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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO4
Molecular Weight 357.4434
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAUDANOSINE

SMILES

COC1=CC2=C(C=C1OC)[C@H](CC3=CC(OC)=C(OC)C=C3)N(C)CC2

InChI

InChIKey=KGPAYJZAMGEDIQ-KRWDZBQOSA-N
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

HIDE SMILES / InChI

Molecular Formula C21H27NO4
Molecular Weight 357.4434
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Laudanosine, a potentially epileptogenic metabolite of the neuromuscular relaxant atracurium besylate with potentially toxic effects. Laudanosine is a non-competitive and voltage-dependent inhibitor of alpha7, alpha4beta2 or alpha4beta4 nicotinic acetylcholine receptors, opioid mu 1 type receptors and possesses a low-affinity to the GABA receptors, but didn’t interact with the benzodiazepine or muscarinic receptors.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: gamma-aminobutyric acid (GABA) receptors
Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57
Gene ID: 4988.0
Gene Symbol: OPRM1
Target Organism: Homo sapiens (Human)
2.7 µM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
PubMed

PubMed

TitleDatePubMed
Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion.
1998 Jan
Blockade and activation of the human neuronal nicotinic acetylcholine receptors by atracurium and laudanosine.
2001 Apr
Concentration-effect relationship of cisatracurium at three different dose levels in the anesthetized patient.
2001 Aug
The pharmacokinetics of cisatracurium in patients with acute respiratory distress syndrome.
2001 Aug
Pharmacokinetic-pharmacodynamic modeling of atracurium in intensive care patients.
2001 Jan
Inhibitory effects of ethaverine, a homologue of papaverine, on monoamine oxidase activity in mouse brain.
2001 Jul
Does ester hydrolysis change the in vitro degradation rate of cisatracurium and atracurium?
2002 Apr
Methyl-laudanosine: a new pharmacological tool to investigate the function of small-conductance Ca(2+)-activated K(+) channels.
2002 Sep
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.
2004 Dec
The insulin pump as murder weapon: a case report.
2004 Jun
The GC-MS detection and characterization of reticuline as a marker of opium use.
2004 Mar 10
The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid.
2004 Oct 11
Perinatal neuroprotection by muscle relaxants against hypoxic-ischemic lesions: is it a possible hypothesis?
2005 Aug
SK channels control the firing pattern of midbrain dopaminergic neurons in vivo.
2005 Dec
Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers.
2005 Feb 15
Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors.
2005 Sep
Chiral separation of norlaudanosoline, laudanosoline, laudanosine, chlorthalidone, and three benzoin derivatives using amino acid based molecular micelles.
2006 Feb
Anesthesiologist suicide with atracurium.
2006 Mar
Simultaneous determination of atracurium and its metabolite laudanosine in post-mortem fluids by liquid chromatography/multiple-stage mass spectrometry on an ion trap.
2007
Bioactive constituents of the roots of Polyalthia cerasoides.
2007 Sep
Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury.
2008
Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling.
2008 Apr 25
[Absorption of papaverine, laudanosine and cepharanthine across human intestine by using human Caco-2 cells monolayers model].
2008 Feb
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.
2008 Feb
Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers.
2008 Jun 1
Use of intrathecal and intravenous clonidine in a case of severe tetanus with acute renal failure.
2009 Apr
Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats.
2010
The biosynthesis of papaverine proceeds via (S)-reticuline.
2010 Aug
Determination of atracurium, cisatracurium and mivacurium with their impurities in pharmaceutical preparations by liquid chromatography with charged aerosol detection.
2010 Feb 19
Evaluation of the enantioselectivity of glycogen-based dual chiral selector systems towards basic drugs in capillary electrophoresis.
2010 Nov 5

Sample Use Guides

In mice and rats: i.v. bolus doses of laudanosine 10-20 mg kg-1, caused convulsions and hind limb extensions
Route of Administration: Intravenous
In Vitro Use Guide
Laudanosine was almost ineffective at [3H]muscimol binding to high-affinity GABA receptors (IC50 = 100 microM). However, laudanosine displayed an inhibitory effect at the low-affinity GABA receptors labeled by [3H]bicuculline methochloride, with an IC50 value of 10 microM. At the opioid receptor subtype, laudanosine lowered radiolabeled opioid binding at the mu 1, mu 2, delta, kappa 1, and kappa 3 receptors with Ki values of 2.7, 13, 5.5, 21, and 24 microM, respectively.
Substance Class Chemical
Created
by admin
on Thu Jul 06 01:21:30 UTC 2023
Edited
by admin
on Thu Jul 06 01:21:30 UTC 2023
Record UNII
DA7R5WVN48
Record Status Validated (UNII)
Record Version
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Name Type Language
LAUDANOSINE
INCI   MI  
INCI  
Official Name English
NSC-35045
Code English
1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-VERATRYLISOQUINOLINE
Systematic Name English
Isoquinoline, 1-[(3,4-dimethoxyphenyl)methyl]-1,2,3,4-tetrahydro-6,7-dimethoxy-2-methyl-, (1S)-
Systematic Name English
LAUDANOSINE [INCI]
Common Name English
(1S)-1-((3,4-DIMETHOXYPHENYL)METHYL)-1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYLISOQUINOLINE
Systematic Name English
LAUDANOSINE [MI]
Common Name English
(S)-(+)-LAUDANOSINE
Common Name English
N-METHYLTETRAHYDROPAPAVERINE
Common Name English
Code System Code Type Description
CAS
2688-77-9
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
SMS_ID
300000043559
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
PUBCHEM
73397
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
NSC
35045
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
EPA CompTox
DTXSID30878577
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
MERCK INDEX
M6706
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY Merck Index
WIKIPEDIA
LAUDANOSINE
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
FDA UNII
DA7R5WVN48
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
ECHA (EC/EINECS)
220-253-2
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
MESH
C001522
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
PRIMARY
CAS
1699-51-0
Created by admin on Thu Jul 06 01:21:30 UTC 2023 , Edited by admin on Thu Jul 06 01:21:30 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
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