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

Details

Stereochemistry ABSOLUTE
Molecular Formula C18H25NO
Molecular Weight 271.3972
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXTROMETHORPHAN

SMILES

COC1=CC=C2C[C@H]3[C@H]4CCCC[C@@]4(CCN3C)C2=C1

InChI

InChIKey=MKXZASYAUGDDCJ-NJAFHUGGSA-N
InChI=1S/C18H25NO/c1-19-10-9-18-8-4-3-5-15(18)17(19)11-13-6-7-14(20-2)12-16(13)18/h6-7,12,15,17H,3-5,8-11H2,1-2H3/t15-,17+,18+/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H25NO
Molecular Weight 271.3972
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry
Defined Stereocenters 3 / 3
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Dextromethorphan is a non-narcotic morphine derivative widely used as an antitussive for almost 40 years. It has attracted attention due to its anticonvulsant and neuroprotective properties. It is a cough suppressant in many over-the-counter cold and cough medicines. In 2010, the FDA approved the combination product dextromethorphan/quinidine for the treatment of pseudobulbar affect. Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Dextromethorphan shows high-affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist and acts as a non-competitive channel blocker. It is one of the widely used antitussives and is used to study the involvement of glutamate receptors in neurotoxicity. Dextromethorphan (DM) is a sigma-1 receptor agonist and an uncompetitive NMDA receptor antagonist. The mechanism by which dextromethorphan exerts therapeutic effects in patients with pseudobulbar affect is unknown. Dextromethorphan should not be taken with monoamine oxidase inhibitors due to the potential for serotonin syndrome. Dextromethorphan is extensively metabolized by CYP2D6 to dextrorphan, which is rapidly glucuronidated and unable to cross the blood-brain barrier.

CNS Activity

Originator

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
205.0 nM [Ki]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
NUEDEXTA
Primary
MUCINEX DM
PubMed

PubMed

TitleDatePubMed
Evidence of significant contribution from CYP3A5 to hepatic drug metabolism.
2004 Dec
[Dextromethorphan enhances analgesic activity of propacetamol--experimental study].
2005
Phenotypical expression of CYP2D6 in amerindians of tepehuano origin from Durango, Mexico.
2005
Epigenetic silencing of DSC3 is a common event in human breast cancer.
2005
High-throughput screening of inhibitory potential of nine cytochrome P450 enzymes in vitro using liquid chromatography/tandem mass spectrometry.
2005
The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan.
2005 Apr
Characterization of microsomal cytochrome P450-dependent monooxygenases in the rat olfactory mucosa.
2005 Aug
Dextromethorphan psychosis, dependence and physical withdrawal.
2005 Dec
MK-801 and dextromethorphan block microglial activation and protect against methamphetamine-induced neurotoxicity.
2005 Jul 19
Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers.
2005 Jun
Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus.
2005 Jun
Dextromethorphan-induced delirium and possible methadone interaction.
2005 Mar
Inhibitory effects of nicardipine to cytochrome P450 (CYP) in human liver microsomes.
2005 May
Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris.
2005 Nov
Side effects of dextromethorphan abuse, a case series.
2005 Sep
Cluster formation as a tool for development in Medicon Valley.
2006 Jan-Feb
Dextromethorphan-induced neurologic illness in a patient with negative toxicology findings.
2006 Jun 27
Randomized, controlled trial of dextromethorphan/quinidine for pseudobulbar affect in multiple sclerosis.
2006 May
Mesenteric artery clamping/unclamping-induced acute lung injury is attenuated by N-methyl-D-aspartate antagonist dextromethorphan.
2006 Nov-Dec
Co-administration of dextromethorphan with methamphetamine attenuates methamphetamine-induced rewarding and behavioral sensitization.
2006 Sep
Bench-to-bedside review: mechanisms and management of hyperthermia due to toxicity.
2007
Immunohistological assessment of the synovial tissue in small joints in rheumatoid arthritis: validation of a minimally invasive ultrasound-guided synovial biopsy procedure.
2007
Cough mixture abuse as a novel cause of folate deficiency: a prospective, community-based, controlled study.
2007 Apr
Effects of dextromethorphan on dopamine dependent behaviours in rats.
2007 Aug
Treatment of the common cold.
2007 Feb 15
Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain.
2007 Jul
In vitro interaction cocktail assay for nine major cytochrome P450 enzymes with 13 probe reactions and a single LC/MSMS run: analytical validation and testing with monoclonal anti-CYP antibodies.
2007 Jul
Free energies of binding of R- and S-propranolol to wild-type and F483A mutant cytochrome P450 2D6 from molecular dynamics simulations.
2007 Jul
[Simultaneous determination of the inhibitory potency of compounds on the activity of five cytochrome P-450 enzymes using a cocktail probe substrates method].
2007 Jun
Challenges for Australia's Bio/Nanopharma Policies: trade deals, public goods and reference pricing in sustainable industrial renewal.
2007 Jun 1
Validated method for rapid inhibition screening of six cytochrome P450 enzymes by liquid chromatography-tandem mass spectrometry.
2007 Jun 1
Prior exposure to uninfected mosquitoes enhances mortality in naturally-transmitted West Nile virus infection.
2007 Nov 14
Effect of sodium ozagrel on the activity of rat CYP2D6.
2007 Nov 14
Ubiquitous computing for remote cardiac patient monitoring: a survey.
2008
Mechanical aspects of a multidirectional, angular stable osteosynthesis system and comparison with four conventional systems.
2008 Apr
Sex differences in NMDA antagonist enhancement of morphine antihyperalgesia in a capsaicin model of persistent pain: comparisons to two models of acute pain.
2008 Apr
Effects of common antitussive drugs on the hERG potassium channel current.
2008 Dec
Sigma ligands, but not N-methyl-D-aspartate antagonists, reduce levodopa-induced dyskinesias.
2008 Jan 8
Anti-inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice.
2008 Jul
Functional expression and comparative characterization of nine murine cytochromes P450 by fluorescent inhibition screening.
2008 Jul
Life-threatening dextromethorphan intoxication associated with interaction with amitriptyline in a poor CYP2D6 metabolizer: a single case re-exposure study.
2008 Jul
Effects of repeated cycles of sterilisation on the mechanical characteristics of titanium miniplates for osteosynthesis.
2008 Sep
Effect of fenofibrate on microcirculation and wound healing in healthy and diabetic mice.
2009
Dextromethorphan reduces oxidative stress and inhibits atherosclerosis and neointima formation in mice.
2009 Apr 1
The diagnostic role of glycosaminoglycans in pleural effusions: a pilot study.
2009 Feb 18
Amyotrophic lateral sclerosis.
2009 Feb 3
Characterization of retrieved orthodontic miniscrew implants.
2009 Jan
Riluzole treatment, survival and diagnostic criteria in Parkinson plus disorders: the NNIPPS study.
2009 Jan
Retrospective analysis of titanium plate-retained prostheses placed after total rhinectomy.
2009 Jan-Feb
[Bone anchored hearing aids (BAHA)].
2009 Mar
Patents

