ACCESSION: MSBNK-Eawag-EA278012
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 75%; R=15000; [M+H]+
DATE: 2014.01.14
AUTHORS: Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2012 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 2780
CH$NAME: Codeine
CH$NAME: (5,6)-3-Methoxy-17-methyl-7,8-didehydro-4,5-epoxymorphinan-6-ol
CH$NAME: Methylmorphine
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C18H21NO3
CH$EXACT_MASS: 299.1521
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: PUBCHEM
CID:5284371
CH$LINK: INCHIKEY
OROGSEYTTFOCAN-DNJOTXNNSA-N
CH$LINK: CHEMSPIDER
4447447
CH$LINK: COMPTOX
DTXSID2020341
AC$INSTRUMENT: LTQ Orbitrap XL Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-ITFT
AC$MASS_SPECTROMETRY: MS_TYPE MS2
AC$MASS_SPECTROMETRY: ION_MODE POSITIVE
AC$MASS_SPECTROMETRY: IONIZATION ESI
AC$MASS_SPECTROMETRY: FRAGMENTATION_MODE HCD
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 75 % (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 15000
AC$CHROMATOGRAPHY: COLUMN_NAME XBridge C18 3.5um, 2.1x50mm, Waters
AC$CHROMATOGRAPHY: FLOW_GRADIENT 90/10 at 0 min, 50/50 at 4 min, 5/95 at 17 min, 5/95 at 25 min, 90/10 at 25.1 min, 90/10 at 30 min
AC$CHROMATOGRAPHY: FLOW_RATE 200 ul/min
AC$CHROMATOGRAPHY: RETENTION_TIME 2.8 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 300.1595
MS$FOCUSED_ION: PRECURSOR_M/Z 300.1594
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: DEPROFILE Spline
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 1.3.1
PK$SPLASH: splash10-015a-0920000000-7eccc8e19d8d88b18128
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0177 C3H3O+ 1 55.0178 -2.2
58.0651 C3H8N+ 1 58.0651 -0.96
67.0542 C5H7+ 1 67.0542 -1.14
69.0334 C4H5O+ 1 69.0335 -1.03
71.0493 C4H7O+ 1 71.0491 1.81
79.0541 C6H7+ 1 79.0542 -1.85
81.0335 C5H5O+ 1 81.0335 0.36
83.0491 C5H7O+ 1 83.0491 -0.62
91.0541 C7H7+ 1 91.0542 -0.95
93.0698 C7H9+ 1 93.0699 -1.15
94.0653 C6H8N+ 1 94.0651 2.38
95.0492 C6H7O+ 1 95.0491 0.51
103.0542 C8H7+ 1 103.0542 0.03
105.0699 C8H9+ 1 105.0699 -0.16
107.0489 C7H7O+ 1 107.0491 -2.72
115.0541 C9H7+ 1 115.0542 -0.75
117.0698 C9H9+ 1 117.0699 -0.91
121.0647 C8H9O+ 1 121.0648 -0.51
128.0619 C10H8+ 1 128.0621 -0.79
129.07 C10H9+ 1 129.0699 0.57
131.0491 C9H7O+ 1 131.0491 -0.01
131.0853 C10H11+ 1 131.0855 -1.58
132.0809 C9H10N+ 1 132.0808 0.71
137.0597 C8H9O2+ 1 137.0597 -0.41
141.0699 C11H9+ 1 141.0699 -0.12
