MassBank Record: AU162311

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Codeine; LC-ESI-QTOF; MS2; HILIC; CE: 50 eV; R=35000; [M+H]+
Mass Spectrum
Chemical Structure
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ACCESSION: AU162311
RECORD_TITLE: Codeine; 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 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$MASS_SPECTROMETRY: COLLISION_ENERGY 50 eV AC$MASS_SPECTROMETRY: RESOLUTION 35000 AC$CHROMATOGRAPHY: COLUMN_NAME ACQUITY UPLC BEH Amide 1.7 um 2.1x100mm, Water AC$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 6.380 min AC$CHROMATOGRAPHY: SOLVENT A Water with 0.01% formic acid and 1mM ammonium formate AC$CHROMATOGRAPHY: SOLVENT B Acetonitrile:Water with 0.01% formic acid and 1mM ammonium formate
MS$FOCUSED_ION: BASE_PEAK 300.1592 MS$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: splash10-0uxr-0910000000-7e8bbdcad9abf73a010c PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm) 115.0536 C9H7+ 1 115.0542 -5.28 116.0592 C9H8+ 1 116.0621 -24.95 117.0692 C9H9+ 1 117.0699 -6.03 118.0404 C8H6O+ 1 118.0413 -7.8 119.0466 C8H7O+ 1 119.0491 -21.24 121.0641 C8H9O+ 1 121.0648 -5.63 122.036 C7H6O2+ 1 122.0362 -1.69 126.0463 C10H6+ 1 126.0464 -0.97 127.0536 C10H7+ 1 127.0542 -4.6 128.0611 C10H8+ 1 128.0621 -7.12 129.0686 C10H9+ 1 129.0699 -9.83 131.0485 C9H7O+ 1 131.0491 -4.58 131.0727 C9H9N+ 2 131.073 -1.73 131.0858 C10H11+ 1 131.0855 1.9 132.0558 C9H8O+ 1 132.057 -8.94 132.0814 C9H10N+ 1 132.0808 4.94 133.0637 C9H9O+ 1 133.0648 -8.54 134.06 C8H8NO+ 1 134.06 -0.51 134.0955 C9H12N+ 2 134.0964 -6.81 135.0438 C8H7O2+ 1 135.0441 -2.08 136.0755 C8H10NO+ 1 136.0757 -1.53 137.059 C8H9O2+ 1 137.0597 -4.96 139.0533 C11H7+ 1 139.0542 -6.47 140.0603 C11H8+ 1 140.0621 -12.7 141.0691 C11H9+ 1 141.0699 -5.26 142.0403 C10H6O+ 1 142.0413 -6.91 142.0752 C11H10+ 1 142.0777 -17.94 143.0481 C10H7O+ 1 143.0491 -7.08 143.0839 C11H11+ 1 143.0855 -11.33 144.0559 C10H8O+ 1 144.057 -7.65 144.0799 C10H10N+ 2 144.0808 -5.87 145.0634 C10H9O+ 1 145.0648 -9.52 146.0353 C9H6O2+ 1 146.0362 -6.56 146.0696 C10H10O+ 1 146.0726 -20.95 146.0946 C7H14O3+ 2 146.0937 5.69 147.0422 C9H7O2+ 1 147.0441 -12.79 147.0788 C10H11O+ 1 147.0804 -11.22 148.0496 C9H8O2+ 1 148.0519 -15.39 148.0738 C9H10NO+ 1 148.0757 -12.72 149.06 C9H9O2+ 1 149.0597 1.83 150.0476 C12H6+ 1 150.0464 8.29 151.0539 C12H7+ 1 151.0542 -2.23 151.074 C9H11O2+ 1 151.0754 -9.21 152.0612 C12H8+ 1 152.0621 -5.85 153.069 C12H9+ 1 153.0699 -5.75 154.0751 C12H10+ 1 154.0777 -16.76 155.0487 C11H7O+ 1 155.0491 -2.92 155.0845 C12H11+ 1 155.0855 -6.7 156.0564 C11H8O+ 1 156.057 -3.43 157.0635 C11H9O+ 1 157.0648 -8.07 157.0899 C11H11N+ 1 157.0886 8.37 157.1004 C12H13+ 1 157.1012 -5.25 158.0715 C11H10O+ 1 158.0726 -7.07 159.0428 C10H7O2+ 1 159.0441 -7.88 159.0792 C11H11O+ 1 159.0804 -7.92 160.0502 