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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

Racemethorphan is racemic mixture of Dextromethorphan and Levomethorphan. Racemethorphan is listed under the Single Convention on Narcotic Drugs 1961 and is therefore listed in the United States as a Controlled Substance, specifically as a Narcotic in Schedule II. Dextromethorphan is a non-narcotic morphine derivative widely used as an antitussive. Dextromethorphan is a cough suppressant in many over-the-counter cold and cough medicines. In 2010, the FDA approved the combination product dextromethorphan/quinidine for the treatment of pseudobulbar affect. Dextromethorphan suppresses the cough reflex by a direct action on the cough center in the medulla of the brain. Levomethorphan is an opioid analgesic of the morphinan family that has never been marketed.

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
Dystonia as acute adverse reaction to cough suppressant in a 3-year-old girl.
2001
High-throughput cytochrome P450 (CYP) inhibition screening via a cassette probe-dosing strategy. VI. Simultaneous evaluation of inhibition potential of drugs on human hepatic isozymes CYP2A6, 3A4, 2C9, 2D6 and 2E1.
2001
Chromatographic analysis of phenethylamine-antihistamine combinations using C8, C18 or cyano columns and micellar sodium dodecyl sulfate-pentanol mixtures.
2001 Apr
Angle closure risk from proprietary medicines.
2001 Apr
Substrate inhibition kinetics for cytochrome P450-catalyzed reactions.
2001 Apr
High-performance liquid chromatography assay for simultaneous determination of dextromethorphan and its main metabolites in urine and in microsomal preparations.
2001 Apr 15
Characterization of biotransformation enzyme activities in primary rat proximal tubular cells.
2001 Apr 16
High-throughput cytochrome P450 (CYP) inhibition screening via cassette probe-dosing strategy. II. Validation of a direct injection/on-line guard cartridge extraction-tandem mass spectrometry method for CYP2D6 inhibition assessment.
2001 Apr 5
Analysis of the CYP2D6 gene polymorphism and enzyme activity in African-Americans in southern California.
2001 Aug
Cytochrome P450 2D6.1 and cytochrome P450 2D6.10 differ in catalytic activity for multiple substrates.
2001 Aug
A fast and efficient determination of amines and preservatives in cough and cold liquid and suspension formulations using a single isocratic ion-pairing high performance [correction of power] liquid chromatography method.
2001 Aug
The use of genetically engineered cells for assessing CYP2D6-related polymorphic effects.
2001 Aug-Oct
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
Expression, purification, and biochemical characterization of a human cytochrome P450 CYP2D6-NADPH cytochrome P450 reductase fusion protein.
2001 Dec 1
Influence of gender and oral contraceptives on CYP2D6 and CYP2C19 activity in healthy volunteers.
2001 Feb
Pharmacokinetics of sabeluzole and dextromethorphan oxidation capacity in patients with severe hepatic dysfunction and healthy volunteers.
2001 Feb
The effect of the NMDA receptor blocker, dextromethorphan, on cribbing in horses.
2001 Jan
Dextromethorphan and ecstasy pills.
2001 Jan 24-31
Improved postoperative pain control in pediatric adenotonsillectomy with dextromethorphan.
2001 Jul
Lack of gender differences and large intrasubject variability in cytochrome P450 activity measured by phenotyping with dextromethorphan.
2001 Jul
NMDA receptor-mediated modulation of ventilation in obese Zucker rats.
2001 Jul
Amantadine, a N-methyl-D-aspartate receptor antagonist, does not enhance postoperative analgesia in women undergoing abdominal hysterectomy.
2001 Jul
Increasing bioanalytical throughput using pcSFC-MS/MS: 10 minutes per 96-well plate.
2001 Jul 1
Clinical case discussion: anesthesia for Cesarean section in a parturient with a large intrathoracic tumour.
2001 Jun
Cold-syrup induced movement disorder.
2001 Jun
Dextromethorphan affects cocaine-mediated behavioral pattern in parallel with a long-lasting Fos-related antigen-immunoreactivity.
2001 Jun 29
Role of the NMDA receptor subunit in the expression of the discriminative stimulus effect induced by ketamine.
2001 Jun 29
Dextromethorphan is an effective cough suppressant.
2001 May
Linezolid: pharmacokinetic and pharmacodynamic evaluation of coadministration with pseudoephedrine HCl, phenylpropanolamine HCl, and dextromethorpan HBr.
2001 May
Cardiovascular sympathomimetic amine interactions in rats treated with monoamine oxidase inhibitors and the novel oxazolidinone antibiotic linezolid.
2001 May
Effects of dextromethorphan on nocturnal behavior and brain c-Fos expression in adolescent rats.
2001 Nov 9
St. John's wort: effect on CYP2D6 activity using dextromethorphan-dextrorphan ratios.
2001 Oct
Application and validation of a computerized cough acquisition system for objective monitoring of acute cough: a meta-analysis.
2001 Oct
Abuse of Coricidin HBP cough & cold tablets: episodes recorded by a poison center.
2001 Oct 1
Dextromethorphan in pregnancy.
2001 Sep
Analgesic effects of dextromethorphan and morphine in patients with chronic pain.
2002 Apr
Differential time course of cytochrome P450 2D6 enzyme inhibition by fluoxetine, sertraline, and paroxetine in healthy volunteers.
2002 Apr
Development of a rapid and sensitive high-performance liquid chromatographic method to determine CYP2D6 phenotype in human liver microsomes.
2002 Feb
Dextromethorphan potentiates the antinociceptive effects of morphine and the delta-opioid agonist SNC80 in squirrel monkeys.
2002 Feb
The African-specific CYP2D617 allele encodes an enzyme with changed substrate specificity.
2002 Jan
Concordance between tramadol and dextromethorphan parent/metabolite ratios: the influence of CYP2D6 and non-CYP2D6 pathways on biotransformation.
2002 Jan
Effect of ketamine, dextromethorphan, and MK-801 on cochlear dysfunction induced by transient ischemia.
2002 Jan
Dextromethorphan can produce false positive phencyclidine testing with HPLC.
2002 Jan
Inhibition kinetics of monoclonal antibodies against cytochromes P450.
2002 Jun
Treatment of codeine dependence with inhibitors of cytochrome P450 2D6.
2002 Jun
The effects of concomitant administration of theophylline and toborinone on the pharmacokinetics of both compounds in poor and extensive metabolizers via CYP2D6.
2002 May
Dextromethorphan and memantine in painful diabetic neuropathy and postherpetic neuralgia: efficacy and dose-response trials.
2002 May
Azithromycin for acute bronchitis: a randomised, double-blind, controlled trial.
2002 May 11
Semi-automated liquid--liquid back-extraction in a 96-well format to decrease sample preparation time for the determination of dextromethorphan and dextrorphan in human plasma.
2002 May 25
Patents

Sample Use Guides

Levomethorphan (dissolved in a mixed solution of 5% Emulphor™ EL-620/5% ethanol/90% isotonic sodium chloride solution, 2.5 mg/mL, rat 4–6) was administered to male DA pigmented rats, which were 5 weeks old and around 90 g mean weight. The drugs were given once daily at 5 mg/kg by intraperitoneal injection for ten successive days.
Route of Administration: Intraperitoneal
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 Wed Jul 05 23:34:19 UTC 2023
Edited
by admin
on Wed Jul 05 23:34:19 UTC 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 Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
DEA NO. 9210
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
Code System Code Type Description
EVMPD
SUB08478MIG
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
WIKIPEDIA
LEVOMETHORPHAN
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
INN
148
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
CHEBI
146176
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
NCI_THESAURUS
C83875
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
ECHA (EC/EINECS)
204-751-7
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
EPA CompTox
DTXSID20872403
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
FDA UNII
7ZZ22K9QE6
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
ChEMBL
CHEMBL1908323
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
MERCK INDEX
M6790
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY Merck Index
SMS_ID
100000082278
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
CAS
125-70-2
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
PUBCHEM
5362449
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
RS_ITEM_NUM
1362359
Created by admin on Wed Jul 05 23:34:20 UTC 2023 , Edited by admin on Wed Jul 05 23:34:20 UTC 2023
PRIMARY
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ACTIVE MOIETY