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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 LEVOMETHORPHAN

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

HIDE SMILES / InChI

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

Description
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

Curator's Comment: https://www.ncbi.nlm.nih.gov/pubmed/16634036

Approval Year

Targets

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
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
Gamma-aminobutyric acid and glutamic acid receptors may mediate theophylline-induced seizures in mice.
1999 Mar
[Acute cholestatic hepatitis induced by dextromethorphan].
1999 Oct
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
Consultation with the specialist: the central serotonin syndrome: paradigm for psychotherapeutic misadventure.
2002 Dec
Expression, purification, biochemical characterization, and comparative function of human cytochrome P450 2D6.1, 2D6.2, 2D6.10, and 2D6.17 allelic isoforms.
2002 Dec
Evaluation of cytochrome P450 probe substrates commonly used by the pharmaceutical industry to study in vitro drug interactions.
2002 Dec
Biotechnology in the Medicon Valley.
2002 Dec 12
Bridging sectors. Medicon Valley.
2002 Dec 12
Broad substrate specificity of human cytochrome P450 46A1 which initiates cholesterol degradation in the brain.
2003 Dec 9
Non-competitive NMDA receptor antagonists moderate seizure-induced c-fos expression in the rat cerebral cortex.
2003 Feb 15
Total and corrected antioxidant capacity in hemodialyzed patients.
2003 Jul 1
mRNA and protein expression of dog liver cytochromes P450 in relation to the metabolism of human CYP2C substrates.
2003 Mar
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
Analysis of pharmacokinetic parameters for assessment of dextromethorphan metabolic phenotypes.
2003 Sep-Oct
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
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
Comparison of various urine collection intervals for caffeine and dextromethorphan phenotyping in children.
2004 Jul
Evaluation of the One-Step ELISA kit for the detection of buprenorphine in urine, blood, and hair specimens.
2004 Jul 16
Validated assays for human cytochrome P450 activities.
2004 Jun
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
Dimemorfan prevents seizures induced by the L-type calcium channel activator BAY k-8644 in mice.
2004 May 5
Bladder emptying over a period of 10-45 years after a traumatic spinal cord injury.
2004 Nov
Evaluation of fresh and cryopreserved hepatocytes as in vitro drug metabolism tools for the prediction of metabolic clearance.
2004 Nov
Treatment of pseudobulbar affect in ALS with dextromethorphan/quinidine: a randomized trial.
2004 Oct 26
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
Effect of dextrometorphan and dextrorphan on nicotine and neuronal nicotinic receptors: in vitro and in vivo selectivity.
2005 Feb
Multiple P450 substrates in a single run: rapid and comprehensive in vitro interaction assay.
2005 Jan
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
Mesenteric artery clamping/unclamping-induced acute lung injury is attenuated by N-methyl-D-aspartate antagonist dextromethorphan.
2006 Nov-Dec
Immunohistological assessment of the synovial tissue in small joints in rheumatoid arthritis: validation of a minimally invasive ultrasound-guided synovial biopsy procedure.
2007
Effects of dextromethorphan on dopamine dependent behaviours in rats.
2007 Aug
Treatment of the common cold.
2007 Feb 15
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
Patents

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 Fri Dec 15 16:06:28 GMT 2023
Edited
by admin
on Fri Dec 15 16:06:28 GMT 2023
Record UNII
7ZZ22K9QE6
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
LEVOMETHORPHAN
INN   MI  
INN  
Official Name English
LEVOMETHORPHAN [MI]
Common Name English
IDS-NL-004
Code English
levomethorphan [INN]
Common Name English
L-METHORPHAN
Common Name English
LEVOMETHORPHAN SOLUTION [USP-RS]
Common Name English
(-)-3-METHOXY-N-METHYLMORPHINAN
Systematic Name English
2H-10,4A-IMINOETHANOPHENANTHRENE, 1,3,4,9,10,10A-HEXAHYDRO-6-METHOXY-11-METHYL-
Systematic Name English
IDS-NL-005
Code English
MORPHINAN, 3-METHOXY-17-METHYL-
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C67413
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
DEA NO. 9210
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
Code System Code Type Description
EVMPD
SUB08478MIG
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
WIKIPEDIA
LEVOMETHORPHAN
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
INN
148
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
CHEBI
146176
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
NCI_THESAURUS
C83875
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
ECHA (EC/EINECS)
204-751-7
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
EPA CompTox
DTXSID20872403
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
FDA UNII
7ZZ22K9QE6
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
ChEMBL
CHEMBL1908323
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
MERCK INDEX
m6790
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY Merck Index
SMS_ID
100000082278
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
CAS
125-70-2
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
PUBCHEM
5362449
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
RS_ITEM_NUM
1362359
Created by admin on Fri Dec 15 16:06:28 GMT 2023 , Edited by admin on Fri Dec 15 16:06:28 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
SALT/SOLVATE -> PARENT
APPROXIMATE PURE ANHYDROUS DRUG CONTENT (IN PERCENT)
Related Record Type Details
PARENT -> IMPURITY
Related Record Type Details
ACTIVE MOIETY