ACCESSION: MSBNK-Eawag-EA278011
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 60%; 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 60 % (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$SPLASH: splash10-0uxr-0973000000-89bc81638a52beefd890
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
58.0651 C3H8N+ 1 58.0651 -0.79
69.0335 C4H5O+ 1 69.0335 -0.45
79.0543 C6H7+ 1 79.0542 0.42
81.0332 C5H5O+ 1 81.0335 -3.22
83.0492 C5H7O+ 1 83.0491 0.71
91.0541 C7H7+ 1 91.0542 -1.61
93.07 C7H9+ 1 93.0699 0.79
103.0541 C8H7+ 1 103.0542 -1.71
115.0538 C9H7+ 1 115.0542 -3.53
121.0648 C8H9O+ 1 121.0648 0.15
129.0698 C10H9+ 1 129.0699 -0.9
131.0489 C9H7O+ 1 131.0491 -1.99
137.0596 C8H9O2+ 1 137.0597 -0.55
141.0698 C11H9+ 1 141.0699 -0.76
143.0492 C10H7O+ 1 143.0491 0.34
144.057 C10H8O+ 1 144.057 0.37
144.0806 C10H10N+ 1 144.0808 -1.5
145.0647 C10H9O+ 1 145.0648 -0.7
146.0601 C9H8NO+ 1 146.06 0.2
149.0592 C9H9O2+ 1 149.0597 -3.6
151.075 C9H11O2+ 1 151.0754 -2.69
153.0698 C12H9+ 1 153.0699 -0.57
154.0777 C12H10+ 1 154.0777 0.18
155.0854 C12H11+ 1 155.0855 -0.95
156.0568 C11H8O+ 1 156.057 -1.32
157.0647 C11H9O+ 1 157.0648 -0.52
158.0724 C11H10O+ 1 158.0726 -1.12
159.0803 C11H11O+ 1 159.0804 -0.64
160.0754 C10H10NO+ 1 160.0757 -1.94
161.0596 C10H9O2+ 1 161.0597 -0.66
162.0908 C10H12NO+ 1 162.0913 -3.4
163.075 C10H11O2+ 1 163.0754 -2.18
164.0707 C9H10NO2+ 1 164.0706 0.34
165.0698 C13H9+ 1 165.0699 -0.53
166.0778 C13H10+ 1 166.0777 0.41
167.0856 C13H11+ 1 167.0855 0.62
168.0569 C12H8O+ 1 168.057 -0.33
169.0646 C12H9O+ 1 169.0648 -1.13
169.1012 C13H13+ 1 169.1012 0.2
170.0725 C12H10O+ 1 170.0726 -0.92
171.0804 C12H11O+ 1 171.0804 -0.48
172.0519 C11H8O2+ 1 172.0519 -0.01
172.0881 C12H12O+ 1 172.0883 -0.79
173.0593 C11H9O2+ 1 173.0597 -2.17
173.0958 C12H13O+ 1 173.0961 -1.97
174.0672 C11H10O2+ 1 174.0675 -1.73
175.0752 C11H11O2+ 1 175.0754 -1.12
177.055 C10H9O3+ 1 177.0546 2.26
177.0698 C14H9+ 1 177.0699 -0.49
177.0778 C10H11NO2+ 1 177.0784 -3.39
178.0775 C14H10+ 1 178.0777 -1.13
178.0857 C10H12NO2+ 1 178.0863 -3.06
179.0854 C14H11+ 1 179.0855 -0.48
180.1014 C10H14NO2+ 1 180.1019 -2.75
181.0647 C13H9O+ 1 181.0648 -0.61
181.1012 C14H13+ 1 181.1012 0.35
182.0724 C13H10O+ 1 182.0726 -0.97
183.0804 C13H11O+ 1 183.0804 -0.5
184.0517 C12H8O2+ 1 184.0519 -1.2
184.0881 C13H12O+ 1 184.0883 -1.18
185.0596 C12H9O2+ 1 185.0597 -0.52
185.096 C13H13O+ 1 185.0961 -0.49
186.0675 C12H10O2+ 1 186.0675 -0.06
187.0752 C12H11O2+ 1 187.0754 -0.62
187.1117 C13H15O+ 1 187.1117 -0.33
