ACCESSION: MSBNK-Athens_Univ-AU162310
RECORD_TITLE: Codeine; LC-ESI-QTOF; MS2; HILIC; CE: 40 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$MASS_SPECTROMETRY: COLLISION_ENERGY 40 eV
AC$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 6.381 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$FOCUSED_ION: BASE_PEAK 300.1592
MS$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: splash10-0gc1-0940000000-b137c53d829ce40b3d5f
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
115.0537 C9H7+ 1 115.0542 -4.27
116.0602 C9H8+ 1 116.0621 -16.34
117.0685 C9H9+ 1 117.0699 -11.89
118.0646 C8H8N+ 2 118.0651 -4.82
120.0822 C8H10N+ 1 120.0808 11.69
121.0641 C8H9O+ 1 121.0648 -5.92
122.0364 C7H6O2+ 1 122.0362 1.12
127.0536 C10H7+ 1 127.0542 -4.99
128.0612 C10H8+ 1 128.0621 -6.53
129.0686 C10H9+ 1 129.0699 -9.6
131.0482 C9H7O+ 1 131.0491 -7.31
131.0846 C10H11+ 1 131.0855 -7.31
132.0803 C9H10N+ 2 132.0808 -3.58
133.0637 C9H9O+ 1 133.0648 -8.36
134.0622 C8H8NO+ 1 134.06 16.47
134.0954 C9H12N+ 2 134.0964 -7.38
136.0736 C8H10NO+ 1 136.0757 -15.08
137.0588 C8H9O2+ 1 137.0597 -6.76
138.063 C7[13]CH9O2+ 1 138.0636 -4.07
139.0536 C11H7+ 1 139.0542 -4.33
140.0607 C11H8+ 1 140.0621 -9.62
141.069 C11H9+ 1 141.0699 -6.52
142.0737 C10[13]CH9+ 1 142.0738 -0.86
143.0479 C10H7O+ 1 143.0491 -8.39
143.0849 C11H11+ 1 143.0855 -4.47
144.0559 C10H8O+ 1 144.057 -7.51
144.0804 C10H10N+ 2 144.0808 -2.76
145.0623 C10H9O+ 1 145.0648 -17.04
145.0875 C10H11N+ 2 145.0886 -7.27
146.0354 C9H6O2+ 1 146.0362 -5.65
146.0595 C9H8NO+ 1 146.06 -3.71
146.0708 C10H10O+ 1 146.0726 -12.52
146.0948 C7H14O3+ 2 146.0937 6.92
147.043 C9H7O2+ 1 147.0441 -7
147.0661 C9H9NO+ 1 147.0679 -11.99
147.0796 C10H11O+ 1 147.0804 -5.47
148.0741 C9H10NO+ 1 148.0757 -10.68
149.0587 C9H9O2+ 1 149.0597 -7.01
149.0831 C9H11NO+ 1 149.0835 -2.59
150.0655 C9H10O2+ 1 150.0675 -13.72
151.0519 C12H7+ 1 151.0542 -15.48
151.075 C9H11O2+ 1 151.0754 -2.56
152.0611 C12H8+ 1 152.0621 -6.24
153.0688 C12H9+ 1 153.0699 -6.75
154.0751 C12H10+ 1 154.0777 -16.83
155.0479 C11H7O+ 1 155.0491 -7.84
155.0587 C7H9NO3+ 1 155.0577 6.21
155.0843 C12H11+ 1 155.0855 -7.79
156.0561 C11H8O+ 1 156.057 -5.8
156.088 C11[13]CH11+ 1 156.0894 -9.42
157.0636 C11H9O+ 1 157.0648 -7.72
157.1004 C12H13+ 1 157.1012 -5.22
158.0713 C11H10O+ 1 158.0726 -8.57
158.0972 C11H12N+ 2 158.0964 4.77
159.0428 C10H7O2+ 1 159.0441 -8.16
159.0792 C11H11O+ 1 159.0804 -8.09
160.0494 C10H8O2+ 1 160.0519 -15.44
160.0762 C10H10NO+ 1 160.0757 3.27
161.0587 C10H9O2+ 1 161.0597 -6.15
162.0628 C9[13]CH9O2+ 1 162.0636 -4.89
