ACCESSION: MSBNK-Athens_Univ-AU153310
RECORD_TITLE: Diacetylmorphine (Heroin); LC-ESI-QTOF; MS2; HILIC; CE: 40 eV; R=35000; [M+H]+
DATE: 2016.02.26
AUTHORS: Nikiforos Alygizakis, 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$LINK: CAS
209-217-7
CH$LINK: CHEBI
27808
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$MASS_SPECTROMETRY: COLLISION_ENERGY 40 eV
AC$MASS_SPECTROMETRY: RESOLUTION 35000
AC$CHROMATOGRAPHY: COLUMN_NAME ACQUITY UPLC BEH Amide 1.7 um 2.1x100mm, Waters
AC$CHROMATOGRAPHY: FLOW_GRADIENT 0/100 at 0-2 min, 95/5 at 12 min, 95/5 at 17 min, 0/100 at 17.1, 0/100 at 25 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 uL/min
AC$CHROMATOGRAPHY: RETENTION_TIME 5.993 min
AC$CHROMATOGRAPHY: SOLVENT A Water with 0.01% formic acid and 1mM ammonium formate
AC$CHROMATOGRAPHY: SOLVENT B Acetonitrile:Water 95:5 with 0.01% formic acid and 1mM 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: splash10-0300-0493000000-90f45b3a7ac00c6a1123
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
123.0447 C7H7O2+ 1 123.0441 5.22
132.0796 C9H10N+ 2 132.0808 -8.56
133.0872 C6H13O3+ 2 133.0859 9.31
137.0596 C8H9O2+ 1 137.0597 -1
141.0701 C11H9+ 1 141.0699 1.55
144.0808 C10H10N+ 2 144.0808 -0.11
145.0651 C10H9O+ 1 145.0648 2.03
146.0942 C7H14O3+ 2 146.0937 3.37
147.0437 C9H7O2+ 1 147.0441 -2.6
152.061 C12H8+ 1 152.0621 -7.23
153.0692 C12H9+ 1 153.0699 -4.18
154.0747 C12H10+ 2 154.0777 -19.5
155.0848 C12H11+ 1 155.0855 -4.98
157.0635 C11H9O+ 1 157.0648 -8.08
158.0948 C8H14O3+ 2 158.0937 6.76
159.1029 C8H15O3+ 2 159.1016 8.28
161.0594 C10H9O2+ 1 161.0597 -1.86
164.108 C10H14NO+ 2 164.107 5.94
165.0692 C13H9+ 1 165.0699 -4.04
166.0732 C12[13]CH9+ 1 166.0738 -3.43
167.0856 C13H11+ 1 167.0855 0.23
168.057 C12H8O+ 1 168.057 -0.07
169.0644 C12H9O+ 1 169.0648 -2.59
173.0591 C11H9O2+ 1 173.0597 -3.34
173.096 C12H13O+ 1 173.0961 -0.34
178.0848 C7H14O5+ 2 178.0836 6.87
179.0855 C14H11+ 1 179.0855 -0.07
181.0644 C13H9O+ 1 181.0648 -2.08
181.1012 C14H13+ 1 181.1012 0.35
182.0699 C13H10O+ 1 182.0726 -14.9
183.08 C13H11O+ 1 183.0804 -2.29
184.0847 C13H12O+ 1 184.0883 -19.23
184.1133 C13H14N+ 2 184.1121 6.66
185.0592 C12H9O2+ 1 185.0597 -2.88
186.066 C12H10O2+ 1 186.0675 -8.41
187.0748 C12H11O2+ 1 187.0754 -3.23
191.0848 C15H11+ 1 191.0855 -3.57
192.088 C14[13]CH11+ 1 192.0894 -7.45
193.0641 C14H9O+ 1 193.0648 -3.37
193.101 C15H13+ 1 193.1012 -0.66
194.0686 C13[13]CH9O+ 1 194.0687 -0.3
197.0583 C13H9O2+ 1 197.0597 -6.96
197.0966 C14H13O+ 1 197.0961 2.33
198.0651 C13H10O2+ 1 198.0675 -12.51
199.0738 C13H11O2+ 1 199.0754 -7.76
201.0902 C13H13O2+ 1 201.091 -4.13
202.0897 C12H12NO2+ 1 202.0863 16.93
203.07 C12H11O3+ 2 203.0703 -1.16
203.0879 C16H11+ 2 203.0855 11.78
207.0795 C15H11O+ 1 207.0804 -4.72
208.0852 C15H12O+ 1 208.0883 -14.62
209.0591 C14H9O2+ 1 209.0597 -2.97
209.0958 C15H13O+ 1 209.0961 -1.54
210.0634 C13[13]CH9O2+ 1 210.0636 -0.99
211.0752 C14H11O2+ 1 211.0754 -0.9
212.0784 C13[13]CH11O2+ 1 212.0793 -4.19
213.0823 C13H11NO2+ 1 213.0784 18.29
213.0895 C14H13O2+ 1 213.091 -6.97
218.0718 C16H10O+ 1 218.0726 -3.89
219.0797 C16H11O+ 1 219.0804 -3.24
220.0835 C15[13]CH11O+ 1 220.0843 -3.76
220.1092 C13H16O3+ 2 220.1094 -0.68
221.0951 C16H13O+ 1 221.0961 -4.4
222.0643 C15H10O2+ 1 222.0675 -14.48
222.0918 C15H12NO+ 2 222.0913 2.05
222.1258 C13H18O3+ 2 222.125 3.53
223.0744 C15H11O2+ 1 223.0754 -4.08
