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ก delta-9-Tetrahydrocannabinol 11-Nor-9-Carboxy-delta-9- Tetrahydrocannabinol Gas Chromatography/Mass Spectrometry กกก กก 2556 หอ

C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

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Page 1: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

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Page 2: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

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Page 3: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

Analysis of delta-9-Tetrahydrocannabinol and 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol in urine samples by Gas Chromatography/Mass Spectrometry

By

Ms. Rossukhon Thanatheerabunjong

A Thesis Submitted in Partial Fulfillment of the Requirements for the Degree Master of Science Program in Forensic Science

Graduate School, Silpakorn University Academic Year 2013

Copyright of Graduate School, Silpakorn University

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����������� ����������ก� ��� ��������������������� "ก���� �!�� delta-

9-Tetrahydrocannabinol 2�! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol ������7��899�!

:;���< Gas Chromatography/Mass Spectrometry" �9��:; ��9��99� ��� ���<�!���E� ��F�

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Page 5: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

52312330: �� �� � � ������ ������: delta-9-Tetrahydrocannabinol, 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol,

TOXI-LAB THC II, Gas Chromatography/Mass Spectrometry (GC/MS)

�?��@� @�@A�BC��D�: ก�� F��BG� delta-9-Tetrahydrocannabinol HIB 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol J����K�L�MN�BOP�� @A Gas Chromatography/Mass Spectrometry. KD����ARM�SกT� ��� U�@�: K. P�. � � ����� �Vก?IFก�A��. 81 G�X.

FMY��AR��Cก��PA�L�KKกZ�@ [J�U\�M�BF]� Cannabis ��^��_�ก����\K�

Tetrahydrocannabinol (THC) J���� D���A_ `PXU�a�� @Aก�� F��BG�GM� ^b delta-9-

Tetrahydrocannabinol HIB11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol J����K�L�MN�B PX��F��� � Gas Chromatography/Mass Spectrometry (GC/MS) FกcC���K�L�DกK^���D���� 15 �� �AR��CM�B��� ก�FUก��� HIB 5 �� DกK^����AR`^L^AM�B��� ก�FUก��� ���K�L��ARDB� F��BG�PX��F��� � GC/MS `PXDกก�ก�PPX���K�FGI� �^PX��ก���JGXFMY��K�?U��@�OP� pentafluoropropionic anhydride HIB pentafluoro-1-propanol J����K�L��_�MN�B�ARdVกF� ^PX���^��e� ^�dGM� ^b�K����_�K��A_`PX�R�dS��BP�C 10 ng/mL ���K�L��_�MN�B��_�G^P`PXfL�ก��PKC�LUCก��� OP�J�X� @A $Cloned enzyme donor

immunoassay, CEDIA+ HIBUC�L 15 ���K�L� JGXfIFMY�C�ก K�L�`�กc�^J����K�L��_�MN�B��_�G^P 20 ���K�L� ^AFUA�� 10 ���K�L� �AR���DUC delta-9-Tetrahydrocannabinol HIB11-Nor-9-

Carboxy-delta-9-Tetrahydrocannabinol OP�F��� � GC/MS �XK^VI�AR`PXDกF��� � GC/MS KP�IXK�ก�CfI�ARFMY�C�ก �G��Cก����AR���DOP�� @A TLC �K��?P���D TOXI- LAB THC II DกfIก��PIK��A_UC�LF��� � GC/MS ^�dJ�XJ�ก��\���� J�ก����DGก���J�fVXFU HIB� @A�A_���^�dJ�XJ�ก�� F��BG�F� �M� ^b�K��กI?L^ Cannabinoids J����K�L�MN�B`PX

�� �� � � ������ C�bg �� ��I�� ^G� ��I��� IMก�I�^\K�\RK��ก�SกT.............................................................. Mhก��SกT 2556 I�^\K�\RKKD����ARM�SกT� ��� U�@� 1....................................................

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Page 6: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

52312330: MAJOR: FORENSIC SCIENCE

KEY WORD: delta-9-Tetrahydrocannabinol / 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol /

TOXI-LAB THC II / Gas Chromatography/Mass Spectrometry (GC/MS)

ROSSUKHON THANATHEERABUNJONG : ANALYSIS OF DELTA-9-TETRA

HYDROCANNABINOL AND 11-NOR-9-CARBOXY- DELTA-9-TETRAHYDROCANNA-

BINOL IN URINE SAMPLES BY GAS CHROMATOGRAPHY/MASS SPECTROMETRY

(GC/MS).THESIS ADVISORS: SIRIRAT CHOOSAKOONKRIANG, Ph.D. 81 pp.

It is well known that Tetrahydrocannabinol (THC) is the active constituent in

Cannabis including marijuana. In this study, the method of Gas Chromatography/Mass

Spectrometry (GC/MS) was developed for the determination of delta-9-Tetrahydrocannabinol and

11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol in urine. Samples were collected from 15

volunteers with known history of marijuana usage and from 5 non-drug-users. Samples for

GC/MS analysis were prepared by liquid extraction followed by derivatization with

pentafluoropropionic anhydride and pentafluoro-1-propanol. In the standard spiked samples, the

amounts of the two components can be measured at the lowest level of 10 ng/mL. All urine

samples collected had been tested for marijuana by BCloned enzyme donor immunoassay,

CEDIAC and it was found that 15 samples showed a positive result. However, amoung these 20

samples, only 10 samples were found to contain delta-9-Tetrahydrocannabinol and 11-Nor-9-

Carboxy-delta-9-Tetrahydrocannabinol with a high amount as measured by the method of

GC/MS.

The GC/MS data conformed with the positive tests for marijuana given by the TLC

method of a commercial TOXI- LAB THC II testing. The results from this study have established

that the GC/MS analysis provides a more definitive proof of marijuana usage and the method

permits quantitative analysis of the cannabinoids in urine samples.

Program of Forensic Science Graduate School, Silpakorn University

StudentDs signature ........................................................ Academic Year 2013

Thesis AdvisorDs signature 1. ..............................................................

