ACCESSION: MSBNK-Eawag-EA278006
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 75%; 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 75 % (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$SPLASH: splash10-015a-0920000000-4f676c9e2b42320493af
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
57.0333 C3H5O+ 1 57.0335 -2.65
58.0651 C3H8N+ 1 58.0651 -0.61
67.0541 C5H7+ 1 67.0542 -1.59
69.0336 C4H5O+ 1 69.0335 1.14
71.0493 C4H7O+ 1 71.0491 2.23
79.0543 C6H7+ 1 79.0542 0.67
81.0335 C5H5O+ 1 81.0335 -0.26
83.0491 C5H7O+ 1 83.0491 -0.02
91.0542 C7H7+ 1 91.0542 -0.07
93.0698 C7H9+ 1 93.0699 -1.25
95.0491 C6H7O+ 1 95.0491 -0.43
103.0544 C8H7+ 1 103.0542 2.07
105.0695 C8H9+ 1 105.0699 -3.68
107.0488 C7H7O+ 1 107.0491 -2.81
115.054 C9H7+ 1 115.0542 -1.62
117.0695 C9H9+ 1 117.0699 -3.3
121.0648 C8H9O+ 1 121.0648 0.24
122.0364 C7H6O2+ 1 122.0362 1.39
128.0621 C10H8+ 1 128.0621 0.14
129.0699 C10H9+ 1 129.0699 0.18
131.0492 C9H7O+ 1 131.0491 0.6
131.0853 C10H11+ 1 131.0855 -1.73
132.0806 C9H10N+ 1 132.0808 -1.56
137.0597 C8H9O2+ 1 137.0597 -0.19
141.0698 C11H9+ 1 141.0699 -0.33
142.0782 C11H10+ 1 142.0777 3.23
143.0494 C10H7O+ 1 143.0491 1.67
143.0861 C11H11+ 1 143.0855 4.08
144.0569 C10H8O+ 1 144.057 -0.18
145.0646 C10H9O+ 1 145.0648 -1.18
146.0605 C9H8NO+ 1 146.06 3.28
146.0728 C10H10O+ 1 146.0726 1.12
147.0801 C10H11O+ 1 147.0804 -2.53
152.0618 C12H8+ 1 152.0621 -1.72
153.0698 C12H9+ 1 153.0699 -0.7
154.0778 C12H10+ 1 154.0777 0.57
155.0494 C11H7O+ 1 155.0491 1.73
155.0601 C10H7N2+ 1 155.0604 -1.9
155.0855 C12H11+ 1 155.0855 -0.11
156.057 C11H8O+ 1 156.057 0.28
157.0646 C11H9O+ 1 157.0648 -1.28
158.0724 C11H10O+ 1 158.0726 -1.12
159.0439 C10H7O2+ 1 159.0441 -0.79
159.0803 C11H11O+ 1 159.0804 -0.83
160.0757 C10H10NO+ 1 160.0757 0
161.0596 C10H9O2+ 1 161.0597 -0.53
162.0918 C10H12NO+ 1 162.0913 2.71
163.0752 C10H11O2+ 1 163.0754 -1.08
164.0712 C9H10NO2+ 1 164.0706 3.63
165.0699 C13H9+ 1 165.0699 -0.04
166.0779 C13H10+ 1 166.0777 1.07
167.0856 C13H11+ 1 167.0855 0.38
168.057 C12H8O+ 1 168.057 -0.04
169.0649 C12H9O+ 1 169.0648 0.41
169.1009 C13H13+ 1 169.1012 -1.4
170.0726 C12H10O+ 1 170.0726 0.02
171.0439 C11H7O2+ 1 171.0441 -1.03
171.0804 C12H11O+ 1 171.0804 -0.24
172.0519 C11H8O2+ 1 172.0519 0.23
172.0884 C12H12O+ 1 172.0883 0.78
173.0594 C11H9O2+ 1 173.0597 -1.71
173.0965 C12H13O+ 1 173.0961 2.19
174.0674 C11H10O2+ 1 174.0675 -0.7
175.0752 C11H11O2+ 1 175.0754 -1.18
177.0701 C14H9+ 1 177.0699 1.32
178.0776 C14H10+ 1 178.0777 -0.52
179.0857 C14H11+ 1 179.0855 1.02
180.0566 C13H8O+ 1 180.057 -2.03
