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
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	12151071
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.	2003 Jan-Feb	12892522
Influence of phenylalanine 120 on cytochrome P450 2D6 catalytic selectivity and regiospecificity: crucial role in 7-methoxy-4-(aminomethyl)-coumarin metabolism.	2004 Dec 1	15498516
Effect of methamphetamine on the pharmacokinetics of dextromethorphan and midazolam in rats.	2005 Jul-Sep	16250257
Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers.	2005 Jun	15988119
3-hydroxymorphinan is neurotrophic to dopaminergic neurons and is also neuroprotective against LPS-induced neurotoxicity.	2005 Mar	15596482
Validation of a liquid chromatography-mass spectrometry method to assess the metabolism of dextromethorphan in rat everted gut sacs.	2005 May 5	15797528
3-Hydroxymorphinan, a metabolite of dextromethorphan, protects nigrostriatal pathway against MPTP-elicited damage both in vivo and in vitro.	2006 Dec	17142799
Selective effects of nitric oxide on the disposition of chlorzoxazone and dextromethorphan in isolated perfused rat livers.	2006 Jul	16621933
Simultaneous analysis of dextromethorphan and its three metabolites in human plasma using an improved HPLC method with fluorometric detection.	2007 Nov 1	17919999
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	18198471
Concise synthesis of dimemorfan (DF) starting from 3-hydroxymorphinan (3-HM).	2008 Jul	18591815
Metabolism of dextrorphan by CYP2D6 in different recombinantly expressed systems and its implications for the in vitro assessment of dextromethorphan metabolism.	2009 Feb	18543297
Inhibitory effect of glutamate release from rat cerebrocortical synaptosomes by dextromethorphan and its metabolite 3-hydroxymorphinan.	2009 Jul	19428798
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	19444798
Neuropsychotoxic and neuroprotective potentials of dextromethorphan and its analogs.	2011	21606622

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

Download

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