C10H8O2+ 1 160.0519 -10.28 160.0759 C10H10NO+ 1 160.0757 1.27 161.059 C10H9O2+ 1 161.0597 -4.16 162.0897 C10H12NO+ 1 162.0913 -10.03 163.0533 C13H7+ 1 163.0542 -5.68 164.0623 C13H8+ 1 164.0621 1.47 165.0692 C13H9+ 1 165.0699 -4.08 166.0744 C13H10+ 1 166.0777 -20.07 167.0489 C12H7O+ 1 167.0491 -1.18 167.0837 C13H11+ 1 167.0855 -11.08 168.0559 C12H8O+ 1 168.057 -6.14 169.0635 C12H9O+ 1 169.0648 -7.59 170.0348 C11H6O2+ 1 170.0362 -8.28 170.0712 C12H10O+ 1 170.0726 -8.05 170.0945 C9H14O3+ 2 170.0937 4.39 171.0429 C11H7O2+ 1 171.0441 -6.89 171.0795 C12H11O+ 1 171.0804 -5.4 172.0509 C11H8O2+ 1 172.0519 -5.82 172.0858 C12H12O+ 1 172.0883 -14.58 173.0572 C11H9O2+ 1 173.0597 -14.38 173.0936 C12H13O+ 1 173.0961 -14.27 174.0659 C11H10O2+ 1 174.0675 -9.45 175.0742 C11H11O2+ 1 175.0754 -6.84 176.0623 C14H8+ 1 176.0621 1.25 177.0695 C14H9+ 1 177.0699 -2.01 178.0767 C14H10+ 1 178.0777 -5.42 179.0592 C9H9NO3+ 1 179.0577 8.15 179.0841 C14H11+ 1 179.0855 -7.94 180.056 C13H8O+ 1 180.057 -5.57 180.0909 C14H12+ 1 180.0934 -13.58 181.0639 C13H9O+ 1 181.0648 -4.81 182.0706 C13H10O+ 1 182.0726 -10.85 183.043 C12H7O2+ 1 183.0441 -6 183.0791 C13H11O+ 1 183.0804 -7.13 184.0506 C12H8O2+ 1 184.0519 -6.88 184.0849 C13H12O+ 1 184.0883 -18.53 185.0585 C12H9O2+ 1 185.0597 -6.72 185.0946 C13H13O+ 1 185.0961 -8.16 186.0309 C11H6O3+ 2 186.0311 -1.14 186.0655 C12H10O2+ 1 186.0675 -10.95 187.074 C12H11O2+ 1 187.0754 -7.2 187.1101 C13H15O+ 1 187.1117 -8.97 189.069 C15H9+ 1 189.0699 -4.45 189.0878 C12H13O2+ 1 189.091 -16.85 190.0762 C15H10+ 1 190.0777 -7.71 191.0838 C15H11+ 1 191.0855 -9 192.0581 C14H8O+ 1 192.057 5.7 192.0905 C15H12+ 1 192.0934 -14.69 193.064 C14H9O+ 1 193.0648 -4.24 193.0989 C15H13+ 1 193.1012 -11.54 194.0712 C14H10O+ 1 194.0726 -7.34 195.0783 C14H11O+ 1 195.0804 -10.74 196.0507 C13H8O2+ 1 196.0519 -5.95 196.0855 C14H12O+ 1 196.0883 -14.35 196.1093 C11H16O3+ 2 196.1094 -0.27 197.0587 C13H9O2+ 1 197.0597 -4.96 197.0949 C14H13O+ 1 197.0961 -5.81 198.0665 C13H10O2+ 1 198.0675 -5.44 198.0929 C13H12NO+ 1 198.0913 7.92 199.0743 C13H11O2+ 1 199.0754 -5.32 200.0457 C12H8O3+ 2 200.0468 -5.68 200.0803 C13H12O2+ 1 200.0832 -14.39 200.1067 C13H14NO+ 1 200.107 -1.24 201.0543 C12H9O3+ 2 201.0546 -1.53 201.0881 C13H13O2+ 1 201.091 -14.27 202.0769 C16H10+ 1 202.0777 -4.11 203.0829 C16H11+ 1 203.0855 -12.89 205.0639 C15H9O+ 1 205.0648 -4.44 205.0925 C15H11N+ 1 205.0886 18.79 206.0714 C15H10O+ 1 206.0726 -5.95 206.0974 C15H12N+ 2 206.0964 4.65 207.0797 C15H11O+ 1 207.0804 -3.66 207.1023 C12H15O3+ 2 207.1016 3.75 208.0512 C14H8O2+ 1 208.0519 -3.44 208.0864 C15H12O+ 1 208.0883 -9.02 208.1088 C12H16O3+ 2 208.1094 -2.76 209.0589 C14H9O2+ 1 209.0597 -3.94 209.0946 C15H13O+ 1 209.0961 -6.91 210.0659 C14H10O2+ 1 210.0675 -7.75 210.0919 C14H12NO+ 1 210.0913 2.87 210.0995 C15H14O+ 1 210.1039 -20.91 211.0382 C13H7O3+ 2 