225.0915 C15H13O2+ 1 225.091 2.37
226.0889 C14H12NO2+ 2 226.0863 11.89
226.0965 C15H14O2+ 1 226.0988 -10.33
227.0695 C14H11O3+ 2 227.0703 -3.34
227.1091 C15H15O2+ 1 227.1067 10.56
229.0857 C14H13O3+ 2 229.0859 -0.94
232.1097 C14H16O3+ 2 232.1094 1.25
235.0972 C13H15O4+ 2 235.0965 3.08
236.1064 C16H14NO+ 2 236.107 -2.62
237.0906 C16H13O2+ 1 237.091 -1.8
238.0942 C16H14O2+ 1 238.0988 -19.43
239.1048 C16H15O2+ 1 239.1067 -7.87
240.1028 C15H14NO2+ 2 240.1019 3.84
240.1376 C16H18NO+ 2 240.1383 -2.92
243.1022 C15H15O3+ 2 243.1016 2.61
248.1044 C14H16O4+ 2 248.1043 0.23
249.1166 C17H15NO+ 2 249.1148 7.05
250.1217 C17H16NO+ 2 250.1226 -3.71
251.1276 C14H19O4+ 2 251.1278 -0.75
252.1048 C16H14NO2+ 2 252.1019 11.31
253.0882 C19H11N+ 3 253.0886 -1.45
253.1077 C13H17O5+ 2 253.1071 2.76
254.1138 C13H18O5+ 3 254.1149 -4.15
255.1023 C16H15O3+ 2 255.1016 2.82
256.1045 C16H16O3+ 1 256.1094 -19.12
266.1179 C17H16NO2+ 2 266.1176 1.16
267.1258 C17H17NO2+ 2 267.1254 1.55
268.1332 C17H18NO2+ 2 268.1332 0.05
269.0798 C16H13O4+ 2 269.0808 -3.96
269.1368 C14H21O5+ 3 269.1384 -5.73
270.1404 C13[13]CH21O5+ 1 270.1423 -7.03
271.0978 C16H15O4+ 2 271.0965 4.86
282.1119 C17H16NO3+ 1 282.1125 -2.1
286.1438 C17H20NO3+ 1 286.1438 0.24
287.1469 C16[13]CH20NO3+ 1 287.1477 -2.61
310.1441 C19H20NO3+ 1 310.1438 0.97
311.149 C18[13]CH20NO3+ 1 311.1477 4.16
328.1545 C19H22NO4+ 1 328.1543 0.57
329.1586 C18[13]CH22NO4+ 1 329.1582 1.23
370.1655 C21H24NO5+ 1 370.1649 1.68
371.168 C20[13]CH24NO5+ 1 371.1688 -2.25
PK$NUM_PEAK: 108
PK$PEAK: m/z int. rel.int.
123.0447 388 18
132.0796 356 17
133.0872 348 17
137.0596 584 28
141.0701 700 34
144.0808 456 22
145.0651 512 25
146.0942 380 18
147.0437 652 31
152.061 520 25
153.0692 856 41
154.0747 304 14
155.0848 956 46
157.0635 860 42
158.0948 312 15
159.1029 304 14
161.0594 1772 86
164.108 348 17
165.0692 8432 412
166.0732 1576 77
167.0856 464 22
168.057 352 17
169.0644 728 35
173.0591 1076 52
173.096 368 17
178.0848 588 28
179.0855 1568 76
181.0644 4360 213
181.1012 932 45
182.0699 664 32
183.08 4180 204
184.0847 520 25
184.1133 352 17
185.0592 1348 65
186.066 508 24
187.0748 1588 77
191.0848 6612 323
192.088 1108 54
193.0641 10540 515
193.101 696 34
194.0686 2004 97
197.0583 372 18
197.0966 448 21
198.0651 364 17
199.0738 804 39
201.0902 3808 186
202.0897 1072 52
203.07 792 38
203.0879 444 21
207.0795 2152 105
208.0852 336 16
209.0591 8520 416
209.0958 2552 124
210.0634 1276 62
211.0752 20304 992
212.0784 3652 178
213.0823 828 40
213.0895 712 34
218.0718 544 26
219.0797 6948 339
220.0835 1244 60
220.1092 300 14
221.0951 1580 77
222.0643 320 15
222.0918 388 18
222.1258 804 39
223.0744 328 16
225.0915 2036 99
226.0889 308 15
226.0965 400 19
227.0695 2728 133
227.1091 556 27
229.0857 3940 192
232.1097 300 14
235.0972 360 17
236.1064 316 15
237.0906 5996 292
238.0942 1792 87
239.1048 1608 78
240.1028 1708 83
240.1376 532 25
243.1022 424 20
248.1044 468 22
249.1166 320 15
250.1217 1536 75
251.1276 504 24
252.1048 620 30
253.0882 432 21
253.1077 1212 59
254.1138 384 18
255.1023 1936 94
256.1045 388 18
266.1179 1556 76
267.1258 1224 59
268.1332 20444 999
269.0798 936 45
269.1368 4592 224
270.1404 508 24
271.0978 344 16
282.1119 324 15
286.1438 3980 194
287.1469 540 26
310.1441 3664 179
311.149 752 36
328.1545 13812 674
329.1586 2380 116
370.1655 19756 965
371.168 5160 252
//