142.0776 C11H10+ 1 142.0777 -0.86
143.049 C10H7O+ 1 143.0491 -1.06
143.0857 C11H11+ 1 143.0855 1.42
144.0569 C10H8O+ 1 144.057 -0.46
144.081 C10H10N+ 1 144.0808 1.83
145.0647 C10H9O+ 1 145.0648 -0.42
146.0599 C9H8NO+ 1 146.06 -0.62
146.0723 C10H10O+ 1 146.0726 -2.03
147.0807 C10H11O+ 1 147.0804 1.83
149.0596 C9H9O2+ 1 149.0597 -0.44
151.0755 C9H11O2+ 1 151.0754 0.89
152.0621 C12H8+ 1 152.0621 0.05
153.0698 C12H9+ 1 153.0699 -0.44
154.0776 C12H10+ 1 154.0777 -0.66
155.0491 C11H7O+ 1 155.0491 -0.27
155.0605 C10H7N2+ 1 155.0604 0.74
155.0854 C12H11+ 1 155.0855 -0.62
156.0569 C11H8O+ 1 156.057 -0.42
157.0646 C11H9O+ 1 157.0648 -1.03
158.0725 C11H10O+ 1 158.0726 -0.55
158.0961 C11H12N+ 1 158.0964 -2.19
159.0438 C10H7O2+ 1 159.0441 -1.29
159.0804 C11H11O+ 1 159.0804 -0.45
160.0521 C10H8O2+ 1 160.0519 1.18
160.0755 C10H10NO+ 1 160.0757 -1.25
161.0596 C10H9O2+ 1 161.0597 -0.6
162.0908 C10H12NO+ 1 162.0913 -3.15
163.0754 C10H11O2+ 1 163.0754 0.21
164.0703 C9H10NO2+ 1 164.0706 -1.68
165.0698 C13H9+ 1 165.0699 -0.34
166.0776 C13H10+ 1 166.0777 -0.37
167.0854 C13H11+ 1 167.0855 -0.7
168.0568 C12H8O+ 1 168.057 -0.81
169.0646 C12H9O+ 1 169.0648 -1.07
169.0758 C11H9N2+ 1 169.076 -1.21
169.1012 C13H13+ 1 169.1012 0.43
170.0725 C12H10O+ 1 170.0726 -0.86
171.0435 C11H7O2+ 1 171.0441 -3.02
171.0804 C12H11O+ 1 171.0804 -0.53
172.0518 C11H8O2+ 1 172.0519 -0.35
172.0882 C12H12O+ 1 172.0883 -0.56
173.0598 C11H9O2+ 1 173.0597 0.43
173.0962 C12H13O+ 1 173.0961 0.68
174.0675 C11H10O2+ 1 174.0675 -0.24
175.0753 C11H11O2+ 1 175.0754 -0.26
177.0698 C14H9+ 1 177.0699 -0.55
178.0776 C14H10+ 1 178.0777 -0.57
179.0854 C14H11+ 1 179.0855 -0.76
180.0569 C13H8O+ 1 180.057 -0.31
180.0933 C14H12+ 1 180.0934 -0.57
181.0647 C13H9O+ 1 181.0648 -0.67
181.1015 C14H13+ 1 181.1012 1.73
182.0726 C13H10O+ 1 182.0726 -0.31
183.0439 C12H7O2+ 1 183.0441 -0.69
183.0804 C13H11O+ 1 183.0804 -0.5
184.0519 C12H8O2+ 1 184.0519 -0.17
184.0883 C13H12O+ 1 184.0883 0.35
185.0596 C12H9O2+ 1 185.0597 -0.46
185.096 C13H13O+ 1 185.0961 -0.44
186.0675 C12H10O2+ 1 186.0675 -0.44
187.0752 C12H11O2+ 1 187.0754 -0.94
187.1117 C13H15O+ 1 187.1117 -0.28
189.0699 C15H9+ 1 189.0699 -0.09
189.0915 C12H13O2+ 1 189.091 2.51
190.0774 C15H10+ 1 190.0777 -1.8
191.0855 C15H11+ 1 191.0855 -0.14
192.0566 C14H8O+ 1 192.057 -1.91
192.1019 C11H14NO2+ 1 192.1019 -0.13
193.0646 C14H9O+ 1 193.0648 -0.99