211.039 -3.75 211.0737 C14H11O2+ 1 211.0754 -7.96 211.1099 C15H15O+ 1 211.1117 -8.68 212.0506 C16H6N+ 2 212.0495 5.21 212.0816 C14H12O2+ 1 212.0832 -7.4 213.0532 C13H9O3+ 2 213.0546 -6.72 213.0893 C14H13O2+ 1 213.091 -8.08 214.0894 C13H12NO2+ 1 214.0863 14.77 215.0694 C13H11O3+ 2 215.0703 -3.87 215.106 C14H15O2+ 1 215.1067 -2.91 218.0715 C16H10O+ 1 218.0726 -5.18 218.0933 C13H14O3+ 2 218.0937 -1.94 219.0795 C16H11O+ 1 219.0804 -4.08 220.0858 C16H12O+ 1 220.0883 -11.21 220.1109 C16H14N+ 2 220.1121 -5.52 221.0597 C15H9O2+ 1 221.0597 0.16 221.0945 C16H13O+ 1 221.0961 -7.14 221.1149 C13H17O3+ 2 221.1172 -10.41 222.0633 C15H10O2+ 1 222.0675 -18.86 222.0913 C15H12NO+ 1 222.0913 -0.03 222.106 C16H14O+ 1 222.1039 9.51 222.1243 C13H18O3+ 2 222.125 -3.53 223.0743 C15H11O2+ 1 223.0754 -4.65 223.101 C15H13NO+ 1 223.0992 8.05 224.08 C15H12O2+ 1 224.0832 -13.98 224.1066 C15H14NO+ 1 224.107 -1.52 225.0535 C14H9O3+ 2 225.0546 -5.02 225.0895 C15H13O2+ 1 225.091 -6.72 226.061 C14H10O3+ 2 226.0624 -6.48 226.0938 C15H14O2+ 1 226.0988 -22.42 227.0694 C14H11O3+ 2 227.0703 -3.96 227.0935 C14H13NO2+ 1 227.0941 -2.56 228.0778 C14H12O3+ 2 228.0781 -1.43 228.1008 C14H14NO2+ 1 228.1019 -4.64 229.0775 C13H11NO3+ 1 229.0733 17.96 234.091 C16H12NO+ 1 234.0913 -1.29 235.0739 C16H11O2+ 1 235.0754 -6.11 235.0993 C16H13NO+ 1 235.0992 0.67 236.0815 C16H12O2+ 1 236.0832 -7.07 236.1046 C16H14NO+ 1 236.107 -10.07 237.0841 C15H11NO2+ 1 237.0784 23.77 238.0962 C16H14O2+ 1 238.0988 -10.88 238.1224 C16H16NO+ 1 238.1226 -0.96 239.0677 C15H11O3+ 2 239.0703 -10.58 239.0995 C15H13NO2+ 1 239.0941 22.78 240.0752 C15H12O3+ 2 240.0781 -11.99 240.1015 C15H14NO2+ 1 240.1019 -1.53 240.1369 C16H18NO+ 1 240.1383 -5.73 241.0853 C15H13O3+ 2 241.0859 -2.74 242.091 C15H14O3+ 2 242.0937 -11.48 242.114 C15H16NO2+ 1 242.1176 -14.77 243.1003 C15H15O3+ 2 243.1016 -5.26 248.1058 C17H14NO+ 1 248.107 -4.83 249.1141 C17H15NO+ 1 249.1148 -2.71 250.1214 C17H16NO+ 1 250.1226 -5.13 251.1032 C17H15O2+ 1 251.1067 -13.76 251.1264 C17H17NO+ 1 251.1305 -16.01 252.1005 C16H14NO2+ 1 252.1019 -5.77 254.116 C16H16NO2+ 1 254.1176 -6.28 266.1169 C17H16NO2+ 1 266.1176 -2.55 267.1226 C17H17NO2+ 1 267.1254 -10.57 268.1287 C17H18NO2+ 1 268.1332 -16.96 282.149 C18H20NO2+ 1 282.1489 0.36 300.1593 C18H22NO3+ 1 300.1594 -0.24 PK$NUM_PEAK: 200 PK$PEAK: m/z int. rel.int. 115.0536 11232 134 116.0592 1816 21 117.0692 972 11 118.0404 952 11 119.0466 496 5 121.0641 2204 26 122.036 1544 18 126.0463 908 10 127.0536 3720 44 128.0611 23716 284 129.0686 9504 113 131.0485 4040 48 131.0727 504 6 131.0858 1040 12 132.0558 1116 13 132.0814 1260 15 133.0637 636 7 134.06 464 5 134.0955 780 9 135.0438 584 6 136.0755 620 7 137.059 7960 95 139.0533 3732 44 140.0603 1720 20 141.0691 24588 294 142.0403 456 5 142.0752 4740 56 143.0481 3744 44 143.0839 1272 15 144.0559 18056 216 144.0799 1388 