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Details

Stereochemistry RACEMIC
Molecular Formula C20H25NO4
Molecular Weight 343.4168
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LAUDANINE

SMILES

COC1=CC2=C(C=C1OC)C(CC3=CC(O)=C(OC)C=C3)N(C)CC2

InChI

InChIKey=MPYHGNAJOKCMAQ-UHFFFAOYSA-N
InChI=1S/C20H25NO4/c1-21-8-7-14-11-19(24-3)20(25-4)12-15(14)16(21)9-13-5-6-18(23-2)17(22)10-13/h5-6,10-12,16,22H,7-9H2,1-4H3

HIDE SMILES / InChI

Approval Year

PubMed

PubMed

TitleDatePubMed
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.
2010-11-18
The biosynthesis of papaverine proceeds via (S)-reticuline.
2010-08
Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling.
2008-04-25
Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD.
2007-11
Bioactive constituents of the roots of Polyalthia cerasoides.
2007-09
Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells.
2007-06
Neutral heroin impurities from tetrahydrobenzylisoquinoline alkaloids.
2006-03
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
(R,S)-Reticuline 7-O-methyltransferase and (R,S)-norcoclaurine 6-O-methyltransferase of Papaver somniferum - cDNA cloning and characterization of methyl transfer enzymes of alkaloid biosynthesis in opium poppy.
2003-12
Separation of opiate alkaloids by electrokinetic chromatography with sulfated-cyclodextrin as a pseudo-stationary phase.
2003-01-24
Name Type Language
COCLANOLINE B
Preferred Name English
LAUDANINE
MI  
Common Name English
2-METHOXY-5-((1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-ISOQUINOLINYL)METHYL)PHENOL
Systematic Name English
(±)-LAUDANINE
Common Name English
DL-LAUDANIDINE
Common Name English
(±)-LAUDANIDINE
Common Name English
LAUDANIDINE, (±)-
Common Name English
PHENOL, 2-METHOXY-5-((1,2,3,4-TETRAHYDRO-6,7-DIMETHOXY-2-METHYL-1-ISOQUINOLINYL)METHYL)-
Systematic Name English
LAUDANINE [MI]
Common Name English
Code System Code Type Description
EPA CompTox
DTXSID00871570
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY
PUBCHEM
92732
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY
FDA UNII
994445H0VB
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY
ECHA (EC/EINECS)
201-620-6
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY
MERCK INDEX
m6705
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY Merck Index
CAS
85-64-3
Created by admin on Mon Mar 31 22:25:21 GMT 2025 , Edited by admin on Mon Mar 31 22:25:21 GMT 2025
PRIMARY