ACCESSION: MSBNK-Eawag-EQ333306
RECORD_TITLE: Dihydrocodeine; LC-ESI-QFT; MS2; CE: 90; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 90 (nominal)
AC$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: splash10-062d-0900000000-c8e88928923875169e0b
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
57.0336 C3H5O+ 1 57.0335 1.73
58.0653 C3H8N+ 1 58.0651 2.66
65.0385 C5H5+ 1 65.0386 -1.18
67.0542 C5H7+ 1 67.0542 -0.55
69.0336 C4H5O+ 1 69.0335 2.3
70.0652 C4H8N+ 1 70.0651 0.63
71.0491 C4H7O+ 1 71.0491 -0.58
77.0384 C6H5+ 1 77.0386 -2.29
78.0465 C6H6+ 1 78.0464 0.75
79.0543 C6H7+ 1 79.0542 0.55
81.07 C6H9+ 1 81.0699 1.15
82.0651 C5H8N+ 1 82.0651 -0.56
83.0493 C5H7O+ 1 83.0491 1.31
91.0543 C7H7+ 1 91.0542 0.48
93.0698 C7H9+ 1 93.0699 -1.04
94.0412 C6H6O+ 1 94.0413 -0.81
94.065 C6H8N+ 1 94.0651 -1.34
95.0492 C6H7O+ 1 95.0491 0.3
95.0857 C7H11+ 1 95.0855 1.51
96.0808 C6H10N+ 1 96.0808 0.46
102.0464 C8H6+ 1 102.0464 -0.02
103.0543 C8H7+ 1 103.0542 0.91
105.0448 C6H5N2+ 1 105.0447 1
105.0699 C8H9+ 1 105.0699 -0.06
107.0492 C7H7O+ 1 107.0491 0.83
109.0647 C7H9O+ 1 109.0648 -0.47
115.0542 C9H7+ 1 115.0542 -0.06
116.062 C9H8+ 1 116.0621 -0.45
117.0699 C9H9+ 1 117.0699 0.46
118.0414 C8H6O+ 1 118.0413 0.62
119.0491 C8H7O+ 1 119.0491 -0.51
121.0648 C8H9O+ 1 121.0648 0.24
122.0363 C7H6O2+ 1 122.0362 0.81
127.0541 C10H7+ 1 127.0542 -1.08
128.0621 C10H8+ 1 128.0621 0.22
129.0699 C10H9+ 1 129.0699 0.18
130.0413 C9H6O+ 1 130.0413 0.03
130.0778 C10H10+ 1 130.0777 0.83
131.0492 C9H7O+ 1 131.0491 0.3
131.0857 C10H11+ 1 131.0855 1.02
132.0571 C9H8O+ 1 132.057 1.32
133.0647 C9H9O+ 1 133.0648 -0.54
137.0597 C8H9O2+ 1 137.0597 0.25
139.0541 C11H7+ 1 139.0542 -1.2
140.0622 C11H8+ 1 140.0621 0.77
141.0699 C11H9+ 1 141.0699 -0.05
142.0778 C11H10+ 1 142.0777 0.83
143.0493 C10H7O+ 1 143.0491 0.83
143.0857 C11H11+ 1 143.0855 1.07
144.0571 C10H8O+ 1 144.057 0.93
145.0649 C10H9O+ 1 145.0648 0.89
146.0362 C9H6O2+ 1 146.0362 -0.07
146.0728 C10H10O+ 1 146.0726 1.6
147.044 C9H7O2+ 1 147.0441 -0.18
147.0805 C10H11O+ 1 147.0804 0.4
151.0753 C9H11O2+ 1 151.0754 -0.37
152.0621 C12H8+ 1 152.0621 0.38
153.07 C12H9+ 1 153.0699 0.48
154.0778 C12H10+ 1 154.0777 0.57
155.0494 C11H7O+ 1 155.0491 1.35
155.0602 C10H7N2+ 1 155.0604 -1.19
155.0856 C12H11+ 1 155.0855 0.41
156.057 C11H8O+ 1 156.057 0.22
157.0649 C11H9O+ 1 157.0648 0.5
157.1011 C12H13+ 1 157.1012 -0.3
158.0727 C11H10O+ 1 158.0726 0.53
159.044 C10H7O2+ 1 159.0441 -0.23
159.0805 C11H11O+ 1 159.0804 0.37
160.0519 C10H8O2+ 1 160.0519 0.37
160.0759 C10H10NO+ 1 160.0757 1.18
161.0598 C10H9O2+ 1 161.0597 0.52