181.0648 C13H9O+ 1 181.0648 -0.17
182.0726 C13H10O+ 1 182.0726 -0.31
183.0434 C12H7O2+ 1 183.0441 -3.42
183.0804 C13H11O+ 1 183.0804 -0.23
184.0517 C12H8O2+ 1 184.0519 -0.82
184.0882 C13H12O+ 1 184.0883 -0.47
185.0596 C12H9O2+ 1 185.0597 -0.46
185.0963 C13H13O+ 1 185.0961 0.96
186.0676 C12H10O2+ 1 186.0675 0.42
187.0754 C12H11O2+ 1 187.0754 0.07
187.1118 C13H15O+ 1 187.1117 0.53
189.0702 C15H9+ 1 189.0699 1.55
190.0777 C15H10+ 1 190.0777 -0.27
191.0855 C15H11+ 1 191.0855 -0.35
193.0656 C14H9O+ 1 193.0648 4.09
193.101 C15H13+ 1 193.1012 -0.76
194.0726 C14H10O+ 1 194.0726 -0.34
195.0804 C14H11O+ 1 195.0804 -0.06
196.0525 C13H8O2+ 1 196.0519 3.26
196.0876 C14H12O+ 1 196.0883 -3.55
197.0596 C13H9O2+ 1 197.0597 -0.74
197.096 C14H13O+ 1 197.0961 -0.62
198.0675 C13H10O2+ 1 198.0675 -0.21
199.0753 C13H11O2+ 1 199.0754 -0.28
200.0829 C13H12O2+ 1 200.0832 -1.5
201.0555 C12H9O3+ 1 201.0546 4.13
201.0903 C13H13O2+ 1 201.091 -3.36
202.0779 C16H10+ 1 202.0777 1.18
203.0857 C16H11+ 1 203.0855 0.95
205.0645 C15H9O+ 1 205.0648 -1.27
207.0801 C15H11O+ 1 207.0804 -1.7
208.0517 C14H8O2+ 1 208.0519 -0.87
208.0883 C15H12O+ 1 208.0883 0.26
209.0596 C14H9O2+ 1 209.0597 -0.51
209.0963 C15H13O+ 1 209.0961 1.19
210.0675 C14H10O2+ 1 210.0675 -0.1
210.1036 C15H14O+ 1 210.1039 -1.27
211.0753 C14H11O2+ 1 211.0754 -0.41
212.0828 C14H12O2+ 1 212.0832 -1.75
213.0542 C13H9O3+ 1 213.0546 -1.79
213.0909 C14H13O2+ 1 213.091 -0.59
215.1064 C14H15O2+ 1 215.1067 -1
216.1009 C13H14NO2+ 1 216.1019 -4.56
218.0719 C16H10O+ 1 218.0726 -3.42
219.0804 C16H11O+ 1 219.0804 -0.1
220.0876 C16H12O+ 1 220.0883 -2.8
220.1115 C16H14N+ 1 220.1121 -2.48
221.0598 C15H9O2+ 1 221.0597 0.47
221.096 C16H13O+ 1 221.0961 -0.28
222.128 C16H16N+ 1 222.1277 1.41
223.0753 C15H11O2+ 1 223.0754 -0.12
224.0831 C15H12O2+ 1 224.0832 -0.41
225.0908 C15H13O2+ 1 225.091 -1.05
226.0626 C14H10O3+ 1 226.0624 0.82
226.099 C15H14O2+ 1 226.0988 0.75
227.0698 C14H11O3+ 1 227.0703 -2.03
228.0784 C14H12O3+ 1 228.0781 1.38
228.1022 C14H14NO2+ 1 228.1019 1.16
235.0759 C16H11O2+ 1 235.0754 2.19
236.0831 C16H12O2+ 1 236.0832 -0.51
237.0911 C16H13O2+ 1 237.091 0.23
238.0983 C16H14O2+ 1 238.0988 -2.15
239.0704 C15H11O3+ 1 239.0703 0.71
239.1066 C16H15O2+ 1 239.1067 -0.28
241.0859 C15H13O3+ 1 241.0859 -0.04
241.1224 C16H17O2+ 1 241.1223 0.18
243.1018 C15H15O3+ 1 243.1016 0.86
250.1226 C17H16NO+ 1 250.1226 -0.08
252.102 C16H14NO2+ 1 252.1019 0.34
266.1175 C17H16NO2+ 1 266.1176 -0.21
267.1252 C17H17NO2+ 1 267.1254 -0.6
282.1477 C18H20NO2+ 1 282.1489 -3.92
PK$NUM_PEAK: 140
PK$PEAK: m/z int. rel.int.
