ACCESSION: MSBNK-Eawag-EA278005
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 60%; 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 60 % (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$SPLASH: splash10-0uxr-0973000000-87d07ddd2ed24b9598d7
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
58.0651 C3H8N+ 1 58.0651 0.25
69.0335 C4H5O+ 1 69.0335 -0.45
71.0491 C4H7O+ 1 71.0491 -1.14
81.0336 C5H5O+ 1 81.0335 1.71
83.049 C5H7O+ 1 83.0491 -1.46
91.0541 C7H7+ 1 91.0542 -1.83
93.0698 C7H9+ 1 93.0699 -0.5
95.0492 C6H7O+ 1 95.0491 0.3
103.0543 C8H7+ 1 103.0542 0.71
121.0648 C8H9O+ 1 121.0648 0.15
129.0701 C10H9+ 1 129.0699 1.58
131.0491 C9H7O+ 1 131.0491 -0.24
132.0807 C9H10N+ 1 132.0808 -0.42
137.0599 C8H9O2+ 1 137.0597 1.05
141.0701 C11H9+ 1 141.0699 1.37
143.0491 C10H7O+ 1 143.0491 -0.01
144.0571 C10H8O+ 1 144.057 0.79
145.0649 C10H9O+ 1 145.0648 0.89
146.0606 C9H8NO+ 1 146.06 3.83
147.0804 C10H11O+ 1 147.0804 -0.42
149.0601 C9H9O2+ 1 149.0597 2.98
151.075 C9H11O2+ 1 151.0754 -2.49
152.0623 C12H8+ 1 152.0621 1.76
153.0699 C12H9+ 1 153.0699 0.02
154.0777 C12H10+ 1 154.0777 -0.14
155.0856 C12H11+ 1 155.0855 0.73
156.0569 C11H8O+ 1 156.057 -0.23
157.0653 C11H9O+ 1 157.0648 3.05
158.0727 C11H10O+ 1 158.0726 0.72
159.0805 C11H11O+ 1 159.0804 0.18
160.0756 C10H10NO+ 1 160.0757 -0.75
161.0598 C10H9O2+ 1 161.0597 0.4
162.0915 C10H12NO+ 1 162.0913 0.98
163.0752 C10H11O2+ 1 163.0754 -0.71
164.0699 C9H10NO2+ 1 164.0706 -4.11
165.07 C13H9+ 1 165.0699 0.63
166.0779 C13H10+ 1 166.0777 1.25
167.0859 C13H11+ 1 167.0855 2.35
168.0571 C12H8O+ 1 168.057 0.74
169.0653 C12H9O+ 1 169.0648 3.13
171.0805 C12H11O+ 1 171.0804 0.52
172.052 C11H8O2+ 1 172.0519 0.46
172.0885 C12H12O+ 1 172.0883 1.12
173.06 C11H9O2+ 1 173.0597 1.93
173.0961 C12H13O+ 1 173.0961 0.11
174.0676 C11H10O2+ 1 174.0675 0.51
175.0754 C11H11O2+ 1 175.0754 0.37
177.0702 C14H9+ 1 177.0699 1.88
181.0648 C13H9O+ 1 181.0648 0.27
181.102 C14H13+ 1 181.1012 4.43
182.0728 C13H10O+ 1 182.0726 0.9
183.0806 C13H11O+ 1 183.0804 0.7
184.0517 C12H8O2+ 1 184.0519 -0.93
184.0884 C13H12O+ 1 184.0883 0.94
185.0599 C12H9O2+ 1 185.0597 1.26
185.0966 C13H13O+ 1 185.0961 2.75
186.0676 C12H10O2+ 1 186.0675 0.21
187.0755 C12H11O2+ 1 187.0754 0.66
187.1119 C13H15O+ 1 187.1117 0.74
189.0918 C12H13O2+ 1 189.091 4.09
191.0855 C15H11+ 1 191.0855 -0.24
