(1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-12-oxa-4-azapentacyclo[9.6.1.01,13.05,17.07,18]octadeca-7(18),8,10,15-tetraen-10-yl acetate

• ChemBase ID: 169872
• Molecular Formular: C21H23NO5
• Molecular Mass: 369.41102
• Monoisotopic Mass: 369.15762284
• SMILES: c1(c2c3c(cc1)C[C@@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)OC(=O)C)O2)CCN1C)OC(=O)C
• Canonical SMILES: CC(=O)O[C@H]1C=C[C@@H]2[C@@]34[C@H]1Oc1c4c(C[C@H]2N(CC3)C)ccc1OC(=O)C
• InChI: InChI=1S/C21H23NO5/c1-11(23)25-16-6-4-13-10-15-14-5-7-17(26-12(2)24)20-21(14,8-9-22(15)3)18(13)19(16)27-20/h4-7,14-15,17,20H,8-10H2,1-3H3/t14-,15+,17-,20-,21-/m0/s1
• InChIKey: GVGLGOZIDCSQPN-PVHGPHFFSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-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-10-yl acetate
• IUPAC Traditional name: (1S,5R,13R,14S,17R)-14-(acetyloxy)-4-methyl-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-10-yl acetate
• Synonyms: (5α,6α)-7,8-Didehydro-4,5-epoxy-17-methylmorphinan-3,6-diol 3,6-Diacetate; Acetomorphine; Diacetylmorphine; Diamorphine; Diaphorm; Eclorion; Morphacetin; Preza; Heroin

Database IDs

• CAS Number: 561-27-3
• PubChem SID: 162264004
• PubChem CID: 5462328

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): -1.697644
• LogD (pH = 7.4): -0.152045
• Log P: 1.549009
• Molar Refractivity: 98.4254 cm^3
• Polarizability: 38.45062 Å^3
• Polar Surface Area: 65.07 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Light Brown Solid
• Melting Point: 154-161°C

Safety Information

• Storage Condition: Controlled Substance, -20°C Freezer

DETAILS

Toronto Research Chemicals - H281180

Narcotic analgesic prepared from morphine and acetic anhydride.Controlled substance (opium derivative).

REFERENCES

• Eddy, N.B., et al.: J. Pharmacol. Exp. Ther., 53, 430 (1935)
• Wyatt, L.T., et al.: Anal. Profiles Drug Subs., 10, 357 (1935)