Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C18H25NO |
| Molecular Weight | 271.3972 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[H][C@@]12CCCC[C@@]13CCN(C)[C@@H]2CC4=CC=C(OC)C=C34
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
| Molecular Formula | C18H25NO |
| Molecular Weight | 271.3972 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 3 / 3 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
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 |
|---|---|---|
| The need for rational therapeutics in the use of cough and cold medicine in infants. | 1992 Apr |
|
| Visual hallucinations after combining fluoxetine and dextromethorphan. | 1992 Oct |
|
| Binding of dimemorfan to sigma-1 receptor and its anticonvulsant and locomotor effects in mice, compared with dextromethorphan and dextrorphan. | 1999 Mar 13 |
|
| The antitussive activity of delta-opioid receptor stimulation in guinea pigs. | 2000 Feb |
|
| Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. | 2000 Jun |
|
| The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches. | 2001 |
|
| Over-the-counter medications for acute cough in children and adults in ambulatory settings. | 2001 |
|
| Dextromethorphan and dexmedetomidine: new agents for the control of perioperative pain. | 2001 Aug |
|
| CYP2D6 polymorphism in a Mexican American population. | 2001 Dec |
|
| Association of polymorphism in the cytochrome CYP2D6 and the efficacy and tolerability of simvastatin. | 2001 Dec |
|
| Important drugs for cough in advanced cancer. | 2001 Nov |
|
| 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 |
|
| Characterization of dextromethorphan O- and N-demethylation catalyzed by highly purified recombinant human CYP2D6. | 2001 Nov |
|
| Effects of dextromethorphan on nocturnal behavior and brain c-Fos expression in adolescent rats. | 2001 Nov 9 |
|
| Application and validation of a computerized cough acquisition system for objective monitoring of acute cough: a meta-analysis. | 2001 Oct |
|
| Co-administration of dextromethorphan during pregnancy and throughout lactation significantly decreases the adverse effects associated with chronic morphine administration in rat offspring. | 2001 Oct 5 |
|
| The role of ionotropic glutamate receptors in nociception with special regard to the AMPA binding sites. | 2002 |
|
| Modulation of human corticomotor excitability by somatosensory input. | 2002 Apr 15 |
|
| Consultation with the specialist: the central serotonin syndrome: paradigm for psychotherapeutic misadventure. | 2002 Dec |
|
| Concordance between tramadol and dextromethorphan parent/metabolite ratios: the influence of CYP2D6 and non-CYP2D6 pathways on biotransformation. | 2002 Jan |
|
| Dextromethorphan can produce false positive phencyclidine testing with HPLC. | 2002 Jan |
|
| Dextromethorphan is effective in the treatment of subacute methotrexate neurotoxicity. | 2002 Jul-Aug |
|
| Is glutamate involved in transient lower esophageal sphincter relaxations? | 2002 Mar |
|
| Substrate specificity for rat cytochrome P450 (CYP) isoforms: screening with cDNA-expressed systems of the rat. | 2002 Mar 1 |
|
| Dextromethorphan and memantine in painful diabetic neuropathy and postherpetic neuralgia: efficacy and dose-response trials. | 2002 May |
|
| Characterization of cytochrome P450 2D6.1 (CYP2D6.1), CYP2D6.2, and CYP2D6.17 activities toward model CYP2D6 substrates dextromethorphan, bufuralol, and debrisoquine. | 2002 May |
|
| Azithromycin for acute bronchitis: a randomised, double-blind, controlled trial. | 2002 May 11 |
|
| Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003 Dec 9 |
|
| Analysis of pharmacokinetic parameters for assessment of dextromethorphan metabolic phenotypes. | 2003 Sep-Oct |
|
| Evidence of significant contribution from CYP3A5 to hepatic drug metabolism. | 2004 Dec |
|
| Effect of dextromethorphan, diphenhydramine, and placebo on nocturnal cough and sleep quality for coughing children and their parents. | 2004 Jul |
|
| Analgesic effect of dextromethorphan in neuropathic pain. | 2004 Mar |
|
| Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. | 2004 May |
|
| [Dextromethorphan enhances analgesic activity of propacetamol--experimental study]. | 2005 |
|
| Epigenetic silencing of DSC3 is a common event in human breast cancer. | 2005 |
|
| Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay. | 2005 Jan |
|
| 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 |
|
| Dextromethorphan-induced neurologic illness in a patient with negative toxicology findings. | 2006 Jun 27 |
|
| Sex differences in the potency of kappa opioids and mixed-action opioids administered systemically and at the site of inflammation against capsaicin-induced hyperalgesia in rats. | 2007 Apr |
|
| 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 |
|
| Effect of sodium ozagrel on the activity of rat CYP2D6. | 2007 Nov 14 |
|
| Ubiquitous computing for remote cardiac patient monitoring: a survey. | 2008 |
|
| Sigma ligands, but not N-methyl-D-aspartate antagonists, reduce levodopa-induced dyskinesias. | 2008 Jan 8 |
|
| Life-threatening dextromethorphan intoxication associated with interaction with amitriptyline in a poor CYP2D6 metabolizer: a single case re-exposure study. | 2008 Jul |
|
| Effect of fenofibrate on microcirculation and wound healing in healthy and diabetic mice. | 2009 |
|
| Retrospective analysis of titanium plate-retained prostheses placed after total rhinectomy. | 2009 Jan-Feb |
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.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 19:03:20 GMT 2023
by
admin
on
Fri Dec 15 19:03:20 GMT 2023
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| Record UNII |
8YB8F78WM1
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| Record Status |
Validated (UNII)
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| Record Version |
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NCI_THESAURUS |
C241
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DEA NO. |
9732
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SUB10233MIG
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DTXSID60872402
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METHORPHAN
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5362449
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CHEMBL22207
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8YB8F78WM1
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C152137
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146177
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208-114-4
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510-53-2
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100000080306
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