162.09 C10H12NO+ 1 162.0913 -8.41
163.0571 C13H7+ 1 163.0542 17.49
163.0721 C10H11O2+ 1 163.0754 -20.2
163.0971 C10H13NO+ 1 163.0992 -12.86
164.0691 C9H10NO2+ 1 164.0706 -9.21
165.0689 C13H9+ 1 165.0699 -5.75
166.0746 C12[13]CH9+ 1 166.0738 5.23
167.0485 C12H7O+ 1 167.0491 -3.71
167.0838 C13H11+ 1 167.0855 -10.15
168.0559 C12H8O+ 1 168.057 -6.54
168.089 C12[13]CH11+ 1 168.0894 -2.43
169.0637 C12H9O+ 1 169.0648 -6.66
169.0999 C13H13+ 1 169.1012 -7.74
170.0359 C11H6O2+ 1 170.0362 -1.95
170.0717 C12H10O+ 1 170.0726 -5.65
170.0954 C12H12N+ 2 170.0964 -6.13
171.044 C11H7O2+ 1 171.0441 -0.15
171.0795 C12H11O+ 1 171.0804 -5.4
172.0506 C11H8O2+ 1 172.0519 -7.47
172.0861 C12H12O+ 1 172.0883 -12.41
173.0569 C11H9O2+ 1 173.0597 -15.98
173.0941 C12H13O+ 1 173.0961 -11.64
174.0672 C11H10O2+ 1 174.0675 -2.02
174.0931 C11H12NO+ 1 174.0913 10.35
175.0742 C11H11O2+ 1 175.0754 -6.37
176.074 C10H10NO2+ 1 176.0706 19.24
177.0538 C10H9O3+ 2 177.0546 -4.7
177.0697 C14H9+ 1 177.0699 -1.03
178.0775 C14H10+ 1 178.0777 -1.23
179.0595 C9H9NO3+ 1 179.0577 10.04
179.0836 C14H11+ 1 179.0855 -10.85
180.0569 C13H8O+ 1 180.057 -0.35
180.0976 C14H12+ 2 180.0934 23.39
181.0638 C13H9O+ 1 181.0648 -5.3
181.1 C14H13+ 1 181.1012 -6.28
182.0705 C13H10O+ 1 182.0726 -11.67
182.1023 C13[13]CH13+ 1 182.1051 -15.06
183.0432 C12H7O2+ 1 183.0441 -4.89
183.0794 C13H11O+ 1 183.0804 -5.5
184.0506 C12H8O2+ 1 184.0519 -6.7
184.0843 C12[13]CH11O+ 1 184.0843 0
185.0585 C12H9O2+ 1 185.0597 -6.4
185.0951 C13H13O+ 1 185.0961 -5.55
186.066 C12H10O2+ 1 186.0675 -8.41
186.0986 C12[13]CH13O+ 1 186.1 -7.58
187.0739 C12H11O2+ 1 187.0754 -7.66
187.1106 C13H15O+ 1 187.1117 -6.07
188.0788 C11[13]CH11O2+ 1 188.0793 -2.62
188.1145 C12[13]CH15O+ 1 188.1156 -6
189.0525 C11H9O3+ 1 189.0546 -11.02
189.0692 C15H9+ 1 189.0699 -3.43
189.089 C12H13O2+ 1 189.091 -10.38
190.0771 C15H10+ 1 190.0777 -3.35
191.0846 C15H11+ 1 191.0855 -4.88
192.0567 C14H8O+ 1 192.057 -1.25
192.0997 C11H14NO2+ 1 192.1019 -11.48
193.0641 C14H9O+ 1 193.0648 -3.44
193.1011 C15H13+ 1 193.1012 -0.38
194.0714 C14H10O+ 1 194.0726 -6.26
195.0781 C14H11O+ 1 195.0804 -11.97
196.0512 C13H8O2+ 1 196.0519 -3.66
196.085 C13[13]CH11O+ 1 196.0843 3.13
196.1096 C11H16O3+ 2 196.1094 1.25
197.0588 C13H9O2+ 1 197.0597 -4.8
197.0949 C14H13O+ 1 197.0961 -5.91
198.0666 C13H10O2+ 1 198.0675 -4.6
198.1004 C14H14O+ 1 198.1039 -17.84
199.0746 C13H11O2+ 1 199.0754 -3.9
200.0804 C12[13]CH11O2+ 1 200.0793 5.58
201.0536 C12H9O3+ 2 201.0546 -5.23
201.0893 C13H13O2+ 1 201.091 -8.65
201.1119 C13H15NO+ 1 201.1148 -14.71
