ACCESSION: MSBNK-Eawag-EQ362905
RECORD_TITLE: delta9-Tetrahydrocannabinol; LC-ESI-QFT; MS2; CE: 75; R=35000; [M+H]+
DATE: 2015.08.25
AUTHORS: Stravs M, Schymanski E, Singer H, Department of Environmental Chemistry, Eawag and Thomaidis N, University of Athens
LICENSE: CC BY
COPYRIGHT: Copyright (C) 2015 Eawag, Duebendorf, Switzerland
COMMENT: CONFIDENCE standard compound
COMMENT: EAWAG_UCHEM_ID 3629
CH$NAME: delta9-Tetrahydrocannabinol
CH$NAME: delta9-THC
CH$NAME: 6,6,9-trimethyl-3-pentyl-6a,7,8,10a-tetrahydrobenzo[c]chromen-1-ol
CH$COMPOUND_CLASS: N/A; Environmental Standard
CH$FORMULA: C21H30O2
CH$EXACT_MASS: 314.22458
CH$SMILES: CCCCCC1=CC2=C(C3C=C(CCC3C(O2)(C)C)C)C(=C1)O
CH$IUPAC: InChI=1S/C21H30O2/c1-5-6-7-8-15-12-18(22)20-16-11-14(2)9-10-17(16)21(3,4)23-19(20)13-15/h11-13,16-17,22H,5-10H2,1-4H3
CH$LINK: CAS
76-03-9
CH$LINK: PUBCHEM
CID:2978
CH$LINK: INCHIKEY
CYQFCXCEBYINGO-UHFFFAOYSA-N
CH$LINK: CHEMSPIDER
2872
AC$INSTRUMENT: Q Exactive Plus Orbitrap Thermo Scientific
AC$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 17.8 min
AC$CHROMATOGRAPHY: SOLVENT A water with 0.1% formic acid
AC$CHROMATOGRAPHY: SOLVENT B methanol with 0.1% formic acid
MS$FOCUSED_ION: BASE_PEAK 391.2837
MS$FOCUSED_ION: PRECURSOR_M/Z 315.2319
MS$FOCUSED_ION: PRECURSOR_TYPE [M+H]+
MS$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$SPLASH: splash10-00xu-8900000000-7dd5d072635bb1e5af61
PK$ANNOTATION: m/z tentative_formula formula_count mass error(ppm)
50.0152 C4H2+ 1 50.0151 1.17
51.0229 C4H3+ 1 51.0229 -0.72
52.0182 C3H2N+ 1 52.0182 -0.3
52.0306 C4H4+ 1 52.0308 -3.1
53.0023 C3HO+ 1 53.0022 1.3
53.0386 C4H5+ 1 53.0386 1.01
53.9975 C2NO+ 1 53.9974 1.11
55.0179 C3H3O+ 1 55.0178 0.89
55.0543 C4H7+ 1 55.0542 0.97
57.0335 C3H5O+ 1 57.0335 0.33
57.0699 C4H9+ 1 57.0699 0.93
59.0492 C3H7O+ 1 59.0491 1.33
65.0386 C5H5+ 1 65.0386 0.98
67.0543 C5H7+ 1 67.0542 0.8
67.9894 C3O2+ 1 67.9893 1.02
69.0336 C4H5O+ 1 69.0335 0.85
69.0699 C5H9+ 1 69.0699 0.63
71.0492 C4H7O+ 1 71.0491 1.25
71.0856 C5H11+ 1 71.0855 0.61
73.0649 C4H9O+ 1 73.0648 0.94
77.0385 C6H5+ 1 77.0386 -0.47
78.0464 C6H6+ 1 78.0464 0.62
79.0543 C6H7+ 1 79.0542 0.55
80.0621 C6H8+ 1 80.0621 0.35
81.0335 C5H5O+ 1 81.0335 0.6
