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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
Differential effects of morphinan drugs on haloperidol-induced catalepsy in rats: a comparative study with an N-methyl-D-aspartate antagonist.
1991 Mar-Apr
[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
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
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
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
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
Comparative metabolic capabilities and inhibitory profiles of CYP2D6.1, CYP2D6.10, and CYP2D6.17.
2007 Aug
Treatment of the common cold.
2007 Feb 15
A placebo double-blind pilot study of dextromethorphan for problematic behaviors in children with autism.
2007 Jan
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
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
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
Dextromethorphan: a review of N-methyl-d-aspartate receptor antagonist in the management of pain.
2007 Spring
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

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