ACCESSION: MSBNK-Athens_Univ-AU153311
RECORD_TITLE: Diacetylmorphine (Heroin); LC-ESI-QTOF; MS2; HILIC; CE: 50 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$MASS_SPECTROMETRY: COLLISION_ENERGY 50 eV
AC$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$FOCUSED_ION: BASE_PEAK 370.1652
MS$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$SPLASH: splash10-015c-0960000000-4efe45d17d1e3c8bd7ff
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
  115.0531 C9H7+ 1 115.0542 -9.4
  117.0684 C9H9+ 1 117.0699 -12.86
  121.0638 C8H9O+ 1 121.0648 -8.56
  123.0438 C7H7O2+ 1 123.0441 -1.95
  128.0627 C10H8+ 1 128.0621 5.4
  131.0478 C9H7O+ 1 131.0491 -10.27
  131.0716 C9H9N+ 2 131.073 -9.99
  132.0791 C6H12O3+ 2 132.0781 7.86
  135.0436 C8H7O2+ 1 135.0441 -3.05
  141.0695 C11H9+ 1 141.0699 -2.61
  144.0581 C10H8O+ 1 144.057 7.98
  144.0798 C10H10N+ 2 144.0808 -6.59
  145.0632 C10H9O+ 1 145.0648 -10.83
  146.0591 C9H8NO+ 2 146.06 -6.55
  146.0695 C10H10O+ 1 146.0726 -21.67
  146.0952 C10H12N+ 2 146.0964 -8.69
  147.0438 C9H7O2+ 1 147.0441 -1.59
  152.0614 C12H8+ 1 152.0621 -4.17
  153.0688 C12H9+ 1 153.0699 -6.82
  154.0748 C12H10+ 2 154.0777 -18.77
  155.0847 C12H11+ 1 155.0855 -5.37
  156.0885 C4H14NO5+ 1 156.0866 11.72
  157.0631 C11H9O+ 1 157.0648 -10.94
  158.0691 C11H10O+ 1 158.0726 -22.25
  158.0968 C11H12N+ 2 158.0964 2.2
  159.1031 C11H13N+ 2 159.1043 -7.37
  160.075 C10H10NO+ 2 160.0757 -4.11
  161.0591 C10H9O2+ 1 161.0597 -3.6
  164.0682 C6H12O5+ 2 164.0679 1.4
  165.0691 C13H9+ 1 165.0699 -4.85
  166.0733 C12[13]CH9+ 1 166.0738 -2.65
  167.0832 C13H11+ 1 167.0855 -13.88
  168.0564 C12H8O+ 1 168.057 -3.46
  169.0638 C12H9O+ 1 169.0648 -6.11
  171.0444 C11H7O2+ 1 171.0441 1.75
  171.0776 C12H11O+ 1 171.0804 -16.33
  173.0585 C11H9O2+ 1 173.0597 -7
  173.0956 C12H13O+ 1 173.0961 -2.67
  176.0711 C10H10NO2+ 2 176.0706 2.93
  178.0778 C14H10+ 1 178.0777 0.67
  179.0852 C14H11+ 1 179.0855 -1.94
  180.0882 C6H14NO5+ 1 180.0866 8.65
  181.0642 C13H9O+ 1 181.0648 -3.48
  181.101 C14H13+ 1 181.1012 -0.81
  182.0674 C12[13]CH9O+ 1 182.0687 -6.86
  183.0797 C13H11O+ 1 183.0804 -3.88
  184.0824 C12[13]CH11O+ 1 184.0843 -10.8
  185.0591 C12H9O2+ 1 185.0597 -3.35
  186.0667 C12H10O2+ 1 186.0675 -4.62
  187.0752 C12H11O2+ 1 187.0754 -0.85
  189.0699 C15H9+ 1 189.0699 0.02
  190.0763 C15H10+ 1 190.0777 -7.25
  191.0848 C15H11+ 1 191.0855 -3.61
  192.0888 C14[13]CH11+ 1 192.0894 -3.52
  193.0636 C14H9O+ 1 193.0648 -5.95
  193.1001 C15H13+ 1 193.1012 -5.48
  194.0688 C14H10O+ 1 194.0726 -19.64
  195.0788 C14H11O+ 1 195.0804 -8.32
  196.0485 C13H8O2+ 1 196.0519 -17.45
  197.0584 C13H9O2+ 1 197.0597 -6.78
  197.0945 C14H13O+ 1 197.0961 -8.28
  198.0657 C13H10O2+ 1 198.0675 -9.46
  198.0926 C13H12NO+ 2 198.0913 6.29
  199.0751 C13H11O2+ 1 199.0754 -1.22
  201.0711 C16H9+ 2 201.0699 6.12
  201.0908 C13H13O2+ 1 201.091 -0.91
  202.0769 C16H10+ 1 202.0777 -3.89
  203.0826 C16H11+ 2 203.0855 -14.63
  203.0881 C16H11+ 2 203.0855 12.64
  205.0667 C15H9O+ 1 205.0648 9.44
  207.0802 C15H11O+ 1 207.0804 -1.32
  208.0848 C15H12O+ 1 208.0883 -16.77
  209.0593 C14H9O2+ 1 209.0597 -1.86
  209.0945 C15H13O+ 1 209.0961 -7.6
  210.0635 C13[13]CH9O2+ 1 210.0636 -0.29
  211.0745 C14H11O2+ 1 211.0754 -3.91
  212.0796 C13[13]CH11O2+ 1 212.0793 1.44
  213.0516 C13H9O3+ 1 213.0546 -14.28
  214.0608 C13H10O3+ 2 214.0624 -7.59
  216.0997 C10H16O5+ 2 216.0992 2.14
  218.072 C16H10O+ 1 218.0726 -2.6
  219.0797 C16H11O+ 1 219.0804 -3.51
  220.0831 C16H12O+ 1 220.0883 -23.35
  220.1105 C13H16O3+ 2 220.1094 4.84
