Codeine

Molecular structure via molpic based on CDK

Conformer []

Conformer structure via 3Dmol.js

Physical properties []
Molecular mass	299.4 g/mol ^[1]
Density	1.32 at 68 °F (NTP, 1992) - Denser than water; will sink g/cm³ ^[1]
Appearance	Orthorhombic crystals from water, dilute alcohol, ether ^[1]
Melting point	309 to 313 °F (after drying at 176 °F) (NTP, 1992) ^[1]
Boiling point	482 ° ^[1]
Decomposition	When heated to decomposition it emits toxic fumes of /nitrogen oxides/. ^[1]
Solubility	less than 1 mg/mL at 70 °F (NTP, 1992) ^[1]
Predicted LogP	1.1 ^[1]

Structural Identifiers []
Molecular formula	C₁₈H₂₁NO₃ ^[1]
IUPAC name	(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 ^[1]
SMILES	CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O ^[1]
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 ^[1]
InChIKey	OROGSEYTTFOCAN-DNJOTXNNSA-N ^[1]

Codeine

Codeine (also known as Methylmorphine, Codeine anhydrous, Codicept, Coducept, Morphine monomethyl ether, O3-Methylmorphine, Morphine 3-methyl ether, codeinum, Codeine base or Morphine-3-methyl ether) is a prodrug and opioid substance of the morphinan class.

Chemistry

Stereochemistry []

Codeine is a absolute mixture

Pharmacology

Codeine acts as a prodrug for:

Active metabolites []
Morphine Codeine-6-glucuronide

Subjective effects []

Physical effects
Constipation Cough suppression Difficulty urinating Itchiness Nausea Pain relief Pupil constriction Respiratory depression Sedation Stomach cramp

Cognitive effects
Anxiety suppression Cognitive euphoria Compulsive redosing Increased music appreciation Thought deceleration

Visual effects
Double vision

External links []

References []

National Center for Biotechnology Information. PubChem Compound Summary for CID 5284371, Codeine. Accessed July 19, 2025. https://pubchem.ncbi.nlm.nih.gov/compound/5284371
U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Codeine. UNII: UX6OWY2V7J. Global Substance Registration System. Accessed July 19, 2025. https://gsrs.ncats.nih.gov/ginas/app/beta/substances/UX6OWY2V7J

Anodyne