ACCESSION: MSBNK-Athens_Univ-AU162303
RECORD_TITLE: Codeine; LC-ESI-QTOF; MS2; CE: 30 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 1623

CH$NAME: Codeine
CH$NAME: (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C₁₈H₂₁NO₃
CH$EXACT_MASS: 299.1521435
CH$SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O
CH$IUPAC: InChI=1S/C18H21NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3-6,11-13,17,20H,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
CH$LINK: CAS 76-57-3
CH$LINK: CHEBI 16714
CH$LINK: KEGG C06174
CH$LINK: PUBCHEM CID:5284371
CH$LINK: INCHIKEY OROGSEYTTFOCAN-DNJOTXNNSA-N
CH$LINK: CHEMSPIDER 4447447
CH$LINK: COMPTOX DTXSID2020341

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$MASS_SPECTROMETRY: COLLISION_ENERGY 30 eV
AC$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 3.570 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$FOCUSED_ION: BASE_PEAK 300.162
MS$FOCUSED_ION: PRECURSOR_M/Z 300.1594
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$SPLASH: splash10-0udi-0459000000-1a92521b38ba51a7fa81
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
  137.0598 C8H9O2+ 1 137.0597 0.49
  144.058 C10H8O+ 1 144.057 7.48
  153.0706 C12H9+ 1 153.0699 4.94
  155.0858 C12H11+ 1 155.0855 1.6
  159.081 C11H11O+ 1 159.0804 3.78
  161.0602 C10H9O2+ 1 161.0597 3.3
  165.0706 C13H9+ 1 165.0699 4.59
  166.0754 C12[13]CH9+ 1 166.0738 9.95
  168.0574 C12H8O+ 1 168.057 2.65
  171.0813 C12H11O+ 1 171.0804 4.75
  172.052 C11H8O2+ 1 172.0519 0.69
  172.0875 C12H12O+ 1 172.0883 -4.33
  174.0684 C11H10O2+ 1 174.0675 5.06
  175.0763 C11H11O2+ 1 175.0754 5.25
  181.0656 C13H9O+ 1 181.0648 4.56
  182.0722 C13H10O+ 1 182.0726 -2.22
  183.0813 C13H11O+ 1 183.0804 4.55
  184.0858 C12[13]CH11O+ 1 184.0843 8.14
  185.0601 C12H9O2+ 1 185.0597 2.07
  186.0677 C12H10O2+ 1 186.0675 0.66
  187.0764 C12H11O2+ 1 187.0754 5.67
  187.1128 C13H15O+ 1 187.1117 5.68
  188.0807 C11[13]CH11O2+ 1 188.0793 7.88
  191.0868 C15H11+ 1 191.0855 6.5
  192.1022 C11H14NO2+ 1 192.1019 1.57
  193.0659 C14H9O+ 1 193.0648 5.79
  193.1028 C15H13+ 1 193.1012 8.57
  194.0727 C14H10O+ 1 194.0726 0.63
  195.0804 C14H11O+ 1 195.0804 0.01
  197.0966 C14H13O+ 1 197.0961 2.62
  198.0682 C13H10O2+ 1 198.0675 3.37
  199.0765 C13H11O2+ 1 199.0754 5.66
  200.0816 C13H12O2+ 1 200.0832 -7.65
  201.0914 C13H13O2+ 1 201.091 2.12
  207.0811 C15H11O+ 1 207.0804 3.37
  209.0614 C14H9O2+ 1 209.0597 8.08
  209.0971 C15H13O+ 1 209.0961 4.99
  210.0664 C14H10O2+ 1 210.0675 -5.61
  211.0763 C14H11O2+ 1 211.0754 4.4
  212.0842 C14H12O2+ 1 212.0832 4.92
  213.0924 C14H13O2+ 1 213.091 6.54
  214.0957 C13[13]CH13O2+ 1 214.0949 3.61
  215.1084 C14H15O2+ 1 215.1067 8
  216.1112 C13[13]CH15O2+ 1 216.1106 2.97
  219.0821 C16H11O+ 1 219.0804 7.44
  220.0882 C16H12O+ 1 220.0883 -0.09
  221.0974 C16H13O+ 1 221.0961 5.86
  223.0768 C15H11O2+ 1 223.0754 6.55
  225.0923 C15H13O2+ 1 225.091 5.82
  226.0957 C14[13]CH13O2+ 1 226.0949 3.67
  236.0846 C16H12O2+ 1 236.0832 6.1
  237.0923 C16H13O2+ 1 237.091 5.25
  239.1074 C16H15O2+ 1 239.1067 3.01
  241.0873 C18H11N+ 2 241.0886 -5.21
  241.1245 C16H17O2+ 1 241.1223 9.04
  242.091 C17[13]CH11N+ 1 242.0925 -6.19
  243.1031 C18H13N+ 2 243.1043 -4.65
  244.1069 C17[13]CH13N+ 1 244.1082 -5.18
  251.108 C17H15O2+ 1 251.1067 5.51
  253.1237 C17H17O2+ 1 253.1223 5.31
  266.119 C17H16NO2+ 1 266.1176 5.31
  267.1271 C17H17NO2+ 1 267.1254 6.51
  269.1199 C17H17O3+ 1 269.1172 10.01
  282.1506 C18H20NO2+ 1 282.1489 6.26
  283.1536 C17[13]CH20NO2+ 1 283.1528 2.99
  300.1621 C18H22NO3+ 1 300.1594 8.92
  301.1651 C17[13]CH22NO3+ 1 301.1633 6.05
  302.1674 C16[13]C2H22NO3+ 1 302.1667 2.44
PK$NUM_PEAK: 68
PK$PEAK: m/z int. rel.int.
  137.0598 5916 9
  144.058 3836 6
  153.0706 6916 11
  155.0858 11068 17
  159.081 9428 15
  161.0602 18664 30
  165.0706 20744 33
  166.0754 4860 7
  168.0574 3828 6
  171.0813 9604 15
  172.052 3172 5
  172.0875 3744 6
  174.0684 3116 5
  175.0763 6352 10
  181.0656 16688 27
  182.0722 5872 9
  183.0813 42984 69
  184.0858 7780 12
  185.0601 5000 8
  186.0677 4772 7
  187.0764 24360 39
  187.1128 9028 14
  188.0807 3236 5
  191.0868 6552 10
  192.1022 4756 7
  193.0659 19556 31
  193.1028 3412 5
  194.0727 10132 16
  195.0804 5324 8
  197.0966 7752 12
  198.0682 4300 6
  199.0765 52056 84
  200.0816 12984 21
  201.0914 6176 9
  207.0811 3660 5
  209.0614 13880 22
  209.0971 6152 9
  210.0664 6384 10
  211.0763 8864 14
  212.0842 7036 11
  213.0924 15004 24
  214.0957 3224 5
  215.1084 108692 175
  216.1112 15724 25
  219.0821 6384 10
  220.0882 3488 5
  221.0974 8016 12
  223.0768 9136 14
  225.0923 51128 82
  226.0957 9660 15
  236.0846 4228 6
  237.0923 3224 5
  239.1074 3172 5
  241.0873 29000 46
  241.1245 3500 5
  242.091 5340 8
  243.1031 70028 113
  244.1069 11904 19
  251.108 7636 12
  253.1237 6708 10
  266.119 7776 12
  267.1271 8364 13
  269.1199 4416 7
  282.1506 22920 37
  283.1536 4672 7
  300.1621 617280 999
  301.1651 109584 177
  302.1674 10732 17
//