Sample Use Guides

In Vivo Use Guide
15-30 mg 3 to 4 times per day (cough) 20-30 mg twice daily (pseudobulbar affect)
Route of Administration: Oral
In Vitro Use Guide
In vitro studies pre- and immature oligodendroglial (OLN-93) cells were subjected to hyperoxic conditions for 48 h after pre-treatment with increasing doses of dextromethorphan.
Substance Class Chemical
Created
by admin
on Mon Oct 21 20:38:37 UTC 2019
Edited
by admin
on Mon Oct 21 20:38:37 UTC 2019
Record UNII
7355X3ROTS
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXTROMETHORPHAN
HSDB   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
BA-2666
Code English
BA 2666
Common Name English
DEX
Common Name English
DEXTROMETHORPHAN [VANDF]
Common Name English
NODEX
Common Name English
DEXTROMETHORPHAN [USP]
Common Name English
DEXTROMETHORPHAN [MI]
Common Name English
D-METHORPHAN
Common Name English
DEXTROMETHORPHAN [WHO-DD]
Common Name English
(+)-DEXTROMETHORPHAN
Common Name English
DEXTROMETHORPHAN [MART.]
Common Name English
MORPHINAN, 3-METHOXY-17-METHYL-, (9.ALPHA.,13.ALPHA.,14.ALPHA.)-
Common Name English
3-METHOXY-17-METHYL-9.ALPHA.,13.ALPHA.,14.ALPHA.-MORPHINAN
Common Name English
DEXTROMETHORPHAN [HSDB]
Common Name English
DEXTROMETHORPHAN [INN]
Common Name English
DEXTROMETHORPHAN [USP-RS]
Common Name English
Classification Tree Code System Code
NDF-RT N0000181821
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
CFR 21 CFR 341.14
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
CFR 21 CFR 341.74
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
WHO-VATC QN07XX59
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
WHO-VATC QR05DA09
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
WHO-ATC R05DA09
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
NDF-RT N0000182149
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
WHO-ATC N07XX59
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
NCI_THESAURUS C2199
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
Code System Code Type Description
NCI_THESAURUS
C62022
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
MERCK INDEX
M4227
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY Merck Index
INN
166
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
LactMed
125-71-3
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
NDF-RT
N0000181819
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY Uncompetitive NMDA Receptor Antagonists [MoA]
EPA CompTox
125-71-3
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
HSDB
125-71-3
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
CAS
125-71-3
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
EVMPD
SUB07051MIG
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
ECHA (EC/EINECS)
204-752-2
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
ChEMBL
CHEMBL52440
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
NDF-RT
N0000182147
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY Sigma-1 Receptor Agonists [MoA]
DRUG BANK
DB00514
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
IUPHAR
6953
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
RXCUI
3289
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
ALTERNATIVE RxNorm
WIKIPEDIA
DEXTROMETHORPHAN
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
MESH
D003915
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
PUBCHEM
5360696
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
RXCUI
236146
Created by admin on Mon Oct 21 20:38:37 UTC 2019 , Edited by admin on Mon Oct 21 20:38:37 UTC 2019
PRIMARY
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SUBSTRATE
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