinical subarachnoid hemorrhage.
PubMed:
Pharmacodynamics and atracurium and laudanosine concentrations during a fixed continuous infusion of atracurium in mechanically ventilated patients with acute respiratory distress syndrome.
PubMed:
Laudanosine, an atracurium and cisatracurium metabolite.
PubMed:
Cerebrospinal fluid concentrations of laudanosine after administration of atracurium.
PubMed:
Electroencephalographic effects of laudanosine in an animal model of epilepsy.
PubMed:
Modification by drugs used in anaesthesia of CNS stimulation induced in mice by laudanosine and strychnine.
PubMed:
Clearance of atracurium and laudanosine in the urine and by continuous venovenous haemofiltration.
PubMed:
Concentrations of atracurium and laudanosine in cerebrospinal fluid and plasma during intracranial surgery.
PubMed:
Laudanosine does not displace receptor-specific ligands from the benzodiazepinergic or muscarinic receptors.
PubMed:
Blockade and activation of the human neuronal nicotinic acetylcholine receptors by atracurium and laudanosine.
PubMed:
Plasma laudanosine levels in patients given atracurium during liver transplantation.
PubMed:
Concentrations of atracurium and laudanosine in cerebrospinal fluid and plasma in three intensive care patients.
PubMed:
Pharmacokinetics of atracurium and laudanosine in the elderly.
PubMed:
Disposition of infusions of atracurium and its metabolite, laudanosine, in patients in renal and respiratory failure in an ITU.
PubMed:
Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers.
PubMed:
Plasma concentrations of laudanosine, but not of atracurium, are increased during the anhepatic phase of orthotopic liver transplantation in pigs.
PubMed:
The distribution of laudanosine in tissues after death from atracurium injection.
PubMed:
High-performance liquid chromatographic method for the determination of atracurium and laudanosine in human plasma. Application to pharmacokinetics.
PubMed:
Transplacental distribution of atracurium, laudanosine and monoquaternary alcohol during elective caesarean section.
PubMed:
High-performance liquid chromatographic assay for laudanosine in biological fluids and tissue for neurotoxic studies in rats.
PubMed:
Modification of central nervous system effects of laudanosine by inhalation anaesthetics.
PubMed:
Pharmacokinetics of atracurium and laudanosine in patients with hepatic cirrhosis.
PubMed:
The metabolic disposition of laudanosine in dog, rabbit, and man.
PubMed:
[Absorption of papaverine, laudanosine and cepharanthine across human intestine by using human Caco-2 cells monolayers model].
PubMed:
Nitrous oxide antagonizes CNS stimulation by laudanosine in mice.
PubMed:
Production of laudanosine following infusion of atracurium in man and its effects on awakening.
PubMed:
Effect of renal failure on laudanosine excretion in man.
PubMed:
Pharmacokinetics of 1R-cis 1'R-cis atracurium besylate (51W89) and plasma laudanosine concentrations in health and chronic renal failure.
PubMed:
Synthesis and radioligand binding studies of C-5- and C-8-substituted 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinoliniums as SK channel blockers related to N-methyl-laudanosine and N-methyl-noscapine.
PubMed:
Clinical experience and plasma laudanosine concentrations during the infusion of atracurium in the intensive therapy unit.
PubMed:
Simultaneous determination of atracurium and its metabolite laudanosine in post-mortem fluids by liquid chromatography/multiple-stage mass spectrometry on an ion trap.
PubMed:
Chiral separation of norlaudanosoline, laudanosoline, laudanosine, chlorthalidone, and three benzoin derivatives using amino acid based molecular micelles.
PubMed:
Identification of laudanosine, an atracurium metabolite, following a fatal drug-related shooting.
PubMed:
Hepatotoxicity testing of atracurium and laudanosine in the isolated, perfused rat liver.
PubMed:
Determination of atracurium and laudanosine in human plasma by high-performance liquid chromatography.
PubMed:
The microbial oxygenation of the benzylisoquinoline alkaloid laudanosine.
PubMed:
Atracurium and laudanosine pharmacokinetics in acute renal failure.
PubMed:
Simplified method for the determination of atracurium and laudanosine in pig plasma by high-performance liquid chromatography and fluorimetric detection.
