ACCESSION: MSBNK-Eawag-EQ333304
RECORD_TITLE: Dihydrocodeine; LC-ESI-QFT; MS2; CE: 60; 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$MASS_SPECTROMETRY: COLLISION_ENERGY 60 (nominal)
AC$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: splash10-0f6t-0941000000-85f127ae74a67d7544d7
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
57.0336 C3H5O+ 1 57.0335 2.08
58.0652 C3H8N+ 1 58.0651 1.11
67.0543 C5H7+ 1 67.0542 0.5
69.0335 C4H5O+ 1 69.0335 -0.6
70.0652 C4H8N+ 1 70.0651 1.2
71.0492 C4H7O+ 1 71.0491 0.4
79.0543 C6H7+ 1 79.0542 0.93
81.0699 C6H9+ 1 81.0699 0.78
82.065 C5H8N+ 1 82.0651 -1.04
83.0492 C5H7O+ 1 83.0491 1.07
84.0808 C5H10N+ 1 84.0808 0.53
91.0543 C7H7+ 1 91.0542 0.7
93.07 C7H9+ 1 93.0699 1.54
95.049 C6H7O+ 1 95.0491 -1.59
95.0855 C7H11+ 1 95.0855 -0.7
96.0809 C6H10N+ 1 96.0808 1.09
97.0649 C6H9O+ 1 97.0648 1.12
103.0543 C8H7+ 1 103.0542 0.52
105.0699 C8H9+ 1 105.0699 0.13
107.0491 C7H7O+ 1 107.0491 -0.01
115.0541 C9H7+ 1 115.0542 -1.36
117.07 C9H9+ 1 117.0699 1.22
121.0648 C8H9O+ 1 121.0648 -0.18
128.0619 C10H8+ 1 128.0621 -1.5
129.0699 C10H9+ 1 129.0699 0.18
131.0491 C9H7O+ 1 131.0491 -0.31
131.0858 C10H11+ 1 131.0855 2.31
133.0644 C9H9O+ 1 133.0648 -2.94
137.0598 C8H9O2+ 1 137.0597 0.32
141.0699 C11H9+ 1 141.0699 -0.12
142.0776 C11H10+ 1 142.0777 -1
143.0492 C10H7O+ 1 143.0491 0.55
143.0857 C11H11+ 1 143.0855 1.35
144.0572 C10H8O+ 1 144.057 1.41
145.0649 C10H9O+ 1 145.0648 1.02
145.1011 C11H13+ 1 145.1012 -0.53
146.0723 C10H10O+ 1 146.0726 -2.03
147.0806 C10H11O+ 1 147.0804 1.08
151.0755 C9H11O2+ 1 151.0754 0.89
152.0619 C12H8+ 1 152.0621 -0.87
153.0699 C12H9+ 1 153.0699 0.09
155.0493 C11H7O+ 1 155.0491 0.7
155.0856 C12H11+ 1 155.0855 0.41
156.057 C11H8O+ 1 156.057 0.41
157.0649 C11H9O+ 1 157.0648 0.63
157.1012 C12H13+ 1 157.1012 0.08
158.0727 C11H10O+ 1 158.0726 0.66
159.0804 C11H11O+ 1 159.0804 -0.07
161.0598 C10H9O2+ 1 161.0597 0.4
161.0962 C11H13O+ 1 161.0961 0.55
162.0675 C10H10O2+ 1 162.0675 0.06
163.0754 C10H11O2+ 1 163.0754 0.45
165.0699 C13H9+ 1 165.0699 0.32
166.0778 C13H10+ 1 166.0777 0.35
167.0856 C13H11+ 1 167.0855 0.5
168.0569 C12H8O+ 1 168.057 -0.57
168.093 C13H12+ 1 168.0934 -2.21
169.0649 C12H9O+ 1 169.0648 0.52
169.0759 C11H9N2+ 1 169.076 -0.68
169.1016 C13H13+ 1 169.1012 2.62
170.0728 C12H10O+ 1 170.0726 0.79
171.0805 C12H11O+ 1 171.0804 0.28
172.0521 C11H8O2+ 1 172.0519 1.22
173.0962 C12H13O+ 1 173.0961 0.4
174.0674 C11H10O2+ 1 174.0675 -0.92
175.0755 C11H11O2+ 1 175.0754 0.71
176.0832 C11H12O2+ 1 176.0832 0.22
177.0699 C14H9+ 1 177.0699 0.24
177.0907 C11H13O2+ 1 177.091 -1.56