202.0602 C12H10O3+ 2 202.0624 -11.22
202.0804 C16H10+ 1 202.0777 13.33
203.0857 C16H11+ 1 203.0855 1
204.1004 C12H14NO2+ 1 204.1019 -7.36
205.0649 C15H9O+ 1 205.0648 0.6
205.1007 C16H13+ 1 205.1012 -2.09
206.0716 C15H10O+ 1 206.0726 -4.82
207.079 C15H11O+ 1 207.0804 -6.91
208.0499 C14H8O2+ 1 208.0519 -9.43
208.0868 C15H12O+ 1 208.0883 -7.18
209.0587 C14H9O2+ 1 209.0597 -4.86
209.0949 C15H13O+ 1 209.0961 -5.85
210.0663 C14H10O2+ 1 210.0675 -5.74
210.0995 C15H14O+ 1 210.1039 -20.92
211.0739 C14H11O2+ 1 211.0754 -6.91
211.1105 C15H15O+ 1 211.1117 -5.98
212.0817 C14H12O2+ 1 212.0832 -6.97
213.0526 C13H9O3+ 2 213.0546 -9.55
213.0899 C14H13O2+ 1 213.091 -5.39
214.0593 C13H10O3+ 1 214.0624 -14.55
214.0938 C13[13]CH13O2+ 1 214.0949 -5.41
215.1057 C14H15O2+ 1 215.1067 -4.41
216.1089 C13[13]CH15O2+ 1 216.1106 -7.51
217.1106 C13H15NO2+ 1 217.1097 3.84
218.0708 C16H10O+ 1 218.0726 -8.18
219.0797 C16H11O+ 1 219.0804 -3.39
220.0876 C16H12O+ 1 220.0883 -3.13
220.1098 C13H16O3+ 2 220.1094 1.89
221.0591 C15H9O2+ 1 221.0597 -2.53
221.0942 C16H13O+ 1 221.0961 -8.53
222.0655 C15H10O2+ 1 222.0675 -8.93
222.0994 C16H14O+ 1 222.1039 -20.17
222.1274 C16H16N+ 2 222.1277 -1.69
223.0742 C15H11O2+ 1 223.0754 -5.13
223.1098 C16H15O+ 1 223.1117 -8.66
224.0797 C15H12O2+ 1 224.0832 -15.45
224.1049 C15H14NO+ 1 224.107 -9.11
225.0903 C15H13O2+ 1 225.091 -3.11
226.0609 C14H10O3+ 2 226.0624 -7
226.0942 C15H14O2+ 1 226.0988 -20.38
227.0685 C14H11O3+ 2 227.0703 -7.79
227.1012 C14[13]CH14O2+ 1 227.1027 -6.9
228.0761 C14H12O3+ 2 228.0781 -8.83
228.1011 C14H14NO2+ 1 228.1019 -3.35
229.076 C13H11NO3+ 1 229.0733 11.71
229.1099 C14H15NO2+ 1 229.1097 0.62
230.1164 C14H16NO2+ 1 230.1176 -4.9
233.0951 C17H13O+ 1 233.0961 -4.44
234.0938 C16H12NO+ 1 234.0913 10.56
235.0735 C16H11O2+ 1 235.0754 -8.08
235.097 C16H13NO+ 1 235.0992 -9.15
236.0826 C16H12O2+ 1 236.0832 -2.67
236.108 C16H14NO+ 1 236.107 4.08
237.0893 C16H13O2+ 1 237.091 -7.07
237.1126 C16H15NO+ 1 237.1148 -9.41
238.096 C16H14O2+ 1 238.0988 -11.96
238.1222 C16H16NO+ 1 238.1226 -2.04
239.0709 C15H11O3+ 2 239.0703 2.53
239.1031 C16H15O2+ 1 239.1067 -15.01
239.1281 C16H17NO+ 1 239.1305 -9.75
240.0748 C15H12O3+ 1 240.0781 -13.92
240.1048 C15H14NO2+ 1 240.1019 12.09
240.1336 C16H18NO+ 1 240.1383 -19.44
241.0852 C15H13O3+ 2 241.0859 -2.83
241.1202 C16H17O2+ 1 241.1223 -8.74
242.088 C14[13]CH13O3+ 1 242.0898 -7.73
242.1171 C15H16NO2+ 1 242.1176 -1.8
243.1007 C15H15O3+ 2 243.1016 -3.72
244.1046 C14[13]CH15O3+ 1 244.1055 -3.59
248.1066 C17H14NO+ 1 248.107 -1.45
249.1119 C17H15NO+ 1 249.1148 -11.83
