ACCESSION: MSBNK-Athens_Univ-AU153305
RECORD_TITLE: Diacetylmorphine (Heroin); LC-ESI-QTOF; MS2; CE: 50 eV; R=35000; [M+H]+
DATE: 2016.02.22
AUTHORS: Nikiforos Alygizakis, Reza Aalizadeh, Nikolaos Thomaidis, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2016 Department of Chemistry, University of Athens
COMMENT: CONFIDENCE standard compound
COMMENT: INTERNAL_ID 1533
CH$NAME: Diacetylmorphine (Heroin)
CH$NAME: Diacetylmorphine
CH$NAME: [(4R,4aR,7S,7aR,12bS)-9-acetyloxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-yl] acetate
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C21H23NO5
CH$EXACT_MASS: 369.1576228
CH$SMILES: CC(=O)Oc1ccc2c3c1O[C@@H]4[C@]35CCN([C@H](C2)[C@@H]5C=C[C@@H]4OC(=O)C)C
CH$IUPAC: 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
CH$LINK: CAS
561-27-3
CH$LINK: CHEBI
27808
CH$LINK: KEGG
D07286
CH$LINK: PUBCHEM
CID:5462328
CH$LINK: INCHIKEY
GVGLGOZIDCSQPN-PVHGPHFFSA-N
CH$LINK: CHEMSPIDER
4575379
CH$LINK: COMPTOX
DTXSID6046761
AC$INSTRUMENT: Bruker maXis Impact
AC$INSTRUMENT_TYPE: LC-ESI-QTOF
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 50 eV
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
AC$CHROMATOGRAPHY: FLOW_GRADIENT 99/1 at 0-1 min, 61/39 at 3 min, 0.1/99.9 at 14-16 min, 99/1 at 16.1-20 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 uL/min at 0-3 min, 400 uL/min at 14 min, 480 uL/min at 16-19 min, 200 uL/min at 19.1-20 min
AC$CHROMATOGRAPHY: RETENTION_TIME 4.820 min
AC$CHROMATOGRAPHY: SOLVENT A 90:10 water:methanol with 0.01% formic acid and 5mM ammonium formate
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.01% formic acid and 5mM ammonium formate
MS$FOCUSED_ION: BASE_PEAK 370.166
MS$FOCUSED_ION: PRECURSOR_M/Z 370.1649
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: RECALIBRATE identity on assigned fragments and MS1
MS$DATA_PROCESSING: WHOLE RMassBank 1.99.10
PK$SPLASH: splash10-014l-0950000000-9cd1cf455c3a42888ee6
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
117.0694 C9H9+ 1 117.0699 -4.34
141.0699 C11H9+ 1 141.0699 0.27
145.0638 C10H9O+ 1 145.0648 -6.68
147.0432 C9H7O2+ 1 147.0441 -6.03
152.062 C12H8+ 1 152.0621 -0.54
153.0697 C12H9+ 1 153.0699 -1.24
154.0718 C4H12NO5+ 1 154.071 5.46
155.0863 C12H11+ 1 155.0855 5.21
157.0645 C11H9O+ 1 157.0648 -2.1
159.0815 C11H11O+ 1 159.0804 6.93
161.0601 C10H9O2+ 1 161.0597 2.21
165.0699 C13H9+ 1 165.0699 0.12
166.0745 C12[13]CH9+ 1 166.0738 4.24
167.0811 C5H13NO5+ 1 167.0788 13.33
168.0562 C12H8O+ 1 168.057 -4.51
169.0647 C12H9O+ 1 169.0648 -0.81
171.0438 C11H7O2+ 1 171.0441 -1.29
173.0576 C11H9O2+ 1 173.0597 -12
174.0642 C11H10O2+ 1 174.0675 -19.21
178.0801 C14H10+ 2 178.0777 13.52
179.0853 C14H11+ 1 179.0855 -1.5
181.0649 C13H9O+ 1 181.0648 0.34
181.1026 C14H13+ 2 181.1012 7.63
182.0688 C13H10O+ 1 182.0726 -20.86
183.0801 C13H11O+ 1 183.0804 -1.72
185.0605 C12H9O2+ 1 185.0597 4.04
