ACCESSION: MSBNK-Eawag-EA278013
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 90%; 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 90 % (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$SPLASH: splash10-0uxr-0910000000-5809a9ed32210bcfa231
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0178 C3H3O+ 1 55.0178 -1.47
57.0334 C3H5O+ 1 57.0335 -1.25
58.0651 C3H8N+ 1 58.0651 -0.79
67.0542 C5H7+ 1 67.0542 -0.1
69.0335 C4H5O+ 1 69.0335 0.42
79.0542 C6H7+ 1 79.0542 -0.34
81.0334 C5H5O+ 1 81.0335 -0.88
83.049 C5H7O+ 1 83.0491 -1.82
91.0542 C7H7+ 1 91.0542 -0.29
93.0698 C7H9+ 1 93.0699 -1.15
94.0417 C6H6O+ 1 94.0413 3.76
94.0649 C6H8N+ 1 94.0651 -1.87
95.0492 C6H7O+ 1 95.0491 0.41
103.0541 C8H7+ 1 103.0542 -1.03
105.0699 C8H9+ 1 105.0699 0.41
107.0489 C7H7O+ 1 107.0491 -2.72
115.0542 C9H7+ 1 115.0542 -0.49
116.0623 C9H8+ 1 116.0621 2.05
117.0696 C9H9+ 1 117.0699 -2.45
121.0645 C8H9O+ 1 121.0648 -2.08
122.0362 C7H6O2+ 1 122.0362 -0.42
127.054 C10H7+ 1 127.0542 -2.1
128.062 C10H8+ 1 128.0621 -0.25
129.0699 C10H9+ 1 129.0699 -0.13
131.0491 C9H7O+ 1 131.0491 -0.39
131.0852 C10H11+ 1 131.0855 -2.65
132.0807 C9H10N+ 1 132.0808 -0.5
137.0596 C8H9O2+ 1 137.0597 -0.7
139.0541 C11H7+ 1 139.0542 -1.2
140.0618 C11H8+ 1 140.0621 -1.87
141.0698 C11H9+ 1 141.0699 -0.47
142.0776 C11H10+ 1 142.0777 -0.93
143.0492 C10H7O+ 1 143.0491 0.13
143.0853 C11H11+ 1 143.0855 -1.72
144.0569 C10H8O+ 1 144.057 -0.53
145.0648 C10H9O+ 1 145.0648 0.06
146.0361 C9H6O2+ 1 146.0362 -0.69
146.0726 C10H10O+ 1 146.0726 -0.32
147.0806 C10H11O+ 1 147.0804 0.81
151.0543 C12H7+ 1 151.0542 0.55
152.062 C12H8+ 1 152.0621 -0.34
153.0697 C12H9+ 1 153.0699 -0.83
154.0776 C12H10+ 1 154.0777 -0.6
155.0491 C11H7O+ 1 155.0491 -0.4
155.0603 C10H7N2+ 1 155.0604 -0.55
155.0854 C12H11+ 1 155.0855 -0.56
156.0569 C11H8O+ 1 156.057 -0.62
157.0647 C11H9O+ 1 157.0648 -0.9
158.0726 C11H10O+ 1 158.0726 -0.36
159.044 C10H7O2+ 1 159.0441 -0.35
159.0803 C11H11O+ 1 159.0804 -0.89
160.052 C10H8O2+ 1 160.0519 0.43
160.0752 C10H10NO+ 1 160.0757 -3.13
161.0596 C10H9O2+ 1 161.0597 -0.53
165.0698 C13H9+ 1 165.0699 -0.59
166.0777 C13H10+ 1 166.0777 -0.07
167.0853 C13H11+ 1 167.0855 -1.42
168.0569 C12H8O+ 1 168.057 -0.39
169.0647 C12H9O+ 1 169.0648 -0.72
169.0758 C11H9N2+ 1 169.076 -1.27
170.0361 C11H6O2+ 1 170.0362 -0.59
170.0724 C12H10O+ 1 170.0726 -1.21
171.0439 C11H7O2+ 1 171.0441 -0.91
171.0804 C12H11O+ 1 171.0804 -0.53
172.0518 C11H8O2+ 1 172.0519 -0.59
172.0882 C12H12O+ 1 172.0883 -0.33