16 145.0634 7392 88 146.0353 2124 25 146.0696 2132 25 146.0946 700 8 147.0422 1036 12 147.0788 1776 21 148.0496 488 5 148.0738 1280 15 149.06 844 10 150.0476 516 6 151.0539 2040 24 151.074 460 5 152.0612 37052 443 153.069 74004 886 154.0751 16564 198 155.0487 7376 88 155.0845 26328 315 156.0564 13188 157 157.0635 9816 117 157.0899 492 5 157.1004 628 7 158.0715 9876 118 159.0428 3624 43 159.0792 8808 105 160.0502 2088 25 160.0759 2736 32 161.059 20752 248 162.0897 1000 11 163.0533 972 11 164.0623 2524 30 165.0692 83404 999 166.0744 17440 208 167.0489 600 7 167.0837 6636 79 168.0559 19140 229 169.0635 18016 215 170.0348 3124 37 170.0712 9700 116 170.0945 688 8 171.0429 6888 82 171.0795 38216 457 172.0509 6140 73 172.0858 10192 122 173.0572 2264 27 173.0936 2856 34 174.0659 3712 44 175.0742 4304 51 176.0623 2016 24 177.0695 3544 42 178.0767 8300 99 179.0592 1772 21 179.0841 7776 93 180.056 5104 61 180.0909 1912 22 181.0639 51080 611 182.0706 22188 265 183.043 16544 198 183.0791 18808 225 184.0506 9944 119 184.0849 4900 58 185.0585 20548 246 185.0946 4572 54 186.0309 756 9 186.0655 6972 83 187.074 7684 92 187.1101 2400 28 189.069 4448 53 189.0878 808 9 190.0762 5644 67 191.0838 8752 104 192.0581 944 11 192.0905 1696 20 193.064 12428 148 193.0989 1840 22 194.0712 16444 196 195.0783 9024 108 196.0507 1380 16 196.0855 2616 31 196.1093 532 6 197.0587 16176 193 197.0949 3036 36 198.0665 22212 266 198.0929 1608 19 199.0743 31516 377 200.0457 496 5 200.0803 9444 113 200.1067 656 7 201.0543 1068 12 201.0881 2784 33 202.0769 2228 26 203.0829 1128 13 205.0639 3716 44 205.0925 424 5 206.0714 1596 19 206.0974 800 9 207.0797 4420 52 207.1023 460 5 208.0512 3880 46 208.0864 3356 40 208.1088 536 6 209.0589 10464 125 209.0946 2824 33 210.0659 13484 161 210.0919 916 10 210.0995 1056 12 211.0382 780 9 211.0737 7588 90 211.1099 488 5 212.0506 452 5 212.0816 6492 77 213.0532 1464 17 213.0893 7728 92 214.0894 2552 30 215.0694 420 5 215.106 7808 93 218.0715 2116 25 218.0933 528 6 219.0795 4020 48 220.0858 2392 28 220.1109 2692 32 221.0597 3932 47 221.0945 1548 18 221.1149 428 5 222.0633 1332 15 222.0913 480 5 222.106 576 6 222.1243 440 5 223.0743 10320 123 223.101 596 7 224.08 2920 34 224.1066 1032 12 225.0535 1304 15 225.0895 9332 111 226.061 2580 30 226.0938 2568 30 227.0694 1412 16 227.0935 428 5 228.0778 872 10 228.1008 1104 13 229.0775 660 7 234.091 1364 16 235.0739 1800 21 235.0993 1108 13 236.0815 2660 31 236.1046 568 6 237.0841 1212 14 238.0962 1020 12 238.1224 712 8 239.0677 856 10 239.0995 788 9 240.0752 524 6 240.1015 556 6 240.1369 660 7 241.0853 7636 91 242.091 1320 15 242.114 820 9 243.1003 1712 20 248.1058 1584 18 249.1141 700 8 250.1214 1840 22 251.1032 956 11 251.1264 556 6 252.1005 1848 22 254.116 548 6 266.1169 4824 57 267.1226 1680 20 268.1287 816 9 282.149 1020 12 300.1593 2980 35 //