ACCESSION: MSBNK-Eawag-EA278014
RECORD_TITLE: Codeine; LC-ESI-ITFT; MS2; CE: 35%; 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$MASS_SPECTROMETRY: FRAGMENTATION_MODE CID
AC$MASS_SPECTROMETRY: COLLISION_ENERGY 35 % (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$SPLASH: splash10-0159-0390000000-a7469c01c0a4ff4179bf
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
121.0647 C8H9O+ 1 121.0648 -0.51
129.0699 C10H9+ 1 129.0699 0.49
132.0811 C9H10N+ 1 132.0808 2.3
137.0597 C8H9O2+ 1 137.0597 -0.26
141.07 C11H9+ 1 141.0699 1.16
143.0493 C10H7O+ 1 143.0491 0.97
144.0567 C10H8O+ 1 144.057 -1.5
144.0809 C10H10N+ 1 144.0808 0.86
145.065 C10H9O+ 1 145.0648 1.16
146.06 C9H8NO+ 1 146.06 -0.14
149.0597 C9H9O2+ 1 149.0597 -0.04
151.0754 C9H11O2+ 1 151.0754 0.22
152.0615 C12H8+ 1 152.0621 -3.56
153.0698 C12H9+ 1 153.0699 -0.31
155.0855 C12H11+ 1 155.0855 -0.3
156.0568 C11H8O+ 1 156.057 -0.94
157.0644 C11H9O+ 1 157.0648 -2.43
158.0729 C11H10O+ 1 158.0726 1.86
158.0961 C11H12N+ 1 158.0964 -1.81
159.0805 C11H11O+ 1 159.0804 0.05
160.0758 C10H10NO+ 1 160.0757 0.62
161.0597 C10H9O2+ 1 161.0597 -0.22
162.0914 C10H12NO+ 1 162.0913 0.24
163.0751 C10H11O2+ 1 163.0754 -1.82
165.0699 C13H9+ 1 165.0699 0.08
167.0855 C13H11+ 1 167.0855 -0.34
168.057 C12H8O+ 1 168.057 0.38
169.0648 C12H9O+ 1 169.0648 -0.24
171.0803 C12H11O+ 1 171.0804 -1
172.0884 C12H12O+ 1 172.0883 0.78
173.0964 C12H13O+ 1 173.0961 1.72
174.0676 C11H10O2+ 1 174.0675 0.51
175.0754 C11H11O2+ 1 175.0754 0.02
177.055 C10H9O3+ 1 177.0546 2.09
177.0785 C10H11NO2+ 1 177.0784 0.51
178.0864 C10H12NO2+ 1 178.0863 1.04
179.0855 C14H11+ 1 179.0855 -0.32
179.0942 C10H13NO2+ 1 179.0941 0.89
180.1018 C10H14NO2+ 1 180.1019 -0.58
181.0648 C13H9O+ 1 181.0648 -0.17
181.1012 C14H13+ 1 181.1012 0.35
182.0728 C13H10O+ 1 182.0726 0.95
183.0804 C13H11O+ 1 183.0804 -0.28
184.0885 C13H12O+ 1 184.0883 1.11
185.0596 C12H9O2+ 1 185.0597 -0.73
185.0957 C13H13O+ 1 185.0961 -1.9
186.0677 C12H10O2+ 1 186.0675 0.75
187.0753 C12H11O2+ 1 187.0754 -0.19
187.1118 C13H15O+ 1 187.1117 0.1
189.0908 C12H13O2+ 1 189.091 -1.2
191.0855 C15H11+ 1 191.0855 -0.09
192.1019 C11H14NO2+ 1 192.1019 -0.29
193.0648 C14H9O+ 1 193.0648 -0.06
193.1014 C15H13+ 1 193.1012 1
194.0725 C14H10O+ 1 194.0726 -0.39
195.0804 C14H11O+ 1 195.0804 -0.11
197.0961 C14H13O+ 1 197.0961 0.2
198.0673 C13H10O2+ 1 198.0675 -1.17
199.0753 C13H11O2+ 1 199.0754 -0.08