189.0907 C12H13O2+ 1 189.091 -1.88
190.0773 C15H10+ 1 190.0777 -2.11
191.0855 C15H11+ 1 191.0855 -0.14
192.1018 C11H14NO2+ 1 192.1019 -0.7
193.0647 C14H9O+ 1 193.0648 -0.68
193.0757 C13H9N2+ 1 193.076 -1.42
193.1011 C15H13+ 1 193.1012 -0.14
194.0726 C14H10O+ 1 194.0726 -0.19
195.0804 C14H11O+ 1 195.0804 -0.42
196.0877 C14H12O+ 1 196.0883 -2.84
197.0598 C13H9O2+ 1 197.0597 0.33
197.096 C14H13O+ 1 197.0961 -0.41
198.0674 C13H10O2+ 1 198.0675 -0.76
198.1035 C14H14O+ 1 198.1039 -2.25
199.0752 C13H11O2+ 1 199.0754 -0.58
200.083 C13H12O2+ 1 200.0832 -0.8
201.0543 C12H9O3+ 1 201.0546 -1.59
201.0908 C13H13O2+ 1 201.091 -1.12
203.0848 C16H11+ 1 203.0855 -3.63
205.065 C15H9O+ 1 205.0648 1.07
207.0804 C15H11O+ 1 207.0804 -0.3
208.0883 C15H12O+ 1 208.0883 0.11
209.0596 C14H9O2+ 1 209.0597 -0.36
209.0961 C15H13O+ 1 209.0961 -0.01
210.0674 C14H10O2+ 1 210.0675 -0.58
211.0752 C14H11O2+ 1 211.0754 -0.79
212.0829 C14H12O2+ 1 212.0832 -1.37
213.0909 C14H13O2+ 1 213.091 -0.5
214.0982 C14H14O2+ 1 214.0988 -2.76
215.1065 C14H15O2+ 1 215.1067 -0.73
218.0718 C16H10O+ 1 218.0726 -3.93
219.0803 C16H11O+ 1 219.0804 -0.6
220.0882 C16H12O+ 1 220.0883 -0.53
221.0599 C15H9O2+ 1 221.0597 0.79
221.0959 C16H13O+ 1 221.0961 -1
223.0753 C15H11O2+ 1 223.0754 -0.34
223.112 C16H15O+ 1 223.1117 1.34
224.0834 C15H12O2+ 1 224.0832 1.02
225.0909 C15H13O2+ 1 225.091 -0.52
226.0613 C14H10O3+ 1 226.0624 -4.98
226.0983 C15H14O2+ 1 226.0988 -2.48
227.0701 C14H11O3+ 1 227.0703 -0.93
227.1067 C15H15O2+ 1 227.1067 0.28
228.0773 C14H12O3+ 1 228.0781 -3.53
228.1013 C14H14NO2+ 1 228.1019 -2.48
230.117 C14H16NO2+ 1 230.1176 -2.54
235.0747 C16H11O2+ 1 235.0754 -2.88
236.0829 C16H12O2+ 1 236.0832 -1.36
237.091 C16H13O2+ 1 237.091 0.1
238.0986 C16H14O2+ 1 238.0988 -0.76
239.07 C15H11O3+ 1 239.0703 -1.01
239.1067 C16H15O2+ 1 239.1067 0.35
241.0858 C15H13O3+ 1 241.0859 -0.58
241.122 C16H17O2+ 1 241.1223 -1.35
243.1014 C15H15O3+ 1 243.1016 -0.74
250.1223 C17H16NO+ 1 250.1226 -1.44
251.1064 C17H15O2+ 1 251.1067 -0.94
251.1309 C17H17NO+ 1 251.1305 1.69
252.1013 C16H14NO2+ 1 252.1019 -2.4
253.1221 C17H17O2+ 1 253.1223 -0.89
254.0941 C16H14O3+ 1 254.0937 1.43
256.1335 C16H18NO2+ 1 256.1332 1.07
266.1174 C17H16NO2+ 1 266.1176 -0.47
267.125 C17H17NO2+ 1 267.1254 -1.54
269.1172 C17H17O3+ 1 269.1172 0
272.1278 C16H18NO3+ 1 272.1281 -1.14
282.1488 C18H20NO2+ 1 282.1489 -0.37
285.1363 C17H19NO3+ 1 285.1359 1.07
300.1591 C18H22NO3+ 1 300.1594 -0.93
PK$NUM_PEAK: 134
PK$PEAK: m/z int. rel.int.
