ACCESSION: MSBNK-Eawag-EQ333305
RECORD_TITLE: Dihydrocodeine; LC-ESI-QFT; MS2; CE: 75; R=35000; [M+H]+
DATE: 2015.08.25
AUTHORS: Otto J, Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3333
CH$NAME: Dihydrocodeine
CH$NAME: (4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,5,6,7,7a,13-octahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinoline-7-ol
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C18H23NO3
CH$EXACT_MASS: 301.16779
CH$SMILES: CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](CC4)O
CH$IUPAC: InChI=1S/C18H23NO3/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19/h3,6,11-13,17,20H,4-5,7-9H2,1-2H3/t11-,12+,13-,17-,18-/m0/s1
CH$LINK: KEGG
D07831
CH$LINK: PUBCHEM
CID:5284543
CH$LINK: INCHIKEY
RBOXVHNMENFORY-DNJOTXNNSA-N
CH$LINK: CHEMSPIDER
4447600
CH$LINK: COMPTOX
DTXSID5022936
AC$INSTRUMENT: Q Exactive Orbitrap Thermo Scientific
AC$INSTRUMENT_TYPE: LC-ESI-QFT
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 35000
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 2.6 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 302.1753
MS$FOCUSED_ION: PRECURSOR_M/Z 302.1751
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$DATA_PROCESSING: DEPROFILE vendor picking in Proteowizard
MS$DATA_PROCESSING: RECALIBRATE loess on assigned fragments and MS1
MS$DATA_PROCESSING: REANALYZE Peaks with additional N2/O included
MS$DATA_PROCESSING: WHOLE RMassBank 1.9.6
PK$SPLASH: splash10-006t-0910000000-fc3b87d3fb93d21f90f4
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
55.0179 C3H3O+ 1 55.0178 0.16
57.0336 C3H5O+ 1 57.0335 2.26
58.0652 C3H8N+ 1 58.0651 2.14
65.0385 C5H5+ 1 65.0386 -0.87
67.0542 C5H7+ 1 67.0542 0.05
70.0652 C4H8N+ 1 70.0651 0.35
71.0491 C4H7O+ 1 71.0491 -0.02
77.0385 C6H5+ 1 77.0386 -0.86
79.0542 C6H7+ 1 79.0542 0.3
81.0699 C6H9+ 1 81.0699 -0.21
83.0491 C5H7O+ 1 83.0491 -0.26
84.0808 C5H10N+ 1 84.0808 0.76
91.0542 C7H7+ 1 91.0542 0.04
93.0698 C7H9+ 1 93.0699 -1.04
94.0412 C6H6O+ 1 94.0413 -1.13
94.0653 C6H8N+ 1 94.0651 2.07
95.049 C6H7O+ 1 95.0491 -0.96
95.0857 C7H11+ 1 95.0855 2.14
96.0807 C6H10N+ 1 96.0808 -0.79
102.0467 C8H6+ 1 102.0464 3.12
103.0543 C8H7+ 1 103.0542 1
105.0699 C8H9+ 1 105.0699 0.51
107.0492 C7H7O+ 1 107.0491 0.55
115.0542 C9H7+ 1 115.0542 -0.06
117.07 C9H9+ 1 117.0699 0.88
119.0495 C8H7O+ 1 119.0491 3.18
119.0855 C9H11+ 1 119.0855 -0.22
121.0647 C8H9O+ 1 121.0648 -0.92
122.0364 C7H6O2+ 1 122.0362 1.55
127.0543 C10H7+ 1 127.0542 0.89
128.062 C10H8+ 1 128.0621 -0.01
129.0699 C10H9+ 1 129.0699 -0.05
130.0778 C10H10+ 1 130.0777 0.91
131.0492 C9H7O+ 1 131.0491 0.6
131.0858 C10H11+ 1 131.0855 2.08
132.081 C9H10N+ 1 132.0808 1.4
133.0649 C9H9O+ 1 133.0648 1.12
137.0597 C8H9O2+ 1 137.0597 0.25
139.0539 C11H7+ 1 139.0542 -2.21
141.0699 C11H9+ 1 141.0699 -0.12
142.0777 C11H10+ 1 142.0777 -0.22
143.0493 C10H7O+ 1 143.0491 0.9
143.0857 C11H11+ 1 143.0855 1.28
144.0571 C10H8O+ 1 144.057 0.72
145.0649 C10H9O+ 1 145.0648 0.82
145.1013 C11H13+ 1 145.1012 0.64
146.0365 C9H6O2+ 1 146.0362 1.71
146.0726 C10H10O+ 1 146.0726 -0.39
146.0965 C10H12N+ 1 146.0964 0.23
147.0441 C9H7O2+ 1 147.0441 0.3
147.0806 C10H11O+ 1 147.0804 1.08
151.0756 C9H11O2+ 1 151.0754 1.68
152.0621 C12H8+ 1 152.0621 0.45
153.0699 C12H9+ 1 153.0699 0.09