PubMed:
The possible neuroprotective effect of laudanosine, an atracurium and cisatracurium metabolite.
PubMed:
High-dose laudanosine enhances liver cell activity and bile flow during reperfusion of the liver.
PubMed:
Determination of atracurium, laudanosine and related compounds in plasma by high-performance liquid chromatography.
PubMed:
The use of cisatracurium in critical care: A review of the literature.
PubMed:
Investigation of chondroitin sulfate D and chondroitin sulfate E as novel chiral selectors in capillary electrophoresis.
PubMed:
[DEHYDRATION OF TERTIARY AMINES WITH HG(II)-EDTA. 8. ON THE CONFIGURATION OF 1-BENZYL-N-TERT-BUTYL-1,2,3,4-TETRAHYDROISOQUINOLINE AND LAUDANOSINE].
PubMed:
[Dehydration of tertiary amines by mercuric acetate in the presence of ethylenediaminetetraacetic acid. 1. The configuration of laudanosine].
PubMed:
Microbial transformations of natural antitumor agents. 2. Studies with d-tetrandrine and laudanosine.
PubMed:
[DEHYDROGENATION OF TERTIARY AMINES WITH HG(II)-EDTA. 6. FURTHER STUDIES ON THE PROCESS OF AROMATIZATION OF LAUDANOSINE WITH HG(III)-EDTA].
PubMed:
[Dehydration of tertiary amines with Hg(II)-EDTA. 4. On the course of aromatization of laudanosine with Hg(II)-EDTA].
PubMed:
Characterization of three O-methyltransferases involved in noscapine biosynthesis in opium poppy.
PubMed:
Synthesis and radioligand binding studies of bis-(8-isopropyl-isoquinolinium) derivatives as ligands for apamin-sensitive sites on cloned SK2 and SK3 channels.
PubMed:
Atracurium infusions in patients with fulminant hepatic failure awaiting liver transplantation.
PubMed:
Anesthesiologist suicide with atracurium.
PubMed:
The in vitro degradation of cisatracurium, the R, cis-R'-isomer of atracurium, in human and rat plasma.
PubMed:
The biosynthesis of papaverine proceeds via (S)-reticuline.
PubMed:
Enantioselective synthesis of tetrahydroprotoberberines and bisbenzylisoquinoline alkaloids from a deprotonated α-aminonitrile.
PubMed:
Identification and quantitation of six non-depolarizing neuromuscular blocking agents by LC-MS in biological fluids.
PubMed:
Pharmacokinetics and dynamics of atracurium infusions after paediatric orthotopic liver transplantation.
PubMed:
Determination of atracurium, cisatracurium and mivacurium with their impurities in pharmaceutical preparations by liquid chromatography with charged aerosol detection.
PubMed:
Perinatal neuroprotection by muscle relaxants against hypoxic-ischemic lesions: is it a possible hypothesis?
PubMed:
Evaluation of the enantioselectivity of glycogen-based dual chiral selector systems towards basic drugs in capillary electrophoresis.
PubMed:
Comparison of the pharmacodynamics and pharmacokinetics of an infusion of cis-atracurium (51W89) or atracurium in critically ill patients undergoing mechanical ventilation in an intensive therapy unit.
PubMed:
In vitro degradation of atracurium in human plasma.
PubMed:
The pharmacokinetics of cisatracurium in patients with acute respiratory distress syndrome.
PubMed:
Effects of neuromuscular blocking agents on excitatory transmission and gamma-aminobutyric acidA-mediated inhibition in the rat hippocampal slice.
PubMed:
Pharmacokinetics of cisatracurium in patients receiving nitrous oxide/opioid/barbiturate anesthesia.
PubMed:
The prolonged use of atracurium in a patient with tetanus.
PubMed:
Pharmacokinetics of atracurium and its metabolites in patients with normal renal function, and in patients in renal failure.
PubMed:
Pharmacophore modelling of structurally unusual diltiazem mimics at L-type calcium channels.
PubMed:
A comparison of the infusion pharmacokinetics and pharmacodynamics of cisatracurium, the 1R-cis 1'R-cis isomer of atracurium, with atracurium besylate in healthy patients.
