NORLEVORPHANOL

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 Search

SMILES

OC1=CC2=C(C[C@H]3NCC[C@@]24CCCC[C@@H]34)C=C1

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

Molecular Formula	C16H21NO
Molecular Weight	243.344
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	3 / 3
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://apps.who.int/iris/bitstream/handle/10665/275695/WHO-EMP-RHT-TSN-2018.1-eng.pdf?sequence=1&isAllowed=y | https://www.drugfuture.com/chemdata/norlevorphanol.html | https://books.google.ru/books?id=4yaGePenGKgC&pg=PA469&lpg=PA469&dq=NORLEVORPHANOL retrieved from The A-Z Encyclopedia of Alcohol and Drug Abuse By Thomas Nordegren, p.469

Norlevorphanol is the levo-isomer of 3-hydroxymorphinan (morphinan-3-ol). It is is an opioid analgesic of the morphinan family. Norlevorphanol is a Schedule I controlled substance (opiate).

Approval Year

PubMed

Title	Date	PubMed
Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs.	2011	21606622
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.	2009-11	19444798
Inhibitory effect of glutamate release from rat cerebrocortical synaptosomes by dextromethorphan and its metabolite 3-hydroxymorphinan.	2009-07	19428798
Metabolism of dextrorphan by CYP2D6 in different recombinantly expressed systems and its implications for the in vitro assessment of dextromethorphan metabolism.	2009-02	18543297
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).	2008-07	18591815
Neuropsychotoxicity of abused drugs: potential of dextromethorphan and novel neuroprotective analogs of dextromethorphan with improved safety profiles in terms of abuse and neuroprotective effects.	2008-01	18198471
Simultaneous analysis of dextromethorphan and its three metabolites in human plasma using an improved HPLC method with fluorometric detection.	2007-11-01	17919999
3-Hydroxymorphinan, a metabolite of dextromethorphan, protects nigrostriatal pathway against MPTP-elicited damage both in vivo and in vitro.	2006-12	17142799
Selective effects of nitric oxide on the disposition of chlorzoxazone and dextromethorphan in isolated perfused rat livers.	2006-07	16621933
Effect of methamphetamine on the pharmacokinetics of dextromethorphan and midazolam in rats.	2005-10-28	16250257
Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers.	2005-06	15988119
Validation of a liquid chromatography-mass spectrometry method to assess the metabolism of dextromethorphan in rat everted gut sacs.	2005-05-05	15797528
3-hydroxymorphinan is neurotrophic to dopaminergic neurons and is also neuroprotective against LPS-induced neurotoxicity.	2005-03	15596482
LC-MS/MS analysis of dextromethorphan metabolism in human saliva and urine to determine CYP2D6 phenotype and individual variability in N-demethylation and glucuronidation.	2004-12-25	15556536
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.	2004-12-01	15498516
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.	2003-08-02	12892522
Determination of dextromethorphan and its metabolites in rat serum by liquid-liquid extraction and liquid chromatography with fluorescence detection.	2003-05-25	12705966
New morphinan derivatives with negligible psychotropic effects attenuate convulsions induced by maximal electroshock in mice.	2003-03-07	12586225
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.	2002-08-22	12151071
The effect of grapefruit juice and seville orange juice on the pharmacokinetics of dextromethorphan: the role of gut CYP3A and P-glycoprotein.	2002-07-26	12095536
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?	2001-11	11602530
High-performance liquid chromatography assay for simultaneous determination of dextromethorphan and its main metabolites in urine and in microsomal preparations.	2001-04-15	11318417

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 19:45:46 GMT 2025` Edited by `admin` on `Mon Mar 31 19:45:46 GMT 2025`
Record UNII	IL94262N7K
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

IDS-NN-006

Preferred Name

English

NORLEVORPHANOL

Official Name

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