154.0778 C12H10+ 1 154.0777 0.31
155.0492 C11H7O+ 1 155.0491 0.57
155.0606 C10H7N2+ 1 155.0604 1.32
155.0856 C12H11+ 1 155.0855 0.41
156.057 C11H8O+ 1 156.057 0.02
157.0649 C11H9O+ 1 157.0648 0.5
157.1013 C12H13+ 1 157.1012 0.78
158.0727 C11H10O+ 1 158.0726 0.34
159.0442 C10H7O2+ 1 159.0441 0.91
159.0805 C11H11O+ 1 159.0804 0.56
160.0521 C10H8O2+ 1 160.0519 1.06
161.0598 C10H9O2+ 1 161.0597 0.34
161.0961 C11H13O+ 1 161.0961 0.24
162.0676 C10H10O2+ 1 162.0675 0.24
163.0754 C10H11O2+ 1 163.0754 0.27
165.07 C13H9+ 1 165.0699 0.57
166.0777 C13H10+ 1 166.0777 0.23
167.0856 C13H11+ 1 167.0855 0.5
168.0572 C12H8O+ 1 168.057 1.33
168.0935 C13H12+ 1 168.0934 0.88
169.0649 C12H9O+ 1 169.0648 0.7
169.0759 C11H9N2+ 1 169.076 -1.03
169.1013 C13H13+ 1 169.1012 0.49
170.0729 C12H10O+ 1 170.0726 1.61
171.0805 C12H11O+ 1 171.0804 0.11
172.0518 C11H8O2+ 1 172.0519 -0.35
172.0883 C12H12O+ 1 172.0883 0.14
173.0962 C12H13O+ 1 173.0961 0.57
174.0675 C11H10O2+ 1 174.0675 -0.41
175.0754 C11H11O2+ 1 175.0754 0.02
176.0622 C14H8+ 1 176.0621 0.96
176.0832 C11H12O2+ 1 176.0832 0.33
177.07 C14H9+ 1 177.0699 0.47
178.0777 C14H10+ 1 178.0777 0.16
179.0699 C10H11O3+ 1 179.0703 -1.96
179.0855 C14H11+ 1 179.0855 0.02
180.0573 C13H8O+ 1 180.057 1.58
181.0648 C13H9O+ 1 181.0648 0.05
181.1015 C14H13+ 1 181.1012 1.62
182.0727 C13H10O+ 1 182.0726 0.57
183.0443 C12H7O2+ 1 183.0441 1.44
183.0806 C13H11O+ 1 183.0804 0.87
184.0521 C12H8O2+ 1 184.0519 0.97
184.0883 C13H12O+ 1 184.0883 0.18
185.0598 C12H9O2+ 1 185.0597 0.72
185.0962 C13H13O+ 1 185.0961 0.53
186.0677 C12H10O2+ 1 186.0675 0.91
187.0754 C12H11O2+ 1 187.0754 0.5
189.0911 C12H13O2+ 1 189.091 0.5
191.0854 C15H11+ 1 191.0855 -0.72
193.0649 C14H9O+ 1 193.0648 0.51
193.0738 C10H11NO3+ 1 193.0733 2.62
193.0754 C13H9N2+ 1 193.076 -2.98
193.1017 C15H13+ 1 193.1012 2.45
194.0727 C14H10O+ 1 194.0726 0.28
195.0806 C14H11O+ 1 195.0804 0.61
196.0884 C14H12O+ 1 196.0883 0.48
197.0599 C13H9O2+ 1 197.0597 1.14
197.0964 C14H13O+ 1 197.0961 1.57
198.0676 C13H10O2+ 1 198.0675 0.45
199.0754 C13H11O2+ 1 199.0754 0.07
200.083 C13H12O2+ 1 200.0832 -0.85
201.0909 C13H13O2+ 1 201.091 -0.33
202.0776 C16H10+ 1 202.0777 -0.4
202.0864 C12H12NO2+ 1 202.0863 0.92
203.085 C16H11+ 1 203.0855 -2.79
203.1067 C13H15O2+ 1 203.1067 0.22
205.0762 C14H9N2+ 1 205.076 0.71
206.0729 C15H10O+ 1 206.0726 1.47
209.0599 C14H9O2+ 1 209.0597 0.93
209.0962 C15H13O+ 1 209.0961 0.52
210.0676 C14H10O2+ 1 210.0675 0.28
211.0756 C14H11O2+ 1 211.0754 1.39
212.0832 C14H12O2+ 1 212.0832 0.23
213.091 C14H13O2+ 1 213.091 -0.22
214.0629 C13H10O3+ 1 214.0624 1.98
214.0992 C14H14O2+ 1 214.0988 1.82
215.1067 C14H15O2+ 1 215.1067 0.39
216.1022 C13H14NO2+ 1 216.1019 1.6
217.1101 C13H15NO2+ 1 217.1097 1.47
217.1225 C14H17O2+ 1 217.1223 0.85
221.0962 C16H13O+ 1 221.0961 0.45
222.104 C16H14O+ 1 222.1039 0.24
223.0754 C15H11O2+ 1 223.0754 0.24
225.0911 C15H13O2+ 1 225.091 0.51
227.1068 C15H15O2+ 1 227.1067 0.46
228.1022 C14H14NO2+ 1 228.1019 1.34
229.0863 C14H13O3+ 1 229.0859 1.79
243.1018 C15H15O3+ 1 243.1016 0.98
245.1177 C15H17O3+ 1 245.1172 1.83
268.134 C17H18NO2+ 1 268.1332 2.85
269.1418 C17H19NO2+ 1 269.141 2.67
284.1653 C18H22NO2+ 1 284.1645 2.94
302.1753 C18H24NO3+ 1 302.1751 0.6
PK$NUM_PEAK: 148
PK$PEAK: m/z int. rel.int.