192.102 C11H14NO2+ 1 192.1019 0.6
193.0652 C14H9O+ 1 193.0648 2.22
193.1012 C15H13+ 1 193.1012 0.22
194.0727 C14H10O+ 1 194.0726 0.48
195.0805 C14H11O+ 1 195.0804 0.4
196.0878 C14H12O+ 1 196.0883 -2.23
197.0594 C13H9O2+ 1 197.0597 -1.7
197.0961 C14H13O+ 1 197.0961 0.09
198.0676 C13H10O2+ 1 198.0675 0.4
198.104 C14H14O+ 1 198.1039 0.52
199.0754 C13H11O2+ 1 199.0754 0.47
200.0833 C13H12O2+ 1 200.0832 0.54
201.0911 C13H13O2+ 1 201.091 0.52
202.0778 C16H10+ 1 202.0777 0.34
203.0849 C16H11+ 1 203.0855 -3.23
205.0644 C15H9O+ 1 205.0648 -1.76
206.0723 C15H10O+ 1 206.0726 -1.58
207.0806 C15H11O+ 1 207.0804 0.72
208.0885 C15H12O+ 1 208.0883 1.27
209.0598 C14H9O2+ 1 209.0597 0.59
209.0964 C15H13O+ 1 209.0961 1.28
210.0678 C14H10O2+ 1 210.0675 1.09
210.1046 C15H14O+ 1 210.1039 3.21
211.0754 C14H11O2+ 1 211.0754 0.45
212.0832 C14H12O2+ 1 212.0832 0.33
213.0911 C14H13O2+ 1 213.091 0.49
214.0982 C14H14O2+ 1 214.0988 -2.76
215.1067 C14H15O2+ 1 215.1067 0.2
219.0807 C16H11O+ 1 219.0804 1.04
220.0886 C16H12O+ 1 220.0883 1.56
221.06 C15H9O2+ 1 221.0597 1.33
221.0959 C16H13O+ 1 221.0961 -0.91
222.104 C16H14O+ 1 222.1039 0.56
222.128 C16H16N+ 1 222.1277 1.41
223.0755 C15H11O2+ 1 223.0754 0.56
223.112 C16H15O+ 1 223.1117 1.11
224.083 C15H12O2+ 1 224.0832 -0.9
225.091 C15H13O2+ 1 225.091 0.2
226.063 C14H10O3+ 1 226.0624 2.28
226.0981 C15H14O2+ 1 226.0988 -3.45
227.0702 C14H11O3+ 1 227.0703 -0.4
227.1074 C15H15O2+ 1 227.1067 3.36
228.0772 C14H12O3+ 1 228.0781 -4.1
228.1019 C14H14NO2+ 1 228.1019 -0.24
229.1105 C14H15NO2+ 1 229.1097 3.53
230.1168 C14H16NO2+ 1 230.1176 -3.24
236.0838 C16H12O2+ 1 236.0832 2.79
237.091 C16H13O2+ 1 237.091 0.06
238.098 C16H14O2+ 1 238.0988 -3.41
239.1062 C16H15O2+ 1 239.1067 -1.82
241.086 C15H13O3+ 1 241.0859 0.41
241.1232 C16H17O2+ 1 241.1223 3.5
243.1017 C15H15O3+ 1 243.1016 0.61
250.1228 C17H16NO+ 1 250.1226 0.56
251.1065 C17H15O2+ 1 251.1067 -0.58
252.1012 C16H14NO2+ 1 252.1019 -2.64
253.1222 C17H17O2+ 1 253.1223 -0.62
254.1175 C16H16NO2+ 1 254.1176 -0.37
266.1178 C17H16NO2+ 1 266.1176 1.03
267.1256 C17H17NO2+ 1 267.1254 0.71
269.1174 C17H17O3+ 1 269.1172 0.63
272.1279 C16H18NO3+ 1 272.1281 -0.62
282.1491 C18H20NO2+ 1 282.1489 0.73
285.1362 C17H19NO3+ 1 285.1359 1.03
300.1599 C18H22NO3+ 1 300.1594 1.7
PK$NUM_PEAK: 126
PK$PEAK: m/z int. rel.int.