193.0761 C13H9N2+ 1 193.076 0.29
193.1014 C15H13+ 1 193.1012 1.05
194.0725 C14H10O+ 1 194.0726 -0.81
195.0803 C14H11O+ 1 195.0804 -0.72
196.0879 C14H12O+ 1 196.0883 -1.66
197.0596 C13H9O2+ 1 197.0597 -0.49
197.096 C14H13O+ 1 197.0961 -0.51
198.0674 C13H10O2+ 1 198.0675 -0.56
199.0753 C13H11O2+ 1 199.0754 -0.48
200.0831 C13H12O2+ 1 200.0832 -0.36
201.0548 C12H9O3+ 1 201.0546 1.09
201.0909 C13H13O2+ 1 201.091 -0.38
202.0779 C16H10+ 1 202.0777 0.98
203.0853 C16H11+ 1 203.0855 -1.31
205.0646 C15H9O+ 1 205.0648 -0.93
206.0734 C15H10O+ 1 206.0726 3.75
207.0802 C15H11O+ 1 207.0804 -1.17
208.052 C14H8O2+ 1 208.0519 0.38
208.088 C15H12O+ 1 208.0883 -1.28
209.0596 C14H9O2+ 1 209.0597 -0.6
209.096 C15H13O+ 1 209.0961 -0.34
210.0674 C14H10O2+ 1 210.0675 -0.81
210.104 C15H14O+ 1 210.1039 0.54
211.0752 C14H11O2+ 1 211.0754 -0.64
212.083 C14H12O2+ 1 212.0832 -0.9
213.054 C13H9O3+ 1 213.0546 -3.1
213.0908 C14H13O2+ 1 213.091 -0.78
214.0987 C14H14O2+ 1 214.0988 -0.71
215.1065 C14H15O2+ 1 215.1067 -0.49
218.0719 C16H10O+ 1 218.0726 -3.28
219.0804 C16H11O+ 1 219.0804 -0.14
220.0882 C16H12O+ 1 220.0883 -0.35
220.1114 C16H14N+ 1 220.1121 -2.98
221.0597 C15H9O2+ 1 221.0597 -0.07
221.0962 C16H13O+ 1 221.0961 0.45
223.0752 C15H11O2+ 1 223.0754 -0.65
223.1115 C16H15O+ 1 223.1117 -1.13
224.0827 C15H12O2+ 1 224.0832 -1.97
224.1061 C15H14NO+ 1 224.107 -3.8
225.0542 C14H9O3+ 1 225.0546 -1.82
225.0909 C15H13O2+ 1 225.091 -0.56
226.0623 C14H10O3+ 1 226.0624 -0.73
226.0985 C15H14O2+ 1 226.0988 -1.69
227.0703 C14H11O3+ 1 227.0703 0.09
227.1064 C15H15O2+ 1 227.1067 -0.91
228.0779 C14H12O3+ 1 228.0781 -0.73
228.1026 C14H14NO2+ 1 228.1019 2.87
235.0752 C16H11O2+ 1 235.0754 -0.58
236.0829 C16H12O2+ 1 236.0832 -1.06
237.091 C16H13O2+ 1 237.091 0.14
238.0992 C16H14O2+ 1 238.0988 1.72
239.0697 C15H11O3+ 1 239.0703 -2.47
239.1071 C16H15O2+ 1 239.1067 1.9
241.0858 C15H13O3+ 1 241.0859 -0.54
241.1217 C16H17O2+ 1 241.1223 -2.51
243.1014 C15H15O3+ 1 243.1016 -0.62
248.1072 C17H14NO+ 1 248.107 0.68
250.1227 C17H16NO+ 1 250.1226 0.36
251.1065 C17H15O2+ 1 251.1067 -0.5
252.1019 C16H14NO2+ 1 252.1019 -0.1
253.1215 C17H17O2+ 1 253.1223 -3.26
266.1173 C17H16NO2+ 1 266.1176 -0.92
267.1252 C17H17NO2+ 1 267.1254 -0.82
268.1341 C17H18NO2+ 1 268.1332 3.34
282.1487 C18H20NO2+ 1 282.1489 -0.69
285.1353 C17H19NO3+ 1 285.1359 -2.33
300.1585 C18H22NO3+ 1 300.1594 -3
PK$NUM_PEAK: 161
PK$PEAK: m/z int. rel.int.