PubMed:
A pharmacokinetic-pharmacodynamic model for a muscle relaxant: atracurium.
PubMed:
Pharmacokinetics of 51W89: preliminary data.
PubMed:
Atracurium-induced neuromuscular block in the isolated arm.
PubMed:
Pharmacokinetics and neuromuscular blocking effects of atracurium besylate and two of its metabolites in patients with normal and impaired renal function.
PubMed:
The pharmacokinetics and pharmacodynamics of atracurium in patients with and without renal failure.
PubMed:
Synthesis of carbon-11 labeled 1-(3,4-dimethoxybenzyl)-2,2-dimethyl-1,2,3,4-tetrahydroisoquinolinium derivatives as new potential PET SKCa channel imaging agents.
PubMed:
Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers.
PubMed:
Risk-based approach for the transfer of quantitative methods: bioanalytical applications.
PubMed:
SK channels control the firing pattern of midbrain dopaminergic neurons in vivo.
PubMed:
Studies of polymerized sodium N-undecylenyl-L-valinate in chiral micellar electrokinetic capillary chromatography of neutral, acidic, and basic compounds.
PubMed:
Pharmacokinetics and pharmacodynamics of cisatracurium in patients with end-stage liver disease undergoing liver transplantation.
PubMed:
Lambda-carrageenan: a novel chiral selector for capillary electrophoresis.
PubMed:
Influence of extreme obesity on the body disposition and neuromuscular blocking effect of atracurium.
PubMed:
Prolonged infusion of atracurium in an infant.
PubMed:
Atracurium overdose in a small infant.
PubMed:
Generation of reactive metabolites during spontaneous degradation of atracurium in vitro.
PubMed:
Pharmacokinetics of atracurium in anaesthetized infants and children.
PubMed:
Relationships between structure and vascular activity in a series of benzylisoquinolines.
PubMed:
Activation of brain acetylcholine receptors by neuromuscular blocking drugs. A possible mechanism of neurotoxicity.
PubMed:
Influence of incubated atracurium on rat liver function.
PubMed:
Residual curarization in the neonate after caesarean section.
PubMed:
Pharmacokinetics and pharmacodynamics of atracurium obtained with arterial and venous blood samples.
PubMed:
Anaesthesia for the treatment of a giant cerebral aneurysm under hypothermic circulatory arrest.
PubMed:
Synthesis and radioligand binding studies of methoxylated 1,2,3,4-tetrahydroisoquinolinium derivatives as ligands of the apamin-sensitive Ca2+-activated K+ channels.
PubMed:
The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid.
PubMed:
Inhibitory effects of ethaverine, a homologue of papaverine, on monoamine oxidase activity in mouse brain.
PubMed:
Effect of dopamine, dimethoxyphenylethylamine, papaverine, and related compounds on mitochondrial respiration and complex I activity.
PubMed:
Identification of urinary and biliary conjugated metabolites of the neuromuscular blocker 51W89 by liquid chromatography/mass spectrometry.
PubMed:
Selective inhibition of calcium entry induced by benzylisoquinolines in rat smooth muscle.
PubMed:
The cardiovascular effects of atracurium and it's metabolite.
PubMed:
Pharmacological action of breakdown products of atracurium and related substances.
PubMed:
Cisatracurium infusion for neuromuscular blockade in the pediatric intensive care unit: A dose-finding study.
PubMed:
Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling.
PubMed:
Bioactive constituents of the roots of Polyalthia cerasoides.
PubMed:
Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors.
PubMed:
Transformation of opium poppy (Papaver somniferum L.) with antisense berberine bridge enzyme gene (anti-bbe) via somatic embryogenesis results in an altered ratio of alkaloids in latex but not in roots.
PubMed:
The GC-MS detection and characterization of reticuline as a marker of opium use.
PubMed:
Instability of pancuronium in postmortem blood and liver taken after a fatal intramuscular Pavulon injection.
PubMed:
The GC-MS detection and characterization of reticuline as a marker of opium use.
PubMed:
Aporphine alkaloids from Guatteria spp. with leishmanicidal activity.
PubMed:
Modulation of small conductance calcium-activated potassium (SK) channels: a new challenge in medicinal chemistry.