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- Duquenois test T7�Q9 delta-9-THC ���ก539Q0�����.WO���.Q0�

2. ก��/��45 TLC

3. ก��/��45 immunoassay

4. ก��/��45 UV spectrum

- Ethanol-cannabidiol N9� 278 nm

- Cannabinol N9� 285 nm

- delta-9-THC N9� 278 nm

5. ก��/��45 GC/MS

- cannabidiol Q9 m/z N9� 231, 246, 314, 232, 121

- cannabinol Q9 m/z N9� 295, 296, 238, 310, 119

- delta-9-THC Q9 m/z N9� 299, 231, 314, 43, 41

ก�� ��1�

��5�P delta-9-THC -.R(�3Q� Q�กก0� 25 ng/ml �ก5R�/0��/'(�1��3�N

LD50 -.�.L (mice) 45 89ก��ก.��� 21.6 g/kg 45 ก��k95K0�.K�.����� 11 g/kg

45 ก��k95�S7��(�5�(��55O���� 0.18 g/kg

KL7�39 69/��กR�ก�`6� /��RP��5�P delta-9-THC -./�P M/ '(�Q7�Q ��� 37.5, 42, 12 µg/g /�Q(O�5�P

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ก��/��ก���S�W./7. 3�Q��TNO�M57�0� 3�5ก �5��g '(�3�Q��T/��1233���O�..Q�ก�� M57 �1U.ก��/����3���3R/5�1U.ก(V0Q MQ03�Q��T��PV6���3��'/0(�6.5-.ก(V0QM57 1233��N9�NO�ก��/����3���3R/5-.��.1���O��. /7��K0�.ก��/��ก���S�W./7.ก0�.NVก�� 1233��N9�/��ก���S�W./7.'(7MQ0RP3���3R/5����MQ0RPS7�3�3� 3�Q��T�� ��.K(ก��/��M570� 8MQ0RP9 (Negative) -.�� N9�/��ก���S�W./7.'(7RP3���3R/5����Q9S7�3�3� �O��1U./7��NO�ก��/��-.S�W./�./0�M1 ���ก��/�� �. �. �R���M57K(ก��/��N9�TLก/7�� '.0.�.'(��ก5��Q V/8��Q'ก0KL7��PP�ก��/��R3L�.� ก��R���]�T����Q�O��1U.-.ก��30�/�� �. �. S�W.ก�P�/TV1��3���S��ก��/�� -.�� S��KL7��PP�ก��/��R3L�.� N9�/7��ก��.O�K(ก��/��-67�1U.�(�กh�.�R��� �. �.-.SP.ก�� V/8��Q ����-67�1U.�(�กh�.-.ก����P���/�PV��( ก�]9��(0�.9W�O��1U.N9�/7��NO�ก��/�� �. �.NVก�� ��กก��/��ก���S�W./7.RP3���3R/5����Q9S7�3�3� '/0-.�� S��KL7��Pก��/��N9�.O�K(ก��/��M1-671��4 6.�N��ก��'RN � ����ก��1~��1��Qก��-673���3R/5 ��NO�ก��[�ก1���/ก��-67 �'(�3���3R/5��กKL7��PP�ก��/��ก0�./�53.-�30�/�� �. �. ก��/�� �. �.����O��1U./7��/���kR��-.�� N9�1o�38ก��-673���3R/5�N0�.�W.

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technique (EMIT) '(� 89 Cloned enzyme donor immunoassay (CEDIA)

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interaction of microparticles in a solution (KIMS) - /5k(�ก57 3��Y(L����3�[g.N� (Fluorescent material) -.89 Fluorescence

polarization immunoassay (FPIA)

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- /5k(�ก57 3��ก�QQ�./���39 (Radioisotope) 125

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Pamprin,Aleve, Naproxen, Haltran, Trendar Cramp Relief Formula, Ketoprofen, Orudis KT,

Marinol, Edecrin, Phenergan, Riboflavin (vitamin B2), Promethegan, Dronabinol, Anaprox,

Tolectin, Feldene, Flurbiprofen, Oxaprozin, Indocin, Ansaid, Ifenoprofen, Lodine, Clinoril,

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16

3. K(ก��/��ก���S�W./7.-67�R���ก��PO�P�5��ก�� ก��/5/�QK(ก����ก�� '(�ก��1~��1��Qก��-673���3R/5�N0�.�W. 4. /7��Q9ก��/�� �. �.NVก���W� ��ก.O�K(ก��/��M1-67-.ก����P���/�PV��( ����-67K(ก��/���1U.�(�กh�.-.SP.ก�� V/8��Q 5. KL7'1(K(ก��/�� '(�KL7-67K(ก��/�� /7���L7'(��S7�-�-.�(�กก�� ����1��ก��KL7�69� 6�`

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�1�9 P�N9 Pก�Pก��/��45 �(�กก�� Gas Chromatography/Mass Spectrometry (GC/MS) Initial Test Cutoff Concentration

SUBSTANCE Initial Test

(IMMUNOASSAY)

Confirming Test

(GC/MS)

Cannabis 50 ng/ml 15 ng/ml

Cocaine 300 ng/ml 150 ng/ml

Opiates 2,000 ng/ml 2,000 ng/ml(morphine), 2,000 ng/ml (codeine),

6-Acetylmorphine

Amphetamines 1,000 ng/ml 500 ng/ml

Phencyclidine 25 ng/ml 25 ng/ml

Notes : Cannabis is detected through its metabolite Delta-9-tetrahydrocannabinol-9-carboxylic

acid. Cocaine is detected by its metabolite Benzoylecgonine. Methamphetamine positive

confirming test requires both 500 ng/ml of methamphetamine and 200 ng/ml of amphetamine

����� : Department of health and human services, 8Mandatory Guidelines for Federal Workplace

Drug Testing Programs,9 Federal Register 69, 71 (April 2004): 19644-19673.

Goldberger BA '(� Cone EJ. M57��ก�� ก��/�� �. �.3O����P3���3R/5-.ก��1oP�/��.45 89 Gas Chromatography/Mass Spectrometry (GC/MS) '.N��ก��1oP�/��./�Q The Mandatory Guidelines for Federal Workplace Drug Testing Programs กO��.5-�7-6789 Gas

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Frazee CC 3rd, Kiscoan M '(� Garg U. M57��ก��ก�����������1�Q�]S�� 11-nor-

9-carboxy-delta-9-tetrahydrocannabinol -.1233��'(��(��545 -6789 Gas Chromato- graphy-

Mass Spectrometry (GC/MS) ก�`6�M57Q���ก-P 5�ก '(�/7.S��R�6 Cannabis sativa 1��ก�P57 3��ก(V0Q��.�P.� 5�Q�กก0� 30 6.5 3��3O���`N9�Q9bN8c/0� ��PP1��3�N��� delta-

9-tetrahydrocannabinol (THC) [��� metabolite S�� THC N9�3O���`��� 11-nor-delta 9-carboxy-

tetrahydrocannabionol (THC-COOH) N9�S�PT0� ��กN��1233�� 3�Q��T/��RPM57-.KL7N9�-67ก�`6� -.ก����ก��M57�8P� T��ก��-67 Internal Standard THC-COOH-d9 -30(�M1-./�� 0��/�� /�Q57 hydrolysis 45 conjugated THC-COOH 57 alkali THC-COOH TLก3ก�5��ก��ก1233�������(��545 -67 liquid-liquid extraction /�Q57 trimethylsilyl-67-.ก��NO� derivatives [���ก���������45 ก��NO� derivatized THC-COOH -�7K(59�Q���-67ก�P89Gas Chromatography

