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Details

Stereochemistry ABSOLUTE
Molecular Formula C16H21NO
Molecular Weight 243.344
Optical Activity ( - )
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NORLEVORPHANOL

SMILES

[H][C@@]12CCCC[C@@]13CCN[C@@H]2CC4=CC=C(O)C=C34

InChI

InChIKey=IYNWSQDZXMGGGI-NUEKZKHPSA-N
InChI=1S/C16H21NO/c18-12-5-4-11-9-15-13-3-1-2-6-16(13,7-8-17-15)14(11)10-12/h4-5,10,13,15,17-18H,1-3,6-9H2/t13-,15+,16+/m0/s1

HIDE SMILES / InChI
PubMed

PubMed

TitleDatePubMed
High-performance liquid chromatography assay for simultaneous determination of dextromethorphan and its main metabolites in urine and in microsomal preparations.
2001 Apr 15
Comparative contribution to dextromethorphan metabolism by cytochrome P450 isoforms in vitro: can dextromethorphan be used as a dual probe for both CTP2D6 and CYP3A activities?
2001 Nov
A sensitive LC-MS/MS assay for the determination of dextromethorphan and metabolites in human urine--application for drug interaction studies assessing potential CYP3A and CYP2D6 inhibition.
2002 Aug 22
The effect of grapefruit juice and seville orange juice on the pharmacokinetics of dextromethorphan: the role of gut CYP3A and P-glycoprotein.
2002 Jul 26
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.
2003 Jan-Feb
New morphinan derivatives with negligible psychotropic effects attenuate convulsions induced by maximal electroshock in mice.
2003 Mar 7
Determination of dextromethorphan and its metabolites in rat serum by liquid-liquid extraction and liquid chromatography with fluorescence detection.
2003 May 25
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.
2004 Dec 1
Effect of methamphetamine on the pharmacokinetics of dextromethorphan and midazolam in rats.
2005 Jul-Sep
Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers.
2005 Jun
3-hydroxymorphinan is neurotrophic to dopaminergic neurons and is also neuroprotective against LPS-induced neurotoxicity.
2005 Mar
Selective effects of nitric oxide on the disposition of chlorzoxazone and dextromethorphan in isolated perfused rat livers.
2006 Jul
Neuropsychotoxicity of abused drugs: potential of dextromethorphan and novel neuroprotective analogs of dextromethorphan with improved safety profiles in terms of abuse and neuroprotective effects.
2008 Jan
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).
2008 Jul
Metabolism of dextrorphan by CYP2D6 in different recombinantly expressed systems and its implications for the in vitro assessment of dextromethorphan metabolism.
2009 Feb
Inhibitory effect of glutamate release from rat cerebrocortical synaptosomes by dextromethorphan and its metabolite 3-hydroxymorphinan.
2009 Jul
A validated SIM GC/MS method for the simultaneous determination of dextromethorphan and its metabolites dextrorphan, 3-methoxymorphinan and 3-hydroxymorphinan in biological matrices and its application to in vitro CYP2D6 and CYP3A4 inhibition study.
2009 Nov
Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs.
2011
Patents

Patents

Name Type Language
NORLEVORPHANOL
INN   MI  
INN  
Official Name English
IDS-NN-006
Code English
2H-10,4A-IMINOETHANOPHENANTHREN-6-OL, 1,3,4,9,10,10A-HEXAHYDRO-
Systematic Name English
norlevorphanol [INN]
Common Name English
(-)-3-HYDROXYMORPHINAN
Systematic Name English
MORPHINAN-3-OL
Systematic Name English
NIH-7539
Code English
NORLEVORPHANOL [MI]
Common Name English
Classification Tree Code System Code
DEA NO. 9634
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
Code System Code Type Description
EVMPD
SUB09375MIG
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
SMS_ID
100000083600
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
INN
873
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
WIKIPEDIA
NORLEVORPHANOL
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY Norlevorphanol is an opioid analgesic of the morphinan class. It was never marketed.
MESH
C054116
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
ECHA (EC/EINECS)
216-236-4
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
PUBCHEM
5463854
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
CAS
1531-12-0
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
NCI_THESAURUS
C170233
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
ChEMBL
CHEMBL2105152
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY
MERCK INDEX
m8066
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY Merck Index
FDA UNII
IL94262N7K
Created by admin on Fri Dec 15 19:29:27 UTC 2023 , Edited by admin on Fri Dec 15 19:29:27 UTC 2023
PRIMARY