Compound: PHOLCODINE
SMILES: O1CCN(CCOc2c3O[C@H]4[C@@H](O)C=C[C@@H]5[C@]64c3c(C[C@H]5N(C)CC6)cc2)CC1
InChIKey: GPFAJKDEDBRFOS-FKQDBXSBSA-N
Synonyms: PHOLCODINE, Homocodeine, Glycodine, Codylin, Folcodine, Neocodine, Weifacodine, Hibernyl, Pholtex, Memine, Morpholinylethylmorphine, Tussokon, Ethnine, Folcodina, Galenphol, 509-67-1, Biocalyptol, Pholcodinum, Dia-Tuss, Ethnine Simplex, 3-Morpholylaethylmorphin, beta-Morpholinoethylmorphine, 3-(2-(4-Morpholinyl)ethyl)morphine, Tetrahydro-1,4-oxazinylmethylcodeine, DEA No. 9314, LPP64AWZ7L, Pavacol-D, CHEBI:53579, DTXSID70198923, IDS-NP-011(SECT.2), 7,8-Didehydro-4,5-alpha-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6-alpha-ol, Evaphol, Tixylix daytime, Evaphol strong, Pholcomed fte, Gppe linct, Sancos co, Tixylix dry cough, Tixylix night-time, (1S,5R,13R,14S,17R)-4-methyl-10-(2-(morpholin-4-yl)ethoxy)-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7(18),8,10,15-tetraen-14-ol, (1S,5R,13R,14S,17R)-4-methyl-10-[2-(morpholin-4-yl)ethoxy]-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7(18),8,10,15-tetraen-14-ol, (4R,4aR,7S,7aR,12bS)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-o, (4R,4aR,7S,7aR,12bS)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-o, Tixylix night cough, RefChem:173208, DTXCID30121414, 7,8-didehydro-4,5 alpha-epoxy-17-methyl-3-(2-morpholinoethoxymorphinan-6 alpha-ol), 208-102-9, Pectolin, Folkodin, Neocodin, Pholcodin, Galphol, Prodromine, Pholcodine (INN), PHOLCODINE [INN], (4R,4aR,7S,7aR,12bS)-3-methyl-9-(2-morpholin-4-ylethoxy)-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol, 3-(2-Morpholinoethyl)morphine, O3-(2-Morpholinoethyl)morphine, Morphine, 3-O-(2-morpholinoethyl)-, Pholcodine (1.0mg/ml in Acetonitrile), Folkodin [Czech], (5alpha,6alpha)-17-methyl-3-[2-(morpholin-4-yl)ethoxy]-7,8-didehydro-4,5-epoxymorphinan-6-ol, Folcodina [Spanish], Pholcodinum [Latin], Pholcodine [INN:BAN], Folcodina [INN-Spanish], Pholcodinum [INN-Latin], UNII-LPP64AWZ7L, beta-Morpholinylethylmorphine, pholcodeine, Adaphol, Codisol, Copholco, Lantuss, Pholcolin, 3-Morpholylaethylmorphin [German], GPFAJKDEDBRFOS-FKQDBXSBSA-N, Covonia Dry Cough, EINECS 208-102-9, O(sup 3)-(2-Morpholinoethyl)morphine, 3-Morpholylathylmorphin, PHOLCODINE [MI], 3-morpholinoethylmorphine, Morphine, O(sup 3)-(2-morpholinoethyl)-, Epitope ID:116651, Pholcodine CRS - * narc, PHOLCODINE [WHO-DD], SCHEMBL154354, GTPL9086, CHEMBL2105224, 03-(2-Morpholinoethyl)-Morphine, 3-O-(2-Morpholinoethyl)-Morphine, MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-17-METHYL-3-(2-(4-MORPHOLINYL)ETHOXY)-, (5.ALPHA.,6.ALPHA.)-, DB09209, D07385, Pholcodine For Peak Identification CRS - * Narc, Q3124290, 17-Methyl-3-[2-(morpholin-4-yl)ethoxy]-5alpha-7,8-didehydro-4,5-epoxymorphinan-6alpha-ol, Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-17-methyl-3-(2-morpholinoethoxy)-
Theoretical properties:
molecular_formula: C23H30N2O4
molecular_weight: 398.5 g/mol
exact_mass: 398.22055744 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 6
rotatable_bond_count: 4
heavy_atom_count: 29
topological_polar_surface_area: 54.4 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
boiling_point: 577.8ºC at 760 mmHg
melting_point: 91ºC
solubility: Slightly soluble
Descriptions:
{"pubchem": "Pholcodine is a morphinane alkaloid that is a derivative of morphine with a 2-morpholinoethyl group at the 3-position. It has a role as an opioid analgesic, an antitussive, a mu-opioid receptor agonist and a drug allergen. It is a morphinane alkaloid and an organic heteropentacyclic compound.", "chebi": "A morphinane alkaloid that is a derivative of morphine with a 2-morpholinoethyl group at the 3-position.", "chembl": "PHOLCODINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Pholcodine is an opioid cough suppressant (antitussive). It helps suppress unproductive coughs and also has a mild sedative effect, but has little or no analgesic effects. It is also known as morpholinylethylmorphine and homocodeine.\nPholcodine is found in certain cough lozenges, and more commonly as an oral solution, typically 5 mg / 5 ml. Adult dosage is 5-10 ml up to 3-4 times daily. Pholcodine now largely replaces the previously more common codeine linctus, as it has a much lower potential for dependence.\nPholcodine has been widely used as an antitussive agent but by 2023 concerns over its association with anaphylaxis in some circumstances meant that it has been withdrawn from sale in many territories. Pholcodine is not prescribed in the United States where it is classed as a Schedule I drug, the most highly controlled drug category.\nFollowing the conclusion of a review of post-marketing safety data by the Medicines and Healthcare products Regulatory Agency, all pholcodine-containing medicines were recalled and withdrawn from the UK as a precaution. The available data has demonstrated that pholcodine use, particularly in the twelve months before general anesthesia with NMBAs (neuromuscular blocking agents), is a risk factor for developing an anaphylactic reaction to NMBAs. In December 2022, the European Medicines Agency recommended their withdrawal in the EU. As of February 2023, the Australian Therapeutic Goods Administration canceled the registration of pholcodine."}