58.0651 477968.2 81
69.0335 44416.5 7
79.0543 35670.1 6
81.0332 22197.9 3
83.0492 30724.6 5
91.0541 29425.9 5
93.07 44107.1 7
103.0541 30687.9 5
115.0538 36981.2 6
121.0648 91527 15
129.0698 34684.1 5
131.0489 39821 6
137.0596 354334.8 60
141.0698 99770.4 17
143.0492 68969 11
144.057 186095.3 31
144.0806 27225.4 4
145.0647 66847.3 11
146.0601 26052.3 4
149.0592 20148.9 3
151.075 22282.4 3
153.0698 335009.7 57
154.0777 39867.4 6
155.0854 653461.6 111
156.0568 48221.9 8
157.0647 67273.8 11
158.0724 94727.8 16
159.0803 596341.1 102
160.0754 36519.7 6
161.0596 845847.9 144
162.0908 38251.8 6
163.075 49615.8 8
164.0707 48629 8
165.0698 927038.1 158
166.0778 94540.6 16
167.0856 119510.4 20
168.0569 207560.1 35
169.0646 81365 13
169.1012 34026.5 5
170.0725 36267.6 6
171.0804 580925.5 99
172.0519 153848.3 26
172.0881 124916 21
173.0593 27273.1 4
173.0958 101430 17
174.0672 140441 24
175.0752 196400.2 33
177.055 37755.1 6
177.0698 43297.7 7
177.0778 25993.8 4
178.0775 42826 7
178.0857 25833.7 4
179.0854 121360.8 20
180.1014 40732.2 6
181.0647 982084.9 168
181.1012 151978.7 26
182.0724 225354.8 38
183.0804 1777434.4 304
184.0517 50237.3 8
184.0881 85380.6 14
185.0596 257387.1 44
185.096 135067 23
186.0675 207088.7 35
187.0752 921293.5 157
187.1117 344555.3 58
189.0907 37545.6 6
190.0773 37469.2 6
191.0855 324165.5 55
192.1018 80804.3 13
193.0647 684149.5 117
193.0757 57348.7 9
193.1011 109817.6 18
194.0726 487664.4 83
195.0804 183061 31
196.0877 37031.6 6
197.0598 79871 13
197.096 338703.3 57
198.0674 269626.3 46
198.1035 52656.4 9
199.0752 2298393 393
200.083 358301.1 61
201.0543 29299.8 5
201.0908 238962.9 40
203.0848 45083.1 7
205.065 29778.2 5
207.0804 145336.9 24
208.0883 104393.1 17
209.0596 538217 92
209.0961 244761.6 41
210.0674 292735.8 50
211.0752 321130 54
212.0829 233113.1 39
213.0909 648275.6 110
214.0982 40738.3 6
215.1065 2988517.9 511
218.0718 23801.6 4
219.0803 247935 42
220.0882 148294.9 25
221.0599 87954.5 15
221.0959 246450.4 42
223.0753 424901.7 72
223.112 42309.4 7
224.0834 47105.7 8
225.0909 1866137.2 319
226.0613 33438.4 5
226.0983 44928.9 7
227.0701 44678.4 7
227.1067 29094.1 4
228.0773 60361.1 10
228.1013 36725 6
230.117 22883.8 3
235.0747 36511 6
236.0829 194841.8 33
237.091 84654.6 14
238.0986 107002.2 18
239.07 27470.7 4
239.1067 89963.1 15
241.0858 1296808 221
241.122 97800.5 16
243.1014 1378827.1 235
250.1223 68473.4 11
251.1064 223810.1 38
251.1309 43583.5 7
252.1013 59833.5 10
253.1221 178525.1 30
254.0941 28928.7 4
256.1335 30352.6 5
266.1174 330099.2 56
267.125 231123.9 39
269.1172 78576.3 13
272.1278 26494.8 4
282.1488 452107.9 77
285.1363 78581.3 13
300.1591 5836649.8 999
//