250.0965 C17H14O2+ 1 250.0988 -9.28
250.1223 C17H16NO+ 1 250.1226 -1.45
251.1056 C17H15O2+ 1 251.1067 -4.29
251.1261 C17H17NO+ 1 251.1305 -17.49
252.1024 C16H14NO2+ 1 252.1019 1.93
253.0831 C16H13O3+ 1 253.0859 -11.23
253.121 C17H17O2+ 1 253.1223 -5.08
254.093 C16H14O3+ 1 254.0937 -2.77
254.1189 C16H16NO2+ 1 254.1176 5.31
254.1521 C17H20NO+ 1 254.1539 -7.35
255.1219 C16H17NO2+ 1 255.1254 -13.69
256.1317 C16H18NO2+ 1 256.1332 -6.06
257.1151 C16H17O3+ 1 257.1172 -8.33
264.0998 C17H14NO2+ 1 264.1019 -7.98
265.1138 C17H15NO2+ 1 265.1097 15.19
266.117 C17H16NO2+ 1 266.1176 -2.21
267.1233 C17H17NO2+ 1 267.1254 -7.78
268.1282 C17H18NO2+ 1 268.1332 -18.69
269.1172 C17H17O3+ 1 269.1172 -0.15
270.1182 C16H16NO3+ 1 270.1125 21.2
272.1259 C16H18NO3+ 1 272.1281 -7.98
280.1327 C18H18NO2+ 1 280.1332 -1.83
282.1478 C18H20NO2+ 1 282.1489 -3.58
283.1507 C17[13]CH20NO2+ 1 283.1528 -7.37
285.134 C17H19NO3+ 1 285.1359 -6.76
286.1414 C17H20NO3+ 1 286.1438 -8.23
298.1432 C18H20NO3+ 1 298.1438 -1.8
300.159 C18H22NO3+ 1 300.1594 -1.52
301.1614 C17[13]CH22NO3+ 1 301.1633 -6.27
302.1651 C16[13]C2H22NO3+ 1 302.1667 -5.13
PK$NUM_PEAK: 233
PK$PEAK: m/z int. rel.int.
115.0537 3932 54
116.0602 896 12
117.0685 596 8
118.0646 436 5
120.0822 368 5
121.0641 2824 38
122.0364 944 12
127.0536 1384 19
128.0612 6520 89
129.0686 4432 60
131.0482 2168 29
131.0846 1512 20
132.0803 1456 20
133.0637 384 5
134.0622 452 6
134.0954 836 11
136.0736 500 6
137.0588 12468 171
138.063 1036 14
139.0536 1072 14
140.0607 464 6
141.069 12896 177
142.0737 1744 23
143.0479 2372 32
143.0849 1476 20
144.0559 13800 189
144.0804 1032 14
145.0623 4584 62
145.0875 560 7
146.0354 1364 18
146.0595 2012 27
146.0708 1680 23
146.0948 732 10
147.043 524 7
147.0661 432 5
147.0796 1360 18
148.0741 1020 14
149.0587 764 10
149.0831 372 5
150.0655 448 6
151.0519 872 11
151.075 1160 15
152.0611 9476 130
153.0688 34424 472
154.0751 7668 105
155.0479 3288 45
155.0587 2228 30
155.0843 30544 419
156.0561 7860 107
156.088 3560 48
157.0636 5580 76
157.1004 788 10
158.0713 8464 116
158.0972 428 5
159.0428 2132 29
159.0792 16312 224
160.0494 1464 20
160.0762 3436 47
161.0587 29244 401
162.0628 3232 44
162.09 1584 21
163.0571 500 6
163.0721 1612 22
163.0971 392 5
164.0691 2648 36
165.0689 66508 913
166.0746 12504 171
167.0485 460 6
167.0838 6504 89
168.0559 12712 174
168.089 896 12
169.0637 7436 102
169.0999 1188 16
170.0359 556 7
170.0717 4964 68
170.0954 1288 17
171.044 2972 40
171.0795 33708 463
172.0506 6880 94
172.0861 10936 150
173.0569 2220 30
173.0941 3396 46
174.0672 5236 71
