Compound: Levomethorphan
SMILES: O(c1cc2c(C[C@H]3N(C)CC[C@]24[C@H]3CCCC4)cc1)C
InChIKey: MKXZASYAUGDDCJ-CGTJXYLNSA-N
Synonyms: Levomethorphan, l-Methorphan, Levomethorphane, Levometorfano, Levomethorphanum, 125-70-2, (-)-3-Methoxy-N-methylmorphinan, 7ZZ22K9QE6, IDS-NL-004, IDS-NL-005, CHEBI:146176, DTXSID20872403, RefChem:924704, DTXCID00820048, 204-751-7, Methorphan, Levometorfano [INN-Spanish], Levomethorphane [INN-French], Levomethorphanum [INN-Latin], 3-Methoxy-17-methylmorphinan, Morphinan, 3-methoxy-17-methyl-, l-, Levomethorphan (INN), Dextromethorfan [Czech], Destrometerfano [DCIT], LEVOMETHORPHAN [INN], Dextrometorphan, Dextrometorfano [INN-Spanish], Dextromethorphan-d3, Tylenol Cough + Decongestant Liquid, Demorphine, Dimacol, Rondec dm, Robitussin CF, Robitussin DM, Levomethorphan (1.0mg/ml in Acetonitrile), Levomethorphan [INN:BAN:DCF], Prestwick_686, Benylin DM (TN), Demorphan hydrobromide, EINECS 204-751-7, UNII-7ZZ22K9QE6, UNII-8YB8F78WM1, 3-Methoxy-17-methylmorphinan, l, Racemetorfano [INN-Spanish], Racemethorphane [INN-French], Racemethorphanum [INN-Latin], Dexyromethorphan, ((-))-3-Methoxy-N-methylmorphinan, DEA No. 9210, Levomethorphan [BAN:DCF:INN], Racemethorphan [INN:BAN:DCF], 2H-10,4a-Iminoethanophenanthrene, 1,3,4,9,10,10a-hexahydro-6-methoxy-11-methyl-, (-)-3-methoxy-17-methylmorphinan, Morphinan, 3-methoxy-N-methyl-, (-)-, EINECS 208-114-4, Morphinan, 3-methoxy-17-methyl-, (-)-, Dextromethorphan Bromhydrate, LEVOMETHORPHAN [MI], RACEMETHORPHAN [MI], RACEMETHORPHAN [INN], SCHEMBL29950, DEA No. 9732, CHEMBL1908323, L-3-methoxy-17-methylmorphinan, SCHEMBL30582488, Morphinan, 3-methoxy-17-methyl-, (+)-3-Methoxy-9a-methylmorphinan, (+-)-3-Methoxy-N-methylmorphinan, 524713-56-2, NSC751452, (+/-)-3-methoxy-17-methylmorphinan, AKOS015969688, dl-cis-1,3,4,9,10,10a-hexahydro-6-methoxy-11-methyl-2H-10,4a-iminoethanophenanthrene, Dextromethorphan hydrobromide [BAN:JAN], AC-13098, Levomethorphan (1 mg/ml in Acetonitrile), (+/-)-3-METHOXY-N-METHYLMORPHINAN, NS00068001, NS00068002, D12696, Q60998690, Levomethorphan, vial of 10 mg, certified reference material, (9S,13S,14S)-6,18-Dideoxy-7,8-dihydro-3-O-methylmorphine, (4aR,10R,10aR)-6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene, DL-CIS-1,2,3,9,10,10A-HEXAHYDRO-6-METHOXY-11-METHYL-4H-10,4A-IMINOETHANOPHENANTHRENE
Theoretical properties:
molecular_formula: C18H25NO
molecular_weight: 271.4 g/mol
exact_mass: 271.193614421 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 2
rotatable_bond_count: 1
heavy_atom_count: 20
topological_polar_surface_area: 12.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 8.51 mg/L
Descriptions:
{"pubchem": "Levomethorphan is 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. It has a role as an opioid analgesic and a prodrug. It is functionally related to a Levorphanol. It is an enantiomer of a dextromethorphan.", "chebi": "A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2<em>H</em>-10,4a-(epiminoethano)phenanthrene in which the stereocenters at positions 4a, 10 and 10a have <i>R</i>-configuration. It is a prodrug of levorphanol and a strong narcotic analgesic, and listed as a schedule II controlled substance.", "chembl": "LEVOMETHORPHAN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 2.0.", "wikipedia": "Levomethorphan (LVM) (INN, BAN) is an opioid analgesic of the morphinan family that has never been marketed. It is the L-stereoisomer of racemethorphan (methorphan). The effects of the two isomers of racemethorphan are quite different, with dextromethorphan (DXM) being an antitussive at low doses and a hallucinogen at much higher doses. Levomethorphan is about five times stronger than morphine.\nLevomethorphan is a prodrug to levorphanol, analogously to DXM acting as a prodrug to dextrorphan or codeine behaving as a prodrug to morphine. As such, levomethorphan has similar effects to levorphanol but is less potent as it must be demethylated to the active form by liver enzymes before being able to produce its effects. As a prodrug of levorphanol, levomethorphan functions as a potent agonist of all three of the opioid receptors, \u03bc, \u03ba (\u03ba1 and \u03ba3 but notably not \u03ba2), and \u03b4, as an NMDA receptor antagonist, and as a serotonin-norepinephrine reuptake inhibitor. Via activation of the \u03ba-opioid receptor, levomethorphan can produce dysphoria and psychotomimetic effects such as dissociation and hallucinations.\nLevomethorphan 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 with a DEA ACSCN of 9210 and a 2014 annual aggregate manufacturing quota of 195 grams, up from 6 grams the year before. The salts in use are the tartrate (free base conversion ratio 0.644) and hydrobromide (0.958). As of February 2026, no levomethorphan pharmaceuticals are marketed in the United States."}