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Details

Stereochemistry ABSOLUTE
Molecular Formula C21H27NO4
Molecular Weight 357.4442
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAUDANOSINE

SMILES

CN1CCc2cc(c(cc2[C@]1([H])Cc3ccc(c(c3)OC)OC)OC)OC

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 357.4442
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
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
Pharmacodynamics and atracurium and laudanosine concentrations during a fixed continuous infusion of atracurium in mechanically ventilated patients with acute respiratory distress syndrome.
2002 Aug
Colominic acid: a novel chiral selector for capillary electrophoresis of basic drugs.
2002 Jul 12
Methyl-laudanosine: a new pharmacological tool to investigate the function of small-conductance Ca(2+)-activated K(+) channels.
2002 Sep
Aporphine alkaloids from Guatteria spp. with leishmanicidal activity.
2003 Jul
Instability of pancuronium in postmortem blood and liver taken after a fatal intramuscular Pavulon injection.
2004 Jul 16
The insulin pump as murder weapon: a case report.
2004 Jun
Identification and quantitation of six non-depolarizing neuromuscular blocking agents by LC-MS in biological fluids.
2004 Mar
The GC-MS detection and characterization of reticuline as a marker of opium use.
2004 Mar 10
The GC-MS detection and characterization of reticuline as a marker of opium use.
2004 May 28
The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid.
2004 Oct 11
Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers.
2005 Feb 15
Anesthesiologist suicide with atracurium.
2006 Mar
Bioactive constituents of the roots of Polyalthia cerasoides.
2007 Sep
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
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 Sat Jun 26 09:45:37 UTC 2021
Edited
by admin
on Sat Jun 26 09:45:37 UTC 2021
Record UNII
DA7R5WVN48
Record Status Validated (UNII)
Record Version
  • Download
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
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 Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
PUBCHEM
73397
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
MERCK INDEX
M6706
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY Merck Index
WIKIPEDIA
LAUDANOSINE
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
FDA UNII
DA7R5WVN48
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
ECHA (EC/EINECS)
220-253-2
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
MESH
C001522
Created by admin on Sat Jun 26 09:45:37 UTC 2021 , Edited by admin on Sat Jun 26 09:45:37 UTC 2021
PRIMARY
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