MassBank Record: AU162304

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Codeine; LC-ESI-QTOF; MS2; CE: 40 eV; R=35000; [M+H]+
Mass Spectrum
Chemical Structure
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ACCESSION: AU162304
RECORD_TITLE: Codeine; 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 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$MASS_SPECTROMETRY: COLLISION_ENERGY 40 eV AC$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 3.548 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$FOCUSED_ION: BASE_PEAK 300.1615 MS$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: splash10-0gc1-0940000000-68cae285315cfe9c7d0e PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm) 115.0546 C9H7+ 1 115.0542 3.36 116.0593 C9H8+ 1 116.0621 -23.96 117.0694 C9H9+ 1 117.0699 -3.75 121.0651 C8H9O+ 1 121.0648 2.31 122.0362 C7H6O2+ 1 122.0362 -0.42 127.0554 C10H7+ 1 127.0542 8.96 128.0626 C10H8+ 1 128.0621 4.18 129.0702 C10H9+ 1 129.0699 2.57 130.0418 C9H6O+ 1 130.0413 4.04 130.0752 C10H10+ 1 130.0777 -19.09 131.05 C9H7O+ 1 131.0491 6.32 131.0738 C9H9N+ 1 131.073 6.33 131.086 C10H11+ 1 131.0855 3.92 132.0826 C9H10N+ 1 132.0808 14 133.0659 C9H9O+ 1 133.0648 8.58 134.0993 C9H12N+ 1 134.0964 21.3 137.0604 C8H9O2+ 1 137.0597 4.9 138.0631 C7[13]CH9O2+ 1 138.0636 -4.04 139.0543 C11H7+ 1 139.0542 0.84 140.0614 C11H8+ 1 140.0621 -4.98 141.0704 C11H9+ 1 141.0699 3.43 142.0758 C11H10+ 1 142.0777 -13.3 143.0498 C10H7O+ 1 143.0491 4.49 143.0867 C11H11+ 1 143.0855 8 144.0576 C10H8O+ 1 144.057 4.68 145.0646 C10H9O+ 1 145.0648 -1.44 146.036 C9H6O2+ 1 146.0362 -1.27 146.062 C9H8NO+ 1 146.06 13.64 146.0716 C10H10O+ 1 146.0726 -7.14 146.0966 C10H12N+ 2 146.0964 1 147.0422 C9H7O2+ 1 147.0441 -12.31 147.066 C9H9NO+ 1 147.0679 -12.87 147.0805 C10H11O+ 1 147.0804 0.21 148.0533 C9H8O2+ 1 148.0519 9.53 148.0755 C9H10NO+ 1 148.0757 -0.99 149.0617 C9H9O2+ 1 149.0597 13.59 150.0473 C12H6+ 1 150.0464 5.71 151.0545 C12H7+ 1 151.0542 1.8 151.078 C9H11O2+ 1 151.0754 17.36 152.0626 C12H8+ 1 152.0621 3.81 153.0705 C12H9+ 1 153.0699 4.34 154.0764 C12H10+ 1 154.0777 -8.21 155.0501 C11H7O+ 1 155.0491 5.88 155.0862 C12H11+ 1 155.0855 4.1 156.0575 C11H8O+ 1 156.057 3.49 156.0901 C11[13]CH11+ 1 156.0894 4.24 157.0649 C11H9O+ 1 157.0648 0.93 157.1028 C12H13+ 1 157.1012 10.56 158.0731 C11H10O+ 1 158.0726 3 158.0979 C11H12N+ 1 158.0964 9.42 159.0453 C10H7O2+ 1 159.0441 7.59 159.0804 