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���� Gas Chromatography/Flame Ionization 45 �0���Q�1U.�37./��S�� THC-COOH � L0-.60� 10 - 300 ng/ml 30.1��3N8f�RS��ก��3ก�545 �k(9� Q�กก0� 85% '(��5�1U.1�Q�]M57�0� correlation coefficient 0.999 3O����P�0� Limit Of Detection '(�ก���O�'.ก(�ก�]��kR��45 -67 GC-MS 3O����P������� metabolite S��3��M57NO�ก��/��T���ก���W� RP0�Q9�0�/�O� ก0� NIDA

guidelines [���Q9�0� cut-off � L0N9� 15 ng/ml

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1. ก�� %ก%�����4���ก#���<������+�������Qก%��� (Electron ionization, EI) ก��Pกก��'/ก/�S��4Q�(กV(�1U.M���.57 � �(gก/��. (electron ionization) Q�ก. Q��9 ก 0�j 0� EI ���Q/7.��ก4Q�(กV(S��3��[������1��ก�P57 Q(/0��j 5��'35�-./����N9� 2.3 �ก5��./�ก� �ก�P��(gก/��.N9�TLกK(/��กQ���กก��-�7ก��'3MYY~�'ก0S5(5S.�5�(gก (filament) 5��'35�-.f�RN9� 2.6 N9����NO�57 4(��N��3�/. (tungsten) ���� ��g.�.9 Q (rhenium) �.NO�-�7S5(5�7�.'5� '(���(gก/��.N9��ก5S�W..9W��TLก��0�57 ��Q/0����ก ����0�� filament '(� ion chamber ��M1N9��1~� (target) P�����W���9 ก0� trap [����1U.S�W'�4.5 (anode) K(�.������กก��Q9'Q0��(gกT�� (N-S) [������ L0-.'.ก����(���.N9�S��ก��'3��(gก/��.N9�1(51(0� Q���ก filament NO�-�7(�ก�]�ก���5.N��S��ก��'3��(gก/��.�1U.�4�7�/0��.����M1����� j NO�-�7�R�Q4�ก�3N9���(gก/��.���ก5��./�ก� �ก�P4Q�(กV(S��3��/�� 0��[�����NO�-�7M57M���.N9��ก5S�W. (ion yield) �R�QQ�กS�W. N9�3f��Q�/�h�.���P�VQ-�7��(gก/��.Q9R(����. 70 ��(gก/��.4(N� (eV) f� -/73f��3V``�ก��3L� 1��Q�] 10-7 - 10-5 N��� ��(gก4N�5K(�ก (repeller electrode) [���� L057�.[7� Q��S��f�RN9� 2.6 NO��.7�N9�-.ก��K(�ก-�7M���.N9��ก5S�W.TLก30�/0�M1 ���.0 �������Q( (mass analyzer) M57�R�QS�W. ก��P.ก���ก5M���.M.�[6��..9W�ก5S�W.f� -.�� ��(� 10-16 - 10-15 .�N9 [�����gก0�60��(�N9�4Q�(กV(3��. (oscillation) S��R�.8�� 0��Q�ก.��.�Q� T�� �L1�0��S��4Q�(กV(MQ0Q9ก���1(9� .'1(�-.���0��ก���ก5 ionization 45 N�� M1 3.- �/���5'(� /5/�Q�kR� �M���.P ก �.�� ����ก1��3N8f�RS��ก��/���5M���.Pก3L�ก0�ก�]9S��M���.(P1��Q�] 103 - 105 �N0� ก�7.-.ก�]9N9�4Q�(กV(N9�1��ก�P57 8�/VN9�Q9�0���(gก4/��.ก�//93L�N9�-67ก��/���5M���.(P �R����R�Q3f�RM-.ก��/���5-�73L�S�W. 1��3N8f�RS��ก��NO�-�74Q�(กV('/ก/��1U.M���.45 N��M1�0�.S7��/�O� ก(0���� 1��Q�] 1 -. 1000 4Q�(กV( f�RN9� 2.7 '35�K(S��R(����.��(gก/��./0�ก���ก5 ionization S��4Q�(กV(45 N��M1. Q��PV1�Q�]R(����.3O����PNO�-�74Q�(กV(�ก5 ionization -.�.0 ��(gก/��.4(/� (eV) 45 1 eV �Q� T�� R(����.��(gก/��.N9���Q/0����ก � 1 4(/�-.�.0 �5 SI 1�Q�] 1 eV �N0�ก�P 1.6 × 10-19 J ��ก �MYY~�3O����Pก���ก5 ionization S��3��30.-� 0̀� L0-.60� 8 - 13 ��(gก/��.4(/� (eV) ��กf�RN9� 2.7 ����g.0� ionization �R�QS�W.� 0��/0��.������ก�0���ก �MYY~�N9�NO�-�7�ก5 ionization '�ก (first ionization potential) M1N9��0�3L�3V51��Q�] 50 - 60 eV '(�ก���ก5ก��'/ก��ก (fragmentation) S��4���3�7��4Q�(กV(�R�QQ�กS�W./�QR(����.S����(gก/��.N9��R�QS�W. ������� mass spectrometer -.P���V0. �Q-�7KL7-673�Q��T�1(9� .'1(�R(����.S����(gก/��. N�W�.9W�R���60 -�7M57M���.4Q�(กV(Q�กS�W.'(�3�Q��T(5ก��'/ก��กS��4Q�(กV(M57 5��-.f�RN9� 2.8 [���M57'35�T��K(S��R(����.

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23

��(gก/��.N9�Q9/0� mass spectrum S�� ethyl acetate ] ��Q/0����ก �Q�/�h�. 70 4(/� ��(gก/��.��M57��PR(����. 70 ��(gก/��.4(/� NO�-�7�ก5 molecule cation radical N9�Q9R(����.�ก.� L0 (excess energy) 1��Q�] 10 - 20 eV N9���NO�-�7�ก5ก��'/กS��4���3�7��4Q�(กV(� 0���/gQN9� 3O����Pก��'/กS��R�.8� C-C -67R(����. 2 - 3 eV ��(gก/��.N9�Q9R(����.3L� 70 eV .9W3�Q��T�ก5��./�ก� �ก�P4Q�(กV([���MQ0Q91���V'(��1U.ก(�� (M) M5745 S]�N9���(gก/��.��(���.N9�K0�.4Q�(กV(�����S7�-ก(74Q�(กV(Q�ก ��NO�-�7��(gก/��. 1 /�TLก5����ก��ก4Q�(กV(�ก5�1U.M���.[���M/0�ก��NO�1oก� � (radical ion) N9�Q91���V�1U.Pก (M+.) 5��'35�-.3Qก��N9� 1

