ACCESSION: MSBNK-Eawag-EA278007
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 90%; R=7500; [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 90 % (nominal)
AC$MASS_SPECTROMETRY: RESOLUTION 7500
AC$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$SPLASH: splash10-0uxr-0910000000-e67964930533268605cd
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0177 C3H3O+ 1 55.0178 -1.66
57.0335 C3H5O+ 1 57.0335 0.86
58.0651 C3H8N+ 1 58.0651 -0.27
69.0335 C4H5O+ 1 69.0335 -0.02
79.054 C6H7+ 1 79.0542 -2.61
81.0337 C5H5O+ 1 81.0335 2.7
83.0489 C5H7O+ 1 83.0491 -3.03
91.0541 C7H7+ 1 91.0542 -0.95
93.0697 C7H9+ 1 93.0699 -1.9
94.0412 C6H6O+ 1 94.0413 -1.34
103.0542 C8H7+ 1 103.0542 -0.45
105.0696 C8H9+ 1 105.0699 -2.44
107.0493 C7H7O+ 1 107.0491 1.3
115.0541 C9H7+ 1 115.0542 -0.93
116.0623 C9H8+ 1 116.0621 2.57
117.0697 C9H9+ 1 117.0699 -1.59
121.0648 C8H9O+ 1 121.0648 0.07
122.0363 C7H6O2+ 1 122.0362 0.81
127.0547 C10H7+ 1 127.0542 3.49
128.062 C10H8+ 1 128.0621 -0.4
129.0699 C10H9+ 1 129.0699 -0.05
131.0491 C9H7O+ 1 131.0491 -0.16
137.0595 C8H9O2+ 1 137.0597 -1.36
139.0544 C11H7+ 1 139.0542 1.1
140.0621 C11H8+ 1 140.0621 0.06
141.0697 C11H9+ 1 141.0699 -1.04
142.0777 C11H10+ 1 142.0777 0.06
143.0494 C10H7O+ 1 143.0491 1.74
144.0568 C10H8O+ 1 144.057 -0.81
145.0646 C10H9O+ 1 145.0648 -1.39
146.036 C9H6O2+ 1 146.0362 -1.31
146.0721 C10H10O+ 1 146.0726 -3.4
151.0539 C12H7+ 1 151.0542 -2.36
152.062 C12H8+ 1 152.0621 -0.14
153.0698 C12H9+ 1 153.0699 -0.7
154.0777 C12H10+ 1 154.0777 0.05
155.0492 C11H7O+ 1 155.0491 0.12
155.0601 C10H7N2+ 1 155.0604 -1.9
155.0855 C12H11+ 1 155.0855 -0.43
156.0569 C11H8O+ 1 156.057 -0.42
157.0649 C11H9O+ 1 157.0648 0.5
158.0727 C11H10O+ 1 158.0726 0.59
159.0439 C10H7O2+ 1 159.0441 -1.23
159.0806 C11H11O+ 1 159.0804 1.12
160.0523 C10H8O2+ 1 160.0519 2.68
160.0755 C10H10NO+ 1 160.0757 -0.88
161.0597 C10H9O2+ 1 161.0597 0.03
165.0698 C13H9+ 1 165.0699 -0.46
166.0776 C13H10+ 1 166.0777 -0.73
167.0856 C13H11+ 1 167.0855 0.68
168.0569 C12H8O+ 1 168.057 -0.16
169.0649 C12H9O+ 1 169.0648 0.64
170.0361 C11H6O2+ 1 170.0362 -0.65
170.0726 C12H10O+ 1 170.0726 -0.27
171.0443 C11H7O2+ 1 171.0441 1.19
171.0804 C12H11O+ 1 171.0804 -0.13
172.0517 C11H8O2+ 1 172.0519 -1.11
172.0884 C12H12O+ 1 172.0883 0.89
173.0599 C11H9O2+ 1 173.0597 0.89
173.0959 C12H13O+ 1 173.0961 -1.34
174.0678 C11H10O2+ 1 174.0675 1.78
175.0755 C11H11O2+ 1 175.0754 0.65
177.0698 C14H9+ 1 177.0699 -0.55
178.0778 C14H10+ 1 178.0777 0.44
179.0855 C14H11+ 1 179.0855 -0.37
180.0569 C13H8O+ 1 180.057 -0.26
180.0935 C14H12+ 1 180.0934 0.66
181.0647 C13H9O+ 1 181.0648 -0.28
182.0725 C13H10O+ 1 182.0726 -0.47
183.0437 C12H7O2+ 1 183.0441 -1.67
183.0805 C13H11O+ 1 183.0804 0.37
184.0517 C12H8O2+ 1 184.0519 -0.87
184.0888 C13H12O+ 1 184.0883 2.95
185.0595 C12H9O2+ 1 185.0597 -1.11
185.0961 C13H13O+ 1 185.0961 0.32
186.0672 C12H10O2+ 1 186.0675 -1.83
187.0752 C12H11O2+ 1 187.0754 -0.73
187.111 C13H15O+ 1 187.1117 -3.91
189.0701 C15H9+ 1 189.0699 1.34
190.0775 C15H10+ 1 190.0777 -1.17
191.0855 C15H11+ 1 191.0855 -0.3
193.0651 C14H9O+ 1 193.0648 1.55
194.0725 C14H10O+ 1 194.0726 -0.7
195.0804 C14H11O+ 1 195.0804 -0.11
196.052 C13H8O2+ 1 196.0519 0.81
197.0597 C13H9O2+ 1 197.0597 -0.28
197.0965 C14H13O+ 1 197.0961 2.02
198.0674 C13H10O2+ 1 198.0675 -0.56
199.0753 C13H11O2+ 1 199.0754 -0.38
