laudanosine
 
Notes:
None found
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CAS Number: 1699-51-0Picture of molecule3D/inchi
ECHA EINECS - REACH Pre-Reg: 216-923-9
Nikkaji Web: J10.989D
XlogP3-AA: 3.70 (est)
Molecular Weight: 357.44999000
Formula: C21 H27 N O4
BioActivity Summary: listing
NMR Predictor: Predict (works with chrome or firefox)
Category: cosmetic ingredient for skin conditioning
 
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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)
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Organoleptic Properties:
 
Odor and/or flavor descriptions from others (if found).
 
 
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Cosmetic Information:
CosIng: cosmetic data
Cosmetic Uses: skin conditioning
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Suppliers:
ExtraSynthese
For experimental / research use only.
DL-Laudanosine (HPLC) ≥95%
Sigma-Aldrich
For experimental / research use only.
Laudanosine EuropePharmacopoeia (EP) Reference Standard
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Safety Information:
 
Hazards identification
 
Classification of the substance or mixture
GHS Classification in accordance with 29 CFR 1910 (OSHA HCS)
None found.
GHS Label elements, including precautionary statements
 
Pictogram
 
Hazard statement(s)
None found.
Precautionary statement(s)
None found.
Oral/Parenteral Toxicity:
Not determined
Dermal Toxicity:
subcutaneous-mouse LDLo 47 mg/kg
BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) BEHAVIORAL: ATAXIA BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Journal of Medicinal Chemistry. Vol. 20, Pg. 894, 1977.

Inhalation Toxicity:
Not determined
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Safety in Use Information:
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.
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Safety References:
EPI System: View
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EPA ACToR: Toxicology Data
EPA Substance Registry Services (SRS): Registry
Laboratory Chemical Safety Summary : 15548
National Institute of Allergy and Infectious Diseases: Data
WGK Germany: 3
 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
Chemidplus: 0001699510
RTECS: NX5070000 for cas# 1699-51-0
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References:
 1-[(3,4-dimethoxyphenyl)methyl]-6,7-dimethoxy-2-methyl-3,4-dihydro-1H-isoquinoline
NIST Chemistry WebBook: Search Inchi
Pubchem (cid): 15548
Pubchem (sid): 134979354
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Other Information:
(IUPAC): Atomic Weights of the Elements 2011 (pdf)
Videos: The Periodic Table of Videos
tgsc: Atomic Weights use for this web site
(IUPAC): Periodic Table of the Elements
CHEMBL: View
HMDB (The Human Metabolome Database): Search
Export Tariff Code: 2939.10.5000
VCF-Online: VCF Volatile Compounds in Food
ChemSpider: View
Wikipedia: View
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Potential Blenders and core components note
 
None Found
 
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Potential Uses:
None Found
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Occurrence (nature, food, other): note
 found in nature
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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
isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratryl-, (+-)-
1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-1-veratrylisoquinoline
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Articles:
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.
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