C11H11O+ 1 159.0804 -0.06 160.0507 C10H8O2+ 1 160.0519 -7.27 160.0832 C10[13]CH11O+ 1 160.0843 -7.44 161.0604 C10H9O2+ 1 161.0597 4.02 162.065 C9[13]CH9O2+ 1 162.0636 8.64 162.0917 C10H12NO+ 1 162.0913 2.16 163.0639 C9H9NO2+ 1 163.0628 6.95 163.076 C10H11O2+ 1 163.0754 4.16 164.0705 C9H10NO2+ 1 164.0706 -0.69 165.0707 C13H9+ 1 165.0699 5.19 166.0761 C12[13]CH9+ 1 166.0738 13.95 167.0505 C12H7O+ 1 167.0491 7.85 167.0855 C13H11+ 1 167.0855 0.08 168.0574 C12H8O+ 1 168.057 2.39 168.0895 C12[13]CH11+ 1 168.0894 0.14 169.0652 C12H9O+ 1 169.0648 2.6 169.1014 C13H13+ 1 169.1012 1.41 170.0366 C11H6O2+ 1 170.0362 2.39 170.0734 C12H10O+ 1 170.0726 4.8 170.0996 C12H12N+ 1 170.0964 18.81 171.0455 C11H7O2+ 1 171.0441 8.38 171.0812 C12H11O+ 1 171.0804 4.49 172.0523 C11H8O2+ 1 172.0519 2.43 172.0876 C12H12O+ 1 172.0883 -3.68 173.0586 C11H9O2+ 1 173.0597 -6.46 173.0955 C12H13O+ 1 173.0961 -3.56 174.0682 C11H10O2+ 1 174.0675 4.11 174.1003 C11[13]CH13O+ 1 174.1 2.01 175.0757 C11H11O2+ 1 175.0754 2.15 176.0794 C10[13]CH11O2+ 1 176.0793 0.93 177.0554 C10H9O3+ 2 177.0546 4.25 177.0715 C14H9+ 1 177.0699 8.89 178.0786 C14H10+ 1 178.0777 4.77 179.0867 C14H11+ 1 179.0855 6.5 180.0577 C13H8O+ 1 180.057 4 180.0935 C13[13]CH11+ 1 180.0894 22.87 181.0657 C13H9O+ 1 181.0648 5.27 181.1024 C14H13+ 1 181.1012 7.02 182.0722 C13H10O+ 1 182.0726 -2.26 182.1057 C13[13]CH13+ 1 182.1051 3.4 183.0454 C12H7O2+ 1 183.0441 7.23 183.0812 C13H11O+ 1 183.0804 4.01 184.0522 C12H8O2+ 1 184.0519 1.91 184.0862 C12[13]CH11O+ 1 184.0843 10.33 185.0604 C12H9O2+ 1 185.0597 3.9 185.0961 C13H13O+ 1 185.0961 -0.15 186.0682 C12H10O2+ 1 186.0675 3.74 186.1005 C12[13]CH13O+ 1 186.1 2.57 187.076 C12H11O2+ 1 187.0754 3.49 187.1126 C13H15O+ 1 187.1117 4.43 188.0807 C11[13]CH11O2+ 1 188.0793 7.5 188.1154 C12[13]CH15O+ 1 188.1156 -1.04 189.0564 C14H7N+ 2 189.0573 -4.52 189.0704 C15H9+ 1 189.0699 2.96 189.0914 C12H13O2+ 1 189.091 1.92 190.0795 C15H10+ 1 190.0777 9.29 191.0863 C15H11+ 1 191.0855 4.27 192.0569 C14H8O+ 1 192.057 -0.15 192.0926 C14[13]CH11+ 1 192.0894 16.63 193.0657 C14H9O+ 1 193.0648 4.89 193.1021 C15H13+ 1 193.1012 4.66 194.0734 C14H10O+ 1 194.0726 4.09 195.0802 C14H11O+ 1 195.0804 -1.49 196.052 C13H8O2+ 1 196.0519 0.5 196.0857 C14H12O+ 1 196.0883 -12.91 197.0608 C13H9O2+ 1 197.0597 5.73 197.0973 C14H13O+ 1 197.0961 5.95 198.0685 C13H10O2+ 1 198.0675 4.7 198.1027 C14H14O+ 1 198.1039 -6.39 199.0764 C13H11O2+ 1 