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
SMILES
[H][C@@]12CC3=C(C=C(OC)C=C3)[C@]4(CCCC[C@@]14[H])CCN2C
InChI
InChIKey=MKXZASYAUGDDCJ-CGTJXYLNSA-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+/m0/s1
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26226106 | https://www.ncbi.nlm.nih.gov/pubmed/23628523 | https://www.ncbi.nlm.nih.gov/pubmed/24142584
Curator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/26226106 | https://www.ncbi.nlm.nih.gov/pubmed/23628523 | https://www.ncbi.nlm.nih.gov/pubmed/24142584
Levomethorphan ( L-stereoisomer of racemethorphan) is an opioid analgesic of the morphinan family that has never been marketed. Levomethorphan is a methylated prodrug of levorphanol, that undergoes hepatic demethylation, converting it to the active form. Levomethorphan (via it’s active form levorphanol)functions as a potent agonist of all three of the opioid receptors, μ, κ (κ1 and κ3 but notably not κ2), and δ, as an NMDA receptor antagonist, and as a serotonin-norepinephrine reuptake inhibitor. Via activation of the KOR, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations. Levomethorphan is listed under the Single Convention on Narcotic Drugs 1961 and is regulated like morphine in most countries. In the United States it is a Schedule II Narcotic controlled substance.
Originator
Sources: https://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19540415&CC=CH&NR=297994A&KC=Ahttps://worldwide.espacenet.com/publicationDetails/biblio?DB=EPODOC&II=0&ND=3&adjacent=true&locale=en_EP&FT=D&date=19480415&CC=CH&NR=254106A&KC=A
Curator's Comment: # F. Hoffmann-La Roche & Co., A.-G.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist. | 1991 Mar-Apr |
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| Evidence of significant contribution from CYP3A5 to hepatic drug metabolism. | 2004 Dec |
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| Effect of dextromethorphan, diphenhydramine, and placebo on nocturnal cough and sleep quality for coughing children and their parents. | 2004 Jul |
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| Comparison of various urine collection intervals for caffeine and dextromethorphan phenotyping in children. | 2004 Jul |
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| Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. | 2004 May |
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| Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance. | 2004 Nov |
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| [Dextromethorphan enhances analgesic activity of propacetamol--experimental study]. | 2005 |
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| Epigenetic silencing of DSC3 is a common event in human breast cancer. | 2005 |
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| The dextromethorphan analog dimemorfan attenuates kainate-induced seizures via sigma1 receptor activation: comparison with the effects of dextromethorphan. | 2005 Apr |
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| Dextromethorphan psychosis, dependence and physical withdrawal. | 2005 Dec |
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| Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity. | 2005 Feb |
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| Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. | 2005 Jan |
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| MK-801 and dextromethorphan block microglial activation and protect against methamphetamine-induced neurotoxicity. | 2005 Jul 19 |
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| Inhibitory effects of nicardipine to cytochrome P450 (CYP) in human liver microsomes. | 2005 May |
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| Recombinant production of human microsomal cytochrome P450 2D6 in the methylotrophic yeast Pichia pastoris. | 2005 Nov |
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| Side effects of dextromethorphan abuse, a case series. | 2005 Sep |
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| Cluster formation as a tool for development in Medicon Valley. | 2006 Jan-Feb |
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| Randomized, controlled trial of dextromethorphan/quinidine for pseudobulbar affect in multiple sclerosis. | 2006 May |
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| Mesenteric artery clamping/unclamping-induced acute lung injury is attenuated by N-methyl-D-aspartate antagonist dextromethorphan. | 2006 Nov-Dec |
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| 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 |
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| Effects of dextromethorphan on dopamine dependent behaviours in rats. | 2007 Aug |
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| Treatment of the common cold. | 2007 Feb 15 |
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| Oral administration of dextromethorphan does not produce neuronal vacuolation in the rat brain. | 2007 Jul |
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| 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 |
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| 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 |
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| Challenges for Australia's Bio/Nanopharma Policies: trade deals, public goods and reference pricing in sustainable industrial renewal. | 2007 Jun 1 |