174.0931 636 8
175.0742 8256 113
176.074 2152 29
177.0538 1124 15
177.0697 2628 36
178.0775 4184 57
179.0595 472 6
179.0836 7588 104
180.0569 2020 27
180.0976 2200 30
181.0638 49292 677
181.1 5552 76
182.0705 20400 280
182.1023 1064 14
183.0432 4564 62
183.0794 44272 608
184.0506 4568 62
184.0843 9476 130
185.0585 17520 240
185.0951 4820 66
186.066 9724 133
186.0986 1104 15
187.0739 20648 283
187.1106 8444 116
188.0788 3656 50
188.1145 1204 16
189.0525 452 6
189.0692 1756 24
189.089 2488 34
190.0771 4244 58
191.0846 10628 146
192.0567 748 10
192.0997 3340 45
193.0641 19400 266
193.1011 3348 46
194.0714 21836 300
195.0781 10876 149
196.0512 1056 14
196.085 2660 36
196.1096 388 5
197.0588 7372 101
197.0949 9188 126
198.0666 18660 256
198.1004 2824 38
199.0746 72708 999
200.0804 17124 235
201.0536 1900 26
201.0893 6112 83
201.1119 408 5
202.0602 432 5
202.0804 1420 19
203.0857 2124 29
204.1004 880 12
205.0649 1912 26
205.1007 644 8
206.0716 1144 15
207.079 5748 78
208.0499 1748 24
208.0868 4708 64
209.0587 17704 243
209.0949 6188 85
210.0663 15920 218
210.0995 1988 27
211.0739 13600 186
211.1105 732 10
212.0817 11248 154
213.0526 1272 17
213.0899 19436 267
214.0593 888 12
214.0938 4428 60
215.1057 49608 681
216.1089 8520 117
217.1106 1000 13
218.0708 1888 25
219.0797 6068 83
220.0876 4192 57
220.1098 1852 25
221.0591 4160 57
221.0942 5208 71
222.0655 1336 18
222.0994 1668 22
222.1274 988 13
223.0742 15564 213
223.1098 1612 22
224.0797 4736 65
224.1049 1272 17
225.0903 42220 580
226.0609 2608 35
226.0942 8556 117
227.0685 2252 30
227.1012 1544 21
228.0761 2552 35
228.1011 1660 22
229.076 1128 15
229.1099 1148 15
230.1164 1180 16
233.0951 592 8
234.0938 536 7
235.0735 1656 22
235.097 660 9
236.0826 4380 60
236.108 716 9
237.0893 3212 44
237.1126 364 5
238.096 3340 45
238.1222 1144 15
239.0709 1272 17
239.1031 3036 41
239.1281 864 11
240.0748 728 10
240.1048 892 12
240.1336 600 8
241.0852 29256 401
241.1202 2096 28
242.088 5480 75
242.1171 908 12
243.1007 19552 268
244.1046 2996 41
248.1066 1320 18
249.1119 1244 17
250.0965 548 7
250.1223 3860 53
251.1056 4172 57
251.1261 2064 28
252.1024 3340 45
253.0831 440 6
253.121 3480 47
254.093 884 12
254.1189 968 13
254.1521 440 6
255.1219 404 5
256.1317 612 8
257.1151 452 6
264.0998 540 7
265.1138 428 5
266.117 10952 150
267.1233 6676 91
268.1282 2220 30
269.1172 1256 17
270.1182 376 5
272.1259 464 6
280.1327 996 13
282.1478 8220 112
283.1507 1612 22
285.134 2428 33
286.1414 368 5
298.1432 560 7
300.159 60984 837
301.1614 11112 152
302.1651 1384 19
//
