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Details

Stereochemistry ABSOLUTE
Molecular Formula C17H23NO
Molecular Weight 257.3706
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTRORPHAN

SMILES

[H][C@]12CCCC[C@]13CCN(C)[C@H]2CC4=C3C=C(O)C=C4

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 257.3706
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

CNS Penetrant
2523
Curator's Comment: Known to be CNS penetrant in bovine brain microvessel endothelial cells. Human data not available

Approval Year

Unknown
134361
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2760
Agonist
2662
 144.0 nM [Ki]
Agonist
2662
 520.0 nM [Ki]
Agonist
2662
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Not Provided
503
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
Anticonvulsant efficacy of N-methyl-D-aspartate antagonists against convulsions induced by cocaine.
1999 May
Pharmacological spinal cord protection with magnesium during replacement of the thoracic and thoracoabdominal aorta.
2001 Dec
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Glutamate AMPA receptor antagonist treatment for ischaemic stroke.
2002
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
Development of a rapid and sensitive high-performance liquid chromatographic method to determine CYP2D6 phenotype in human liver microsomes.
2002 Feb
Assessment of the effect of dextromethorphan and ketamine on the acute nociceptive threshold and wind-up of the second pain response in healthy male volunteers.
2002 Jun
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
Affinity and specificity of N-methyl- D-aspartate channel blockers affect their ability to disrupt prepulse inhibition of acoustic startle in rats.
2003 Feb
Determination of dextromethorphan and its metabolite dextrorphan in human urine by capillary gas chromatography without derivatization.
2003 Feb 5
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
High-throughput inhibition screening of major human cytochrome P450 enzymes using an in vitro cocktail and liquid chromatography-tandem mass spectrometry.
2003 Jan 1
Metabolism to dextrorphan is not essential for dextromethorphan's anticonvulsant activity against kainate in mice.
2003 Jan 3
Discrimination of a single dose of morphine followed by naltrexone: substitution of other agonists for morphine and other antagonists for naltrexone in a rat model of acute dependence.
2003 Mar
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
Characterization of the non-competitive antagonist binding site of the NMDA receptor in dark Agouti rats.
2004 Aug 6
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
Modulation of morphine analgesia by site-specific N-methyl-D-aspartate receptor antagonists: dependence on sex, site of antagonism, morphine dose, and time.
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
Comparison of the effects of dextromethorphan, dextrorphan, and levorphanol on the hypothalamo-pituitary-adrenal axis.
2004 May
Pharmacokinetics of dextromethorphan after single or multiple dosing in combination with quinidine in extensive and poor metabolizers.
2004 Oct
Measurement of CYP2D6 and CYP3A4 activity in vivo with dextromethorphan: sources of variability and predictors of adverse effects in 419 healthy subjects.
2005 Dec
Differential binding properties of [3H]dextrorphan and [3H]MK-801 in heterologously expressed NMDA receptors.
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
Validation of a liquid chromatography-mass spectrometry method to assess the metabolism of dextromethorphan in rat everted gut sacs.
2005 May 5
Potential interactions of methylphenidate and atomoxetine with dextromethorphan.
2006 Jul-Aug
Opioid peptides and receptors in joint tissues: study in the rat.
2006 Jun
Comparative effects of dextromethorphan and dextrorphan on nicotine discrimination in rats.
2006 Nov
Patents

Patents

JP2002517462A
7

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 Thu Jul 06 01:20:44 UTC 2023
Edited
by admin
on Thu Jul 06 01:20:44 UTC 2023
Record UNII
04B7QNO9WS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXTRORPHAN
INN   MART.   WHO-DD  
INN  
Official 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
DEXTROMETHORPHAN HYDROBROMIDE IMPURITY B [EP IMPURITY]
Common Name English
17-METHYL-9.ALPHA.,13.ALPHA.,14.ALPHA.-MORPHINAN-3-OL
Common Name English
DEXTRORPHAN [MART.]
Common Name English
ENT-17-METHYLMORPHINAN-3-OL
Common Name English
Dextrorphan [WHO-DD]
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
Common Name English
D-LEVORPHANOL
Common Name English
Code System Code Type Description
CAS
125-73-5
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
WIKIPEDIA
DEXTRORPHAN
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
ChEMBL
CHEMBL1254766
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
EVMPD
SUB07054MIG
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
NCI_THESAURUS
C171857
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
CHEBI
29133
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
EPA CompTox
DTXSID301014178
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-754-3
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
FDA UNII
04B7QNO9WS
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
DRUG BANK
DB14682
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
SMS_ID
100000082899
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
MERCK INDEX
M6794
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY Merck Index
PUBCHEM
5360697
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
INN
111
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
MESH
D003917
Created by admin on Thu Jul 06 01:20:45 UTC 2023 , Edited by admin on Thu Jul 06 01:20:45 UTC 2023
PRIMARY
Related Record Type Details
Structure of DEXTRORPHAN HYDROCHLORIDE
SALT/SOLVATE -> PARENT
Structure of DEXTRORPHAN SULFATE
SALT/SOLVATE -> PARENT
Related Record Type Details
Structure of Dextromethorphan
PARENT -> METABOLITE ACTIVE
Related Record Type Details
Structure of DEXTROMETHORPHAN HYDROBROMIDE
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
Structure of DEXTRORPHAN
ACTIVE MOIETY
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