199.0754 5.41 200.082 C13H12O2+ 1 200.0832 -5.85 201.0556 C12H9O3+ 2 201.0546 5.03 201.0729 C16H9+ 1 201.0699 15.16 201.091 C13H13O2+ 1 201.091 0.17 202.0598 C12H10O3+ 1 202.0624 -13.17 202.0799 C16H10+ 1 202.0777 10.93 203.0727 C15H9N+ 2 203.073 -1.33 203.0859 C16H11+ 1 203.0855 2 204.1026 C12H14NO2+ 1 204.1019 3.4 205.0656 C15H9O+ 1 205.0648 4.05 205.1015 C16H13+ 1 205.1012 1.81 206.0718 C15H10O+ 1 206.0726 -3.89 207.0815 C15H11O+ 1 207.0804 5.22 207.1024 C12H15O3+ 2 207.1016 4.16 208.0542 C14H8O2+ 1 208.0519 11.07 208.0882 C15H12O+ 1 208.0883 -0.55 209.0609 C14H9O2+ 1 209.0597 5.66 209.0972 C15H13O+ 1 209.0961 5.26 210.0678 C14H10O2+ 1 210.0675 1.34 210.1043 C15H14O+ 1 210.1039 1.88 211.0758 C14H11O2+ 1 211.0754 2.23 211.1089 C15H15O+ 1 211.1117 -13.53 212.0479 C13H8O3+ 2 212.0468 5.38 212.084 C14H12O2+ 1 212.0832 4.02 213.0541 C13H9O3+ 2 213.0546 -2.31 213.0916 C14H13O2+ 1 213.091 2.68 214.0617 C13H10O3+ 2 214.0624 -3.47 214.0962 C13[13]CH13O2+ 1 214.0949 6.01 215.108 C14H15O2+ 1 215.1067 6.36 216.111 C13[13]CH15O2+ 1 216.1106 2.26 217.1103 C12[13]C2H15O2+ 1 217.1139 -16.88 218.0733 C16H10O+ 1 218.0726 3.03 219.0814 C16H11O+ 1 219.0804 4.43 220.0881 C16H12O+ 1 220.0883 -0.81 220.1123 C16H14N+ 2 220.1121 1.19 221.0604 C15H9O2+ 1 221.0597 2.99 221.0975 C16H13O+ 1 221.0961 6.41 222.0666 C15H10O2+ 1 222.0675 -4.12 222.1015 C16H14O+ 1 222.1039 -10.82 222.1275 C16H16N+ 2 222.1277 -1.05 223.0768 C15H11O2+ 1 223.0754 6.38 223.1129 C16H15O+ 1 223.1117 5.01 224.0822 C15H12O2+ 1 224.0832 -4.5 224.1081 C15H14NO+ 1 224.107 5.1 225.0923 C15H13O2+ 1 225.091 5.83 226.0632 C14H10O3+ 2 226.0624 3.25 226.0965 C15H14O2+ 1 226.0988 -10.35 227.0724 C17H9N+ 2 227.073 -2.33 227.1053 C14[13]CH14O2+ 1 227.1027 11.15 228.0787 C14H12O3+ 2 228.0781 2.81 228.1035 C14H14NO2+ 1 228.1019 7.12 229.0783 C13H11NO3+ 1 229.0733 21.74 229.1094 C14H15NO2+ 1 229.1097 -1.64 230.1197 C14H16NO2+ 1 230.1176 9.41 234.0926 C16H12NO+ 1 234.0913 5.4 235.0773 C16H11O2+ 1 235.0754 8.23 235.099 C16H13NO+ 1 235.0992 -0.6 236.0844 C16H12O2+ 1 236.0832 5.13 236.1081 C16H14NO+ 1 236.107 4.7 237.0907 C16H13O2+ 1 237.091 -1.32 238.1007 C16H14O2+ 1 238.0988 7.74 238.1248 C16H16NO+ 1 238.1226 8.91 239.0706 C15H11O3+ 2 239.0703 1.34 239.1067 C16H15O2+ 1 239.1067 0.19 239.1326 C16H17NO+ 1 239.1305 8.85 240.0807 C18H10N+ 2 240.0808 -0.41 240.1106 C16H16O2+ 1 240.1145 -16.24 240.1382 C16H18NO+ 1 240.1383 -0.46 241.0869 C15H13O3+ 