178.0777 C14H10+ 1 178.0777 0.05
179.0701 C10H11O3+ 1 179.0703 -0.9
181.0649 C13H9O+ 1 181.0648 0.32
181.1012 C14H13+ 1 181.1012 0.18
182.0724 C13H10O+ 1 182.0726 -1.08
183.0806 C13H11O+ 1 183.0804 0.65
184.0519 C12H8O2+ 1 184.0519 -0.17
184.0883 C13H12O+ 1 184.0883 0.29
185.06 C12H9O2+ 1 185.0597 1.86
185.0962 C13H13O+ 1 185.0961 0.69
186.0677 C12H10O2+ 1 186.0675 0.91
187.0754 C12H11O2+ 1 187.0754 0.4
188.083 C12H12O2+ 1 188.0832 -0.7
189.0911 C12H13O2+ 1 189.091 0.66
191.0856 C15H11+ 1 191.0855 0.54
192.1019 C11H14NO2+ 1 192.1019 0.13
193.065 C14H9O+ 1 193.0648 0.93
193.0737 C10H11NO3+ 1 193.0733 2
193.1012 C15H13+ 1 193.1012 0.33
194.0727 C14H10O+ 1 194.0726 0.64
195.0805 C14H11O+ 1 195.0804 0.56
196.0885 C14H12O+ 1 196.0883 0.99
197.0596 C13H9O2+ 1 197.0597 -0.74
197.0965 C14H13O+ 1 197.0961 2.23
198.0677 C13H10O2+ 1 198.0675 1.06
199.0754 C13H11O2+ 1 199.0754 0.12
199.1116 C14H15O+ 1 199.1117 -0.51
200.0829 C13H12O2+ 1 200.0832 -1.3
201.0909 C13H13O2+ 1 201.091 -0.33
202.0986 C13H14O2+ 1 202.0988 -1.29
203.07 C12H11O3+ 1 203.0703 -1.43
203.1063 C13H15O2+ 1 203.1067 -1.85
204.1021 C12H14NO2+ 1 204.1019 1.15
205.0764 C14H9N2+ 1 205.076 1.98
209.0587 C14H9O2+ 1 209.0597 -4.91
209.0962 C15H13O+ 1 209.0961 0.61
210.104 C15H14O+ 1 210.1039 0.25
211.0754 C14H11O2+ 1 211.0754 0.35
211.1122 C15H15O+ 1 211.1117 2.41
212.0831 C14H12O2+ 1 212.0832 -0.29
213.091 C14H13O2+ 1 213.091 0.02
214.0624 C13H10O3+ 1 214.0624 -0.35
214.099 C14H14O2+ 1 214.0988 0.84
215.1069 C14H15O2+ 1 215.1067 1.04
217.11 C13H15NO2+ 1 217.1097 1.2
217.1223 C14H17O2+ 1 217.1223 0.11
219.1019 C13H15O3+ 1 219.1016 1.27
221.0965 C16H13O+ 1 221.0961 2.03
222.1038 C16H14O+ 1 222.1039 -0.39
223.0756 C15H11O2+ 1 223.0754 0.91
223.1122 C16H15O+ 1 223.1117 1.97
224.0836 C15H12O2+ 1 224.0832 1.78
225.0911 C15H13O2+ 1 225.091 0.64
226.0986 C15H14O2+ 1 226.0988 -1.02
227.1067 C15H15O2+ 1 227.1067 0.19
228.1022 C14H14NO2+ 1 228.1019 1.34
229.0862 C14H13O3+ 1 229.0859 1.04
229.1221 C15H17O2+ 1 229.1223 -1.12
238.0992 C16H14O2+ 1 238.0988 1.42
241.1224 C16H17O2+ 1 241.1223 0.18
243.1018 C15H15O3+ 1 243.1016 0.86
245.1174 C15H17O3+ 1 245.1172 0.69
252.1386 C17H18NO+ 1 252.1383 1.19
253.1224 C17H17O2+ 1 253.1223 0.49
256.1093 C16H16O3+ 1 256.1094 -0.33
256.1334 C16H18NO2+ 1 256.1332 0.6
268.1327 C17H18NO2+ 1 268.1332 -2.07
269.1412 C17H19NO2+ 1 269.141 0.74
271.133 C17H19O3+ 1 271.1329 0.33
274.1438 C16H20NO3+ 1 274.1438 0.07
284.1647 C18H22NO2+ 1 284.1645 0.65
287.1516 C17H21NO3+ 1 287.1516 0.12
302.1752 C18H24NO3+ 1 302.1751 0.5
PK$NUM_PEAK: 142
PK$PEAK: m/z int. rel.int.