200.083 C13H12O2+ 1 200.0832 -0.7
202.0774 C16H10+ 1 202.0777 -1.69
205.0645 C15H9O+ 1 205.0648 -1.62
207.0801 C15H11O+ 1 207.0804 -1.7
208.0518 C14H8O2+ 1 208.0519 -0.2
208.088 C15H12O+ 1 208.0883 -1.09
209.0596 C14H9O2+ 1 209.0597 -0.65
209.0966 C15H13O+ 1 209.0961 2.24
210.0677 C14H10O2+ 1 210.0675 0.66
211.0753 C14H11O2+ 1 211.0754 -0.08
212.0829 C14H12O2+ 1 212.0832 -1.47
213.054 C13H9O3+ 1 213.0546 -2.96
213.0905 C14H13O2+ 1 213.091 -2.52
218.0719 C16H10O+ 1 218.0726 -3.06
219.0809 C16H11O+ 1 219.0804 2.28
220.1118 C16H14N+ 1 220.1121 -1.48
221.0597 C15H9O2+ 1 221.0597 0.11
223.0754 C15H11O2+ 1 223.0754 0.24
224.0828 C15H12O2+ 1 224.0832 -1.7
225.0909 C15H13O2+ 1 225.091 -0.56
235.0763 C16H11O2+ 1 235.0754 4.06
236.0839 C16H12O2+ 1 236.0832 3.17
241.0856 C15H13O3+ 1 241.0859 -1.25
248.1068 C17H14NO+ 1 248.107 -0.97
266.1166 C17H16NO2+ 1 266.1176 -3.7
PK$NUM_PEAK: 114
PK$PEAK: m/z int. rel.int.
55.0177 43269.7 13
57.0335 56065.6 17
58.0651 206437.5 64
69.0335 48671 15
79.054 58371.3 18
81.0337 56254.6 17
83.0489 51190.8 16
91.0541 213493 66
93.0697 33584 10
94.0412 27391.7 8
103.0542 172969.6 54
105.0696 76812.4 24
107.0493 71096.8 22
115.0541 587605.9 183
116.0623 91360.8 28
117.0697 84418.1 26
121.0648 117402.2 36
122.0363 70781.8 22
127.0547 37276 11
128.062 866556.6 271
129.0699 460858.5 144
131.0491 161575.2 50
137.0595 266557.6 83
139.0544 62644.7 19
140.0621 54200.2 16
141.0697 1102695.9 344
142.0777 196224.4 61
143.0494 158926.7 49
144.0568 834459.3 260
145.0646 161129.3 50
146.036 133400.5 41
146.0721 40506.9 12
151.0539 46166.3 14
152.062 1142284.3 357
153.0698 2890070.5 903
154.0777 570064.2 178
155.0492 381019.3 119
155.0601 217800.1 68
155.0855 1067065.1 333
156.0569 647399.7 202
157.0649 314883.6 98
158.0727 433958.2 135
159.0439 209532.6 65
159.0806 256194 80
160.0523 47580 14
160.0755 33903.4 10
161.0597 894926.6 279
165.0698 3194276.5 999
166.0776 544008.1 170
167.0856 208128.1 65
168.0569 720955.9 225
169.0649 607803.8 190
170.0361 88165.6 27
170.0726 348158 108
171.0443 283382.4 88
171.0804 1506582.5 471
172.0517 209218.5 65
172.0884 252650.6 79
173.0599 98253.4 30
173.0959 61882.3 19
174.0678 102539.2 32
175.0755 96629.3 30
177.0698 96944.1 30
178.0778 291629.8 91
179.0855 263909.2 82
180.0569 194745.9 60
180.0935 56929.7 17
181.0647 1850348.4 578
182.0725 693156 216
183.0437 749637.1 234
183.0805 558394.1 174
184.0517 338204.1 105
184.0888 57977.6 18
185.0595 756024 236
185.0961 141043 44
186.0672 166703 52
187.0752 182910.8 57
187.111 41642.6 13
189.0701 188464.4 58
190.0775 234338 73
191.0855 280137 87
193.0651 440205.6 137
194.0725 524543.3 164
195.0804 281735.9 88
196.052 62275 19
197.0597 765530 239
197.0965 105019.5 32
198.0674 769187.1 240
199.0753 927895.3 290
200.083 189838.5 59
202.0774 83080.1 25
205.0645 129924.5 40
207.0801 155091.8 48
208.0518 171108.4 53
208.088 91591.2 28
209.0596 381415.1 119
209.0966 64482.1 20
210.0677 400121.9 125
211.0753 236117.6 73
212.0829 189318.2 59
213.054 39881.4 12
213.0905 194333.3 60
218.0719 52051.2 16
219.0809 119324.5 37
220.1118 118556 37
221.0597 162771.7 50
223.0754 340104.4 106
224.0828 47268 14
225.0909 236761.2 74
235.0763 64630.4 20
236.0839 59203.2 18
241.0856 142298.4 44
248.1068 68079.1 21
266.1166 88542.5 27
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