ACCESSION: MSBNK-Athens_Univ-AU162305
RECORD_TITLE: Codeine; LC-ESI-QTOF; MS2; CE: 50 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$MASS_SPECTROMETRY: COLLISION_ENERGY 50 eV
AC$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 3.532 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$FOCUSED_ION: BASE_PEAK 300.1623
MS$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: splash10-0uxs-0910000000-b0c288c76c616e1a54d3
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
115.055 C9H7+ 1 115.0542 6.64
116.0605 C8[13]CH7+ 1 116.0581 20.64
117.0698 C9H9+ 1 117.0699 -0.82
118.0429 C8H6O+ 1 118.0413 13.12
121.0647 C8H9O+ 1 121.0648 -0.72
122.0377 C7H6O2+ 1 122.0362 12.31
126.0481 C10H6+ 1 126.0464 13.13
127.0548 C10H7+ 1 127.0542 4.84
128.0627 C10H8+ 1 128.0621 4.82
129.0695 C10H9+ 1 129.0699 -2.97
130.0426 C9H6O+ 1 130.0413 9.58
130.0754 C9[13]CH9+ 1 130.0738 12.59
131.0504 C9H7O+ 1 131.0491 9.29
131.0747 C9H9N+ 1 131.073 13.41
131.0857 C10H11+ 1 131.0855 1.01
132.0574 C9H8O+ 1 132.057 3.11
132.0809 C9H10N+ 2 132.0808 0.91
133.0649 C9H9O+ 1 133.0648 0.8
134.0971 C9H12N+ 1 134.0964 5.18
136.0766 C8H10NO+ 1 136.0757 6.69
137.0605 C8H9O2+ 1 137.0597 5.85
138.0644 C8H10O2+ 1 138.0675 -22.63
139.0554 C11H7+ 1 139.0542 8.57
140.0621 C11H8+ 1 140.0621 0.41
141.0707 C11H9+ 1 141.0699 5.63
142.0758 C10[13]CH9+ 1 142.0738 14.14
143.05 C10H7O+ 1 143.0491 6.14
143.085 C11H11+ 1 143.0855 -3.52
144.0577 C10H8O+ 1 144.057 5.04
145.0652 C10H9O+ 1 145.0648 2.79
146.0363 C9H6O2+ 1 146.0362 0.51
146.0715 C10H10O+ 1 146.0726 -7.97
146.0964 C10H12N+ 2 146.0964 -0.42
147.0434 C9H7O2+ 1 147.0441 -4.52
147.081 C10H11O+ 1 147.0804 3.6
148.0761 C9H10NO+ 1 148.0757 2.75
149.0595 C9H9O2+ 1 149.0597 -1.47
150.0486 C12H6+ 1 150.0464 14.47
151.0547 C12H7+ 1 151.0542 3.13
152.0629 C12H8+ 1 152.0621 5.35
153.0706 C12H9+ 1 153.0699 4.83
154.0771 C12H10+ 1 154.0777 -3.58
155.0501 C11H7O+ 1 155.0491 6.28
155.0862 C12H11+ 1 155.0855 4.34
156.0577 C11H8O+ 1 156.057 4.72
156.0895 C11[13]CH11+ 1 156.0894 0.6
157.0653 C11H9O+ 1 157.0648 2.94
158.0736 C11H10O+ 1 158.0726 6.46
159.0455 C10H7O2+ 1 159.0441 9.21
159.0806 C11H11O+ 1 159.0804 1.27
160.0526 C10H8O2+ 1 160.0519 4.26
160.0816 C10[13]CH11O+ 1 160.0843 -16.94
161.0607 C10H9O2+ 1 161.0597 6.38
162.0644 C9[13]CH9O2+ 1 162.0636 4.81
162.0914 C10H12NO+ 1 162.0913 0.43
163.0545 C13H7+ 1 163.0542 1.66