55.0177 22412.3 11
58.0651 252961.1 127
67.0542 34878 17
69.0334 52883.1 26
71.0493 17196.7 8
79.0541 34425.8 17
81.0335 24135.9 12
83.0491 40737.6 20
91.0541 105571.7 53
93.0698 53995.6 27
94.0653 14537.5 7
95.0492 24523.6 12
103.0542 64049.6 32
105.0699 31233.2 15
107.0489 31546.6 15
115.0541 129176.9 65
117.0698 30131.1 15
121.0647 133018.9 67
128.0619 132239.8 66
129.07 142780.5 71
131.0491 51531.1 25
131.0853 34134.9 17
132.0809 17057.2 8
137.0597 336831.6 169
141.0699 396652.7 199
142.0776 43718.4 22
143.049 73846.5 37
143.0857 45202.3 22
144.0569 412991.8 208
144.081 23759.3 11
145.0647 128697.1 64
146.0599 22953.5 11
146.0723 28937.2 14
147.0807 46661.1 23
149.0596 34073.9 17
151.0755 21033.1 10
152.0621 150771.9 75
153.0698 1221273.6 615
154.0776 210488.2 106
155.0491 94457.1 47
155.0605 58893.8 29
155.0854 1081757 545
156.0569 298501.7 150
157.0646 144290.4 72
158.0725 314574.6 158
158.0961 19938.4 10
159.0438 99612.3 50
159.0804 484432.4 244
160.0521 27022.6 13
160.0755 35248 17
161.0596 745888.7 375
162.0908 22005.1 11
163.0754 17173.2 8
164.0703 22108.6 11
165.0698 1982256.8 999
166.0776 265291 133
167.0854 180000.6 90
168.0568 420015.8 211
169.0646 192467 96
169.0758 41316.8 20
169.1012 25939.6 13
170.0725 163509.1 82
171.0435 83827.7 42
171.0804 1270877.9 640
172.0518 190740.1 96
172.0882 250029.5 126
173.0598 56184.6 28
173.0962 87062.1 43
174.0675 135753.1 68
175.0753 198497.9 100
177.0698 73964.8 37
178.0776 141019.2 71
179.0854 166881 84
180.0569 63674.4 32
180.0933 28950.5 14
181.0647 1538634.7 775
181.1015 125654 63
182.0726 479115.9 241
183.0439 139608.9 70
183.0804 970349.8 489
184.0519 156460.8 78
184.0883 101838.3 51
185.0596 465228.8 234
185.096 167740.4 84
186.0675 254229 128
187.0752 417629.7 210
187.1117 161496.6 81
189.0699 46901.7 23
189.0915 36247.2 18
190.0774 113476.1 57
191.0855 321685.1 162
192.0566 15727.7 7
192.1019 22871.6 11
193.0646 429174.1 216
193.0761 102292.2 51
193.1014 49211.5 24
194.0725 608647.8 306
195.0803 260564.6 131
196.0879 43355.8 21
197.0596 301617.5 152
197.096 219275 110
198.0674 552682.9 278
199.0753 1552320.1 782
200.0831 293275.8 147
201.0548 44310.7 22
201.0909 106246.3 53
202.0779 50344.8 25
203.0853 29441.5 14
205.0646 60044.9 30
206.0734 19097.2 9
207.0802 107092.8 53
208.052 49641.5 25
208.088 93568.9 47
209.0596 338734.5 170
209.096 129700.4 65
210.0674 405822.6 204
210.104 30260.8 15
211.0752 228422.6 115
212.083 237310.5 119
213.054 33507.4 16
213.0908 436904.2 220
214.0987 25782.9 12
215.1065 687451.3 346
218.0719 35683.9 17
219.0804 128390.6 64
220.0882 107538.5 54
220.1114 70776.8 35
221.0597 112498 56
221.0962 69531.4 35
223.0752 391394.3 197
223.1115 27412.1 13
224.0827 54119.5 27
224.1061 15839.3 7
225.0542 45156.5 22
225.0909 757488.9 381
226.0623 66387.1 33
226.0985 40930.9 20
227.0703 46288.5 23
227.1064 16932.8 8
228.0779 52796.9 26
228.1026 17680 8
235.0752 49314.2 24
236.0829 116613.5 58
237.091 47739.4 24
238.0992 17233.6 8
239.0697 19475.8 9
239.1071 24564.8 12
241.0858 584547.2 294
241.1217 35938.6 18
243.1014 185912.9 93
248.1072 41638.6 20
250.1227 65823.8 33
251.1065 37792.2 19
252.1019 46683.1 23
253.1215 24260.8 12
266.1173 192200.7 96
267.1252 82500.9 41
268.1341 22312.2 11
282.1487 40593.6 20
285.1353 20440.2 10
300.1585 338705.5 170
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