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
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 |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/27139517https://www.ncbi.nlm.nih.gov/pubmed/21311876Curator'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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/27139517https://www.ncbi.nlm.nih.gov/pubmed/21311876
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.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24142584
Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/16634036
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
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19345586 |
3360.0 nM [Ki] | ||
Target ID: CHEMBL287 Sources: https://www.ncbi.nlm.nih.gov/pubmed/15723099 |
205.0 nM [Ki] | ||
Target ID: CHEMBL4787 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2897648 |
|||
Target ID: CHEMBL2094124 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19345586 |
3360.0 nM [Ki] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21311876 |
Primary | Unknown Approved UseUnknown |
||
PubMed
Title | Date | PubMed |
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The need for rational therapeutics in the use of cough and cold medicine in infants. | 1992 Apr |
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Visual hallucinations after combining fluoxetine and dextromethorphan. | 1992 Oct |
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Gamma-aminobutyric acid and glutamic acid receptors may mediate theophylline-induced seizures in mice. | 1999 Mar |
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[Acute cholestatic hepatitis induced by dextromethorphan]. | 1999 Oct |
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Dextromethorphan and its metabolite dextrorphan block alpha3beta4 neuronal nicotinic receptors. | 2000 Jun |
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The role of glutamatergic transmission in the pathogenesis of levodopa-induced dyskinesias. Potential therapeutic approaches. | 2001 |
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Consultation with the specialist: the central serotonin syndrome: paradigm for psychotherapeutic misadventure. | 2002 Dec |
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Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms. | 2002 Dec |
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Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions. | 2002 Dec |
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Biotechnology in the Medicon Valley. | 2002 Dec 12 |
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Bridging sectors. Medicon Valley. | 2002 Dec 12 |
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Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain. | 2003 Dec 9 |
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Non-competitive NMDA receptor antagonists moderate seizure-induced c-fos expression in the rat cerebral cortex. | 2003 Feb 15 |
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Total and corrected antioxidant capacity in hemodialyzed patients. | 2003 Jul 1 |
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mRNA and protein expression of dog liver cytochromes P450 in relation to the metabolism of human CYP2C substrates. | 2003 Mar |
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Combined phenotypic assessment of cytochrome p450 1A2, 2C9, 2C19, 2D6, and 3A, N-acetyltransferase-2, and xanthine oxidase activities with the "Cooperstown 5+1 cocktail". | 2003 Nov |
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Analysis of pharmacokinetic parameters for assessment of dextromethorphan metabolic phenotypes. | 2003 Sep-Oct |
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Effect of St John's wort on the activities of CYP1A2, CYP3A4, CYP2D6, N-acetyltransferase 2, and xanthine oxidase in healthy males and females. | 2004 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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Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens. | 2004 Jul 16 |
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Validated assays for human cytochrome P450 activities. | 2004 Jun |
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Analgesic effect of dextromethorphan in neuropathic pain. | 2004 Mar |
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Potential of pranlukast and zafirlukast in the inhibition of human liver cytochrome P450 enzymes. | 2004 May |
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Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice. | 2004 May 5 |
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Bladder emptying over a period of 10-45 years after a traumatic spinal cord injury. | 2004 Nov |
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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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Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial. | 2004 Oct 26 |
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Phenotypical expression of CYP2D6 in amerindians of tepehuano origin from Durango, Mexico. | 2005 |
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Epigenetic silencing of DSC3 is a common event in human breast cancer. | 2005 |
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High-throughput screening of inhibitory potential of nine cytochrome P450 enzymes in vitro using liquid chromatography/tandem mass spectrometry. | 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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Characterization of microsomal cytochrome P450-dependent monooxygenases in the rat olfactory mucosa. | 2005 Aug |
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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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Evaluation of dextromethorphan metabolism using hepatocytes from CYP2D6 poor and extensive metabolizers. | 2005 Jun |
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Cytochrome P450 2D6 (CYP2D6) inhibitory constituents of Catharanthus roseus. | 2005 Jun |
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Dextromethorphan-induced delirium and possible methadone interaction. | 2005 Mar |
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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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Mesenteric artery clamping/unclamping-induced acute lung injury is attenuated by N-methyl-D-aspartate antagonist dextromethorphan. | 2006 Nov-Dec |
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Immunohistological assessment of the synovial tissue in small joints in rheumatoid arthritis: validation of a minimally invasive ultrasound-guided synovial biopsy procedure. | 2007 |
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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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Ubiquitous computing for remote cardiac patient monitoring: a survey. | 2008 |
|
Functional expression and comparative characterization of nine murine cytochromes P450 by fluorescent inhibition screening. | 2008 Jul |
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/21311876
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 16:06:28 GMT 2023
by
admin
on
Fri Dec 15 16:06:28 GMT 2023
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Record UNII |
7ZZ22K9QE6
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Record Status |
Validated (UNII)
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Record Version |
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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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Related Record | Type | Details | ||
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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SALT/SOLVATE -> PARENT |
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
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PARENT -> IMPURITY |
Related Record | Type | Details | ||
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ACTIVE MOIETY |