173.0599 C11H9O2+ 1 173.0597 0.89
173.0957 C12H13O+ 1 173.0961 -2.32
174.0676 C11H10O2+ 1 174.0675 0.28
175.0753 C11H11O2+ 1 175.0754 -0.61
177.0699 C14H9+ 1 177.0699 -0.15
178.0776 C14H10+ 1 178.0777 -0.68
179.0854 C14H11+ 1 179.0855 -0.76
180.0567 C13H8O+ 1 180.057 -1.26
180.094 C14H12+ 1 180.0934 3.71
181.0647 C13H9O+ 1 181.0648 -0.5
182.0725 C13H10O+ 1 182.0726 -0.58
183.0439 C12H7O2+ 1 183.0441 -0.63
183.0803 C13H11O+ 1 183.0804 -0.55
184.0518 C12H8O2+ 1 184.0519 -0.6
184.0883 C13H12O+ 1 184.0883 0.07
185.0596 C12H9O2+ 1 185.0597 -0.79
185.0961 C13H13O+ 1 185.0961 -0.01
186.0673 C12H10O2+ 1 186.0675 -1.3
187.0752 C12H11O2+ 1 187.0754 -1.05
187.1119 C13H15O+ 1 187.1117 0.9
189.0699 C15H9+ 1 189.0699 -0.04
190.0777 C15H10+ 1 190.0777 -0.06
191.0854 C15H11+ 1 191.0855 -0.61
192.0568 C14H8O+ 1 192.057 -1.07
193.0648 C14H9O+ 1 193.0648 -0.21
193.076 C13H9N2+ 1 193.076 -0.08
193.1019 C15H13+ 1 193.1012 3.8
194.0725 C14H10O+ 1 194.0726 -0.7
195.0804 C14H11O+ 1 195.0804 -0.26
196.0518 C13H8O2+ 1 196.0519 -0.57
196.0886 C14H12O+ 1 196.0883 1.85
197.0596 C13H9O2+ 1 197.0597 -0.49
197.096 C14H13O+ 1 197.0961 -0.31
198.0674 C13H10O2+ 1 198.0675 -0.81
199.0753 C13H11O2+ 1 199.0754 -0.48
200.083 C13H12O2+ 1 200.0832 -1
201.0911 C13H13O2+ 1 201.091 0.37
202.0771 C16H10+ 1 202.0777 -2.78
203.0862 C16H11+ 1 203.0855 3.46
205.0649 C15H9O+ 1 205.0648 0.43
206.0724 C15H10O+ 1 206.0726 -1.24
207.0802 C15H11O+ 1 207.0804 -1.21
208.052 C14H8O2+ 1 208.0519 0.48
208.0881 C15H12O+ 1 208.0883 -0.66
209.0597 C14H9O2+ 1 209.0597 -0.12
209.096 C15H13O+ 1 209.0961 -0.39
210.0674 C14H10O2+ 1 210.0675 -0.67
211.0752 C14H11O2+ 1 211.0754 -0.69
212.083 C14H12O2+ 1 212.0832 -0.67
213.054 C13H9O3+ 1 213.0546 -3.05
213.0909 C14H13O2+ 1 213.091 -0.5
215.107 C14H15O2+ 1 215.1067 1.69
218.0728 C16H10O+ 1 218.0726 0.75
219.0801 C16H11O+ 1 219.0804 -1.56
220.1121 C16H14N+ 1 220.1121 0.11
221.0599 C15H9O2+ 1 221.0597 0.97
221.0962 C16H13O+ 1 221.0961 0.67
223.0752 C15H11O2+ 1 223.0754 -0.7
225.0546 C14H9O3+ 1 225.0546 -0.05
225.0909 C15H13O2+ 1 225.091 -0.25
226.0628 C14H10O3+ 1 226.0624 1.79
227.0696 C14H11O3+ 1 227.0703 -3.09
235.0754 C16H11O2+ 1 235.0754 0.19
236.0822 C16H12O2+ 1 236.0832 -4.11
239.07 C15H11O3+ 1 239.0703 -1.17
241.0856 C15H13O3+ 1 241.0859 -1.41
248.1073 C17H14NO+ 1 248.107 1.33
250.1224 C17H16NO+ 1 250.1226 -0.88
252.1021 C16H14NO2+ 1 252.1019 0.61
266.1178 C17H16NO2+ 1 266.1176 0.92
300.1587 C18H22NO3+ 1 300.1594 -2.33
PK$NUM_PEAK: 137
PK$PEAK: m/z int. rel.int.