e- + M M.+ + 2e- (1) �.��� ก��6.���0����(gก/��.'(�4Q�(กV(-.ก�]9.9W ���W��.����� TLก��9 ก0� _ก��'/ก/��1U.M���.�.������กK(S��ก��1�N�ก�P��(gก/��.a (electron-impact ionization) N�W�j N9�-.��Q�1U.���'(7 ก��'/ก/��1U.M���.���� ionization N9��ก5S�W.5��ก(0� MQ0M57�1U.K(��กก��1�N�ก�P��(gก/��. '/0�ก5��ก��./�ก� ����0��3.�QS����(gก/��.'(�4Q�(กV(N9�R(����. 70 eV -.3f����Q�1U.3V``�ก��3L� ��./�ก� ����0����(gก/��.'(�4Q�(กV(NO�-�7M57M���.4Q�(กV( (M·+) Q9R(����.Q�กR�N9���NO�-�74Q�(กV('/ก��ก�1U.30. 0� j (fragment) M57M���.N9�Q9Q(.7� (� (A+, B+ '(����.j) 5��'35�-.3Qก��N9� 2 ก��'/กS��4���3�7��4Q�(กV(����ก5��กก��'/กS��R�.8�'PP�0� j ��������ก5��กก��P.ก����54���3�7��4Q�(กV(-�Q0 (rearrangement) EI T���1U.ก��P.ก�� ionization �R9 �6.5�59 �N0�.�W.N9�3�Q��T-�7 mass spectrum N9��1U.Q�/�h�. 45 3�Q��T-�7 spectrum N9�'NP����Q��.�5QNVก���W� (reproducible) 'Q7ก��N�����ก/0��������� mass spectrometer ก�.กg/�Q ��3�Q��T.O�Q��1�9 P�N9 Pก�.M57 '(�-�7S7�QL( spectrum N9�3�Q��T-�7�� (���9 557�.4���3�7��S��4Q�(กV(��ก�L1'PPก��'/ก/� (fragmentation pattern) 57 ��/VK(5��ก(0�S7��/7. ���NO�-�7Q9ก��3�7��'(�-67h�.S7�QL( mass spectrum 3O����Pก��3�P�7.�� (mass spectrum pattern library database) 4���3�7��S��3��45 -67S7�QL( EI � 0��'R�0�(� NO�-�7Q91��4 6.�� 0��Q�ก45 �kR��3O����P�V]f�R��������R���-�7N��PT��6.5S��3�� 45 MQ0���1U./7������ 3��Q�/�h�.Q��1�9 P�N9 P N�W�.9W�.������ก'Q33�1ก/��Q EI �1U.3QP�/�kR��/�3O����P3��'/0(�6.5 �1�9 P�3Q��.S7�QL((� .WQ�� 5���60. mass spectrum 6.5 EI S�� Acetone '35�-.f�RN9� 2.9 N9�Q9 fragment A Q9 m/z �N0�ก�P 58 T���1U.M���.4Q�(กV(N9��1U.1���VPก ���-673�`(�ก�]� M+· �R����ก5��ก4Q�(กV( Acetone [���Q9Q(4Q�(กV( 58 3L`�39 ��(gก/��.M11 /� �.������ก��(gก/��. 1 /�Q9Q(.7� Q�ก (9.1093897 × 10-28

Page 37: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

ก4(ก��Q ���� 0.0005485712 M570�'NP��MQ0Q9ก���1(9� .'1(�-.Q(4Q�(กV(�ก5S�W. 45 ����Q9Q(�N0�ก�P 30. fragment B �ก5��ก4Q�(กV( �59 ���0������P�.S���QL0�N0�ก�PK(/0��S��Q(4Q�(กV('(�Q(S���QL0�QN( M-15

f�RN9� 2.6 '�(0�กO��.5M���. N9�Q� : I. Lavagnini et al., 2006)

0.0005485712 5�(/�.) �Q����N9 Pก�PQ(S����/�Q/0��j -.'�[4/. ������ก(0�M570�'NP��MQ0Q9ก���1(9� .'1(�-.Q(4Q�(กV(�ก5S�W. 45 ����Q9Q(�N0�ก�P

�ก5��ก4Q�(กV( Acetone 3L`�39 fragment S���QL0�QN(�.������กก��'/กR�.8��59 ���0������P�.S���QL0����P�.(ก�(����P�.S���QL0�QN( NO�-�7M57 �N0�ก�PK(/0��S��Q(4Q�(กV('(�Q(S���QL0�QN( ([���Q9Q(�N0�กก�P 15) ���TLก��9 ก0�

e- + M M·+ + 2e- A+,B+,�

'�(0�กO��.5M���. (Ion source) 6.5 Electron Ionization Lavagnini et al., Quantitative Applications of Mass Spectrometry

24

�Q����N9 Pก�PQ(S����/�Q/0��j -.'�[4/. ������ก(0�M570�'NP��MQ0Q9ก���1(9� .'1(�-.Q(4Q�(กV(�ก5S�W. 45 ����Q9Q(�N0�ก�P 58 45 1��Q�]

S���QL0�QN(�.������กก��'/กR�.8�����P�.(ก�(����P�.S���QL0�QN( NO�-�7M57 fragment [���Q9Q(

���TLก��9 ก0� fragment

(2)

Quantitative Applications of Mass Spectrometry (New Delhi: Wiley,

Page 38: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

25

/����N9� 2.3 �0�Q((���9 5 (Exact Mass) '(���Q�V5Q-.8��Q6�/ (Natural Abundance) -.�.0 �7� (�S��M�4[4N18�/V (Element) /0��j

Element Exact Mass Isotopic Composition (%) 1H 2H

4He 12C 13C 14N 15N 16O 18O 19F

23Na 28Si 29Si 30Si 31P 32S 34S

35Cl 37Cl 39K

40Ar

1.007825 2.0140 4.0026

12.00000 13.003355 14.003074 15.000108 15.994915 17.999160 18.998403 22.989767 27.976927 28.976495 29.973770 30.973762 31.972070 33.967866 34.968852 36.965903 38.963707 39.962384

99.985 0.015

99.999 98.90 1.10

99.634 0.366

99.762 0.200 100 100

92.23 4.67 3.10 100

95.02 4.21

75.77 24.23

93.2581 99.6

N9�Q� : 'Q7. �Q�3N8c '(��]�, 0��กก�� ��������ก���������0*�"�����=����=� (ก�V��NR�: 6.RQR� 50, 2555)

Page 39: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

f�RN9� 2.7 K(S��R(����./0N9�Q� : Michael Oehme, (Heidelberg: Hüthig, 1998)

f�RN9� 2.8 K(S��R(����.��(gก/��.N9�Q9/0�N9�Q�: J.R. Chapman, Practical organic mass spectrometry: A guide for chemical and biochemical analysis (New York: John Wiley & Sons, 1997)

K(S��R(����./0�ก���ก5 Ionization S��4Q�(กV( Michael Oehme, Practical Introduction to GC-MS Analysis with Quadrupoles

(Heidelberg: Hüthig, 1998)

K(S��R(����.��(gก/��.N9�Q9/0� Mass Spectrum S�� Ethyl Acetate Practical organic mass spectrometry: A guide for chemical and

(New York: John Wiley & Sons, 1997)