200.0831 C13H12O2+ 1 200.0832 -0.16
201.0543 C12H9O3+ 1 201.0546 -1.64
201.0704 C16H9+ 1 201.0699 2.65
201.0909 C13H13O2+ 1 201.091 -0.53
203.0855 C16H11+ 1 203.0855 0.07
205.1014 C16H13+ 1 205.1012 0.89
206.0725 C15H10O+ 1 206.0726 -0.56
207.0803 C15H11O+ 1 207.0804 -0.54
208.0885 C15H12O+ 1 208.0883 1.12
209.0598 C14H9O2+ 1 209.0597 0.35
209.0961 C15H13O+ 1 209.0961 -0.05
210.0675 C14H10O2+ 1 210.0675 -0.15
211.0753 C14H11O2+ 1 211.0754 -0.12
212.0834 C14H12O2+ 1 212.0832 1.22
213.091 C14H13O2+ 1 213.091 -0.12
215.1066 C14H15O2+ 1 215.1067 -0.17
216.1011 C13H14NO2+ 1 216.1019 -3.86
218.0729 C16H10O+ 1 218.0726 1.35
219.0803 C16H11O+ 1 219.0804 -0.6
220.0881 C16H12O+ 1 220.0883 -0.62
221.096 C16H13O+ 1 221.0961 -0.19
222.1042 C16H14O+ 1 222.1039 1.32
222.1275 C16H16N+ 1 222.1277 -0.88
223.0754 C15H11O2+ 1 223.0754 0.02
223.1119 C16H15O+ 1 223.1117 0.58
224.0831 C15H12O2+ 1 224.0832 -0.32
224.108 C15H14NO+ 1 224.107 4.46
225.0909 C15H13O2+ 1 225.091 -0.47
226.0989 C15H14O2+ 1 226.0988 0.44
227.0707 C14H11O3+ 1 227.0703 1.85
227.1066 C15H15O2+ 1 227.1067 -0.29
228.0789 C14H12O3+ 1 228.0781 3.53
229.11 C14H15NO2+ 1 229.1097 1.05
230.1175 C14H16NO2+ 1 230.1176 -0.2
235.0752 C16H11O2+ 1 235.0754 -0.88
236.0831 C16H12O2+ 1 236.0832 -0.39
237.091 C16H13O2+ 1 237.091 -0.03
237.1273 C17H17O+ 1 237.1274 -0.26
238.0988 C16H14O2+ 1 238.0988 -0.05
239.0702 C15H11O3+ 1 239.0703 -0.21
239.1066 C16H15O2+ 1 239.1067 -0.11
240.1382 C16H18NO+ 1 240.1383 -0.38
241.0859 C15H13O3+ 1 241.0859 -0.09
241.1222 C16H17O2+ 1 241.1223 -0.32
242.1176 C15H16NO2+ 1 242.1176 0.19
243.1015 C15H15O3+ 1 243.1016 -0.37
250.0988 C17H14O2+ 1 250.0988 0.08
250.1223 C17H16NO+ 1 250.1226 -1.24
251.1066 C17H15O2+ 1 251.1067 -0.18
251.1299 C17H17NO+ 1 251.1305 -2.25
252.102 C16H14NO2+ 1 252.1019 0.22
253.1223 C17H17O2+ 1 253.1223 -0.06
254.1168 C16H16NO2+ 1 254.1176 -3.09
254.1533 C17H20NO+ 1 254.1539 -2.44
256.1334 C16H18NO2+ 1 256.1332 0.8
257.1166 C16H17O3+ 1 257.1172 -2.3
257.1404 C16H19NO2+ 1 257.141 -2.3
265.1224 C18H17O2+ 1 265.1223 0.2
266.1175 C17H16NO2+ 1 266.1176 -0.32
267.1254 C17H17NO2+ 1 267.1254 0.04
268.1339 C17H18NO2+ 1 268.1332 2.55
269.1171 C17H17O3+ 1 269.1172 -0.6
272.1281 C16H18NO3+ 1 272.1281 -0.11
272.1648 C17H22NO2+ 1 272.1645 1.23
280.133 C18H18NO2+ 1 280.1332 -0.63
282.1488 C18H20NO2+ 1 282.1489 -0.23
285.1355 C17H19NO3+ 1 285.1359 -1.7
PK$NUM_PEAK: 126
PK$PEAK: m/z int. rel.int.
