ACCESSION: MSBNK-Eawag-EA278001
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 35%; 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$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 35 % (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$SPLASH: splash10-0159-0390000000-ac30542a576060b3373c
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
103.0544 C8H7+ 1 103.0542 1.59
121.0646 C8H9O+ 1 121.0648 -1.25
132.0809 C9H10N+ 1 132.0808 0.79
137.0597 C8H9O2+ 1 137.0597 0.03
141.0699 C11H9+ 1 141.0699 -0.19
144.0803 C10H10N+ 1 144.0808 -3.44
145.0644 C10H9O+ 1 145.0648 -2.56
146.06 C9H8NO+ 1 146.06 0.07
151.0753 C9H11O2+ 1 151.0754 -0.11
153.0701 C12H9+ 1 153.0699 1.59
155.0856 C12H11+ 1 155.0855 0.73
156.0571 C11H8O+ 1 156.057 0.6
158.0726 C11H10O+ 1 158.0726 -0.36
158.0963 C11H12N+ 1 158.0964 -0.61
159.0805 C11H11O+ 1 159.0804 0.31
161.0597 C10H9O2+ 1 161.0597 0.21
162.0915 C10H12NO+ 1 162.0913 0.74
165.0699 C13H9+ 1 165.0699 -0.16
167.086 C13H11+ 1 167.0855 2.89
168.057 C12H8O+ 1 168.057 -0.1
171.0805 C12H11O+ 1 171.0804 0.46
172.0517 C11H8O2+ 1 172.0519 -0.94
172.0884 C12H12O+ 1 172.0883 0.78
173.0963 C12H13O+ 1 173.0961 1.32
174.0676 C11H10O2+ 1 174.0675 0.45
175.0755 C11H11O2+ 1 175.0754 0.65
177.0541 C10H9O3+ 1 177.0546 -3.17
178.0857 C10H12NO2+ 1 178.0863 -3.29
180.102 C10H14NO2+ 1 180.1019 0.58
181.0646 C13H9O+ 1 181.0648 -1
182.0734 C13H10O+ 1 182.0726 4.25
183.0805 C13H11O+ 1 183.0804 0.27
184.0885 C13H12O+ 1 184.0883 1.38
185.0603 C12H9O2+ 1 185.0597 3.32
186.0681 C12H10O2+ 1 186.0675 3
187.0754 C12H11O2+ 1 187.0754 0.4
187.1118 C13H15O+ 1 187.1117 0.21
191.0855 C15H11+ 1 191.0855 -0.14
192.1021 C11H14NO2+ 1 192.1019 0.96
193.0648 C14H9O+ 1 193.0648 -0.01
193.1012 C15H13+ 1 193.1012 0.22
194.0727 C14H10O+ 1 194.0726 0.53
195.0804 C14H11O+ 1 195.0804 -0.42
197.0959 C14H13O+ 1 197.0961 -1.12
199.0754 C13H11O2+ 1 199.0754 0.17
200.0833 C13H12O2+ 1 200.0832 0.69
201.0695 C16H9+ 1 201.0699 -1.62
201.091 C13H13O2+ 1 201.091 -0.08
202.0773 C16H10+ 1 202.0777 -2.09
203.0856 C16H11+ 1 203.0855 0.36
205.1013 C16H13+ 1 205.1012 0.55
207.0808 C15H11O+ 1 207.0804 1.83
208.0891 C15H12O+ 1 208.0883 3.86
209.0599 C14H9O2+ 1 209.0597 0.78
209.0961 C15H13O+ 1 209.0961 0.04
210.0675 C14H10O2+ 1 210.0675 -0.24
211.0755 C14H11O2+ 1 211.0754 0.68
212.0829 C14H12O2+ 1 212.0832 -1.33
213.0911 C14H13O2+ 1 213.091 0.25
215.1066 C14H15O2+ 1 215.1067 -0.08
219.0804 C16H11O+ 1 219.0804 -0.42
220.0882 C16H12O+ 1 220.0883 -0.12
221.096 C16H13O+ 1 221.0961 -0.59
222.128 C16H16N+ 1 222.1277 1.41
223.0752 C15H11O2+ 1 223.0754 -0.61
223.1113 C16H15O+ 1 223.1117 -1.89
224.0831 C15H12O2+ 1 224.0832 -0.27
225.0909 C15H13O2+ 1 225.091 -0.38
227.1072 C15H15O2+ 1 227.1067 2.39
236.0836 C16H12O2+ 1 236.0832 1.86
237.0912 C16H13O2+ 1 237.091 0.69
238.099 C16H14O2+ 1 238.0988 0.54
239.0693 C15H11O3+ 1 239.0703 -4.19