81.0699 C6H9+ 1 81.0699 0.78
83.0128 C4H3O2+ 1 83.0128 0.41
83.0492 C5H7O+ 1 83.0491 0.23
83.0856 C6H11+ 1 83.0855 0.76
85.0285 C4H5O2+ 1 85.0284 0.75
85.0648 C5H9O+ 1 85.0648 -0.13
91.0543 C7H7+ 1 91.0542 1.03
92.0622 C7H8+ 1 92.0621 1.07
93.07 C7H9+ 1 93.0699 1.32
94.0415 C6H6O+ 1 94.0413 2.17
94.0778 C7H10+ 1 94.0777 1.15
95.0492 C6H7O+ 1 95.0491 0.83
95.0856 C7H11+ 1 95.0855 0.88
97.0286 C5H5O2+ 1 97.0284 1.69
97.0649 C6H9O+ 1 97.0648 1.02
97.1013 C7H13+ 1 97.1012 1.58
103.0543 C8H7+ 1 103.0542 1
105.0449 C6H5N2+ 1 105.0447 1.29
105.07 C8H9+ 1 105.0699 1.17
106.0779 C8H10+ 1 106.0777 1.96
107.0492 C7H7O+ 1 107.0491 0.83
107.0856 C8H11+ 1 107.0855 0.68
108.0571 C7H8O+ 1 108.057 1.33
109.0286 C6H5O2+ 1 109.0284 1.6
109.0649 C7H9O+ 1 109.0648 1
109.1013 C8H13+ 1 109.1012 0.85
111.0441 C6H7O2+ 1 111.0441 0.67
115.0541 C9H7+ 1 115.0542 -0.75
116.0622 C9H8+ 1 116.0621 1.02
117.0699 C9H9+ 1 117.0699 0.54
119.0493 C8H7O+ 1 119.0491 0.91
119.0605 C7H7N2+ 1 119.0604 1.14
119.0857 C9H11+ 1 119.0855 1.2
120.0572 C8H8O+ 1 120.057 2.28
120.0934 C9H12+ 1 120.0934 0.57
121.0649 C8H9O+ 1 121.0648 1.06
121.1013 C9H13+ 1 121.1012 1.18
123.0441 C7H7O2+ 1 123.0441 0.68
124.052 C7H8O2+ 1 124.0519 0.96
125.0599 C7H9O2+ 1 125.0597 1.31
128.0623 C10H8+ 1 128.0621 1.63
129.07 C10H9+ 1 129.0699 0.88
130.0779 C10H10+ 1 130.0777 1.37
131.0492 C9H7O+ 1 131.0491 0.52
131.0856 C10H11+ 1 131.0855 0.79
132.0571 C9H8O+ 1 132.057 0.86
133.0285 C8H5O2+ 1 133.0284 0.63
133.0649 C9H9O+ 1 133.0648 0.67
133.1013 C10H13+ 1 133.1012 0.62
135.0441 C8H7O2+ 1 135.0441 0.62
135.0805 C9H11O+ 1 135.0804 0.73
135.1169 C10H15+ 1 135.1168 0.62
136.052 C8H8O2+ 1 136.0519 1.1
137.0599 C8H9O2+ 1 137.0597 1.12
139.1116 C9H15O+ 1 139.1117 -0.87
141.0699 C11H9+ 1 141.0699 0.02
142.0779 C11H10+ 1 142.0777 1.33
143.0857 C11H11+ 1 143.0855 1.07
144.0574 C10H8O+ 1 144.057 2.73
144.0936 C11H12+ 1 144.0934 1.51
145.0648 C10H9O+ 1 145.0648 0.34
145.1012 C11H13+ 1 145.1012 0.09
146.0727 C10H10O+ 1 146.0726 0.78
147.0442 C9H7O2+ 1 147.0441 0.84
147.0805 C10H11O+ 1 147.0804 0.47
147.1171 C11H15+ 1 147.1168 1.99
148.052 C9H8O2+ 1 148.0519 0.47
149.0598 C9H9O2+ 1 149.0597 0.7
149.0962 C10H13O+ 1 149.0961 0.86
151.0756 C9H11O2+ 1 151.0754 1.81
