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

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
Maintenance of liver functions in rat hepatocytes cultured as spheroids in a rotating wall vessel.	2003 Jan-Feb	12892522
New morphinan derivatives with negligible psychotropic effects attenuate convulsions induced by maximal electroshock in mice.	2003 Mar 7	12586225
Determination of dextromethorphan and its metabolites in rat serum by liquid-liquid extraction and liquid chromatography with fluorescence detection.	2003 May 25	12705966
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
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 Dec 25	15556536
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

Patents

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