55.0179 102668.7 1
57.0336 571726.3 8
58.0652 424601.5 6
65.0385 115141.8 1
67.0542 1110821.8 16
70.0652 198566.8 2
71.0491 233945.2 3
77.0385 127596.7 1
79.0542 810198.6 11
81.0699 210895 3
83.0491 437264.5 6
84.0808 229797.1 3
91.0542 1429285 20
93.0698 203693.4 2
94.0412 103296.5 1
94.0653 113486.5 1
95.049 187130.3 2
95.0857 113955.9 1
96.0807 201903.7 2
102.0467 108382.4 1
103.0543 1254752.4 18
105.0699 539586.4 7
107.0492 542553.6 7
115.0542 3743934.8 54
117.07 586190.3 8
119.0495 144769.2 2
119.0855 184212.6 2
121.0647 1176915 17
122.0364 122036.2 1
127.0543 109285.6 1
128.062 7182474 105
129.0699 5610847 82
130.0778 552905.2 8
131.0492 2010321.6 29
131.0858 447418 6
132.081 118526.9 1
133.0649 213993 3
137.0597 4576521.5 67
139.0539 119803.6 1
141.0699 13536234 198
142.0777 1195929.8 17
143.0493 2634400 38
143.0857 1982692.1 29
144.0571 2794163.2 40
145.0649 2019319.2 29
145.1013 254771.1 3
146.0365 567659.1 8
146.0726 208463.4 3
146.0965 116603.8 1
147.0441 181262.4 2
147.0806 990793.9 14
151.0756 511606.2 7
152.0621 3329464.8 48
153.0699 4745809 69
154.0778 967486 14
155.0492 1264594 18
155.0606 588120.2 8
155.0856 4450343 65
156.057 4998336 73
157.0649 4197528 61
157.1013 1639280.2 24
158.0727 16266865 238
159.0442 369838.8 5
159.0805 4345171 63
160.0521 640869.7 9
161.0598 8727075 127
161.0961 1652578.6 24
162.0676 197885.1 2
163.0754 987995.2 14
165.07 13420503 196
166.0777 1577179.8 23
167.0856 11156216 163
168.0572 1660328.2 24
168.0935 528131.8 7
169.0649 3789660.5 55
169.0759 1440033.5 21
169.1013 700730.6 10
170.0729 1276877.8 18
171.0805 41777504 612
172.0518 1443478.2 21
172.0883 233896.5 3
173.0962 13056983 191
174.0675 818427.7 11
175.0754 2240769.2 32
176.0622 550856.4 8
176.0832 145444.8 2
177.07 3990827 58
178.0777 1329120.2 19
179.0699 160734.4 2
179.0855 414647.2 6
180.0573 198563.9 2
181.0648 2960765.2 43
181.1015 592638.6 8
182.0727 1632592.1 23
183.0443 1186034.9 17
183.0806 11000965 161
184.0521 1998945.6 29
184.0883 3707772.5 54
185.0598 3053199.8 44
185.0962 3701260.8 54
186.0677 4363917.5 63
187.0754 4426803 64
189.0911 3934423.8 57
191.0854 217528.9 3
193.0649 1810621.2 26
193.0738 133280.9 1
193.0754 114421 1
193.1017 555939.6 8
194.0727 2936200.2 43
195.0806 9675040 141
196.0884 3935854.8 57
197.0599 1988469.6 29
197.0964 1584492.1 23
198.0676 4245651 62
199.0754 68173448 999
200.083 554388.9 8
201.0909 17783778 260
202.0776 182375.1 2
202.0864 221486.9 3
203.085 337907.6 4
203.1067 443458.3 6
205.0762 180764 2
206.0729 134786 1
209.0599 189788.7 2
209.0962 1165522 17
210.0676 594204.6 8
211.0756 1793414.2 26
212.0832 2927729.2 42
213.091 2235935.5 32
214.0629 835036.8 12
214.0992 254456.7 3
215.1067 1021975.3 14
216.1022 163671.8 2
217.1101 449629.2 6
217.1225 831787.5 12
221.0962 669693.8 9
222.104 211484.9 3
223.0754 525807.4 7
225.0911 3178550.5 46
227.1068 7344824 107
228.1022 480105.6 7
229.0863 166610.8 2
243.1018 1921714.5 28
245.1177 1312143.8 19
268.134 678295.9 9
269.1418 173168.5 2
284.1653 189512.3 2
302.1753 2739468.8 40
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