121.0647 49779.5 3
129.0699 15822 1
132.0811 24352 1
137.0597 224630.7 17
141.07 14543.4 1
143.0493 30330.1 2
144.0567 24222.6 1
144.0809 49589.9 3
145.065 31895.1 2
146.06 75758.3 6
149.0597 13683.6 1
151.0754 59922.3 4
152.0615 17113.5 1
153.0698 92250.2 7
155.0855 421656.1 33
156.0568 39069 3
157.0644 17090.2 1
158.0729 19339.2 1
158.0961 32584.6 2
159.0805 240809.2 19
160.0758 31220.6 2
161.0597 1058526.9 83
162.0914 97842.2 7
163.0751 28558.7 2
165.0699 525841 41
167.0855 66967.1 5
168.057 46824.4 3
169.0648 21900.5 1
171.0803 128055.7 10
172.0884 54952.8 4
173.0964 30443 2
174.0676 60942.9 4
175.0754 616089 48
177.055 32241.7 2
177.0785 13688.6 1
178.0864 32647.4 2
179.0855 57787.8 4
179.0942 58446.5 4
180.1018 146282.4 11
181.0648 258193.2 20
181.1012 51243.9 4
182.0728 51286.1 4
183.0804 3352944.6 265
184.0885 28480.3 2
185.0596 98937.3 7
185.0957 28990.1 2
186.0677 45142.4 3
187.0753 1411282 111
187.1118 292756.3 23
189.0908 17452.6 1
191.0855 441266.2 34
192.1019 209263.5 16
193.0648 1060592.4 84
193.1014 201704 15
194.0725 182802.1 14
195.0804 119510 9
197.0961 290361.5 23
198.0673 24229.6 1
199.0753 1627958.1 128
200.0831 293792.1 23
201.0543 20102.8 1
201.0704 29270 2
201.0909 212779.2 16
203.0855 118474.6 9
205.1014 73519.3 5
206.0725 18193.6 1
207.0803 222784.5 17
208.0885 35449 2
209.0598 250735.3 19
209.0961 193105.2 15
210.0675 42848.8 3
211.0753 456502.9 36
212.0834 45932.7 3
213.091 350273.2 27
215.1066 12610916.4 999
216.1011 41100.1 3
218.0729 35663.4 2
219.0803 444363.8 35
220.0881 98754.9 7
221.096 641839.1 50
222.1042 67626.6 5
222.1275 26903.1 2
223.0754 272232 21
223.1119 72848.1 5
224.0831 31637.6 2
224.108 12686.1 1
225.0909 4224835.6 334
226.0989 28839.9 2
227.0707 20461.6 1
227.1066 59638.3 4
228.0789 19939.5 1
229.11 46110.8 3
230.1175 71443.9 5
235.0752 15357.1 1
236.0831 139546.8 11
237.091 180258.5 14
237.1273 61532.9 4
238.0988 145840.8 11
239.0702 34341.8 2
239.1066 148238.5 11
240.1382 26712.7 2
241.0859 345662.1 27
241.1222 156385.8 12
242.1176 29700.6 2
243.1015 5196006.6 411
250.0988 149861.8 11
250.1223 145806.7 11
251.1066 572624.2 45
251.1299 50291.5 3
252.102 51699.8 4
253.1223 829183.4 65
254.1168 29852.6 2
254.1533 22447.1 1
256.1334 39513.4 3
257.1166 70335.6 5
257.1404 22035 1
265.1224 149645 11
266.1175 324189.5 25
267.1254 632816.5 50
268.1339 22443.5 1
269.1171 217664.5 17
272.1281 27256.4 2
272.1648 30940.2 2
280.133 41076.1 3
282.1488 3793643.9 300
285.1355 80451.5 6
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