{"ATC Code":"R05DA04","Abbreviation":"","Actives":["Morphine","Codeine-6-glucuronide"],"Aliases":["Methylmorphine","Codeine anhydrous","Codicept","Coducept","Morphine monomethyl ether","O3-Methylmorphine","Morphine 3-methyl ether","codeinum","Codeine base","Morphine-3-methyl ether","Norcodine, N-methyl","Norcodeine, N-methyl","Codeine polistirex","codeina","O(3)-methylmorphine","Codeinum monohydricum","Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5α,6α)-","Ids-nc-005(sect.-2)","7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol","7,8-didehydro-4,5α-epoxy-3-methoxy-17-methylmorphinan-6α-ol","Morphinan-6α-ol, 7,8-didehydro-4,5α-epoxy-3-methoxy-17-methyl-","(5α,6α)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol","Morphinan-6-α-ol, 7,8-didehydro-4,5-α-epoxy-3-methoxy-17-methyl-","Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-α,6-α)-","N Methylmorphine"],"Biological Half-Life":"Plasma half-lives of codeine and its metabolites have been reported to be approximately 3 hours.","Boiling Point":"482 °","CAS":"76-57-3","ChEBI":"CHEBI:16714","ChEMBL":"CHEMBL369475","ChemicalClasses":["morphinan"],"Chirality":"absolute","Classes":["Prodrug","Opioid"],"Color/Form":"Orthorhombic crystals from water, dilute alcohol, ether","DEA no":9050,"Decomposition":"When heated to decomposition it emits toxic fumes of /nitrogen oxides/.","Density":"1.32 at 68 °F (NTP, 1992) - Denser than water; will sink g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Classes":"Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics; Antitussive Agents","Drug Indication":"Codeine sulfate is a form of this drug that is commonly used. It is available in tablet form and indicated for the relief of mild to moderately severe pain, where the use of an opioid analgesic is appropriate.  The solution form is used by itself or combined in a syrup with other drugs and is used as a cough suppressant in adults aged 18 and above,.","Drug Warnings":"The U.S. Food and Drug Administration (FDA) is warning about several safety issues with the entire class of opioid pain medicines. These safety risks are potentially harmful interactions with numerous other medications, problems with the adrenal glands, and decreased sex hormone levels. We are requiring changes to the labels of all opioid drugs to warn about these risks. Opioids can interact with antidepressants and migraine medicines to cause a serious central nervous system reaction called serotonin syndrome, in which high levels of the chemical serotonin build up in the brain and cause toxicity. Taking opioids may lead to a rare, but serious condition in which the adrenal glands do not produce adequate amounts of the hormone cortisol. Cortisol helps the body respond to stress. Long-term use of opioids may be associated with decreased sex hormone levels and symptoms such as reduced interest in sex, impotence, or infertility.","EINECS":"200-969-1","Erowid Experience Reports":null,"Esters":[],"European Community (EC) Number":"200-969-1","FDA Pharmacological Classification":"UX6OWY2V7J","Flash Point":"167 °F (NTP, 1992)","Formating":[],"HMDB ID":"HMDB0004995","HeavyAtomCount":22,"Human Drugs":"Breast Feeding; Lactation; Milk, Human; Analgesics, Opioid; Narcotics; Antitussive Agents","IUPACName":"(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","InChI":"InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1","InChIKey":"OROGSEYTTFOCAN-DNJOTXNNSA-N","MeSH Pharmacological Classification":"Compounds with activity like OPIATE ALKALOIDS, acting at OPIOID RECEPTORS. Properties include induction of ANALGESIA or NARCOSIS. (See all compounds classified as Analgesics, Opioid.)","Melting Point":"309 to 313 °F (after drying at 176 °F) (NTP, 1992)","MolecularFormula":"C\u003csub\u003e18\u003c/sub\u003eH\u003csub\u003e21\u003c/sub\u003eNO\u003csub\u003e3\u003c/sub\u003e","MolecularWeight":"299.4 g/mol","Opticalactivity":"UNSPECIFIED","Pharmacodynamics":"**General effects**  Codeine is a weak narcotic pain reliever and cough suppressant that is similar to morphine and hydrocodone. A small amount of ingested codeine is converted to morphine in the body. Codeine increases tolerance to pain, reducing existing discomfort. In addition to decreasing pain, codeine also causes sedation, drowsiness, and respiratory depression.   **Antitussive activity**  This drug has shown antitussive activity in clinical trials and has been effective in cough secondary to tuberculosis and insomnia due to coughing. Codeine suppresses the cough reflex through a direct effect on the cough center in the medulla.  **Effects on intestinal motility**  Codeine may reduce intestinal motility through both a local and possibly central mechanism of action. This may possibly lead to constipation. The chronic use of opioids, including codeine sulfate, may lead to obstructive bowel disease, particularly in patients with underlying disorders of intestinal motility.   **Effects on the central nervous system**  Codeine phosphate is an opioid analgesic with uses similar to those of morphine, but is much less potent as an analgesic. Its primary site of action is at the _mu_ opioid receptors distributed throughout the central nervous system. The sedative activities of codeine are less potent than those of morphine. Codeine may cause respiratory system depression by the activation of μ-opioid receptors at specific sites in the central nervous system.  **Effects on blood pressure**  This drug poses an increased risk of compromised ability to maintain blood pressure due to peripheral vasodilation and other mechanisms.   **Effects on chronic cancer pain and other types of pain**  Codeine is an opioid analgesic with similar indications to those of morphine, however, is much less potent in its pain alleviating properties. Its primary action takes place at the mu opioid receptors, which are distributed throughout the central nervous system. The average duration of action is about 4 hours.  Regular dosing of opioid analgesics such as codeine in patients with severe cancer pain has been well documented to improve symptoms,.","Physical Description":"Codeine appears as colorless to white crystalline solid or white powder. Sublimes at 284 °F. Odorless. Bitter taste. pH (saturated aqueous solution) 9.8. (NTP, 1992)","PubChemId":5284371,"RefCount":3,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Codeine","Name":"Codeine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/drugs/DB00318","Name":"Codeine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/5284371","Name":"Codeine","Sub":false}]},{"Name":"ChEMBL","Urls":[{"Link":"https://www.ebi.ac.uk/chembl/explore/compound/CHEMBL369475","Name":"Codeine","Sub":false}]},{"Name":"ChEBI","Urls":[{"Link":"https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16714","Name":"Codeine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=76-57-3","Name":"Codeine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0004995","Name":"Codeine","Sub":false}]},{"Name":"KEGG","Urls":[{"Link":"https://www.kegg.jp/entry/C06174","Name":"Codeine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/UX6OWY2V7J","Name":"Codeine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID2020341","Name":"Codeine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 5284371, Codeine. Accessed July 19, 2025. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/5284371\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/5284371\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Codeine. UNII: UX6OWY2V7J. Global Substance Registration System. Accessed July 19, 2025. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/UX6OWY2V7J\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/UX6OWY2V7J\u003c/a\u003e"],"Reported Fatal Dose":"In adults, ingestion of 7 to 14 mg/kg may cause death. Much higher doses may be tolerated by chronic users. Ingestion of more than 1 mg/kg of codeine in children is capable of producing symptoms, and doses more than 5 mg/kg have caused respiratory arrest.","SMILES":"CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O","SaltData":[],"Salts":[],"Solubility":"less than 1 mg/mL at 70 °F (NTP, 1992)","Stability/Shelf Life":"Stable under recommended storage conditions. /Codeine monohydrate/","StereoisomerData":[],"Stereoisomers":[],"Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 80.574 95.144\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#ff0d0d\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h81v96H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m79.55 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1.221-.53.387-.536.387-1.459 0-.928-.387-1.452-.381-.524-1.209-.524-.833 0-1.226.524t-.393 1.452M4.305 94.512h-.62v-2.286H1.173v2.286H.56v-4.899h.613v2.071h2.512v-2.071h.62z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m74.921 72.632 2.315 5.065M73.143 65.059l-.114-5.742\" class=\"hi\"/\u003e\u003cpath stroke=\"#ff0d0d\" d=\"m9.931 18 4.989 2.81M6.596 12.223l-.059-5.654M7.824 50.38l6.093-5.765\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":{"Cognitive Effects":["Cognitive euphoria","Thought deceleration","Anxiety suppression","Compulsive redosing","Increased music appreciation"],"Physical Effects":["Respiratory depression","Pain relief","Itchiness","Constipation","Cough suppression","Sedation","Nausea","Pupil constriction","Stomach cramp","Difficulty urinating"],"Visual Effects":["Double vision"]},"Therapeutic Uses":"Analgesics, Opioid; Antitussive Agents; Narcotics","Title":"Codeine","UNII":"UX6OWY2V7J","Wikipedia":"Codeine","XLogP":1.1}