55.0178 23570.1 10
57.0334 26387.4 11
58.0651 144849 63
67.0542 28457.6 12
69.0335 49384.8 21
79.0542 47201.5 20
81.0334 19791.9 8
83.049 30207.9 13
91.0542 149328.7 65
93.0698 26340 11
94.0417 15616.2 6
94.0649 19721.9 8
95.0492 27562.1 12
103.0541 102643.9 44
105.0699 18504.9 8
107.0489 39724.8 17
115.0542 416850.1 182
116.0623 56374.9 24
117.0696 31297.7 13
121.0645 83906 36
122.0362 42281.8 18
127.054 35600.1 15
128.062 653234.6 286
129.0699 357661.2 156
131.0491 123543.2 54
131.0852 29078.2 12
132.0807 26079.6 11
137.0596 218767.8 95
139.0541 47704.3 20
140.0618 23562 10
141.0698 807781.5 353
142.0776 112219.1 49
143.0492 112585.1 49
143.0853 39281.9 17
144.0569 519377 227
145.0648 128828.6 56
146.0361 68669.6 30
146.0726 49016.7 21
147.0806 28603.5 12
151.0543 20111.1 8
152.062 748789.8 327
153.0697 2146541.6 939
154.0776 401200.3 175
155.0491 235626.8 103
155.0603 186859 81
155.0854 801466.5 350
156.0569 432588.5 189
157.0647 222118.5 97
158.0726 343649.1 150
159.044 160458.6 70
159.0803 226763.2 99
160.052 44940.2 19
160.0752 23832.5 10
161.0596 616872.9 270
165.0698 2281743.3 999
166.0777 301378.2 131
167.0853 166545.7 72
168.0569 464981.9 203
169.0647 403512 176
169.0758 42056.9 18
170.0361 88451.3 38
170.0724 237198.6 103
171.0439 170540.3 74
171.0804 1137910 498
172.0518 177081 77
172.0882 154532 67
173.0599 29272.4 12
173.0957 29179.7 12
174.0676 76436.3 33
175.0753 88285.7 38
177.0699 49469.7 21
178.0776 237946.4 104
179.0854 182452.4 79
180.0567 160582 70
180.094 31612.3 13
181.0647 1293411.4 566
182.0725 520709 227
183.0439 605100 264
183.0803 337293.2 147
184.0518 208054.2 91
184.0883 87880.7 38
185.0596 479409.9 209
185.0961 99776 43
186.0673 151604.3 66
187.0752 167860.8 73
187.1119 35165.1 15
189.0699 129152.3 56
190.0777 139778.8 61
191.0854 177202 77
192.0568 23188.7 10
193.0648 288737.2 126
193.076 37791.4 16
193.1019 24182.3 10
194.0725 316233.4 138
195.0804 175384.1 76
196.0518 34914.2 15
196.0886 36926.7 16
197.0596 511113.7 223
197.096 62827.6 27
198.0674 624943.6 273
199.0753 673408.2 294
200.083 121260.3 53
201.0911 23028.6 10
202.0771 34538.7 15
203.0862 18715.9 8
205.0649 97929.1 42
206.0724 24054.1 10
207.0802 93113.6 40
208.052 103179.3 45
208.0881 51511.8 22
209.0597 231635.3 101
209.096 35271.5 15
210.0674 245374.6 107
211.0752 144161.2 63
212.083 100175.7 43
213.054 33268.9 14
213.0909 110350.1 48
215.107 86047.4 37
218.0728 30593.1 13
219.0801 89735.8 39
220.1121 98685.3 43
221.0599 105351.8 46
221.0962 27466 12
223.0752 235186.1 102
225.0546 45576.7 19
225.0909 204090.6 89
226.0628 52816.2 23
227.0696 30263 13
235.0754 44287.9 19
236.0822 36492.5 15
239.07 31362 13
241.0856 101532.8 44
248.1073 46943.3 20
250.1224 33949.8 14
252.1021 27258.3 11
266.1178 63844.7 27
300.1587 33201.2 14
//