163.0749 C10H11O2+ 1 163.0754 -2.85
164.0633 C13H8+ 1 164.0621 7.59
165.0709 C13H9+ 1 165.0699 6.28
166.0764 C12[13]CH9+ 1 166.0738 15.81
167.0493 C12H7O+ 1 167.0491 0.95
167.0854 C13H11+ 1 167.0855 -0.7
168.0578 C12H8O+ 1 168.057 4.96
168.0885 C12[13]CH11+ 1 168.0894 -5.67
169.0652 C12H9O+ 1 169.0648 2.69
170.0363 C11H6O2+ 1 170.0362 0.52
170.0733 C12H10O+ 1 170.0726 4.16
171.0452 C11H7O2+ 1 171.0441 6.52
171.0814 C12H11O+ 1 171.0804 5.42
172.0524 C11H8O2+ 1 172.0519 2.88
172.0874 C12H12O+ 1 172.0883 -5.14
173.0588 C11H9O2+ 1 173.0597 -5.24
173.0946 C11[13]CH12O+ 1 173.0922 13.85
174.0688 C11H10O2+ 1 174.0675 7.04
174.095 C11H12NO+ 1 174.0913 21.1
175.0759 C11H11O2+ 1 175.0754 3.29
176.0637 C14H8+ 1 176.0621 9.31
177.0705 C14H9+ 1 177.0699 3.36
178.0786 C14H10+ 1 178.0777 5.11
179.062 C9H9NO3+ 1 179.0577 23.88
179.0862 C14H11+ 1 179.0855 3.92
180.0579 C13H8O+ 1 180.057 5.19
180.0924 C14H12+ 1 180.0934 -5.52
181.0662 C13H9O+ 1 181.0648 7.56
182.0725 C13H10O+ 1 182.0726 -0.4
183.0451 C12H7O2+ 1 183.0441 5.74
183.081 C13H11O+ 1 183.0804 3.08
184.0528 C12H8O2+ 1 184.0519 5.08
184.087 C13H12O+ 1 184.0883 -6.73
185.0604 C12H9O2+ 1 185.0597 3.79
185.0974 C13H13O+ 1 185.0961 7.05
186.0325 C14H4N+ 2 186.0338 -6.88
186.0669 C12H10O2+ 1 186.0675 -3.42
186.1011 C12[13]CH13O+ 1 186.1 5.91
187.0759 C12H11O2+ 1 187.0754 3.13
187.1129 C13H15O+ 1 187.1117 6.45
188.0818 C11[13]CH11O2+ 1 188.0793 13.77
189.0705 C15H9+ 1 189.0699 3.36
189.0912 C12H13O2+ 1 189.091 1.18
190.0785 C15H10+ 1 190.0777 4.1
191.0865 C15H11+ 1 191.0855 4.86
192.0588 C14H8O+ 1 192.057 9.67
192.0899 C14[13]CH11+ 1 192.0894 2.32
193.0659 C14H9O+ 1 193.0648 5.86
193.1035 C15H13+ 1 193.1012 12.24
194.0735 C14H10O+ 1 194.0726 4.81
195.0805 C14H11O+ 1 195.0804 0.2
196.0524 C13H8O2+ 1 196.0519 2.75
196.0872 C14H12O+ 1 196.0883 -5.66
197.0611 C13H9O2+ 1 197.0597 7.11
197.0979 C14H13O+ 1 197.0961 8.98
198.0686 C13H10O2+ 1 198.0675 5.42
199.0765 C13H11O2+ 1 199.0754 5.58
200.0828 C13H12O2+ 1 200.0832 -1.87
201.0572 C15H7N+ 2 201.0573 -0.54
201.0699 C16H9+ 1 201.0699 -0.04
201.0913 C12[13]CH12O2+ 1 201.0871 20.73
202.0802 C16H10+ 1 202.0777 12.19
203.0859 C16H11+ 1 203.0855 2.04
205.0654 C15H9O+ 1 205.0648 2.78
206.0704 C15H10O+ 1 206.0726 -10.91
206.0991 C15H12N+ 1 206.0964 12.82
207.0815 C15H11O+ 1 207.0804 4.91
208.053 C14H8O2+ 1 208.0519 5.33
208.0894 C15H12O+ 1 208.0883 5.23
