Compound: codeine
SMILES: O1c2c(OC)ccc3c2[C@@]45[C@@H]1[C@@H](O)C=C[C@H]4[C@H](N(C)CC5)C3
InChIKey: OROGSEYTTFOCAN-DNJOTXNNSA-N
Synonyms: codeine, Methylmorphine, Codicept, Codeine anhydrous, 76-57-3, Coducept, l-Codeine, Morphine monomethyl ether, (-)-Codeine, O3-Methylmorphine, codeinum, CODEINE BASE, Morphine 3-methyl ether, Norcodine, N-methyl, Norcodeine, N-methyl, Codeine polistirex, Morphine-3-methyl ether, codeina, UX6OWY2V7J, Codeinum monohydricum, O(3)-methylmorphine, DTXSID2020341, CHEBI:16714, IDS-NC-005(SECT.-2), 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol, DTXCID40341, Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-, Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-, DEA No. 9050, (5alpha,6alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol, Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-, Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)-, (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol, N Methylmorphine, (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-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)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo(9.6.1.0^(1,13).0^(5,17).0^(7,18))octadeca-7,9,11(18),15-tetraen-14-ol, (1S,5R,13R,14S,17R)-10-methoxy-4-methyl-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)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0^{1,13}.0^{5,17}.0^{7,18}]octadeca-7,9,11(18),15-tetraen-14-ol, (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-ol, NSC11427, RefChem:6413, (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinoline-7-ol, 200-969-1, Q830PW7520, Codein, CCRIS 7555, HSDB 3043, Codeine Anhydrate, Codeine (1.0 mg/mL in Methanol), Morphine-3-methyl ester, CHEMBL369475, (5alpha,6alpha)-17-methyl-3-(methyloxy)-7,8-didehydro-4,5-epoxymorphinan-6-ol, Codeine (CRM), Codeine [INN:BAN], EINECS 200-969-1, UNII-UX6OWY2V7J, (Codeine), Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5.alpha.,6.alpha.)-, 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(Codeine), 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol[codeine], MYTUSSIN, KODELAK FITO, CODEINE [HSDB], CODEINE [MI], Codeine CRS - * narc, Pholcodine EP Impurity B, CODEINE [WHO-DD], CHEMBL485, Epitope ID:120369, Codeine polistirex [USAN], SCHEMBL3257, SS85U8K5ZN, GTPL1673, 831 - Opiates in poppy seeds, Codeine 0.1 mg/ml in Methanol, Codeine 1.0 mg/ml in Methanol, SCHEMBL29394600, Codeine (1 mg/mL in Methanol), Tox21_200082, 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol, BDBM50019351, BDBM50105098, AKOS015955539, DB00318, CAS-76-57-3, NCGC00248518-01, NCGC00257636-01, AC-11114, DB-318946, DB-318947, NS00000391, C-0010, C06174, MORPHINE SULFATE IMPURITY A [EP IMPURITY], Q174723, MORPHINE HYDROCHLORIDE IMPURITY A [EP IMPURITY], Codeine, European Pharmacopoeia (EP) Reference Standard, ETHYLMORPHINE HYDROCHLORIDE IMPURITY C [EP IMPURITY], DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A [EP IMPURITY], 3-Methoxy-17-methyl-5alpha-7,8-didehydro-4,5-epoxymorphinan-6alpha-ol, HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C [EP IMPURITY], Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)- (9CI), Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl- (8CI), (1S,13R,14S,17R)-10-methoxy-4-methyl-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)-9-methoxy-3-methyl-2,3,4,4a,7,7a-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol, (codeine)10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol, 10-methoxy-4-methyl-(13R,14S)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10-trien-14-ol(Dihydrocodeine), 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol, 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol phosphate(codeine), 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(codeine (H3PO4)), 10-methoxy-4-methyl-(1S,5R,13R,14S,17R)-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-14-ol(codeine phosphate)
Theoretical properties:
molecular_formula: C18H21NO3
molecular_weight: 299.4 g/mol
exact_mass: 299.15214353 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 22
topological_polar_surface_area: 41.9 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Orthorhombic crystals from water, dilute alcohol, ether
color: Orthorhombic crystals from water, dilute alcohol, ether
boiling_point: 482 °F at 22 mmHg (sublimes) (NTP, 1992)
melting_point: 309 to 313 °F (after drying at 176 °F) (NTP, 1992)
density: 1.32 at 68 °F (NTP, 1992) - Denser than water; will sink
solubility: less than 1 mg/mL at 70 °F (NTP, 1992)
flash_point: 167 °F (NTP, 1992)
Descriptions:
{"pubchem": "Codeine is a morphinane alkaloid found in the opium poppy, Papaver somniferum var. album; has analgesic, anti-tussive and anti-diarrhoeal properties. It has a role as an opioid analgesic, a xenobiotic, a prodrug, an antitussive, an opioid receptor agonist, an environmental contaminant and a drug allergen. It is a morphinane alkaloid and an organic heteropentacyclic compound. It is functionally related to a morphine. It is a conjugate base of a codeine(1+).", "chebi": "A  morphinane alkaloid found in the opium poppy, <em>Papaver somniferum var. album</em>; has analgesic, anti-tussive and anti-diarrhoeal properties.", "chembl": "CODEINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Codeine is an opiate and prodrug of morphine mainly used to treat pain, coughing, and diarrhea. It is commonly used as a recreational drug. It is found naturally in the sap of the opium poppy, Papaver somniferum. It is typically used to treat mild to moderate degrees of pain. Greater benefit may occur when combined with paracetamol (acetaminophen) as codeine/paracetamol or a nonsteroidal anti-inflammatory drug (NSAID) such as aspirin or ibuprofen. Evidence does not support its use for acute cough suppression in children. In Europe, it is not recommended as a cough medicine for those under 12 years of age. It is generally taken orally. It usually starts working after half an hour, with maximum effect at two hours. Its effects last for about four to six hours. Codeine exhibits abuse potential similar to other opioid medications, including a risk of addiction and overdose. \nCommon side effects include nausea, vomiting, constipation, itchiness, lightheadedness, and drowsiness. Serious side effects may include breathing difficulties and addiction. Whether it can be used safely during pregnancy  is unclear. Care should be used during breastfeeding, as it may result in opiate toxicity in the baby. Its use as of 2016 is not recommended for children. Codeine works by being broken down by the liver into morphine; how quickly this occurs depends on a person's genetics.\nCodeine was discovered in 1832 by Pierre Jean Robiquet. In 2013, about 361,000 kg (795,000 lb) of codeine were produced while 249,000 kg (549,000 lb) were used, which made it the most commonly taken opiate. It is on the World Health Organization's List of Essential Medicines. Codeine occurs naturally and makes up about 2% of opium.\n\n"}