26

MS Analysis with Quadrupoles

cetate

Practical organic mass spectrometry: A guide for chemical and

Page 40: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

27

��ก mass spectrum -.�L1'PP bar-graph 5��'35�-.f�RN9� 10 ����g.0��0�3L�3V5S��'ก. ionization �Q (total ionization) �N0�ก�P 47% .��.�Q� T��0�R9��(�ก (base peak) N9� m/z 43 �5�1U.�7� (� 47 S�� ionization N�W��Q5 45.���Q/�W�'/0 m/z 12 M1�.T��R9�M�4[4N1 (isotope peak) S��M���.4Q�(กV( N9� m/z 58 �0�S��'ก. ionization �Q�O�.]��ก��/��30.S����Q�S7Q3�QR�N8� (relative intensity, RI) S��R9��(�ก/0��0�ก��'3M���.�Q (total ion current, TIC) -.P�����W�S7�QL( mass spectrum ���TLก.O�Q��3.�-.�L1/���� 5���60. S7�QL( mass spectrum S�� Acetone -.f�RN9� 10 �Q���.O�Q��3.�-.�L1'PPS��/����5��'35�-./����N9� 6 5��N9�ก(0�S7��/7. ก��'/ก/�S��4Q�(กV(�1U.M���.57 EI 30.-� 0̀���ก9� S7��ก�PM���.Pก�N0�.�W. '/03O����P3��P��6.5N9�Q9� L0�0�.S7���O�ก�5 ก��P.ก��'/ก/�S��4Q�(กV(�1U.M���.���M57�.Vf��M���.(P (negative radical-anion) 5��'35�-.3Qก��N9� 3

e- + M M- (3)

ก��'/ก/�S��4Q�(กV(�1U.M���.57 ก��P.ก�� EI ��TLก�P�VQ3f��-�7�ก5S�W. -.3f����Q�1U.3V``�ก��3L� ก(0���� N9���Q5�./�O� 45 N��M1����ก����5�P��Q5�.S��'�(0�กO��.5M���.M7N9�1��Q�] 10-6 N��� (torr) N�W�.9W�R���1~��ก�.MQ0-�7M���.4Q�(กV( (M·+) N9��ก5��ก��./�ก� ����0��ก��'3S����(gก/��.'(�4Q�(กV( (M) M16.ก�P4Q�(กV(N9��1U.ก(�����.j ก0�.N9�M���.4Q�(กV(��TLก�P�VQ-�7�5.N���ก��ก'�(0�กO��.5M���.M1 ���.0 �������Q(S��������� mass spectrometer

Page 41: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

f�RN9� 2.9 Mass SpectrumN9�Q�: J. Throck Watson, 1997) /����N9� 2.4 S7�QL( Mass SpectrumTabular mass spectrum of A

m/z RI 12 13 14 15 16 18 19 20 24 25

0.160.644.22

34.220.360.200.160.160.201.04

N9�Q� : J. Throck Watson, 1997)

pectrum EI S�� Acetone : J. Throck Watson, Introduction to mass spectrometry (New York: Lippincott

Mass Spectrum EI S�� Acetone -.�L1'PP/���� ectrum of Acetone (TIC � 0212)

m/z RI m/z 0.16 0.64 4.22

34.22 0.36 0.20 0.16 0.16 0.20 1.04

26 27 28 29 31 36 37 38 39 40 41

4.50 6.06 1.68 3.34 0.36 0.50 1.38 1.96 3.44 0.74 1.82

42 43 44 45 52 53 55 57 58 59 63

J. Throck Watson, Introduction to mass spectrometry (New York: Lippincott

28

(New York: Lippincott-Raven,

RI

6.32 99.94 2.20 0.20 0.16 0.30 0.20 1.08

32.46 1.08 0.16

(New York: Lippincott-Raven,

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29

2. 0�.���������0*��� (Mass analyzer) ��"��+��� Mass Spectrometer �.0 ' กQ(S��������� mass spectrometer NO��.7�N9�' กM���./�Q�0�Q(/0�1���V (m/z) '(�6.5S�� mass analyzer ���1U./�กO��.56.5S�� mass spectrometer /0��j [���Q9� L0�(�ก�(� 'PP'(��L1�0�� M57'ก0 magnetic sector, quadrupole, ion trap, time-of-flight '(� fourier transform; mass spectrometer 6.5 magnetic sector '(� quadrupole TLก-67� 0��'R�0�(� ก���(��ก mass analyzer ���� 6.5S�� mass spectrometer S�W.� L0ก�P��Q�O��1U.-.ก��-67��.-.57�..�W.j M57'ก0 3f�RM-.ก��/���53�� ��Q(���9 5S���0�Q(3��N9��5 60�Q(3��N9�3.-��5 ��Q��g-.ก��3'ก.Q( /(�5�.R(����.N9�-67��ก��ก��'/ก/�4���3�7��S��4Q�(กV( �60. T7�/7��ก��-�7M���.N9�3.-��ก5ก��'/ก/�S��4���3�7���.������กก��6. (collisionally activated dissociation) 3O����Pก��/���5'PP tandem mass spectrometry [���P�����W���9 ก0� mass spectrometry/mass spectrometry ������9 ก 0�j 0� MS/MS N9�R(����.3L� (Q�กก0� 1,000 eV) �O��1U./7��-67 mass spectrometer 6.5 magnetic sector '/0-.ก�]9/��S7�Q T7�/7��ก����ก��ก��'/ก/�S��4���3�7��4Q�(กV(�.������กก��6.N9�R(����./�O� (N9���5�P 10 eV) ���-67 mass spectrometer 6.5 triple quadrupole ���� ion trap 2.1 ��������93�ก�� �ก��� (Mass Resolution) �.7�N9��(�กS���.0 �������Q( (mass analyzer) ��� ก��' กM���.N9��ก5S�W.-.'�(0�กO��.5M���./�Q��/��30.S��Q(/0�1���V (m/z) S��M���. ��Q3�Q��T-.ก��' ก (resolution, R) S�� mass analyzer ������Q3�Q��T-.ก��' ก 2 R9� [����Q� T����/��30.S��Q(S��R9� (M1) /0���Q'/ก/0��S��Q(���0��R9�.�W.'(�R9�/5ก�.N9�Q9Q(3L�ก0� (M2) 5��'35�-.f�RN9� 11 '(�3�Q��T�O�.]5��'35�-.3Qก��N9� 4

R � ��

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�Q��� R = ��Q3�Q��T-.ก��' กQ( (mass resolution) M1 = Q(S��R9�N9�3.-� M2 = Q(S��R9�N9�� L0/5ก�.[����1U.R9�N9�Q9Q(Q�กก0� �R���-�7�S7�-�T����Q�Q� S����Q3�Q��T-.ก��' กQ(M5759 ��S�W. ��S� กก�]9/�� 0�� -.�L1'PPN9��0� N9�3V5/0�ก��NO���Q�S7�-� ��� ก�]9S��M���.N9�Q91���V�1U. 1 [���T7�M���. Q9 m/z 1000 ��3�Q��TTLก' ก��ก��กM���.N9�Q91���V�1U. 1 [���Q9 m/z 1001 M57