209.0609 C14H9O2+ 1 209.0597 5.63
209.0962 C15H13O+ 1 209.0961 0.3
210.0685 C14H10O2+ 1 210.0675 4.82
210.1005 C15H14O+ 1 210.1039 -16.23
211.0403 C13H7O3+ 2 211.039 6.13
211.0763 C14H11O2+ 1 211.0754 4.4
212.0493 C16H6N+ 2 212.0495 -0.92
212.0836 C14H12O2+ 1 212.0832 2.21
212.1052 C14H14NO+ 1 212.107 -8.65
213.0573 C16H7N+ 2 213.0573 -0.16
213.092 C14H13O2+ 1 213.091 4.72
214.0623 C13H10O3+ 2 214.0624 -0.53
214.0954 C14H14O2+ 1 214.0988 -15.81
215.0702 C13H11O3+ 2 215.0703 -0.46
215.1079 C14H15O2+ 1 215.1067 5.56
216.1116 C13[13]CH15O2+ 1 216.1106 5.03
218.0739 C16H10O+ 1 218.0726 5.91
218.0956 C16H12N+ 2 218.0964 -3.56
219.0825 C16H11O+ 1 219.0804 9.34
220.0877 C16H12O+ 1 220.0883 -2.63
220.1138 C16H14N+ 2 220.1121 7.72
221.0616 C15H9O2+ 1 221.0597 8.36
221.0959 C16H13O+ 1 221.0961 -0.86
221.1186 C13H17O3+ 2 221.1172 6.02
222.0659 C15H10O2+ 1 222.0675 -7.14
223.0774 C15H11O2+ 1 223.0754 9.29
224.0815 C14[13]CH11O2+ 1 224.0793 9.97
224.1087 C15H14NO+ 1 224.107 7.79
225.056 C14H9O3+ 2 225.0546 5.92
225.0923 C15H13O2+ 1 225.091 5.92
226.0651 C17H8N+ 2 226.0651 -0.32
226.0966 C15H14O2+ 1 226.0988 -9.95
227.0712 C14H11O3+ 2 227.0703 3.94
227.103 C15H15O2+ 1 227.1067 -15.99
228.0794 C17H10N+ 2 228.0808 -5.84
228.1071 C14H14NO2+ 1 228.1019 22.7
234.0928 C16H12NO+ 1 234.0913 6.15
235.0776 C16H11O2+ 1 235.0754 9.56
235.1011 C16H13NO+ 1 235.0992 8.09
236.0844 C16H12O2+ 1 236.0832 5.15
236.1082 C16H14NO+ 1 236.107 5.27
237.0917 C16H13O2+ 1 237.091 2.76
238.0975 C16H14O2+ 1 238.0988 -5.39
239.0702 C15H11O3+ 2 239.0703 -0.36
239.0937 C15H13NO2+ 1 239.0941 -1.68
239.1285 C16H17NO+ 1 239.1305 -8.28
240.1046 C15H14NO2+ 1 240.1019 11.4
240.139 C16H18NO+ 1 240.1383 3.11
241.0878 C18H11N+ 2 241.0886 -3.25
241.1197 C16H17O2+ 1 241.1223 -10.86
242.09 C17[13]CH11N+ 1 242.0925 -10.53
242.1218 C15H16NO2+ 1 242.1176 17.5
243.1042 C18H13N+ 2 243.1043 -0.13
248.1081 C17H14NO+ 1 248.107 4.52
249.1151 C17H15NO+ 1 249.1148 1.34
250.1244 C17H16NO+ 1 250.1226 7.05
251.1065 C17H15O2+ 1 251.1067 -0.8
251.1327 C17H17NO+ 1 251.1305 9.04
252.1044 C16H14NO2+ 1 252.1019 9.81
266.1198 C17H16NO2+ 1 266.1176 8.51
267.1277 C16[13]CH16NO2+ 1 267.1215 23.5
268.1363 C17H18NO2+ 1 268.1332 11.49
282.1508 C18H20NO2+ 1 282.1489 6.91
300.1629 C18H22NO3+ 1 300.1594 11.62
301.1633 C17[13]CH22NO3+ 1 301.1633 -0.24
PK$NUM_PEAK: 190
PK$PEAK: m/z int. rel.int.
