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
SMILES
COC1=C(OC)C=C(C[C@@H]2N(C)CCC3=CC(OC)=C(OC)C=C23)C=C1
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
| 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.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: gamma-aminobutyric acid (GABA) receptors |
|||
Target ID: CHEMBL1907589 |
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Target ID: P35372|||G8XRH8|||Q5TDA1|||Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) |
2.7 µM [Ki] | ||
Target ID: CHEMBL1907591 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
PubMed
| Title | Date | PubMed |
|---|---|---|
| Evaluation of the enantioselectivity of glycogen-based dual chiral selector systems towards basic drugs in capillary electrophoresis. | 2010-11-05 |
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| The biosynthesis of papaverine proceeds via (S)-reticuline. | 2010-08 |
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| Determination of atracurium, cisatracurium and mivacurium with their impurities in pharmaceutical preparations by liquid chromatography with charged aerosol detection. | 2010-02-19 |
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| Laudanosine has no effects on respiratory activity but induces non-respiratory excitement activity in isolated brainstem-spinal cord preparation of neonatal rats. | 2010 |
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| Use of intrathecal and intravenous clonidine in a case of severe tetanus with acute renal failure. | 2009-04 |
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| Bis-tetrahydroisoquinoline derivatives: AG525E1, a new step in the search for non-quaternary non-peptidic small conductance Ca(2+)-activated K(+) channel blockers. | 2008-06-01 |
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| Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling. | 2008-04-25 |
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| [Absorption of papaverine, laudanosine and cepharanthine across human intestine by using human Caco-2 cells monolayers model]. | 2008-02 |
|
| 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. | 2008-02 |
|
| Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury. | 2008 |
|
| Bioactive constituents of the roots of Polyalthia cerasoides. | 2007-09 |
|
| Simultaneous determination of atracurium and its metabolite laudanosine in post-mortem fluids by liquid chromatography/multiple-stage mass spectrometry on an ion trap. | 2007 |
|
| Anesthesiologist suicide with atracurium. | 2006-03 |
|
| Chiral separation of norlaudanosoline, laudanosoline, laudanosine, chlorthalidone, and three benzoin derivatives using amino acid based molecular micelles. | 2006-02 |
|
| SK channels control the firing pattern of midbrain dopaminergic neurons in vivo. | 2005-12 |
|
| Evaluation of benzyltetrahydroisoquinolines as ligands for neuronal nicotinic acetylcholine receptors. | 2005-09 |
|
| Perinatal neuroprotection by muscle relaxants against hypoxic-ischemic lesions: is it a possible hypothesis? | 2005-08 |
|
| Synthesis and biological evaluation of N-methyl-laudanosine iodide analogues as potential SK channel blockers. | 2005-02-15 |
|
| 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. | 2004-12 |
|
| The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid. | 2004-10-11 |
|
| Instability of pancuronium in postmortem blood and liver taken after a fatal intramuscular Pavulon injection. | 2004-07-16 |
|
| The insulin pump as murder weapon: a case report. | 2004-06 |
|
| The GC-MS detection and characterization of reticuline as a marker of opium use. | 2004-05-28 |
|
| The GC-MS detection and characterization of reticuline as a marker of opium use. | 2004-03-10 |
|
| Identification and quantitation of six non-depolarizing neuromuscular blocking agents by LC-MS in biological fluids. | 2004-03 |
|
| Aporphine alkaloids from Guatteria spp. with leishmanicidal activity. | 2003-07 |
|
| The possible neuroprotective effect of laudanosine, an atracurium and cisatracurium metabolite. | 2003-07 |
|
| Cerebrospinal fluid concentrations of atracurium, laudanosine and vecuronium following clinical subarachnoid hemorrhage. | 2002-11 |
|
| Methyl-laudanosine: a new pharmacological tool to investigate the function of small-conductance Ca(2+)-activated K(+) channels. | 2002-09 |
|
| Pharmacodynamics and atracurium and laudanosine concentrations during a fixed continuous infusion of atracurium in mechanically ventilated patients with acute respiratory distress syndrome. | 2002-08 |
|
| Colominic acid: a novel chiral selector for capillary electrophoresis of basic drugs. | 2002-07-12 |
|
| Laudanosine, an atracurium and cisatracurium metabolite. | 2002-07 |
|
| Does ester hydrolysis change the in vitro degradation rate of cisatracurium and atracurium? | 2002-04 |
|
| Concentration-effect relationship of cisatracurium at three different dose levels in the anesthetized patient. | 2001-08 |
|
| The pharmacokinetics of cisatracurium in patients with acute respiratory distress syndrome. | 2001-08 |
|
| Inhibitory effects of ethaverine, a homologue of papaverine, on monoamine oxidase activity in mouse brain. | 2001-07 |
|
| Blockade and activation of the human neuronal nicotinic acetylcholine receptors by atracurium and laudanosine. | 2001-04 |
|
| Pharmacokinetic-pharmacodynamic modeling of atracurium in intensive care patients. | 2001-01 |
|
| Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion. | 1998-01 |
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
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
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Edited
Mon Mar 31 19:02:03 GMT 2025
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| Record UNII |
DA7R5WVN48
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| Record Status |
Validated (UNII)
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2688-77-9
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300000043559
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DTXSID30878577
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m6706
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LAUDANOSINE
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DA7R5WVN48
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220-253-2
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C001522
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1699-51-0
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NON-SPECIFIC STEREOCHEMISTRY |
| Related Record | Type | Details | ||
|---|---|---|---|---|
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PARENT -> METABOLITE ACTIVE |