161.0963 C11H13O+ 1 161.0961 1.42
162.0676 C10H10O2+ 1 162.0675 0.61
163.0754 C10H11O2+ 1 163.0754 0.02
164.0613 C13H8+ 1 164.0621 -4.64
165.07 C13H9+ 1 165.0699 0.57
166.0777 C13H10+ 1 166.0777 -0.07
167.0856 C13H11+ 1 167.0855 0.44
168.0571 C12H8O+ 1 168.057 0.62
168.0934 C13H12+ 1 168.0934 0.35
169.0649 C12H9O+ 1 169.0648 0.76
169.0759 C11H9N2+ 1 169.076 -0.68
169.101 C13H13+ 1 169.1012 -1.34
170.0363 C11H6O2+ 1 170.0362 0.29
170.0729 C12H10O+ 1 170.0726 1.73
171.0442 C11H7O2+ 1 171.0441 0.61
171.0805 C12H11O+ 1 171.0804 0.17
172.0519 C11H8O2+ 1 172.0519 0.23
172.0884 C12H12O+ 1 172.0883 1.01
173.0962 C12H13O+ 1 173.0961 0.4
174.0674 C11H10O2+ 1 174.0675 -0.52
175.0754 C11H11O2+ 1 175.0754 0.54
176.0622 C14H8+ 1 176.0621 0.79
177.07 C14H9+ 1 177.0699 0.58
178.0777 C14H10+ 1 178.0777 0.05
179.0605 C12H7N2+ 1 179.0604 0.7
179.0855 C14H11+ 1 179.0855 -0.43
181.0647 C13H9O+ 1 181.0648 -0.28
182.073 C13H10O+ 1 182.0726 1.94
183.0442 C12H7O2+ 1 183.0441 0.73
183.0806 C13H11O+ 1 183.0804 0.87
184.052 C12H8O2+ 1 184.0519 0.65
184.0883 C13H12O+ 1 184.0883 0.18
185.0599 C12H9O2+ 1 185.0597 0.89
185.0961 C13H13O+ 1 185.0961 0.26
186.0677 C12H10O2+ 1 186.0675 0.75
187.0754 C12H11O2+ 1 187.0754 0.5
188.0832 C12H12O2+ 1 188.0832 0.1
189.0696 C15H9+ 1 189.0699 -1.62
189.091 C12H13O2+ 1 189.091 0.02
190.0779 C15H10+ 1 190.0777 0.94
191.0854 C15H11+ 1 191.0855 -0.56
193.0649 C14H9O+ 1 193.0648 0.3
193.076 C13H9N2+ 1 193.076 -0.18
193.1009 C15H13+ 1 193.1012 -1.64
194.0727 C14H10O+ 1 194.0726 0.28
195.0805 C14H11O+ 1 195.0804 0.4
196.0523 C13H8O2+ 1 196.0519 2.39
196.0884 C14H12O+ 1 196.0883 0.78
197.0599 C13H9O2+ 1 197.0597 0.88
197.0962 C14H13O+ 1 197.0961 0.6
198.0676 C13H10O2+ 1 198.0675 0.2
199.0754 C13H11O2+ 1 199.0754 0.12
200.0834 C13H12O2+ 1 200.0832 1.29
201.091 C13H13O2+ 1 201.091 0.12
202.0777 C16H10+ 1 202.0777 -0.16
202.0864 C12H12NO2+ 1 202.0863 0.67
205.0651 C15H9O+ 1 205.0648 1.46
207.0804 C15H11O+ 1 207.0804 -0.01
209.0598 C14H9O2+ 1 209.0597 0.26
209.096 C15H13O+ 1 209.0961 -0.29
210.0676 C14H10O2+ 1 210.0675 0.42
211.0754 C14H11O2+ 1 211.0754 0.3
212.0835 C14H12O2+ 1 212.0832 1.5
213.0911 C14H13O2+ 1 213.091 0.39
214.0625 C13H10O3+ 1 214.0624 0.07
215.1067 C14H15O2+ 1 215.1067 0.02
221.0959 C16H13O+ 1 221.0961 -0.73
223.0756 C15H11O2+ 1 223.0754 0.96
225.0913 C15H13O2+ 1 225.091 1.17
227.1067 C15H15O2+ 1 227.1067 0.37
228.1024 C14H14NO2+ 1 228.1019 2.34
243.102 C15H15O3+ 1 243.1016 1.68
268.133 C17H18NO2+ 1 268.1332 -0.69
302.1746 C18H24NO3+ 1 302.1751 -1.52
PK$NUM_PEAK: 145
PK$PEAK: m/z int. rel.int.