PubMed:
Colominic acid: a novel chiral selector for capillary electrophoresis of basic drugs.
PubMed:
Pharmacokinetic-pharmacodynamic modeling of atracurium in intensive care patients.
PubMed:
Approaching a million-fold sensitivity increase in capillary electrophoresis with direct ultraviolet detection: cation-selective exhaustive injection and sweeping
PubMed:
Comparative evaluation of capillary electrophoresis and high-performance liquid chromatography for the separation of cis-cis, cis-trans, and trans-trans isomers of atracurium besylate.
PubMed:
[Cisatracurium].
PubMed:
[The clinical pharmacology of new benzylisoquinoline-diester compounds, with special consideration of cisatracurium and mivacurium].
PubMed:
[New muscle relaxants].
PubMed:
Approaches to short-acting neuromuscular blocking agents: nonsymmetrical bis-tetrahydroisoquinolinium mono- and diesters.
PubMed:
Simple high-performance liquid chromatographic method for the analysis of the non-depolarizing neuromuscular blocking drugs in clinical anaesthesia.
PubMed:
Pharmacokinetics of atracurium metabolites.
PubMed:
Review of atracurium by continuous i.v. infusion.
PubMed:
High pressure liquid chromatographic determination of the five major alkaloids in Papaver somniferum L. and thebaine in Papaver bracteatum Lindl. capsular tissue.
PubMed:
Hofmann elimination with diazomethane on curare bases and selected quaternary tetrahydroisoquinoline alkaloids.
PubMed:
A relatively simple differential screening test for GABA or glycine antagonists using rat electroretinography.
PubMed:
Alkaloids of Hernandia voyronii: chloroquine-potentiating activity and structure elucidation of herveline D.
PubMed:
Neutral heroin impurities from tetrahydrobenzylisoquinoline alkaloids.
PubMed:
The roles of latex and the vascular bundle in morphine biosynthesis in the opium poppy, Papaver somniferum.
PubMed:
The insulin pump as murder weapon: a case report.
PubMed:
Does ester hydrolysis change the in vitro degradation rate of cisatracurium and atracurium?
PubMed:
Concentration-effect relationship of cisatracurium at three different dose levels in the anesthetized patient.
PubMed:
[Effects of priming technique on onset profile of cisatracurium].
PubMed:
In vitro degradation of atracurium and cisatracurium at pH 7.4 and 37 degrees C depends on the composition of the incubating solutions.
PubMed:
Importance of the organ-independent elimination of cisatracurium.
PubMed:
Simultaneous determination of dextrorphan and guaifenesin in human plasma by liquid chromatography with fluorescence detection.
PubMed:
Is 51W89 an improvement compared with atracurium?
PubMed:
Inhibition of purine nucleobase transport in human erythrocytes and cell lines by papaverine. Investigation of structure-activity relationship.
PubMed:
Simple and rapid high-performance liquid chromatography method for the determination of alcuronium in human plasma and urine.
PubMed:
Inhibition of hepatic microsomal drug metabolism by atracurium administration in the rat.
PubMed:
Separation of eight alkaloids and meconic acid and quantitation of five principal alkaloids in gum opium by gradient reversed-phase high-performance liquid chromatography.
PubMed:
Effects of atracurium, vecuronium or pancuronium pretreatment on lignocaine seizure thresholds in cats.
PubMed:
Preponderance of hydrolysis in inactivation of atracurium: questions remain.
PubMed:
Status epilepticus following enflurane anaesthesia.
PubMed:
Atracurium infusions in patients with renal failure on an ITU.
PubMed:
Pharmacokinetics of atracurium and its metabolites.
PubMed:
Atracurium: an overview.
PubMed:
The cerebral effects of pancuronium and atracurium in halothane-anesthetized dogs.
PubMed:
Magic bullets, science, and medicine.
PubMed:
[Metabolism and pharmacokinetics of atracurium].
PubMed:
Stereochemical preferences for curarimimetic neuromuscular junction blockade IV: Monoquaternary ammonium probes possessing carbon and nitrogen asymmetry.
PubMed:
Stereochemical preferences for curarimimetic neuromuscular junction blockade I: enantiomeric monoquaternary amines as probes.