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| Development and full validation of six inhibition assays for five major cytochrome P450 enzymes in human liver microsomes using an automated 96-well microplate incubation format and LC-MS/MS analysis. | 2007 May 9 |
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| Prior exposure to uninfected mosquitoes enhances mortality in naturally-transmitted West Nile virus infection. | 2007 Nov 14 |
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| Effect of sodium ozagrel on the activity of rat CYP2D6. | 2007 Nov 14 |
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| Dextromethorphan: a review of N-methyl-d-aspartate receptor antagonist in the management of pain. | 2007 Spring |
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| Ubiquitous computing for remote cardiac patient monitoring: a survey. | 2008 |
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| Mechanical aspects of a multidirectional, angular stable osteosynthesis system and comparison with four conventional systems. | 2008 Apr |
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| 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 |
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| Effects of common antitussive drugs on the hERG potassium channel current. | 2008 Dec |
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| Sigma ligands, but not N-methyl-D-aspartate antagonists, reduce levodopa-induced dyskinesias. | 2008 Jan 8 |
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| Anti-inflammatory effects of dimemorfan on inflammatory cells and LPS-induced endotoxin shock in mice. | 2008 Jul |
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| Functional expression and comparative characterization of nine murine cytochromes P450 by fluorescent inhibition screening. | 2008 Jul |
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| Life-threatening dextromethorphan intoxication associated with interaction with amitriptyline in a poor CYP2D6 metabolizer: a single case re-exposure study. | 2008 Jul |
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| Effects of repeated cycles of sterilisation on the mechanical characteristics of titanium miniplates for osteosynthesis. | 2008 Sep |
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| Effect of fenofibrate on microcirculation and wound healing in healthy and diabetic mice. | 2009 |
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| Dextromethorphan reduces oxidative stress and inhibits atherosclerosis and neointima formation in mice. | 2009 Apr 1 |
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| The diagnostic role of glycosaminoglycans in pleural effusions: a pilot study. | 2009 Feb 18 |
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| Amyotrophic lateral sclerosis. | 2009 Feb 3 |
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| Characterization of retrieved orthodontic miniscrew implants. | 2009 Jan |
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| Riluzole treatment, survival and diagnostic criteria in Parkinson plus disorders: the NNIPPS study. | 2009 Jan |
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| Retrospective analysis of titanium plate-retained prostheses placed after total rhinectomy. | 2009 Jan-Feb |
|
| [Bone anchored hearing aids (BAHA)]. | 2009 Mar |
Sample Use Guides
Dextromethorphan -- 15-30 mg 3 to 4 times per day (cough)
Dextromethorphan -- 20-30 mg twice daily (pseudobulbar affect)
Route of Administration:
Oral
Liver microsomes from individual male dark agouti (DA) rats (n=4, 6 weeks old, around 125 g mean weight) were prepared by ultracentrifugation. For the in vitro experiments with rat and human liver microsomes, the reaction mixture consisted of 0.1 M potassium phosphate buffer (pH 7.4) with an NADPH generating system (1.3 mM NADP, 3.3 mM G-6-P, 0.4 U/ mL G-6-PDH, 3.3 mM MgCl2), 50 μM substrate (dextromethorphan or levomethorphan), and 0.5 mg protein/mL microsomes (rat or human liver microsomes) in a final volume of 200 μL. Dextromethorphan and levomethorphan were dissolved in methanol, and the final concentration of the organic solvent was 0.1%. The incubation was started by adding the microsomal fraction and then continued for 0, 5, 10, or 20 min. The reaction was terminated by adding an equal volume of a mixed organic solution of 50% acetonitrile and 50% methanol, including 10 μM levallorphan (IS), and vigorous shaking.
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| Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C67413
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DEA NO. |
9210
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SUB08478MIG
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LEVOMETHORPHAN
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148
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146176
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C83875
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204-751-7
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DTXSID20872403
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7ZZ22K9QE6
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CHEMBL1908323
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m6790
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100000082278
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125-70-2
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5362449
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1362359
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ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)