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T7�������� mass spectrometer 1 [���Q9 m/z 2000 ��/7��ก�� [���Q9 m/z 2001 M57 -.S]�N9�M���.N9�Q91���V�1U. �R���-�73�Q��TTLก' ก��ก��กM���.N9�Q91���V�1U.

magnetic sector Q�ก�8P� 57 N9� 2.10 �Q� T�� ก��N9� 2 ��ก��กก�.�Q�����Q3L�S�� S��ก����PV resolution [���. Q-67.7� ก0� ��� ก����PV spectrometer 6.5 quadrupole mass unit) M57� 0��M�กg/�Q��Qก7��.7�S���N�4.4( 9 1��P1�V� mass resolution R9� (peak width) �60. N9���Qก7��R9� FWHM (full width half maximum)

f�RN9� 2.10 ก��' กQ( N9�Q� : Hans-Joachim Hubschmann, York: Wiley-VCH, 2001)

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M57 -.S]�N9�M���.N9�Q91���V�1U. 1 [���Q9 m/z 100 ��/7��ก�� �R���-�73�Q��TTLก' ก��ก��กM���.N9�Q91���V�1U. 1 [���Q9 m/z 101

��Q3�Q��T-.ก��' กQ(-.ก�]9S�� mass spectrometer Q�ก�8P� 57 _valley definitiona 45 N9� resolution N9� 10% valley

2 R9�[���Q9��Q�S7QS��3�``�] (intensity) �N0�ก�. ��TLกR���]�0�' ก��ก��กก�.�Q�����Q3L�S�� valley ���0��R9��1U. 10% S����Q3L�S��R9� �9ก��Q�Q� �.���

[���. Q-67.7� ก0� ��� ก����PV resolution N9� 50% valley quadrupole '(� time-of-flight 45 N��M1MQ03�Q��T-�7 resolution

M57� 0��M�กg/�Q��Qก7��.7�S���N�4.4( 9 time-of-flight -.12��VP�.NO�-�73�Q��Tmass resolution M5759S�W.Q�ก NO�-�7Q9ก����PV mass resolution -.(�ก�]�S����Qก7��

�60. N9���Qก7��R9� 0.5 amu [����5N9�������.���S�� �5R9� ����N9� FWHM (full width half maximum)

ก��' กQ( (Mass Resolution) N9� 10% Valley Definition Joachim Hubschmann, Handbook of GC: Fundamentals and applicationVCH, 2001)

Mass Spectrometer "��+ Quadrupol ������� mass spectrometer 6.5 quadrupole M57��P��Q. Q-.ก��-67��.

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30

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Handbook of GC: Fundamentals and application (New

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(DC) '(���ก �MYY~�3(�PN9�/��ก�P��QT9��(��.N V '35�-.f�RN9� 2.11 45 ก���1(9� .��QT9�S��3.�QMYY~� ��NO�-�7M���.N9�Q9�0�Q(/0�1���V��ก/�O�M13L��0� j N � ��(���.N9�-.(�ก�]�S���(��. 'N0�'(�TLก/���545 1���V NO�-�7M57S7�QL( mass spectrum

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31

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32

-./O�'�.0���ก��ก'ก. (off-axis) S��'.ก����(���.N9�S��M���.��ก�.0 �������Q(�R���(53�``�]�Pก. [�����NO�-�7M573Q��T.�ก��/���53L�3V5 detector N9�M57��P��Q. QQ�กN9�3V5 ��� electron multiplier 3.1 Detector "��+ Electron Multiplier Detector 6.5 electron mutiplier Q9� L0 2 �L1'PP ��� �L1'PPN9�Q9�O�..M54�.5�O�ก�5 (discrete dynode) '(��L1'PP4�.5'PP/0��.���� (continuous dynode) Electron multiplier -.�L1'PPN9�Q9�O�..M54�.5�O�ก�5 (discrete dynode) 5��'35�-.f�RN9� 2.13 (ก) 1��ก�P57 6V5S����(gก4N�5N9���9 ก0� _M54�.5a (dynode) ��9 �/0�ก�.1��Q�] 12 - 20 M54�.5N9�NO�57 beryllium-copper [���Q93QP�/N9�59-.ก��1(51(0� ��(gก/��.���� �(�กก��NO���.ก����0�M���.[����ก5S�W.N9�'�(0�กO��.5M���.'(�TLก' ก45 �.0 �������Q(3�� -�7�5.N��M1N9�M54�.5 (dynode) /�'�ก [���Q�ก. Q��9 ก0� _conversion dynodea K(��กก����0�-�7 M���.��M16.N9�KS��M54�.5 NO�-�7M���.3L`�39 1���V Q93f�R�1U.ก(��N��MYY~� '(�NO�-�7M57��(gก/��.1hQfLQ (primary electrons) �(� /��(V5��กQ���กKS��M54�.5 45 ก����ก'PP-�7Q9��ก �MYY~�N9�M54�.5(O�5�PT�5M1�R�QS�W.� 0��/0��.���� NO�-�7��(gก/��.'/0(�/�N9��ก5S�W.5��ก(0�TLก��0�-�7��M16.N9�KS��M54�.5(O�5�PT�5M1 '(�NO�-�7M57��(gก/��.NV/ fLQ (secondary electrons) �(� /��ก5S�W.� 0��/0��.���� �O�..��(gก/��.NV/ fLQN9��ก5S�W..9WS�W.� L0ก�P6.5S���35VN9�-67NO�M54�.5 ��ก �MYY~�S��M54�.5'(�R(����.ก��6. (collision energy) S��M���. Electron multiplier -.�L1'PP/0��.���� (continuous dynode) �1U. detector N9�Q9(�ก�]��L1N���(7� '/� (horn) 5��'35�-.f�RN9� 2.13 (S) NO���.45 ���� �(�กก����0�57 ��Q/0����ก �-�7M���.[�����(���.N9���ก��ก�.0 �������Q(M1N9�57�.1�กS�� detector '(�3W.3V5ก���5.N��N9�57�.���S���L1N��'/�[����1U.S�W3�``�] (signal lead) M���.TLกS�P��(���.45 ก����0�N9����Q/7.45 /�K(�ก (repeller) N9�'�(0�กO��.5M���. M���.TLก5��-�7��(���.N9�Q�3L0 electron multiplier 57 ��ก �MYY~�ก��'3/�� (dc potential) N9�Q9�0�3L�'(��1U.(P (�.������ก45 N��M1�1U.ก��/���5M���.Pก) 45 N��M1��ก �MYY~� ] 30.��P��(gก/��. (electron collector) Q9�0��1U.�L. � �(����กN9�M���.��6.Kf� -.S��'/�[�����(��P57 /�ก����กM[5� (lead oxide) ��NO�-�7�ก5��(gก/��.1hQfLQ�(� /��(V5��กQ���กKf� -.S��'/� ��(gก/��.1hQfLQ��TLก��0�-�7��M1N9�1(� '�Pj S��'/� '(�6.N9�Kf� -.S��'/�N9���(��P57 � L0 NO�-�7�ก5��(gก/��.NV/ fLQ�ก5S�W.� 0��/0��.���� กO�(��S � (gain) 3L�3V5S�� electron multiplier Q9Q�กก0� 106 �N0� S�W.� L0ก�P��ก �MYY~�N9�-67 �R���-�7M57��QM-.ก��/���5M���.

