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

[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

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
High-performance liquid chromatography assay for simultaneous determination of dextromethorphan and its main metabolites in urine and in microsomal preparations.	2001 Apr 15	11318417
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	11602530
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
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	12095536
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
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

Name

Type

Language

NORLEVORPHANOL

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