  221.0586 C15H9O2+ 1 221.0597 -4.99
  221.0958 C16H13O+ 1 221.0961 -1.15
  222.0684 C15H10O2+ 1 222.0675 4.1
  222.0917 C15H12NO+ 2 222.0913 1.61
  222.1281 C16H16N+ 3 222.1277 1.77
  223.0736 C15H11O2+ 1 223.0754 -8
  225.0902 C15H13O2+ 1 225.091 -3.8
  227.07 C14H11O3+ 2 227.0703 -1.11
  227.1038 C15H15O2+ 1 227.1067 -12.69
  228.0762 C14H12O3+ 2 228.0781 -8.48
  228.1008 C14H14NO2+ 2 228.1019 -4.92
  229.0844 C14H13O3+ 2 229.0859 -6.64
  230.0852 C13H12NO3+ 1 230.0812 17.35
  234.0909 C16H12NO+ 2 234.0913 -2.07
  235.0985 C16H13NO+ 2 235.0992 -2.9
  236.1053 C13H16O4+ 2 236.1043 4.24
  237.0898 C16H13O2+ 1 237.091 -5.27
  238.0937 C16H14O2+ 1 238.0988 -21.48
  239.0952 C15H13NO2+ 2 239.0941 4.72
  240.1027 C15H14NO2+ 2 240.1019 3.12
  240.1385 C16H18NO+ 2 240.1383 0.93
  250.1211 C14H18O4+ 2 250.12 4.43
  251.1265 C14H19O4+ 2 251.1278 -5.21
  252.1043 C16H14NO2+ 2 252.1019 9.69
  253.1072 C13H17O5+ 3 253.1071 0.41
  255.098 C16H15O3+ 2 255.1016 -13.88
  266.117 C17H16NO2+ 2 266.1176 -2.13
  267.1231 C14H19O5+ 3 267.1227 1.45
  268.1335 C17H18NO2+ 2 268.1332 1.12
  269.0815 C16H13O4+ 2 269.0808 2.31
  269.1359 C16[13]CH18NO2+ 1 269.1371 -4.54
  286.1435 C17H20NO3+ 1 286.1438 -1.02
  328.1545 C19H22NO4+ 1 328.1543 0.56
  329.1565 C19H23NO4+ 1 329.1622 -17.15
  370.1665 C21H24NO5+ 1 370.1649 4.44
PK$NUM_PEAK: 119
PK$PEAK: m/z int. rel.int.
  115.0531 644 41
  117.0684 408 26
  121.0638 528 34
  123.0438 376 24
  128.0627 408 26
  131.0478 496 31
  131.0716 392 25
  132.0791 316 20
  135.0436 308 19
  141.0695 1812 116
  144.0581 352 22
  144.0798 328 21
  145.0632 940 60
  146.0591 428 27
  146.0695 328 21
  146.0952 300 19
  147.0438 1080 69
  152.0614 936 60
  153.0688 3152 203
  154.0748 516 33
  155.0847 2820 181
  156.0885 400 25
  157.0631 1360 87
  158.0691 496 31
  158.0968 412 26
  159.1031 344 22
  160.075 344 22
  161.0591 1084 69
  164.0682 312 20
  165.0691 15500 999
  166.0733 2908 187
  167.0832 636 40
  168.0564 600 38
  169.0638 1220 78
  171.0444 440 28
  171.0776 444 28
  173.0585 1016 65
  173.0956 484 31
  176.0711 436 28
  178.0778 1252 80
  179.0852 1780 114
  180.0882 548 35
  181.0642 8396 541
  181.101 768 49
  182.0674 1732 111
  183.0797 4924 317
  184.0824 880 56
  185.0591 2044 131
  186.0667 752 48
  187.0752 1300 83
  189.0699 876 56
  190.0763 1436 92
  191.0848 7848 505
  192.0888 1420 91
  193.0636 7088 456
  193.1001 744 47
  194.0688 1944 125
  195.0788 544 35
  196.0485 332 21
  197.0584 816 52
  197.0945 868 55
  198.0657 348 22
  198.0926 328 21
  199.0751 1036 66
  201.0711 676 43
  201.0908 2772 178
  202.0769 548 35
  203.0826 348 22
  203.0881 388 25
  205.0667 316 20
  207.0802 1148 73
  208.0848 356 22
  209.0593 7620 491
  209.0945 2068 133
  210.0635 2032 130
  211.0745 9136 588
  212.0796 2056 132
  213.0516 308 19
  214.0608 632 40
  216.0997 316 20
  218.072 832 53
  219.0797 3348 215
  220.0831 816 52
  220.1105 484 31
  221.0586 324 20
  221.0958 968 62
  222.0684 724 46
  222.0917 412 26
  222.1281 536 34
  223.0736 300 19
  225.0902 1028 66
  227.07 2156 138
  227.1038 396 25
  228.0762 308 19
  228.1008 388 25
  229.0844 1652 106
  230.0852 520 33
  234.0909 552 35
  235.0985 432 27
  236.1053 300 19
  237.0898 3060 197
  238.0937 680 43
  239.0952 380 24
  240.1027 836 53
  240.1385 492 31
  250.1211 652 42
  251.1265 420 27
  252.1043 896 57
  253.1072 876 56
  255.098 580 37
  266.117 1188 76
  267.1231 556 35
  268.1335 5168 333
  269.0815 316 20
  269.1359 1532 98
  286.1435 984 63
  328.1545 2104 135
  329.1565 464 29
  370.1665 904 58
//