2 241.0859 3.97 241.1226 C16H17O2+ 1 241.1223 1.29 242.0901 C14[13]CH13O3+ 1 242.0898 1.05 242.1185 C15H16NO2+ 1 242.1176 3.92 243.1026 C15H15O3+ 2 243.1016 4.42 244.1058 C15H16O3+ 1 244.1094 -14.82 245.1083 C14[13]CH16O3+ 1 245.1133 -20.39 248.1081 C17H14NO+ 1 248.107 4.38 249.1153 C17H15NO+ 1 249.1148 1.78 250.1228 C17H16NO+ 1 250.1226 0.7 251.1088 C17H15O2+ 1 251.1067 8.56 251.1308 C17H17NO+ 1 251.1305 1.46 252.1044 C16H14NO2+ 1 252.1019 9.98 253.1252 C17H17O2+ 1 253.1223 11.27 254.0946 C16H14O3+ 1 254.0937 3.38 254.1198 C16H16NO2+ 1 254.1176 8.7 256.1329 C16H18NO2+ 1 256.1332 -1 266.1196 C17H16NO2+ 1 266.1176 7.6 267.1252 C17H17NO2+ 1 267.1254 -0.77 268.1321 C16[13]CH17NO2+ 1 268.1293 10.54 269.1188 C17H17O3+ 1 269.1172 5.82 270.121 C17H18O3+ 1 270.125 -14.88 272.1323 C16H18NO3+ 1 272.1281 15.27 280.1316 C18H18NO2+ 1 280.1332 -5.72 282.1499 C18H20NO2+ 1 282.1489 3.86 283.1518 C17[13]CH20NO2+ 1 283.1528 -3.55 285.1371 C17H19NO3+ 1 285.1359 3.96 300.1613 C18H22NO3+ 1 300.1594 6.34 301.1641 C17[13]CH22NO3+ 1 301.1633 2.64 302.1674 C16[13]C2H22NO3+ 1 302.1667 2.53 PK$NUM_PEAK: 219 PK$PEAK: m/z int. rel.int. 115.0546 3728 52 116.0593 676 9 117.0694 452 6 121.0651 1864 26 122.0362 684 9 127.0554 1692 23 128.0626 7840 110 129.0702 4312 60 130.0418 364 5 130.0752 636 8 131.05 3048 42 131.0738 432 6 131.086 792 11 132.0826 880 12 133.0659 488 6 134.0993 360 5 137.0604 8976 125 138.0631 800 11 139.0543 984 13 140.0614 744 10 141.0704 10928 153 142.0758 2316 32 143.0498 2684 37 143.0867 1056 14 144.0576 12732 178 145.0646 4040 56 146.036 1068 14 146.062 840 11 146.0716 1064 14 146.0966 452 6 147.0422 660 9 147.066 428 6 147.0805 1460 20 148.0533 376 5 148.0755 648 9 149.0617 776 10 150.0473 516 7 151.0545 396 5 151.078 756 10 152.0626 9656 135 153.0705 29796 418 154.0764 9016 126 155.0501 3844 53 155.0862 29704 416 156.0575 8588 120 156.0901 4024 56 157.0649 5104 71 157.1028 500 7 158.0731 9472 132 158.0979 528 7 159.0453 2364 33 159.0804 17248 242 160.0507 1212 17 160.0832 2276 31 161.0604 31420 440 162.065 2992 41 162.0917 668 9 163.0639 532 7 163.076 1476 20 164.0705 1736 24 165.0707 61436 862 166.0761 11348 159 167.0505 436 6 167.0855 6044 84 168.0574 13276 186 168.0895 980 13 169.0652 7316 102 169.1014 1676 23 170.0366 900 12 170.0734 5524 77 170.0996 596 8 171.0455 3288 46 171.0812 34880 489 172.0523 5932 83 172.0876 10644 149 173.0586 1800 25 173.0955 4400 61 