LAUDANINE

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 Search

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

Molecular Formula	C20H25NO4
Molecular Weight	343.4168
Charge	0
Count

Stereochemistry	RACEMIC
Additional Stereochemistry	No
Defined Stereocenters	0 / 1
E/Z Centers	0
Optical Activity	( + / - )

Approval Year

PubMed

Title	Date	PubMed
Integration of deep transcriptome and proteome analyses reveals the components of alkaloid metabolism in opium poppy cell cultures.	2010-11-18	21083930
The biosynthesis of papaverine proceeds via (S)-reticuline.	2010-08	20494383
Applicability of ultra-performance liquid chromatography-tandem mass spectrometry for heroin profiling.	2008-04-25	18374345
Biotransformation of phenolic 1-benzyl-N-methyltetrahydroisoquinolines in plant cell cultures followed by LC/NMR, LC/MS, and LC/CD.	2007-11	17988098
Bioactive constituents of the roots of Polyalthia cerasoides.	2007-09	17845001
Knockdown of berberine bridge enzyme by RNAi accumulates (S)-reticuline and activates a silent pathway in cultured California poppy cells.	2007-06	17103244
Neutral heroin impurities from tetrahydrobenzylisoquinoline alkaloids.	2006-03	16566764
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	15672841
(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	14675446
Separation of opiate alkaloids by electrokinetic chromatography with sulfated-cyclodextrin as a pseudo-stationary phase.	2003-01-24	12580518

Substance Class	Chemical Created by `admin` on `Mon Mar 31 22:25:21 GMT 2025` Edited by `admin` on `Mon Mar 31 22:25:21 GMT 2025`
Record UNII	994445H0VB
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

COCLANOLINE B

Preferred Name

English

LAUDANINE

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