186.0655 C12H10O2+ 1 186.0675 -10.71
187.0749 C12H11O2+ 1 187.0754 -2.44
189.0713 C15H9+ 2 189.0699 7.32
190.0765 C15H10+ 1 190.0777 -6.37
191.0851 C15H11+ 1 191.0855 -1.98
192.0883 C7H14NO5+ 1 192.0866 8.56
193.0655 C14H9O+ 1 193.0648 3.48
193.1026 C15H13+ 2 193.1012 7.53
194.0713 C14H10O+ 1 194.0726 -6.53
195.0801 C14H11O+ 1 195.0804 -1.54
197.0584 C13H9O2+ 1 197.0597 -6.77
199.0762 C13H11O2+ 1 199.0754 4.15
201.0905 C13H13O2+ 1 201.091 -2.46
202.0806 C16H10+ 2 202.0777 14.28
203.0868 C16H11+ 2 203.0855 6.44
207.0786 C15H11O+ 1 207.0804 -8.85
208.0514 C14H8O2+ 1 208.0519 -2.32
209.06 C14H9O2+ 1 209.0597 1.29
209.094 C15H13O+ 1 209.0961 -10.18
211.0755 C14H11O2+ 1 211.0754 0.74
212.0817 C14H12O2+ 1 212.0832 -6.81
218.0728 C16H10O+ 1 218.0726 0.81
219.081 C16H11O+ 1 219.0804 2.35
220.0861 C16H12O+ 1 220.0883 -9.65
221.0972 C16H13O+ 1 221.0961 4.93
222.0688 C15H10O2+ 1 222.0675 5.52
222.1282 C16H16N+ 3 222.1277 2.36
225.0865 C15H13O2+ 1 225.091 -20.08
227.0717 C17H9N+ 2 227.073 -5.61
229.0856 C14H13O3+ 2 229.0859 -1.23
237.0919 C16H13O2+ 1 237.091 3.74
238.096 C16H14O2+ 1 238.0988 -11.97
239.1047 C16H15O2+ 1 239.1067 -8.24
240.1019 C15H14NO2+ 2 240.1019 0.08
240.1395 C16H18NO+ 2 240.1383 4.94
250.124 C17H16NO+ 2 250.1226 5.26
252.1006 C16H14NO2+ 2 252.1019 -5.01
253.1102 C16H15NO2+ 2 253.1097 1.72
254.1151 C13H18O5+ 3 254.1149 0.75
266.1204 C17H16NO2+ 2 266.1176 10.63
268.1326 C17H18NO2+ 2 268.1332 -2.34
269.1379 C14H21O5+ 3 269.1384 -1.5
286.1453 C17H20NO3+ 1 286.1438 5.49
328.1552 C19H22NO4+ 1 328.1543 2.79
329.1585 C19H23NO4+ 1 329.1622 -11.07
370.1652 C21H24NO5+ 1 370.1649 0.79
PK$NUM_PEAK: 72
PK$PEAK: m/z int. rel.int.
117.0694 304 33
141.0699 576 63
145.0638 708 77
147.0432 416 45
152.062 528 57
153.0697 2056 225
154.0718 432 47
155.0863 1448 158
157.0645 816 89
159.0815 308 33
161.0601 368 40
165.0699 9120 999
166.0745 1396 152
167.0811 400 43
168.0562 500 54
169.0647 744 81
171.0438 324 35
173.0576 768 84
174.0642 312 34
178.0801 612 67
179.0853 956 104
181.0649 4172 456
181.1026 492 53
182.0688 768 84
183.0801 3000 328
185.0605 800 87
186.0655 504 55
187.0749 860 94
189.0713 412 45
190.0765 932 102
191.0851 5152 564
192.0883 720 78
193.0655 3720 407
193.1026 500 54
194.0713 960 105
195.0801 324 35
197.0584 416 45
199.0762 832 91
201.0905 1892 207
202.0806 460 50
203.0868 416 45
207.0786 724 79
208.0514 380 41
209.06 3852 421
209.094 1060 116
211.0755 4412 483
212.0817 980 107
218.0728 312 34
219.081 2432 266
220.0861 492 53
221.0972 416 45
222.0688 340 37
222.1282 508 55
225.0865 452 49
227.0717 1396 152
229.0856 1228 134
237.0919 1364 149
238.096 300 32
239.1047 360 39
240.1019 312 34
240.1395 392 42
250.124 336 36
252.1006 424 46
253.1102 308 33
254.1151 304 33
266.1204 536 58
268.1326 3040 333
269.1379 832 91
286.1453 432 47
328.1552 1248 136
329.1585 516 56
370.1652 424 46
//