174.0682 4572 64 174.1003 548 7 175.0757 7240 101 176.0794 1320 18 177.0554 1024 14 177.0715 2608 36 178.0786 5436 76 179.0867 6168 86 180.0577 1676 23 180.0935 1324 18 181.0657 47836 671 181.1024 3908 54 182.0722 15984 224 182.1057 932 13 183.0454 4200 58 183.0812 42940 602 184.0522 4900 68 184.0862 8080 113 185.0604 14316 200 185.0961 5848 82 186.0682 10488 147 186.1005 1112 15 187.076 18904 265 187.1126 6860 96 188.0807 2556 35 188.1154 1288 18 189.0564 680 9 189.0704 1700 23 189.0914 1376 19 190.0795 3048 42 191.0863 11120 156 192.0569 704 9 192.0926 2332 32 193.0657 17264 242 193.1021 3292 46 194.0734 21452 301 195.0802 10864 152 196.052 948 13 196.0857 3024 42 197.0608 7780 109 197.0973 8248 115 198.0685 16584 232 198.1027 2136 29 199.0764 71176 999 200.082 19076 267 201.0556 1644 23 201.0729 1200 16 201.091 7408 103 202.0598 512 7 202.0799 2280 32 203.0727 524 7 203.0859 2192 30 204.1026 472 6 205.0656 2160 30 205.1015 536 7 206.0718 1356 19 207.0815 5784 81 207.1024 416 5 208.0542 1696 23 208.0882 4556 63 209.0609 16264 228 209.0972 6516 91 210.0678 14388 201 210.1043 1976 27 211.0758 11196 157 211.1089 736 10 212.0479 560 7 212.084 11028 154 213.0541 1064 14 213.0916 20368 285 214.0617 620 8 214.0962 4476 62 215.108 52648 738 216.111 7936 111 217.1103 692 9 218.0733 1328 18 219.0814 5728 80 220.0881 4768 66 220.1123 2728 38 221.0604 3712 52 221.0975 4248 59 222.0666 1348 18 222.1015 1508 21 222.1275 412 5 223.0768 14972 210 223.1129 1068 14 224.0822 4608 64 224.1081 748 10 225.0923 34952 490 226.0632 3180 44 226.0965 8260 115 227.0724 1820 25 227.1053 1140 16 228.0787 2096 29 228.1035 1616 22 229.0783 1004 14 229.1094 844 11 230.1197 616 8 234.0926 664 9 235.0773 1180 16 235.099 604 8 236.0844 5268 73 236.1081 644 9 237.0907 2584 36 238.1007 2780 39 238.1248 576 8 239.0706 1120 15 239.1067 2324 32 239.1326 468 6 240.0807 696 9 240.1106 808 11 240.1382 448 6 241.0869 28972 406 241.1226 1716 24 242.0901 4724 66 242.1185 840 11 243.1026 19556 274 244.1058 3536 49 245.1083 508 7 248.1081 1720 24 249.1153 796 11 250.1228 2620 36 251.1088 3568 50 251.1308 1040 14 252.1044 2532 35 253.1252 1604 22 254.0946 888 12 254.1198 1252 17 256.1329 676 9 266.1196 8820 123 267.1252 4752 66 268.1321 1424 19 269.1188 1192 16 270.121 400 5 272.1323 368 5 280.1316 364 5 282.1499 5716 80 283.1518 1100 15 285.1371 1368 19 300.1613 59992 842 301.1641 11744 164 302.1674 1532 21 //