(1S,5S,13R,14S,17R)-4-acetyl-14-(acetyloxy)-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: 159387
• Molecular Formular: C22H23NO6
• Molecular Mass: 397.42112
• Monoisotopic Mass: 397.15253746
• SMILES: c1(c2c3c(cc1)C[C@H]1[C@H]4[C@@]3([C@H]([C@H](C=C4)OC(=O)C)O2)CCN1C(=O)C)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(=O)C)ccc1OC(=O)C
• InChI: InChI=1S/C22H23NO6/c1-11(24)23-9-8-22-15-5-7-18(28-13(3)26)21(22)29-20-17(27-12(2)25)6-4-14(19(20)22)10-16(15)23/h4-7,15-16,18,21H,8-10H2,1-3H3/t15-,16-,18-,21-,22-/m0/s1
• InChIKey: LJFIFOPYTFFRKD-CAUQANCSSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (1S,5S,13R,14S,17R)-4-acetyl-14-(acetyloxy)-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,5S,13R,14S,17R)-4-acetyl-14-(acetyloxy)-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: 1-[(5α,6α)-3,6-Bis(acetyloxy)-7,8-didehydro-4,5-epoxymorphinan-17-yl]ethanone; N,3,6-Triacetylnormorphine; N,O3,O6-Triacetylnormorphine; N-Acetylnorheroin

Database IDs

• CAS Number: 65846-34-6
• PubChem SID: 162253522
• PubChem CID: 71312965

CALCULATED PROPERTIES

• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.7759013
• LogD (pH = 7.4): 0.7759032
• Log P: 0.7759033
• Molar Refractivity: 102.6966 cm^3
• Polarizability: 40.089516 Å^3
• Polar Surface Area: 82.14 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A187290

A pyrolysis product of street heroin observed during the act of “chasing the dragon”.

REFERENCES

• Brenneisen, R., et al.: J. Forens. Sci., 47, 885 (2002)
• Klous, M., et al.: J. Anal. Toxicol., 30, 6 (2002)