239.1064 C16H15O2+ 1 239.1067 -1.15
240.1387 C16H18NO+ 1 240.1383 1.75
241.0857 C15H13O3+ 1 241.0859 -0.71
241.1222 C16H17O2+ 1 241.1223 -0.27
243.1015 C15H15O3+ 1 243.1016 -0.13
250.0985 C17H14O2+ 1 250.0988 -1.16
250.1235 C17H16NO+ 1 250.1226 3.28
251.1067 C17H15O2+ 1 251.1067 -0.02
253.1224 C17H17O2+ 1 253.1223 0.53
254.0927 C16H14O3+ 1 254.0937 -3.92
254.1179 C16H16NO2+ 1 254.1176 1.16
256.132 C16H18NO2+ 1 256.1332 -4.74
257.1181 C16H17O3+ 1 257.1172 3.26
257.1414 C16H19NO2+ 1 257.141 1.36
265.1221 C18H17O2+ 1 265.1223 -0.74
266.1176 C17H16NO2+ 1 266.1176 0.13
267.1255 C17H17NO2+ 1 267.1254 0.45
269.1173 C17H17O3+ 1 269.1172 0.29
272.1294 C16H18NO3+ 1 272.1281 4.78
272.1652 C17H22NO2+ 1 272.1645 2.66
280.1343 C18H18NO2+ 1 280.1332 4.09
282.149 C18H20NO2+ 1 282.1489 0.44
285.135 C17H19NO3+ 1 285.1359 -3.42
PK$NUM_PEAK: 96
PK$PEAK: m/z int. rel.int.
103.0544 43617.3 1
121.0646 109122.1 4
132.0809 71158 3
137.0597 549993.5 23
141.0699 53708.8 2
144.0803 88381.5 3
145.0644 40052.4 1
146.06 155696.7 6
151.0753 73734.7 3
153.0701 199831.3 8
155.0856 717982.9 30
156.0571 48524.6 2
158.0726 49563.3 2
158.0963 86292.3 3
159.0805 445847.4 18
161.0597 1960390.7 82
162.0915 281257.5 11
165.0699 1049392.7 44
167.086 120467.8 5
168.057 68932.6 2
171.0805 233260 9
172.0517 34403.8 1
172.0884 124571.8 5
173.0963 65384.6 2
174.0676 82278.7 3
175.0755 1103911.1 46
177.0541 56842.3 2
178.0857 116015.3 4
180.102 254147.7 10
181.0646 504762.7 21
182.0734 66412.3 2
183.0805 5754015.4 243
184.0885 62244.1 2
185.0603 134226.5 5
186.0681 87700.2 3
187.0754 2605721.3 110
187.1118 574655.9 24
191.0855 849905.9 35
192.1021 357037.9 15
193.0648 2093372.5 88
193.1012 364486.2 15
194.0727 328494.8 13
195.0804 227741.5 9
197.0959 586996.2 24
199.0754 3201560 135
200.0833 528693.5 22
201.0695 83093.9 3
201.091 400998.3 16
202.0773 44255.4 1
203.0856 203725.8 8
205.1013 180857.7 7
207.0808 400263.8 16
208.0891 62447.3 2
209.0599 564580.9 23
209.0961 477754.4 20
210.0675 87073.1 3
211.0755 761534.3 32
212.0829 81293.2 3
213.0911 680086.4 28
215.1066 23600250.2 999
219.0804 852536.1 36
220.0882 216360.8 9
221.096 1196963 50
222.128 42987.8 1
223.0752 530255.8 22
223.1113 90634 3
224.0831 60058.7 2
225.0909 7788631.6 329
227.1072 138941.3 5
236.0836 268381.6 11
237.0912 364259.4 15
238.099 238549.6 10
239.0693 61540.4 2
239.1064 362018 15
240.1387 61263.7 2
241.0857 736374.2 31
241.1222 379570.7 16
243.1015 9606663.6 406
250.0985 372133.3 15
250.1235 257586.2 10
251.1067 1103069.4 46
253.1224 1706123.6 72
254.0927 61026.6 2
254.1179 84427.8 3
256.132 74213.8 3
257.1181 84763.6 3
257.1414 43394.2 1
265.1221 268108.3 11
266.1176 612417.5 25
267.1255 1216190.9 51
269.1173 312297 13
272.1294 73919.9 3
272.1652 48421.9 2
280.1343 86959.4 3
282.149 6788398.7 287
285.135 139300.7 5
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