58.0651 608314.2 82
69.0335 51331.3 6
71.0491 23841.4 3
81.0336 34759.3 4
83.049 29316.3 3
91.0541 39705.3 5
93.0698 57297.5 7
95.0492 28316.7 3
103.0543 23636.9 3
121.0648 195713.7 26
129.0701 38278 5
131.0491 42775.5 5
132.0807 35182.5 4
137.0599 426362.4 57
141.0701 148219 20
143.0491 59183.5 8
144.0571 215692.4 29
145.0649 76021.4 10
146.0606 51691.7 7
147.0804 35319.9 4
149.0601 33662.3 4
151.075 55230.3 7
152.0623 32296 4
153.0699 391442.8 53
154.0777 51017.3 6
155.0856 755768.8 102
156.0569 110852.1 15
157.0653 79556.4 10
158.0727 170644.5 23
159.0805 657422.9 89
160.0756 62261.4 8
161.0598 1043753.5 141
162.0915 41487.3 5
163.0752 39322.5 5
164.0699 27019.1 3
165.07 1267686.7 172
166.0779 96934.2 13
167.0859 170310.5 23
168.0571 274394.3 37
169.0653 114757 15
171.0805 674173.4 91
172.052 173984.6 23
172.0885 201112 27
173.06 40662 5
173.0961 110253.9 14
174.0676 190009.7 25
175.0754 297613.2 40
177.0702 70703.9 9
181.0648 1174916.3 159
181.102 222387.7 30
182.0728 303516.3 41
183.0806 2063869.9 280
184.0517 51685.6 7
184.0884 102283.2 13
185.0599 300232.7 40
185.0966 164308.2 22
186.0676 311850.6 42
187.0755 1113975.2 151
187.1119 423507.7 57
189.0918 58318.4 7
191.0855 403705.4 54
192.102 192635.9 26
193.0652 868025.3 117
193.1012 156368 21
194.0727 583227.5 79
195.0805 285394.8 38
196.0878 36301.2 4
197.0594 89154.7 12
197.0961 420704.6 57
198.0676 318155.8 43
198.104 34251.7 4
199.0754 2940821.3 399
200.0833 420456.5 57
201.0911 269723 36
202.0778 32984.6 4
203.0849 63725.4 8
205.0644 60409.1 8
206.0723 24387.4 3
207.0806 234141 31
208.0885 119408.6 16
209.0598 693525.3 94
209.0964 283697.5 38
210.0678 285230.9 38
210.1046 54533.4 7
211.0754 456944.7 62
212.0832 354352.1 48
213.0911 799057.5 108
214.0982 64591.9 8
215.1067 3742662.6 508
219.0807 265924.8 36
220.0886 150982.6 20
221.06 78524.7 10
221.0959 253595.7 34
222.104 25587.6 3
222.128 28746.5 3
223.0755 527292 71
223.112 45746 6
224.083 74985.4 10
225.091 2267063.8 307
226.063 29048.3 3
226.0981 86731 11
227.0702 83062.3 11
227.1074 59312 8
228.0772 83793.4 11
228.1019 63106.1 8
229.1105 33154.1 4
230.1168 34327.2 4
236.0838 201340.5 27
237.091 119083.9 16
238.098 133539.2 18
239.1062 119179.9 16
241.086 1539229.5 209
241.1232 117023.7 15
243.1017 1675043.7 227
250.1228 121320.2 16
251.1065 297585.5 40
252.1012 78566.2 10
253.1222 205766.9 27
254.1175 48896.7 6
266.1178 361716.6 49
267.1256 278642.2 37
269.1174 101478.6 13
272.1279 28836.7 3
282.1491 529074.4 71
285.1362 77146.4 10
300.1599 7357139.1 999
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