Codeine

Details

• Internal ID: 2f04eece-38e8-489c-9651-5468f807087d
• Taxonomy: Alkaloids and derivatives > Morphinans
• 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
• SMILES (Canonical): CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O
• SMILES (Isomeric): 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
• InChI Key: OROGSEYTTFOCAN-DNJOTXNNSA-N
• Popularity: 17,527 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₈H₂₁NO₃
• Molecular Weight: 299.40 g/mol
• Exact Mass: 299.15214353 g/mol
• Topological Polar Surface Area (TPSA): 41.90 Ų
• XlogP: 1.10

Synonyms

• Methylmorphine
• Codeine anhydrous
• Codicept
• Coducept
• l-Codeine
• 76-57-3
• Morphine monomethyl ether
• O3-Methylmorphine
• (-)-Codeine
• Morphine 3-methyl ether
• codeinum
• CODEINE BASE
• Codein
• Morphine-3-methyl ether
• Norcodine, N-methyl
• Norcodeine, N-methyl
• Codeine polistirex
• codeina
• codeine monohydrate
• CCRIS 7555
• HSDB 3043
• O(3)-methylmorphine
• metilmorfina
• Morphine-3-methyl ester
• CHEBI:16714
• UNII-UX6OWY2V7J
• UX6OWY2V7J
• N-methylnorcodeine
• EINECS 200-969-1
• N-methyl norcodine
• Codeine (CRM)
• Codeinum monohydricum
• MYTUSSIN
• DTXSID2020341
• KODELAK FITO
• Codeine [INN:BAN]
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5alpha,6alpha)-
• IDS-NC-005(SECT.-2)
• 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
• SS85U8K5ZN
• DTXCID40341
• 3-o-methylmorphine monohydrate
• CODEINE PHOSPHATE
• Codeine Anhydrate
• 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methylmorphinan-6alpha-ol
• Morphinan-6alpha-ol, 7,8-didehydro-4,5alpha-epoxy-3-methoxy-17-methyl-
• DEA No. 9050
• Codeine [BAN]
• LEAN
• Morphinan-6-alpha-ol, 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methyl-
• CODEINE SULFATE
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5-alpha,6-alpha)-
• Codeine phosphate hydrate
• CODEINE (MART.)
• Codeine phosphate anhydrous
• Ardinex
• 3-methoxy-17-methyl-7,8-didehydro-4,5alpha-epoxymorphinan-6alpha-ol
• N Methylmorphine
• 7,8-didehydro-4,5-alpha-epoxy-3-methoxy-17-methylmorphinan-6-alpha-ol
• CHEMBL369475
• CODEINE (USP MONOGRAPH)
• (5alpha,6alpha)-17-methyl-3-(methyloxy)-7,8-didehydro-4,5-epoxymorphinan-6-ol
• 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
• CODEINE COMPONENT OF TUZISTRA
• TUZISTRA COMPONENT OF CODEINE
• CODEINE MONOHYDRATE (EP MONOGRAPH)
• Calcidrine
• Actacode
• codein-
• DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A (EP IMPURITY)
• DIHYDROCODEINE HYDROGEN TARTRATE IMPURITY A [EP IMPURITY]
• Novahistine DH
• Codeine Alkaloid
• HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C (EP IMPURITY)
• HYDROCODONE HYDROGEN TARTRATE 2.5-HYDRATE IMPURITY C [EP IMPURITY]
• Codeine USP
• (Codeine)
• (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
• (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
• 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]
• N-methyl-nordoceine
• Codeine (anhydrous)
• Codalgin Forte Codate
• NSC11427
• 7,8-Didehydro-4,5-epoxy-3-methoxy-17-methyl-(5,6)-morphinan-6-ol
• Norcodeine, N-methyl-
• CODEINE [HSDB]
• CODEINE [MI]
• morphine monomethy l ether
• CODEINE [WHO-DD]
• CHEMBL485
• D03DIG
• Epitope ID:120369
• Codeine polistirex [USAN]
• SCHEMBL3257
• GTPL1673
• Codeine 0.1 mg/ml in Methanol
• Codeine 1.0 mg/ml in Methanol
• OROGSEYTTFOCAN-DNJOTXNNSA-N
• (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
• Tox21_200082
• BDBM50019351
• BDBM50105098
• AKOS015955539
• Morphinan-6-ol, 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-, (5?,6?)-
• CS-T-56966
• DB00318
• LS-1695
• CAS-76-57-3
• NCGC00248518-01
• NCGC00257636-01
• AC-11114
• C06174
• MORPHINE SULFATE IMPURITY A [EP IMPURITY]
• Q174723
• Codeine, European Pharmacopoeia (EP) Reference Standard
• 7,8-didehydro-4,5-ep oxy-3-methoxy-17-methylmorphinan-6-ol
• CODEINE (SEE ALSO: CODEINE PHOSPHATE (CAS 52-28-8))
• (5-alpha,6-alpha)-7,8-Didehydro-4,5-epoxy-3-methoxy-17-methylmorphinan-6-ol
• (6alpha,13alpha)-3-methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
• 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-(5 ALPHA, 6 ALPHA)-MORPHINAN 6-OL
• 7,8-didehydro-4,5-epoxy-3-methoxy-17-methyl-(5alpha, 6alpha)-morphinan 6-ol
• MORPHINAN-6-OL, 7,8-DIDEHYDRO-4,5-EPOXY-3-METHOXY-17-METHYL-(5 ALPHA, 6
• 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,5R,13R,14S,17R)-10-methoxy-4-methyl-12-oxa-4-azapentacyclo[9.6.1.0?,??.0?,??.0?,??]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
• (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)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
No predicted properties yet!

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL237	P41145	Kappa opioid receptor	15000 nM	IC50	PMID: 12502358
CHEMBL233	P35372	Mu opioid receptor	105 nM	IC50	PMID: 12502358

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	99.53%	96.09%
CHEMBL5608	Q16288	NT-3 growth factor receptor	93.35%	95.89%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	90.99%	95.56%
CHEMBL1293249	Q13887	Kruppel-like factor 5	88.02%	86.33%
CHEMBL2635	P51452	Dual specificity protein phosphatase 3	87.36%	94.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	87.33%	94.45%
CHEMBL225	P28335	Serotonin 2c (5-HT2c) receptor	85.85%	89.62%
CHEMBL253	P34972	Cannabinoid CB2 receptor	85.18%	97.25%
CHEMBL4829	O00763	Acetyl-CoA carboxylase 2	84.46%	98.00%
CHEMBL5469	Q14289	Protein tyrosine kinase 2 beta	83.78%	91.03%
CHEMBL4895	P30530	Tyrosine-protein kinase receptor UFO	82.20%	90.95%
CHEMBL3492	P49721	Proteasome Macropain subunit	81.63%	90.24%
CHEMBL2096618	P11274	Bcr/Abl fusion protein	81.58%	85.83%
CHEMBL2335	P42785	Lysosomal Pro-X carboxypeptidase	80.98%	100.00%
CHEMBL4478	Q00975	Voltage-gated N-type calcium channel alpha-1B subunit	80.49%	97.14%

Plants that contains it

• Aloe microstigma
• Chrozophora plicata
• Papaver bracteatum
• Papaver somniferum
• Papaver somniferum subsp. setigerum

Cross-Links

• PubChem: 5284371
• NPASS: NPC43069
• ChEMBL: CHEMBL485
• LOTUS: LTS0225213
• wikiData: Q105152313