(1S,5R,13R,14S,17R)-4-methyl-10-[2-(morpholin-4-yl)ethoxy]-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7,9,11(18),15-tetraen-14-ol

• ChemBase ID: 130431
• Molecular Formular: C23H30N2O4
• Molecular Mass: 398.4953
• Monoisotopic Mass: 398.22055745
• SMILES: O(c1ccc2c3c1O[C@H]1[C@@H](O)C=C[C@H]4[C@H](N(C)CC[C@]314)C2)CCN1CCOCC1
• Canonical SMILES: CN1CC[C@@]23[C@@H]4[C@H]1Cc1c3c(O[C@H]2[C@H](C=C4)O)c(cc1)OCCN1CCOCC1
• InChI: InChI=1S/C23H30N2O4/c1-24-7-6-23-16-3-4-18(26)22(23)29-21-19(5-2-15(20(21)23)14-17(16)24)28-13-10-25-8-11-27-12-9-25/h2-5,16-18,22,26H,6-14H2,1H3/t16-,17+,18-,22-,23-/m0/s1
• InChIKey: GPFAJKDEDBRFOS-FKQDBXSBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-4-methyl-10-[2-(morpholin-4-yl)ethoxy]-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7,9,11(18),15-tetraen-14-ol; (1S,5R,13R,14S,17R)-4-methyl-10-[2-(morpholin-4-yl)ethoxy]-12-oxa-4-azapentacyclo[9.6.1.0^1,^1^3.0^5,^1^7.0^7,^1^8]octadeca-7(18),8,10,15-tetraen-14-ol
• IUPAC Traditional name: morpholinylethylmorphine
• Synonyms: Pholcodine; (5α,6α)-7,8-Didehydro-4,5-epoxy-17-methyl-3-[2-(4-morpholinyl)ethoxy]morphinan-6-ol; 7,8-Didehydro-4,5α-epoxy-17-methyl-3-(2-morpholinoethoxy)morphinan-6α-ol; 3-O-(2-Morpholinoethyl)morphine; 3-[2-(4-Morpholinyl)ethyl]morphine; Biocalyptol; Codylin; Ethnine; Folcodin; Folcodine; Galenphol; Galphol; Glycodine; Hibernyl; Homocodeine; Memine; Morpholinylethylmorphine; Neocodine; O-2-Morpholinoethylmorphine; Pectolin; Pholtex; Tussokon; Weifacodine; β-Morpholinylethylmorphine

Database IDs

• CAS Number: 509-67-1
• PubChem SID: 162224710
• PubChem CID: 5311356
• CHEBI ID: 53579
• ATC CODE: R05DA08
• Chemspider ID: 4470854
• KEGG ID: D07385
• Unique Ingredient Identifier: LPP64AWZ7L
• Wikipedia Title: Pholcodine

CALCULATED PROPERTIES

• Acid pKa: 13.78274
• H Acceptors: 6
• H Donor: 1
• LogD (pH = 5.5): -3.0236862
• LogD (pH = 7.4): -0.6806895
• Log P: 1.1430954
• Molar Refractivity: 111.6983 cm^3
• Polarizability: 43.3123 Å^3
• Polar Surface Area: 54.4 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 48-52°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

Pharmacology Properties

• Admin Routes: Oral
• Bioavailability: Maximum plasma conc. attained 4-8 hours after oral dose.
• Dependency Liability: Low
• Excretion: Renal
• Half Life: 32-43 hours; volume of distribution is 36-49L/kg.
• Metabolism: Hepatic
• Protein Bound: 23.5%
• Legal Status: Class B (UK); Schedule I (US)
• Pregnancy Category: A (Australia)

DETAILS

Toronto Research Chemicals - P351500

Antitussive; an opioid cough suppressant. Controlled Substance.

REFERENCES

• Findlay, J.W.A.: J. Clin. Pharm. Therap., 13, 5 (1988)
• Chen, Z.R. et al.: Br. J. Clin. Pharmacol., 26, 445 (1988)
• Maurer, H.H. et al.: Arzneim.-Forsch., 40, 546 (1988)