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Codeine

Athanor · official

C18H21NO3 · 299.4 g/mol

IUPAC name: (4R,4aR,7R,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol

Also called methylmorphine, opiate

DrugsNatural products
Open in Athanor
The structure of Codeine
Drawn from its SMILES with RDKit
Acute toxicityHarmful or irritantDangerToxic if swallowed · Harmful if swallowed · Toxic if inhaled

Names and identifiers

IUPAC name
(4R,4aR,7R,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol
Synonyms
methylmorphine, opiate, Isocodeine
+ 26 more

XWN5Y2Y8ZQ, DTXSID10858973, NSC-76434, (5alpha,6beta)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol, (4R,4aR,7R,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro(3,2-e)isoquinolin-7-ol, (4R,4aR,7R,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol, RefChem:149197, DTXCID101474455, 208-101-3, Ardinex, Isocodein, Iso-Codeine, EINECS 208-101-3, NSC 76434, UNII-XWN5Y2Y8ZQ, .ALPHA.-ISOCODEINE, SCHEMBL29390493, (5.alpha.,6.beta.)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol, Morphinan-6.beta.-ol, 7,8-didehydro-4,5.alpha.-epoxy-3-methoxy-17-methyl-, Isocodeine 0.1 mg/ml in Methanol, Morphinan-6-beta-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-, FI161208, NS00080708, Q6085506, 3-Methoxy-17-methyl-5alpha-7,8-didehydro-4,5-epoxymorphinan-6beta-ol, Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6beta)-

Molecular formula
C18H21NO3
Empirical formula
C18H21NO3
Molecular weight
299.4 g/mol
Exact mass
299.15214
CAS number
76-57-3
PubChem CID
5324288
Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
Isomeric SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@@H](C=C4)O
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-KEMUOJQUSA-N
Molfile

Names, InChI and the identifiers from PubChem, retrieved 2026-10-14.

Calculated

Heavy atoms
22
Rings
5
Aromatic rings
1
Fraction sp³ carbons (Fsp3)
0.56
H-bond donors
1
H-bond acceptors
4
Rotatable bonds
1
TPSA (Ų)
41.9
Formal charge
0
XLogP3
1.1 PubChem
Complexity
509 PubChem
Stereocenters
5 definedCIP: C8: R · C9: R · C12: R · C14: R · C18: S
Double-bond geometry
None specified
Point group
C1 of one 3D conformer with its hydrogens, by Athanor’s engine (as in the app)

Elemental analysis

  • C72.22%
  • H7.07%
  • N4.68%
  • O16.03%

Isotope pattern

100%299.15220%300.1552.5%301.158302.161

Each peak is a nominal mass with its abundance-weighted exact mass, as a percentage of the tallest, from IUPAC natural isotope abundances.

Computed from the structure with RDKit 2026.09 when this page was built, beside PubChem's own computed values from its record; where the two differ, both are shown.

Predicted

log P
1.5 Crippen (Wildman and Crippen 1999)
log S (water solubility)
-2.78 ESOL (Delaney 2004), log mol/L
Synthetic accessibility
5.16 SA score, 1 easy to 10 hard (Ertl and Schuffenhauer 2009)

Drug-likeness: Lipinski’s rule of five

  • Molecular weight ≤ 500: 299.37
  • log P ≤ 5 (Crippen): 1.5
  • H-bond donors ≤ 5: 1
  • H-bond acceptors ≤ 10: 4

Passes all four rules.

¹³C NMR shifts, predicted

Predictions, not measurements; each names its method. A measured log P, where a source reports one, is under Physical properties.

Safety

Danger

Most widely reported: 2 company reports to ECHA. Source [1].

  • Acute toxicity
  • Harmful or irritant
  • H301Toxic if swallowed (50% of reports)
  • H302Harmful if swallowed (50% of reports)
  • H331Toxic if inhaled (50% of reports)

Precautionary statements: P261, P264, P270, P271, P301+P316, P301+P317, P304+P340, P316, P321, P330, P403+P233, P405, P501

Always read the supplier’s safety data sheet before working with it.

Spectra

Experimental spectra held by these sources; each link opens the source's own record.

Literature

Reading PubChem, OpenAlex and GSRS…

Bioactivity

Reading ChEMBL…

References

  1. [1]European Chemicals Agency (ECHA) · ECHA legal notice: reuse with acknowledgement · via PubChem · retrieved 2026-10-14
  2. [2]NMRShiftDB · Linked only · via PubChem · retrieved 2026-10-14
  3. ·Calculated values: computed by Athanor with RDKit 2026.09 from the structure.
  4. ·Literature on PubChem

Data last updated 2026-10-14.