152.0625 C12H8+ 1 152.0621 3.08
153.0699 C12H9+ 1 153.0699 0.02
155.0606 C10H7N2+ 1 155.0604 1.13
155.0856 C12H11+ 1 155.0855 0.73
156.0935 C12H12+ 1 156.0934 1.01
157.0651 C11H9O+ 1 157.0648 1.97
157.1013 C12H13+ 1 157.1012 0.97
158.0728 C11H10O+ 1 158.0726 1.23
159.0806 C11H11O+ 1 159.0804 1.25
159.1173 C12H15+ 1 159.1168 2.78
160.0521 C10H8O2+ 1 160.0519 1.56
160.0885 C11H12O+ 1 160.0883 1.52
161.0599 C10H9O2+ 1 161.0597 0.89
161.0963 C11H13O+ 1 161.0961 1.42
162.0674 C10H10O2+ 1 162.0675 -0.62
163.0756 C10H11O2+ 1 163.0754 1.74
163.1119 C11H15O+ 1 163.1117 0.67
165.0702 C13H9+ 1 165.0699 1.84
165.0912 C10H13O2+ 1 165.091 1.36
165.1275 C11H17O+ 1 165.1274 0.47
169.065 C12H9O+ 1 169.0648 1.41
169.076 C11H9N2+ 1 169.076 -0.15
169.1014 C13H13+ 1 169.1012 1.62
170.0725 C12H10O+ 1 170.0726 -0.92
171.0805 C12H11O+ 1 171.0804 0.63
171.1171 C13H15+ 1 171.1168 1.42
172.0886 C12H12O+ 1 172.0883 1.82
173.0599 C11H9O2+ 1 173.0597 0.83
173.0965 C12H13O+ 1 173.0961 2.13
174.0677 C11H10O2+ 1 174.0675 0.97
175.0756 C11H11O2+ 1 175.0754 1.28
175.1119 C12H15O+ 1 175.1117 1.13
177.0913 C11H13O2+ 1 177.091 1.43
177.1276 C12H17O+ 1 177.1274 1.18
183.0808 C13H11O+ 1 183.0804 1.9
184.0883 C13H12O+ 1 184.0883 0.29
185.0963 C13H13O+ 1 185.0961 1.07
187.0755 C12H11O2+ 1 187.0754 0.98
188.0834 C12H12O2+ 1 188.0832 1.16
189.091 C12H13O2+ 1 189.091 0.07
189.1278 C13H17O+ 1 189.1274 2.42
191.1433 C13H19O+ 1 191.143 1.3
193.1225 C12H17O2+ 1 193.1223 1.16
197.0963 C14H13O+ 1 197.0961 1.16
201.0912 C13H13O2+ 1 201.091 1.06
202.0989 C13H14O2+ 1 202.0988 0.34
203.1074 C13H15O2+ 1 203.1067 3.81
203.1433 C14H19O+ 1 203.143 1.07
205.1226 C13H17O2+ 1 205.1223 1.38
207.1382 C13H19O2+ 1 207.138 1.22
211.1123 C15H15O+ 1 211.1117 2.5
215.1068 C14H15O2+ 1 215.1067 0.53
215.1435 C15H19O+ 1 215.143 2.13
217.1226 C14H17O2+ 1 217.1223 1.58
225.1272 C16H17O+ 1 225.1274 -0.98
229.1223 C15H17O2+ 1 229.1223 0.15
231.1383 C15H19O2+ 1 231.138 1.4
233.1541 C15H21O2+ 1 233.1536 2.12
241.1589 C17H21O+ 1 241.1587 0.74
243.1384 C16H19O2+ 1 243.138 1.91
244.1457 C16H20O2+ 1 244.1458 -0.33
245.153 C16H21O2+ 1 245.1536 -2.31
259.1695 C17H23O2+ 1 259.1693 0.94
PK$NUM_PEAK: 158
PK$PEAK: m/z int. rel.int.