57.0336 203809 2
58.0652 1182405.4 13
67.0543 977327.5 11
69.0335 95919.6 1
70.0652 200865.6 2
71.0492 727542.8 8
79.0543 752953.1 8
81.0699 222378.2 2
82.065 93141.8 1
83.0492 516668.1 6
84.0808 152762.7 1
91.0543 265436.3 3
93.07 117243.7 1
95.049 129106.3 1
95.0855 247891.2 2
96.0809 144804.7 1
97.0649 119505.7 1
103.0543 505770.8 5
105.0699 421094.8 4
107.0491 142725 1
115.0541 1051857.6 12
117.07 133288.1 1
121.0648 969789.1 11
128.0619 1162120.1 13
129.0699 1767878.4 20
131.0491 1039688.8 12
131.0858 142518.2 1
133.0644 138323.7 1
137.0598 5564734 64
141.0699 2548782.2 29
142.0776 363410.1 4
143.0492 2327835.2 27
143.0857 757018.7 8
144.0572 487007.2 5
145.0649 809847.4 9
145.1011 138380.2 1
146.0723 133875.6 1
147.0806 653892.3 7
151.0755 651691.8 7
152.0619 793917.9 9
153.0699 1640360 19
155.0493 223973.7 2
155.0856 1506345.8 17
156.057 504176 5
157.0649 4148002 48
157.1012 1447799.1 16
158.0727 5427356 63
159.0804 1991745.5 23
161.0598 6635788 77
161.0962 1435575.1 16
162.0675 197798 2
163.0754 2702332 31
165.0699 3708090 43
166.0778 483757.5 5
167.0856 9363505 109
168.0569 526261.2 6
168.093 172799.2 2
169.0649 2882546.8 33
169.0759 222337.9 2
169.1016 820297.3 9
170.0728 437677.2 5
171.0805 16606376 193
172.0521 569218.9 6
173.0962 10267405 119
174.0674 198621.5 2
175.0755 3218442.5 37
176.0832 418263.2 4
177.0699 2999013.8 34
177.0907 814111.1 9
178.0777 502985.4 5
179.0701 499706.1 5
181.0649 3705950.5 43
181.1012 845848.6 9
182.0724 606708.4 7
183.0806 15919833 185
184.0519 249720.8 2
184.0883 2994042.5 34
185.06 1798474.2 20
185.0962 7636877 89
186.0677 2969787.8 34
187.0754 6481931 75
188.083 159086.3 1
189.0911 9081888 105
191.0856 169514.5 1
192.1019 183303.7 2
193.065 1973368.6 22
193.0737 150769.9 1
193.1012 1068181.6 12
194.0727 1591503.9 18
195.0805 18071940 210
196.0885 4394662.5 51
197.0596 1062313.5 12
197.0965 1892330.9 22
198.0677 2631100 30
199.0754 85716120 999
199.1116 7246212 84
200.0829 251778.3 2
201.0909 42654508 497
202.0986 453452.5 5
203.07 197445.7 2
203.1063 962542.7 11
204.1021 420455.3 4
205.0764 118516.3 1
209.0587 132883.5 1
209.0962 2160103.8 25
210.104 178656.2 2
211.0754 3769333.8 43
211.1122 190167.8 2
212.0831 3409372 39
213.091 6536170 76
214.0624 726631.1 8
214.099 593840.4 6
215.1069 2059026.1 23
217.11 773991.2 9
217.1223 4227943 49
219.1019 142840.8 1
221.0965 952808.1 11
222.1038 595256.6 6
223.0756 159621.2 1
223.1122 176377.3 2
224.0836 148669.6 1
225.0911 5298132.5 61
226.0986 222638.3 2
227.1067 24355026 283
228.1022 244141 2
229.0862 643009.2 7
229.1221 196665 2
238.0992 434191.9 5
241.1224 673288.9 7
243.1018 7532524.5 87
245.1174 14694061 171
252.1386 177258.3 2
253.1224 1240071.5 14
256.1093 431309.6 5
256.1334 131019.2 1
268.1327 516471.7 6
269.1412 1963186.1 22
271.133 382854.3 4
274.1438 805085 9
284.1647 2056391.9 23
287.1516 443273 5
302.1752 37959000 442
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