57.0333 41254.2 16
58.0651 372155.3 148
67.0541 34415 13
69.0336 77046.3 30
71.0493 26119.9 10
79.0543 71059.8 28
81.0335 61916.9 24
83.0491 62186.6 24
91.0542 129602.8 51
93.0698 49319.9 19
95.0491 46477.8 18
103.0544 104347.3 41
105.0695 59446.1 23
107.0488 25216.2 10
115.054 194943 77
117.0695 41236.8 16
121.0648 167717.2 66
122.0364 30099.4 12
128.0621 227284.1 90
129.0699 199759.6 79
131.0492 68751.5 27
131.0853 48557.9 19
132.0806 23635.2 9
137.0597 466815.8 186
141.0698 594491.6 237
142.0782 73266.7 29
143.0494 75237.5 30
143.0861 53374.2 21
144.0569 581467.1 232
145.0646 113526.9 45
146.0605 23677.9 9
146.0728 37096.8 14
147.0801 49716.4 19
152.0618 215071.6 85
153.0698 1645442.7 656
154.0778 322348 128
155.0494 144855.3 57
155.0601 82751.2 33
155.0855 1499509.7 598
156.057 381083.3 152
157.0646 196825.1 78
158.0724 412068.7 164
159.0439 116547.7 46
159.0803 616392.2 245
160.0757 61850.9 24
161.0596 1097160.8 437
162.0918 23862 9
163.0752 30399.4 12
164.0712 34198.5 13
165.0699 2503649.8 999
166.0779 328992.1 131
167.0856 252396.4 100
168.057 519083.8 207
169.0649 234413.2 93
169.1009 41890.5 16
170.0726 247737.6 98
171.0439 124022.7 49
171.0804 1594905.2 636
172.0519 243432 97
172.0884 332444.1 132
173.0594 74957.2 29
173.0965 129490.9 51
174.0674 234975.9 93
175.0752 227678 90
177.0701 101904.6 40
178.0776 231227.1 92
179.0857 264242.5 105
180.0566 135524.9 54
181.0648 1948245.3 777
182.0726 670223.2 267
183.0434 188840.5 75
183.0804 1221991.3 487
184.0517 225006.5 89
184.0882 138594.8 55
185.0596 713179.1 284
185.0963 242248.1 96
186.0676 355657.4 141
187.0754 611574.5 244
187.1118 220827.1 88
189.0702 54498.8 21
190.0777 150154.2 59
191.0855 420958.8 167
193.0656 631725.7 252
193.101 90250 36
194.0726 817522.9 326
195.0804 307287.1 122
196.0525 35102.1 14
196.0876 49071.4 19
197.0596 359878.8 143
197.096 270604.9 107
198.0675 796226 317
199.0753 2172198.5 866
200.0829 426491.2 170
201.0555 53070.9 21
201.0903 132287.4 52
202.0779 46708.5 18
203.0857 41693.4 16
205.0645 103566.2 41
207.0801 137840.4 55
208.0517 96428.9 38
208.0883 144100.8 57
209.0596 565940.6 225
209.0963 139056.3 55
210.0675 536672.4 214
210.1036 30308.2 12
211.0753 357375.8 142
212.0828 402721.2 160
213.0542 50432.7 20
213.0909 569346.5 227
215.1064 983952.2 392
216.1009 28007.3 11
218.0719 75420.7 30
219.0804 207940 82
220.0876 129769.8 51
220.1115 96729.9 38
221.0598 153777.5 61
221.096 108234.5 43
222.128 39878.2 15
223.0753 571653.8 228
224.0831 83112.2 33
225.0908 904229.7 360
226.0626 106695.9 42
226.099 43407.1 17
227.0698 51691.3 20
228.0784 45661 18
228.1022 46316.5 18
235.0759 80960.6 32
236.0831 152473 60
237.0911 44305.8 17
238.0983 61421.3 24
239.0704 39098.3 15
239.1066 47032.4 18
241.0859 804738.4 321
241.1224 43793.8 17
243.1018 281855.5 112
250.1226 85431 34
252.102 68242.5 27
266.1175 250988.4 100
267.1252 66669.6 26
282.1477 66525.2 26
//