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6.5 Electron Mulitplier (ก) -.�L1'PPN9�Q9�O�..M54�.5�O�ynode) (S) -.�L1'PP/0��.���� (Continuous dynode)

Michael Oehme, Practical Introduction to GC-MS Analysis with Quadrupoles(Heidelberg: Hüthig, 1998)

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33

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4. 40�+ก���/����3� Mass Spectrometry Mass Spectrometer 3�Q��TNO���.M57-.�(� _4�Q5S��ก��NO���.a (operating mode) ����P�����W���9 ก0� _4�Q5S��ก��M57S7�QL(a (acquisition mode) NO�-�7M57��Q�O��R��-.ก��/���53��'(�3f�RM-.ก��/���5.�W.'/ก/0��ก�. ก��P�.N�กS7�QL(-.��PPmass spectrometer 30.-� 0̀�1U.ก��3'ก.[WO�j ก�.� 0��/0��.����45 ก��-67��/��ก��P�.N�กS7�QL(45 N��M11��Q�] 0.1 - 1.5 .�N9/3'ก. S7�QL(��Q��g-.ก��3'ก.�O��1U.��/7��3L�R�N9�45 N��M1����M57�O�..S7�QL( (data point) MQ0.7� ก0� 10 �V5/0�R9��R���N9���M57 chromatogram N9�Q9��Q(���9 5�R9 �R� ��Qก7��S��R9�N9�M57��กกก��-67��(�Q.� GC 6.5��1Z((��9 (capillary) 1��Q�] 5 - 20 .�N9 5��.�W.�O��1U./7��Q9��Q��g-.ก��3'ก.MQ0.7� ก0� 1 - 2 3'ก./0�.�N9 '/0(�3'ก.��M57 mass spectrum �กgP� L0-.�.0 ��Q�O�S����QR�/�����PPS7�QL( (data system) 3O����P������� GC-MS Q9��Q3�Q��T-.ก��'35�S7�QL(M57�(� �L1'PP�R���-�73�Q��T�������K(M57-.S]�กO�(��P�.N�กS7�QL( (real time analysis) '(�f� �(��ก��P�.N�ก /0�M1.9W��S�ก(0�T��4�Q5S��ก��NO���.6.5/0��j -. mass spectrometry 4.1 Scanning Mode 4�Q53'ก. (scanning mode) ����P�����W���9 ก0� full scan �1U.ก��3'ก.-.60�Q( (mass range) N9�กO��.5�R���-�7M57 mass spectrum N9�3�Q��T.O�Q�-67-.57�.�V]f�R������� �60. 45 ก���N9 Pก�Ph�.S7�QL( mass spectrum �R���-�7N��PT��6.5����4���3�7��N����Q9S��4Q(�(กV(�������-. mode S�� full scan 3O����P mass spectrometer N9�-67-.��.1���O�45 N��M1 M57'ก0 6.5 quadrupole '(� magnetic sector ��� ก��Q93�530.S���O�..M���.N9�TLกP�.N�ก45 detector �N9 Pก�P�O�..M��.6.5�59 ก�.N9��ก5N9�'�(0�K(/M���. N9�/�O�Q�ก �.������กM���.30.-� 0̀[���Q9�0�Q(/0�1���V.�ก60�Q(N9�กO��.5��TLกกO���5��ก��ก�.0 �������Q( ���MQ03�Q��T�5.N��T�� detector M57 4.2 Selected Ion Monitoring (SIM) Q�ก. Q��9 ก 0�j 0� SIM �1U.4�Q5S��ก��NO���.N9�/��/5/�Q (monitoring) �kR��M���.N9��(��ก�R9 �MQ0ก9�M���.N9�-67�1U./�'N.3��1��ก�PN9�/7��ก����������6�1�Q�] 45 �kR��N9���5�P��Q�S7QS7./�O�j T���1U.4�Q5S��ก��NO���.����6.5S��ก���������N9�QV0��.7.N9���/���53��1��ก�P�1~��Q� �N0�.�W. (target compound analysis) SIM Q93f�RM-.ก��/���53L�ก0�4�Q53'ก.-.ก�]9N9�-67 mass spectrometer 6.5 quadrupole ���� magnetic sector �R���0�-67�(�Q�กS�W.-.ก��/��/5/�QQ(/0�1���V (m/z) N9��(��ก

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spectrum S�� o-xylene, m-xylene '(� p-xylene �1U./7. [���Q9 mass spectrum �(7� �(��ก�.Q�ก -.N��1oP�/���'ก7MS12`��.9W57 ก��1��P3f��-.ก��' ก-.N�� chromatography '(�ก���(��ก-67��(�Q.� 2.1.3 ��QM-.ก���5'(�1�Q�]/�O�3V5N9�3�Q��T�������M57 ��QM-.ก���5 (sensitivity) '(�1�Q�]/�O�3V5N9�3�Q��T�������M57 (detection limits) S�W.� L0ก�P ionization method '(� detection mode 45 N��M1/7��ก��1�Q�]3��3O����P'/0(�����1��ก�PN9��O��1U.3O����Pก��/���51��Q�] 0.1 - 100 ng �������k953��/�� 0����/4.Q�/ (Automatic Samplers ���� Autosamplers) 3O����P-.ก�]9N9�Q93��/�� 0���O�..Q�กj '(�/7��NO�ก���������/5/0�ก�.�1U.�(�.�. ก��-67�������k95��/4.Q�/���Q9��Q��Q��3Q �R���NO�-�73�5ก'(�M57K(�������TLก/7��ก0� 57 ��/V.9W���NO�-�7Q9KL7. Q-67ก�.�1U.�O�..Q�ก P���NKL7K(/������� GC N�W��(� ���1��5�h��������Q��.9W��กQ�S� N��M1 Q9N�W�6.5N9�3�Q��T41�'ก�Q�(�-.ก��k953��/�� 0��M5757 '(�Q96.5N9�-67 syringe '(�-�73��/�� 0��M�(K0�. syringe �1U./7. 5��f�RN9� 2.14 (ก) ������� Autoinjector '(� (S) ������� Autosampler '(�f�RN9� 2.15 (�ก�]�S��������� CombiPAL with Liquid injection, CombiPAL with HeadSpace'(� CombiPAL with SPME HeadSpace .�ก��ก.9W ��3�Q��T�(��ก�O�..���W�S��ก���������'/0(�3��/�� 0�� � 0��M�3��/�� 0����-30M7-.T�5 (tray) N9��QV.M57 '/0T7�3��/�� 0���1U.'กn3กg��-67�1U. automatic gas-sampling valves �60. -.ก���������/�� 0��'กn3��ก4��' ก'กn38��Q6�/ �1U./7.