115.055 11984 125
116.0605 1588 16
117.0698 936 9
118.0429 1320 13
121.0647 1332 13
122.0377 1280 13
126.0481 712 7
127.0548 3892 40
128.0627 25856 270
129.0695 9972 104
130.0426 504 5
130.0754 1184 12
131.0504 4788 50
131.0747 520 5
131.0857 1312 13
132.0574 860 9
132.0809 640 6
133.0649 684 7
134.0971 604 6
136.0766 868 9
137.0605 5608 58
138.0644 932 9
139.0554 3348 35
140.0621 2500 26
141.0707 26884 281
142.0758 5420 56
143.05 4248 44
143.085 2044 21
144.0577 21640 226
145.0652 8228 86
146.0363 3032 31
146.0715 1992 20
146.0964 592 6
147.0434 936 9
147.081 1540 16
148.0761 624 6
149.0595 664 6
150.0486 772 8
151.0547 2392 25
152.0629 38340 401
153.0706 83260 871
154.0771 20300 212
155.0501 9608 100
155.0862 30520 319
156.0577 16420 171
156.0895 4420 46
157.0653 10148 106
158.0736 11496 120
159.0455 4496 47
159.0806 10872 113
160.0526 2132 22
160.0816 1644 17
161.0607 24964 261
162.0644 2692 28
162.0914 632 6
163.0545 988 10
163.0749 656 6
164.0633 2636 27
165.0709 95388 999
166.0764 20456 214
167.0493 872 9
167.0854 6824 71
168.0578 19856 207
168.0885 1344 14
169.0652 20500 214
170.0363 3360 35
170.0733 11596 121
171.0452 8512 89
171.0814 40596 425
172.0524 8080 84
172.0874 11216 117
173.0588 2648 27
173.0946 2548 26
174.0688 3916 41
174.095 652 6
175.0759 5056 52
176.0637 2144 22
177.0705 3936 41
178.0786 9552 100
179.062 1180 12
179.0862 7796 81
180.0579 5992 62
180.0924 2356 24
181.0662 53328 558
182.0725 25168 263
183.0451 18124 189
183.081 21548 225
184.0528 10084 105
184.087 5964 62
185.0604 20708 216
185.0974 5004 52
186.0325 648 6
186.0669 8320 87
186.1011 1076 11
187.0759 8964 93
187.1129 2728 28
188.0818 1428 14
189.0705 4720 49
189.0912 788 8
190.0785 5768 60
191.0865 10020 104
192.0588 1168 12
192.0899 2272 23
193.0659 13724 143
193.1035 1984 20
194.0735 19760 206
195.0805 10536 110
196.0524 1732 18
196.0872 2836 29
197.0611 20556 215
197.0979 4304 45
198.0686 25188 263
199.0765 40860 427
200.0828 11512 120
201.0572 1116 11
201.0699 1592 16
201.0913 2324 24
202.0802 2548 26
203.0859 1144 11
205.0654 3584 37
206.0704 2076 21
206.0991 672 7
207.0815 4356 45
208.053 4440 46
208.0894 3636 38
209.0609 9840 103
209.0962 2868 30
210.0685 16084 168
210.1005 1096 11
211.0403 744 7
211.0763 8396 87
212.0493 1156 12
212.0836 6848 71
212.1052 616 6
213.0573 1332 13
213.092 8492 88
214.0623 688 7
214.0954 2472 25
215.0702 532 5
215.1079 8428 88
216.1116 1324 13
218.0739 2220 23
218.0956 644 6
219.0825 4744 49
220.0877 2600 27
220.1138 2600 27
221.0616 4780 50
221.0959 1808 18
221.1186 924 9
222.0659 1576 16
223.0774 12340 129
224.0815 2764 28
224.1087 944 9
225.056 1864 19
225.0923 9604 100
226.0651 2896 30
226.0966 2948 30
227.0712 1820 19
227.103 572 5
228.0794 1444 15
228.1071 688 7
234.0928 812 8
235.0776 1764 18
235.1011 800 8
236.0844 2380 24
236.1082 648 6
237.0917 1844 19
238.0975 1028 10
239.0702 996 10
239.0937 596 6
239.1285 484 5
240.1046 612 6
240.139 932 9
241.0878 7380 77
241.1197 604 6
242.09 1468 15
242.1218 544 5
243.1042 2852 29
248.1081 1572 16
249.1151 1068 11
250.1244 1840 19
251.1065 936 9
251.1327 480 5
252.1044 1328 13
266.1198 4576 47
267.1277 1224 12
268.1363 852 8
282.1508 516 5
300.1629 3084 32
301.1633 856 8
//
