Compound: dextromethorphan
SMILES: O(c1cc2c(C[C@@H]3N(C)CC[C@@]24[C@@H]3CCCC4)cc1)C
InChIKey: MKXZASYAUGDDCJ-NJAFHUGGSA-N
Synonyms: dextromethorphan, d-Methorphan, 125-71-3, delta-Methorphan, Dextromorphan, Dextromethorfan, Dextrometorfano, Dextromethorphane, Albutussin, Destrometerfano, Dextromethorphanum, BA 2666, Balminil DM, (+)-Dextromethorphan, 3-Methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan, Morphinan, 3-methoxy-17-methyl-, (9alpha,13alpha,14alpha)-, DXM [Antitussive], BA-2666, 7355X3ROTS, CHEBI:4470, (+)-3-Methoxy-N-methylmorphinon, NSC-751452, DTXSID3022908, DXM (Antitussive), (+)-cis-1,3,4,9,10,10a-Hexahydro-6-methoxy-11-methyl-2H-10,4alpha-iminoethanophenanthren, (+)-3-methoxy-17-methyl-9alpha,13alpha,14alpha-morphinan, RoboTablets, RefChem:6417, Delsym (dextromethorphan), Soothe Comfort I Cough Syrup, Hydrochloride, Dextromethorphan, Soothe Comfort II Cough Syrup, DTXCID202908, Soothe Comfort I Cough Syrup Original, Soothe Comfort II Cough Syrup Herbal Mint, LIBI AIR VIRLAZA Dextromethorphan Cough Suppressant, (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo(7.5.3.01,10.02,7)heptadeca-2(7),3,5-triene, 204-752-2, Nodex, HSDB 3056, Dextromethorfan [Czech], Destrometerfano [DCIT], Dextrometorphan, Dextrometorfano [INN-Spanish], (+)-3-Methoxy-17-methylmorphinan, (1S,9S,10S)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.01,10.02,7]heptadeca-2(7),3,5-triene, Morphinan, 3-methoxy-17-methyl-, (9.alpha.,13.alpha.,14.alpha.)-, DXM, Dextromethorphane [INN-French], Dextromethorphanum [INN-Latin], Dextromethorphan [USP:INN:BAN], ( )-3-Methoxy-N-methylmorphinon, Dextromethorphan (USP), EINECS 204-752-2, BRN 0088549, UNII-7355X3ROTS, Calmylin, Delsym (Salt/Mix), Medicon (Salt/Mix), Romilar (Salt/Mix), Tusilan (Salt/Mix), 9alpha,13alpha,14alpha-Morphinan, 3-methoxy-17-methyl-, Prestwick0_000359, Prestwick1_000359, Prestwick2_000359, Prestwick3_000359, Lopac-D-2531, Epitope ID:549279, Racemethorphan [as d-form], ( )-cis-1,3,4,9,10,10a-Hexahydro-6-methoxy-11-methyl-2H-10,4alpha-iminoethanophenanthren, SCHEMBL29949, BSPBio_000457, DEXTROMETHORPHAN [MI], 4-21-00-01367 (Beilstein Handbook Reference), CHEMBL52440, DEXTROMETHORPHAN [INN], SPBio_002378, DEXTROMETHORPHAN [HSDB], BPBio1_000503, GTPL6953, DEXTROMETHORPHAN [VANDF], DEXTROMETHORPHAN [MART.], SCHEMBL29357059, CHEBI:92579, (+)-3-methoxy-n-methylmorphinan, DEXTROMETHORPHAN [USP-RS], DEXTROMETHORPHAN [WHO-DD], (9alpha,13alpha,14alpha)-17-methyl-3-(methyloxy)morphinan, 9-alpha,13-alpha,14-alpha-Morphinan, 3-methoxy-17-methyl-, HMS2090C08, LSM-2726, Morphinan, 3-methoxy-17-methyl-, (9-alpha,13-alpha,14-alpha)-, BDBM50366613, Dextromethorphan, 1mg/ml in Methanol, MFCD00866862, AKOS025311415, DB00514, FM36326, NSC 751452, DEXTROMETHORPHAN [USP MONOGRAPH], NCGC00015333-01, NCGC00015333-02, 3-Methoxy-17-methyl-9a,13a,14a-morphinan, NS00008569, (9a,13a,14a)-3-Methoxy-17-methylmorphinan, C06947, D03742, 9-alpha,-14-alpha-3-Methoxy-17-methylmorphinan, Q407781, 3-Methoxy-17-methyl-9.alpha.,13.alpha.-morphinan, BRD-K33211335-004-01-7, BRD-K33211335-337-03-7, (9alpha,13alpha,14alpha)-3-Methoxy-17-methylmorphinan, Morphinan, 3-methoxy-17-methyl-, (9?,13?,14?)-, 3-Methoxy-17-methyl-9.alpha.,13.alpha.,14.alpha.-morphinan, 9.alpha.,13.alpha.,14.alpha.-Morphinan, 3-methoxy-17-methyl-, 9alpha,13alpha,14alpha-Morphinan, 3-methoxy-17-methyl- (8CI), 3-Methoxy-17-methylmorphinan-, (9.alpha.,13.alpha.,14.alpha.)- #, 4-methoxy-12-methyl-12-azatetracyclo[9.3^1.10^.0^2.7^] heptadeca-2(7),3,5-triene, (1R,9R,10R)-4-methoxy-17-methyl-17-azatetracyclo[7.5.3.0^{1,10}.0^{2,7}]heptadeca-2,4,6-triene, (4aS,10S,10aS)-6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene, (4bS,8aS,9S)-3-methoxy-11-methyl-6,7,8,8a,9,10-hexahydro-5H-9,4b-(epiminoethano)phenanthrene, 4NQ
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:
physical_state: White to slightly yellow crystalline powder
color: White to slightly yellow crystalline powder
odor: Odorless
melting_point: 122-124
Descriptions:
{"pubchem": "Dextromethorphan is a 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough. It has a role as a oneirogen, a xenobiotic, a prodrug, a neurotoxin, an antitussive, a NMDA receptor antagonist and an environmental contaminant. It is functionally related to a dextrorphan. It is an enantiomer of a levomethorphan.", "chebi": "A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2<em>H</em>-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have <i>S</i>-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.", "chembl": "DEXTROMETHORPHAN is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Dextromethorphan is a cough suppressant used in many cough and cold medicines. In 2022, the US Food and Drug Administration (FDA) approved the combination dextromethorphan/bupropion to serve as a rapid-acting antidepressant in people with major depressive disorder.\nIt is in the morphinan class of medications with dissociative and stimulant properties (at lower doses). Dextromethorphan does not have a significant affinity for the mu-opioid receptor activity typical of morphinan compounds and exerts its therapeutic effects through several other receptors. In its pure form, dextromethorphan occurs as a white powder.\nWhen exceeding approved dosages, dextromethorphan acts as a dissociative hallucinogen. It has multiple mechanisms of action, including actions as a nonselective serotonin\u2013norepinephrine reuptake inhibitor and a sigma-1 receptor agonist. Dextromethorphan and its major metabolite dextrorphan also block the NMDA receptor at high doses, producing effects similar to those of other dissociative anesthetics such as ketamine, nitrous oxide, and phencyclidine.\nIt was patented in 1949 and approved for medical use in 1953. In 2023, the combination with promethazine was the 252nd most commonly prescribed medication in the United States, with more than 1 million prescriptions; and the combination with brompheniramine and pseudoephedrine was the 281st most commonly prescribed medication in the United States, with more than 700,000 prescriptions.\n\n"}