LAUDANOSINE

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/12113608 | https://www.ncbi.nlm.nih.gov/pubmed/8069669

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	Potency
gamma-aminobutyric acid (GABA) receptors 1 Target ID: gamma-aminobutyric acid (GABA) receptors Sources: https://www.ncbi.nlm.nih.gov/pubmed/8069669	Binding Agent 1064
Neuronal acetylcholine receptor; alpha4/beta2 76 Target ID: CHEMBL1907589 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15980871	Inhibitor 8297
Mu-type opioid receptor 61 Target ID: P35372\|\|\|G8XRH8\|\|\|Q5TDA1\|\|\|Q9UN57 Gene ID: 4988.0 Gene Symbol: OPRM1 Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/8069669	Inhibitor 8297	2.7 µM [Ki]
Neuronal acetylcholine receptor; alpha4/beta4 7 Target ID: CHEMBL1907591 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15980871	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Unknown 2578

PubMed

Title	Date	PubMed
Laudanosine and atracurium concentrations in a patient receiving long-term atracurium infusion.	1998 Jan	9428564
Pharmacokinetic-pharmacodynamic modeling of atracurium in intensive care patients.	2001 Jan	11144993
Inhibitory effects of ethaverine, a homologue of papaverine, on monoamine oxidase activity in mouse brain.	2001 Jul	11456127
Colominic acid: a novel chiral selector for capillary electrophoresis of basic drugs.	2002 Jul 12	12198966
The GC-MS detection and characterization of reticuline as a marker of opium use.	2004 May 28	15272474
The efficient synthesis of morphinandienone alkaloids by using a combination of hypervalent iodine(III) reagent and heteropoly acid.	2004 Oct 11	15372696
Bioactive constituents of the roots of Polyalthia cerasoides.	2007 Sep	17845001
Clinical review: Drug metabolism and nonrenal clearance in acute kidney injury.	2008	19040780

Sample Use Guides

In Vivo Use Guide

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.

Name

Type

Language

LAUDANOSINE

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