50.0152 21063.1 4
51.0229 10908.5 2
52.0182 6080.8 1
52.0306 5856.9 1
53.0023 138223.1 26
53.0386 240224.4 45
53.9975 32167.2 6
55.0179 318824.1 60
55.0543 887269.6 168
57.0335 29950.3 5
57.0699 269372.2 51
59.0492 37868.4 7
65.0386 191891.9 36
67.0543 1615053 306
67.9894 28475.7 5
69.0336 169848.3 32
69.0699 1991879.6 378
71.0492 24331.7 4
71.0856 91731.7 17
73.0649 18275.6 3
77.0385 187096 35
78.0464 9493.4 1
79.0543 1342718.2 255
80.0621 30931.7 5
81.0335 142070.6 27
81.0699 1867355.5 354
83.0128 96113.9 18
83.0492 212506.4 40
83.0856 28351.8 5
85.0285 6866.2 1
85.0648 8401 1
91.0543 1670537.1 317
92.0622 22837.2 4
93.07 2233776.2 424
94.0415 16713.8 3
94.0778 26313.4 5
95.0492 1216785.4 231
95.0856 442480.5 84
97.0286 31287.4 5
97.0649 104891.6 19
97.1013 53835.2 10
103.0543 72199.5 13
105.0449 368494.2 70
105.07 725059.4 137
106.0779 7344.7 1
107.0492 623782.3 118
107.0856 1054836 200
108.0571 40261.4 7
109.0286 83190.5 15
109.0649 670790.8 127
109.1013 272283.1 51
111.0441 173170.6 32
115.0541 55943.2 10
116.0622 26793.1 5
117.0699 129568.4 24
119.0493 46849 8
119.0605 112153.6 21
119.0857 312331.2 59
120.0572 7532 1
120.0934 49949.1 9
121.0649 452428.4 85
121.1013 266354.4 50
123.0441 5256357.5 999
124.052 40776.8 7
125.0599 34200 6
128.0623 64302.3 12
129.07 90666.9 17
130.0779 10378.3 1
131.0492 43054.6 8
131.0856 151515.8 28
132.0571 9782.3 1
133.0285 6967 1
133.0649 130040.9 24
133.1013 79242.5 15
135.0441 109618.7 20
135.0805 106990.7 20
135.1169 110061 20
136.052 178773.4 33
137.0599 635353.3 120
139.1116 17524.7 3
141.0699 49246.4 9
142.0779 42334.7 8
143.0857 88307.7 16
144.0574 25459.1 4
144.0936 8927.5 1
145.0648 57700.1 10
145.1012 70126.4 13
146.0727 40072 7
147.0442 122895.5 23
147.0805 88085.7 16
147.1171 28874.1 5
148.052 32165.3 6
149.0598 65536 12
149.0962 53822.4 10
151.0756 52166.8 9
152.0625 6763.4 1
153.0699 6153 1
155.0606 19329.2 3
155.0856 27041.6 5
156.0935 23469.5 4
157.0651 25284.6 4
157.1013 43083.3 8
158.0728 25391.1 4
159.0806 118709.2 22
159.1173 31370.1 5
160.0521 123592.3 23
160.0885 7984.3 1
161.0599 287712.7 54
161.0963 47798.4 9
162.0674 31991.9 6
163.0756 48460.9 9
163.1119 18172.1 3
165.0702 7087.3 1
165.0912 113473.4 21
165.1275 17558.8 3
169.065 21410.8 4
169.076 10852.4 2
169.1014 8303.5 1
170.0725 8664.9 1
171.0805 79418.7 15
171.1171 7571.6 1
172.0886 5595.4 1
173.0599 43161.8 8
173.0965 22631.9 4
174.0677 263884.8 50
175.0756 150181.6 28
175.1119 29361.7 5
177.0913 33114.1 6
177.1276 155290.2 29
183.0808 31270.4 5
184.0883 56660.2 10
185.0963 20342.3 3
187.0755 95654.7 18
188.0834 73687.7 14
189.091 28598.4 5
189.1278 22095.7 4
191.1433 9153.6 1
193.1225 970373.8 184
197.0963 19670.8 3
201.0912 39450.4 7
202.0989 81900.2 15
203.1074 7088.6 1
203.1433 10862.5 2
205.1226 10310.1 1
207.1382 26320.5 5
211.1123 10634.4 2
215.1068 6220.2 1
215.1435 8637.3 1
217.1226 126155.6 23
225.1272 8004.8 1
229.1223 21710.3 4
231.1383 203702.6 38
233.1541 8022.5 1
241.1589 21834.2 4
243.1384 23907.3 4
244.1457 22843 4
245.153 19043.5 3
259.1695 67628.8 12
//