ACCESSION: MSBNK-Athens_Univ-AU153304
RECORD_TITLE: Diacetylmorphine (Heroin); LC-ESI-QTOF; MS2; CE: 40 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$MASS_SPECTROMETRY: COLLISION_ENERGY 40 eV
AC$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 4.836 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$FOCUSED_ION: BASE_PEAK 370.1671
MS$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$SPLASH: splash10-0303-0593000000-b8c7c4e8760df849eeb2
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
  145.0622 C10H9O+ 1 145.0648 -18.15
  152.0613 C12H8+ 1 152.0621 -4.9
  153.0701 C12H9+ 1 153.0699 1.34
  155.0867 C12H11+ 1 155.0855 7.87
  157.0645 C11H9O+ 1 157.0648 -2.16
  161.06 C10H9O2+ 1 161.0597 1.73
  165.0702 C13H9+ 1 165.0699 2.19
  166.075 C13H10+ 2 166.0777 -16.07
  173.0617 C11H9O2+ 1 173.0597 11.79
  178.0839 C7H14O5+ 2 178.0836 1.56
  179.0854 C14H11+ 1 179.0855 -0.62
  181.0633 C13H9O+ 1 181.0648 -7.96
  183.0802 C13H11O+ 1 183.0804 -1.17
  184.0846 C13H12O+ 1 184.0883 -19.77
  185.0612 C12H9O2+ 1 185.0597 7.96
  187.0743 C12H11O2+ 1 187.0754 -5.65
  190.0779 C15H10+ 1 190.0777 1.27
  191.0854 C15H11+ 1 191.0855 -0.64
  192.09 C14[13]CH11+ 1 192.0894 3
  193.0644 C14H9O+ 1 193.0648 -2.05
  193.1011 C15H13+ 1 193.1012 -0.26
  194.07 C13[13]CH9O+ 1 194.0687 6.5
  199.0768 C13H11O2+ 1 199.0754 7.19
  201.0929 C13H13O2+ 1 201.091 9.26
  202.0893 C12H12NO2+ 1 202.0863 15.28
  207.08 C15H11O+ 1 207.0804 -1.97
  208.091 C15H12O+ 1 208.0883 13.32
  209.0604 C14H9O2+ 1 209.0597 3.21
  209.0979 C15H13O+ 1 209.0961 8.86
  210.0639 C14H10O2+ 1 210.0675 -17.47
  211.0758 C14H11O2+ 1 211.0754 2
  212.0809 C13[13]CH11O2+ 1 212.0793 7.86
  218.0757 C16H10O+ 1 218.0726 14.04
  219.0809 C16H11O+ 1 219.0804 2.04
  221.0943 C16H13O+ 1 221.0961 -8.06
  223.0726 C15H11O2+ 1 223.0754 -12.43
  225.0905 C15H13O2+ 1 225.091 -2.17
  227.0716 C14H11O3+ 2 227.0703 5.8
  227.1079 C15H15O2+ 1 227.1067 5.64
  229.0867 C14H13O3+ 2 229.0859 3.24
  229.1078 C11H17O5+ 2 229.1071 3.07
  230.0889 C14H14O3+ 1 230.0937 -21.13
  237.0921 C16H13O2+ 1 237.091 4.57
  238.0935 C16H14O2+ 1 238.0988 -22.25
  239.1073 C16H15O2+ 1 239.1067 2.66
  240.1042 C15H14NO2+ 2 240.1019 9.65
  250.1247 C17H16NO+ 2 250.1226 8.29
  253.0865 C16H13O3+ 2 253.0859 2.23
  253.1094 C16H15NO2+ 2 253.1097 -1.47
  255.101 C16H15O3+ 2 255.1016 -2.09
  266.1185 C17H16NO2+ 2 266.1176 3.38
  267.1292 C17H17NO2+ 2 267.1254 14.19
  268.1335 C17H18NO2+ 2 268.1332 1.06
  269.1384 C16[13]CH18NO2+ 1 269.1371 4.78
  286.1447 C17H20NO3+ 1 286.1438 3.31
  310.145 C19H20NO3+ 1 310.1438 4.12
  311.1508 C19H21NO3+ 1 311.1516 -2.53
  328.1554 C19H22NO4+ 1 328.1543 3.18
  329.158 C18[13]CH22NO4+ 1 329.1582 -0.62
  370.1673 C21H24NO5+ 1 370.1649 6.58
  371.1699 C20[13]CH24NO5+ 1 371.1688 2.86
PK$NUM_PEAK: 61
PK$PEAK: m/z int. rel.int.
  145.0622 428 46
  152.0613 440 48
  153.0701 496 54
  155.0867 404 44
  157.0645 380 41
  161.06 528 57
  165.0702 3564 391
  166.075 752 82
  173.0617 680 74
  178.0839 336 36
  179.0854 608 66
  181.0633 1660 182
  183.0802 2744 301
  184.0846 344 37
  185.0612 796 87
  187.0743 1068 117
  190.0779 432 47
  191.0854 3612 396
  192.09 620 68
  193.0644 5284 580
  193.1011 444 48
  194.07 1028 112
  199.0768 388 42
  201.0929 2076 227
  202.0893 376 41
  207.08 832 91
  208.091 320 35
  209.0604 3460 379
  209.0979 1068 117
  210.0639 596 65
  211.0758 9100 999
  212.0809 1528 167
  218.0757 308 33
  219.0809 2820 309
  221.0943 700 76
  223.0726 444 48
  225.0905 732 80
  227.0716 704 77
  227.1079 300 32
  229.0867 2244 246
  229.1078 304 33
  230.0889 476 52
  237.0921 2492 273
  238.0935 712 78
  239.1073 856 93
  240.1042 740 81
  250.1247 448 49
  253.0865 384 42
  253.1094 604 66
  255.101 932 102
  266.1185 476 52
  267.1292 416 45
  268.1335 8768 962
  269.1384 1732 190
  286.1447 1084 119
  310.145 1448 158
  311.1508 412 45
  328.1554 5196 570
  329.158 1016 111
  370.1673 8156 895
  371.1699 2220 243
//