U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3713
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTRORPHAN

SMILES

CN1CC[C@]23CCCC[C@]3([H])[C@]1([H])Cc4ccc(cc42)O

InChI

InChIKey=JAQUASYNZVUNQP-PVAVHDDUSA-N
InChI=1S/C17H23NO/c1-18-9-8-17-7-3-2-4-14(17)16(18)10-12-5-6-13(19)11-15(12)17/h5-6,11,14,16,19H,2-4,7-10H2,1H3/t14-,16+,17+/m1/s1

HIDE SMILES / InChI

Molecular Formula C17H23NO
Molecular Weight 257.3713
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Dextrorphan is an active metabolite of dextromethorphan, is an antitussive agent, which was found in cough medicines. Dextrorphan is a noncompetitive N-methyl-D-aspartate receptor (NMDAR) antagonist, sigma 1 receptor agonist, so as is an agonist of mu and kappa opioid receptors. In addition was found, that dextrorphan possessed anticonvulsive and neuroprotective effects.

CNS Activity

Curator's Comment:: Known to be CNS penetrant in bovine brain microvessel endothelial cells. Human data not available

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991 Mar-Apr
Glutamate receptor antagonists block cocaine-induced convulsions and death.
1991 Nov
Inhibition of cocaine intoxication by excitatory amino acid receptor antagonists.
1992 May 11
CYP2D6 inhibition by selective serotonin reuptake inhibitors: analysis of achievable steady-state plasma concentrations and the effect of ultrarapid metabolism at CYP2D6.
2002 Aug
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
Evaluation of dextromethorphan N-demethylation activity as a biomarker for cytochrome P450 3A activity in man.
2002 Feb
Rapid and quantitative determination of metabolites from multiple cytochrome P450 probe substrates by gradient liquid chromatography-electrospray ionization-ion trap mass spectrometry.
2002 Nov 25
Multiple-dose administration of Ginkgo biloba did not affect cytochrome P-450 2D6 or 3A4 activity in normal volunteers.
2003 Dec
On-line turbulent-flow chromatography-high-performance liquid chromatography-mass spectrometry for fast sample preparation and quantitation.
2003 Dec 5
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.
2003 Feb
Melperone is an inhibitor of the CYP2D6 catalyzed O-demethylation of venlafaxine.
2003 Jan
Attenuation of the stimulant and convulsant effects of cocaine by 17-substituted-3-hydroxy and 3-alkoxy derivatives of dextromethorphan.
2003 Jan
Metabolism to dextrorphan is not essential for dextromethorphan's anticonvulsant activity against kainate in mice.
2003 Jan 3
Physiologically based modelling of inhibition of metabolism and assessment of the relative potency of drug and metabolite: dextromethorphan vs. dextrorphan using quinidine inhibition.
2003 Jul
New morphinan derivatives with negligible psychotropic effects attenuate convulsions induced by maximal electroshock in mice.
2003 Mar 7
Discriminative stimulus effects of acute morphine followed by naltrexone in the squirrel monkey.
2003 May
Determination of dextromethorphan and its metabolites in rat serum by liquid-liquid extraction and liquid chromatography with fluorescence detection.
2003 May 25
Effect of St John's wort on drug metabolism by induction of cytochrome P450 3A4 enzyme.
2003 Sep 17
Analysis of pharmacokinetic parameters for assessment of dextromethorphan metabolic phenotypes.
2003 Sep-Oct
Influence of concomitant quinidine administration on dextromethorphan disposition in rats.
2004 Apr
Clinical inhibition of CYP2D6-catalysed metabolism by the antianginal agent perhexiline.
2004 Apr
Simple chromatography method for simultaneous determination of dextromethorphan and its main metabolites in human plasma with fluorimetric detection.
2004 Apr 5
[Determination of dextrorphan in human plasma and pharmacokinetic study].
2004 Jun
Validated assays for human cytochrome P450 activities.
2004 Jun
Metabolic activity of dextromethorphan O-demethylation in healthy Japanese volunteers carrying duplicated CYP2D6 genes: duplicated allele of CYP2D6*10 does not increase CYP2D6 metabolic activity.
2004 Jun
Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice.
2004 May 5
Plasma profile and pharmacokinetics of dextromethorphan after intravenous and oral administration in healthy dogs.
2004 Oct
Pharmacokinetics of dextromethorphan after single or multiple dosing in combination with quinidine in extensive and poor metabolizers.
2004 Oct
Development of a chromatographic bioreactor based on immobilized beta-glucuronidase on monolithic support for the determination of dextromethorphan and dextrorphan in human urine.
2004 Sep 3
On-line solid phase extraction using the Prospekt-2 coupled with a liquid chromatography/tandem mass spectrometer for the determination of dextromethorphan, dextrorphan and guaifenesin in human plasma.
2005
High-throughput biological sample analysis using on-line turbulent flow extraction combined with monolithic column liquid chromatography/tandem mass spectrometry.
2005
Conserved structural and functional control of N-methyl-D-aspartate receptor gating by transmembrane domain M3.
2005 Aug 19
Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity.
2005 Feb
Differential binding properties of [3H]dextrorphan and [3H]MK-801 in heterologously expressed NMDA receptors.
2005 Jul
Dextromethorphan to dextrorphan urinary metabolic ratio does not reflect dextromethorphan oral clearance.
2005 Jul
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
[Pharmacogenetic study of the response to flecainide and propafenone in patients with atrial fibrillation].
2005 Jun
Frequency distribution of dextromethorphan O-demethylation in a Greek population.
2005 Mar
Validation of a liquid chromatography-mass spectrometry method to assess the metabolism of dextromethorphan in rat everted gut sacs.
2005 May 5
The effect of CYP2D6 polymorphisms on dextromethorphan metabolism in Mexican Americans.
2005 Nov
[The action of dextrorphan and sigma ligands on the spontaneous secretion of interleukins by jurkat cell line].
2005 Oct
Enhancing the uptake of dextromethorphan in the CNS of rats by concomitant administration of the P-gp inhibitor verapamil.
2005 Oct 21
Agents that act by different mechanisms modulate the activity of protein kinase CbetaII isozyme in the rat spinal cord during peripheral inflammation.
2006
Dextromethorphan, 3-methoxymorphinan, and dextrorphan have local anaesthetic effect on sciatic nerve blockade in rats.
2006 Aug 21
Potential interactions of methylphenidate and atomoxetine with dextromethorphan.
2006 Jul-Aug
Comparative effects of dextromethorphan and dextrorphan on nicotine discrimination in rats.
2006 Nov
CYP2D6 genotype and phenotype relationship in South Indians.
2006 Oct-Dec
Standardization of method for the analysis of dextromethorphan in urine.
2006 Sep 12
Simultaneous determination of dextromethorphan, dextrorphan, and guaifenesin in human plasma using semi-automated liquid/liquid extraction and gradient liquid chromatography tandem mass spectrometry.
2007 Jan 17
Patents

Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Dextrorphan (DX) was evaluated for antiepileptic properties in vitro. Interictal bursts and prolonged ictal epileptiform afterdischarges, induced by perfusion of guinea pig neocortical brain slices with Mg2+-free solution, were blocked by DX (1-250 microM). Intracellular records showed that DX blocked N-methyl-D-aspartate (NMDA)-induced depolarizations without altering intrinsic membrane properties. DX blocked NMDA but not quisqualate-evoked multi-unit excitatory responses.
Substance Class Chemical
Created
by admin
on Sat Jun 26 10:39:54 UTC 2021
Edited
by admin
on Sat Jun 26 10:39:54 UTC 2021
Record UNII
04B7QNO9WS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXTRORPHAN
INN   MART.   WHO-DD  
INN  
Official Name English
DEXTROMETHORPHAN HYDROBROMIDE SPECIFIED IMPURITY B [EP]
Common Name English
LEVORPHANOL D-FORM
MI  
Common Name English
DEXTRO-DROMORAN
Common Name English
MORPHINAN-3-OL, 17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.) -
Systematic Name English
(+)-N-METHYLMORPHINAN-3-OL
Systematic Name English
17-METHYL-9.ALPHA.,13.ALPHA.,14.ALPHA.-MORPHINAN-3-OL
Common Name English
DEXTROMETHORPHAN HYDROBROMIDE IMPURITY B [EP]
Common Name English
DEXTRORPHAN [MART.]
Common Name English
ENT-17-METHYLMORPHINAN-3-OL
Common Name English
RO-1-6794
Code English
MORPHINAN-3-OL, 17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-
Common Name English
DEXTRORPHAN [INN]
Common Name English
RO 1-6794
Code English
LEVORPHANOL D-FORM [MI]
Common Name English
DEXTRORPHAN [WHO-DD]
Common Name English
(+)-DEXTRORPHAN
Common Name English
D-LEVORPHANOL
Common Name English
Code System Code Type Description
CAS
125-73-5
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
WIKIPEDIA
DEXTRORPHAN
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL1254766
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
EVMPD
SUB07054MIG
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
NCI_THESAURUS
C171857
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
ECHA (EC/EINECS)
204-754-3
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
FDA UNII
04B7QNO9WS
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
DRUG BANK
DB14682
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
MERCK INDEX
M6794
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY Merck Index
PUBCHEM
5360697
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
INN
111
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
MESH
D003917
Created by admin on Sat Jun 26 10:39:54 UTC 2021 , Edited by admin on Sat Jun 26 10:39:54 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> METABOLITE ACTIVE
Related Record Type Details
PARENT -> IMPURITY
and not more than 1 such peak has an area greater than 0.5 times the area of the principal peak in the chromatogram obtained with reference solution (b) (0.25 per cent)
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY