CHEBI:146176 - levomethorphan

ChEBI IDCHEBI:146176
ChEBI Namelevomethorphan
Stars
DefinitionA 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the stereocenters at positions 4a, 10 and 10a have R-configuration. It is a prodrug of levorphanol and a strong narcotic analgesic, and listed as a schedule II controlled substance.
Last Modified14 February 2020
SubmitterAdnan
DownloadsMolfile
FormulaC18H25NO
Net Charge0
Average Mass271.404
Monoisotopic Mass271.19361
SMILES[H][C@@]12CCCC[C@@]13CCN(C)[C@@H]2Cc1ccc(OC)cc13
InChIInChI=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
InChIKeyMKXZASYAUGDDCJ-CGTJXYLNSA-N
Wikipedia
Roles Classification
Biological Roles:
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
metabolite  Any intermediate or product resulting from metabolism. The term 'metabolite' subsumes the classes commonly known as primary and secondary metabolites.
Applications:
prodrug  A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug.
opioid analgesic  A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood.
ChEBI Ontology
Outgoing Relation(s)
levomethorphan (CHEBI:146176) has functional parent Levorphanol (CHEBI:6444)
levomethorphan (CHEBI:146176) has role opioid analgesic (CHEBI:35482)
levomethorphan (CHEBI:146176) has role prodrug (CHEBI:50266)
levomethorphan (CHEBI:146176) is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene (CHEBI:146178)
levomethorphan (CHEBI:146176) is enantiomer of dextromethorphan (CHEBI:4470)
Incoming Relation(s)
racemethorphan (CHEBI:146177) has part levomethorphan (CHEBI:146176)
dextromethorphan (CHEBI:4470) is enantiomer of levomethorphan (CHEBI:146176)
IUPAC Names 
3-methoxy-17-methylmorphinan
(4aR,10R,10aR)-6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene
INNs  Source
levomethorphanWHO MedNet
lévométhorphaneWHO MedNet
levomethorphanumWHO MedNet
levometorfanoWHO MedNet
Synonyms  Source
(−)-3-methoxy-17-methylmorphinanChEBI
(−)-3-methoxy-N-methylmorphinanChemIDplus
L-3-methoxy-17-methylmorphinanChEBI
L-methorphanChemIDplus
Manual XrefsDatabases
LevomethorphanWikipedia
Registry NumbersSources
CAS:125-70-2ChemIDplus
CAS:125-70-2NIST Chemistry WebBook
Citations