57.0336 821726.5 17
58.0653 477802.1 10
65.0385 124083.3 2
67.0542 1061818.8 22
69.0336 118299.7 2
70.0652 143645.1 3
71.0491 140264.6 2
77.0384 105478.7 2
78.0465 111859.6 2
79.0543 1138015.6 24
81.07 487147.9 10
82.0651 148176.9 3
83.0493 694370.5 14
91.0543 3044295.2 64
93.0698 173436 3
94.0412 471788.5 10
94.065 113617.7 2
95.0492 766839.8 16
95.0857 114374.1 2
96.0808 116414.4 2
102.0464 197302 4
103.0543 3149428.2 67
105.0448 387810.5 8
105.0699 1104677.8 23
107.0492 811212.6 17
109.0647 395310.4 8
115.0542 16575747 352
116.062 907285.1 19
117.0699 1433636 30
118.0414 848543.7 18
119.0491 203601 4
121.0648 1666052.6 35
122.0363 893663.9 19
127.0541 464243.5 9
128.0621 29448104 626
129.0699 9293342 197
130.0413 153789.5 3
130.0778 1564197.5 33
131.0492 2790032.8 59
131.0857 654276.7 13
132.0571 423890.8 9
133.0647 243754.2 5
137.0597 3486532.8 74
139.0541 557401.4 11
140.0622 768491.8 16
141.0699 30972458 659
142.0778 2316225.5 49
143.0493 3343138.2 71
143.0857 3143588.8 66
144.0571 4603485.5 98
145.0649 3812461.8 81
146.0362 1377797.8 29
146.0728 812774.6 17
147.044 139458.2 2
147.0805 691494.9 14
151.0753 236784.4 5
152.0621 8582023 182
153.07 9583361 204
154.0778 1925952.4 41
155.0494 2627682 55
155.0602 2072837.9 44
155.0856 5124092.5 109
156.057 12488948 265
157.0649 4175577.8 88
157.1011 595720.4 12
158.0727 24683276 525
159.044 482634.8 10
159.0805 4743056.5 100
160.0519 591127.8 12
160.0759 142453.5 3
161.0598 9733138 207
161.0963 1017860.1 21
162.0676 245476.7 5
163.0754 405936.2 8
164.0613 121377.4 2
165.07 23131834 492
166.0777 3088736.2 65
167.0856 7480649 159
168.0571 4270001.5 90
168.0934 429666.9 9
169.0649 5312784 113
169.0759 1715667.2 36
169.101 370278.7 7
170.0363 681530 14
170.0729 1432271.9 30
171.0442 2745724.8 58
171.0805 46922580 999
172.0519 2096877 44
172.0884 662836.7 14
173.0962 7772352.5 165
174.0674 960855.4 20
175.0754 1465483 31
176.0622 1561669.5 33
177.07 3593956.2 76
178.0777 2396101.8 51
179.0605 169827.4 3
179.0855 481019.2 10
181.0647 3794035.2 80
182.073 2519657.5 53
183.0442 3391913.5 72
183.0806 6381849 135
184.052 4496037 95
184.0883 2749116.5 58
185.0599 3204588.8 68
185.0961 1275452.2 27
186.0677 2908394.8 61
187.0754 2176904.8 46
188.0832 188389.3 4
189.0696 202313.2 4
189.091 1282024.8 27
190.0779 189617 4
191.0854 170977.6 3
193.0649 1201674.2 25
193.076 476847.8 10
193.1009 411702.2 8
194.0727 3152840.8 67
195.0805 4102614 87
196.0523 148050.8 3
196.0884 2242006.2 47
197.0599 2658387.2 56
197.0962 720523.6 15
198.0676 3796453.8 80
199.0754 30592598 651
200.0834 540876.6 11
201.091 5188857.5 110
202.0777 607004.5 12
202.0864 167241.4 3
205.0651 113419.9 2
207.0804 457632.5 9
209.0598 416184.2 8
209.096 205963.4 4
210.0676 574641.6 12
211.0754 1236416.9 26
212.0835 1355472.6 28
213.0911 633297.6 13
214.0625 683611.4 14
215.1067 177937.3 3
221.0959 186870.1 3
223.0756 220317.9 4
225.0913 1327181.2 28
227.1067 1196490.4 25
228.1024 181195.6 3
243.102 129736.1 2
268.133 166374.1 3
302.1746 115265.2 2
//
