levomethorphan (CHEBI:146176)

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ChEBI Name	levomethorphan

ChEBI ID	CHEBI:146176

Definition	A 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.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C18H25NO

Net Charge

Average Mass

271.404

Monoisotopic Mass

271.19361

InChI

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

InChIKey

MKXZASYAUGDDCJ-CGTJXYLNSA-N

SMILES

C=1C=2C[C@@H]3[C@]4([C@@](C2C=C(C1)OC)(CCCC4)CCN3C)[H]

Roles Classification
Biological Role(s):	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. (via alkaloid )

Application(s):	opioid analgesic A narcotic or opioid substance, synthetic or semisynthetic agent producing profound analgesia, drowsiness, and changes in mood. 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.

ChEBI Ontology
Outgoing	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	racemethorphan (CHEBI:146177) has part levomethorphan (CHEBI:146176) dextromethorphan (CHEBI:4470) is enantiomer of levomethorphan (CHEBI:146176)

IUPAC Names

(4aR,10R,10aR)-6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene

3-methoxy-17-methylmorphinan

Last Modified

14 February 2020