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f�RN9� 2.15 (�ก�]�S��������� CombiPAL with Liquid injection, CombiPAL with HeadSpace '(� CombiPAL with SPME HeadSpace N9�Q� : Accessed March 9, 2014. Available from http: www.agilent.com/chem/ctc.

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2. 3��/�� 0�����5L5[�P (absorb) ����3(� /�N9� injection port ����-.��(�Q.� ����N9�59�N��/��� T7�Q93����(0�.9W�ก5S�W.ก�����������1�Q�]���K5R(�5M57 3. 3f�R�������S�� GC T7�/�Q3f�RS���������MQ059 ก���P�VQ ก���5/0��j 0�Q�ก5��QK5R(�5M57 4. ก��k953��/�� 0���S7�������� GC

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1.2.1 ก��U�กP)�40�ก4^��� U.412344��Y:�X:r�2s6 V/�6 60 ml �:��8� MILLIONANT

1.2.2 Cups 4^��� U.412344�� V/�6 3 ml �:��8� Thermo SCIENTIFIC 1.2.3 TOXI GRAM BLANK THC II �2L/(l1/ Chromatogram Y:�.78(�ก��Y:� 08��ก��Y64�U �:��8� Agilent Technologies 1.2.4 TOXI DISCS �2L/ disc standard Y:�X:4�� ∆8

THC-COOH ()� dye marker �:��8� Agilent Technologies 1.2.5 Spec C18 Extraction Cartridge with Sample Reservoirs �2L/ Solid Phase Extraction Cartridge �:��8� Agilent Technologies 1.2.6 OMEGA-12 Extraction Solvent Concentrator with Screen �2L/ Solvent concentrator Y:�X: 12 �)MX 4^��� U Disposable Concentration Cups and screen cover �:��8� Varian 1.2.7 Disposable Concentration Cups �2L/ Disposable aluminum cups�:��8� Varian 1.2.8 Chromatography jar �:��8� SUPELCO 1.2.9 Test tube �:��8� PYREX 1.2.10 Screw Cap Vial V/�6 2 ml �:��8� La-Pha-Pack 1.2.11 Screw Caps /Center hole Red Rubber 1.0 mm ()� Septa �:��8� Neumann-

Neuander

1.2.12 pM�X�� Examination Gloves �:��8� SemperMed 1.2.13 Micro-Insert V/�6 0.1ml �:��8� La-Pha-Pack

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48

1.2.14 Micro Pipette -adjustable volumn V/�6 0.5-10 µl, 5-50 µl, 10-100 µl,

20-200 µl ()� 100-1,000 µl �:��8� SOCOREX 1.2.15 �)�6(ก8(UU�ก):� X:r�2s6 V/�6 10 ml �:��8� PYREX 1.2.16 Pasteur Pipette V/�6 1.5 ml �:��8� Delta Lab 1.2.17 U:��ก��� V/�6 20 ml, 50 ml, 100 ml, 500 ml ()� 1,000 ml �:��8� PYREX 1.2.18 Measuring Cylinder V/�6 50 ml, 100 ml ()� 1,000 ml �:��8� Witeg 1.2.19 Rack 4^��� U.41�)�6(ก8 �:��8� LabMaster 1.2.20 /�w�ก�� U�)� �:��8� CITIZEN 2. &�� ������&����'�(��

2.1 CEDIA THC R1 ()� THC R2 �:��8� Thermo SCIENTIFIC

2.2 CEDIA THC 50 ()� THC 100 Calibrator (Urine Human : 11-nor-∆9- THC-COOH ) �:��8� Thermo SCIENTIFIC

2.3 CEDIA MULTI-DRUG Calibrator (Negative, Intermediate, High) �:��8� Thermo SCIENTIFIC

2.4 CEDIA MULTI-DRUG Calibrator(Clinical Cutoffs) �:��8� Thermo SCIENTIFIC

2.5 Hydrolysis ��X�V8XV8/ 11.8 N KOH, Analysis grade �:��8�Agilent Technologies

2.6 Glacial acetic acid, Analysis grade �:��8� Merck 2.7 Heptane, Analysis grade �:��8� Merck 2.8 Acetone, Analysis grade �:��8� Merck 2.9 Dichloromethane, Analysis grade �:��8� Merck 2.10 Concenteate Hydrochloric acid, Analysis grade �:��8� Merck 2.11 Diethylamine, Analysis grade �:��8� Merck

2.12 Fast Blue BB �:��8� Agilent Technologies 2.13 n-Hexane, Analysis grade �:��8� Merck

2.14 Ethyl acetate, Analysis grade �:��8� Merck 2.15 Potassium hydroxide, Pellets Analysis grade �:��8� Merck

Page 62: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

49

2.16 Pentafluoropropionic anhydride 99 % , �:��8� Aldrich product no.252387-5G

2.17 2,2,3,3-Pentafluoro-1-propanol 97 % , �:��8� Aldrich product no.257478-25G

2.18 ∆8 THC-COOH control 200 ul. �:��8�Agilent Technologies l4Xก U

Distilled water 6 ml. ��X:��X�V8XV8/�2L/ 25 ng/ml.

2.19 4��X�0�\�/ ∆9-Tetrahydrocannabinol ; 1 mg/1 ml ethanol �:��8� Lipomed Product no.135.1B64.5L1

2.20 4��X�0�\�/ (-)-11- Nor-∆9-THC carboxylic acid ; 1 mg/1 ml methanol �:��8� Lipomed Product no.136.1B13.1L1

2.21 4�� Internal Standard ∆9-Tetrahydrocannabinol xD3; 1 mg/1 ml ethanol

�:��8� Lipomed Product no.135.1B2.3L1

2.22 4�� Internal Standard d,l-11- Nor-∆9-THC carboxylic acid-D3 ; 1 mg/1 ml

methanol �:��8� Lipomed Product no.750.1B5.1L1

3. ���ก������

3.1 '����)��'��� 3.1.1 0 ��1��2344��Y:��กyU��ก�/2ก0� Y:�zX1X:2�� 0�ก���4Pก q7� `���X:l)ก��

0��ก���V k/08/��ก q7�./2344��56��9: Cloned enzyme donor immunoassay (CEDIA) `���.78�) กก��Y����XX{5/(�4�4�� (Immunoassay) Y:�.�8l)ก��0�� (Negative) 56�z68�กyU� ก�z8./

0{8��y/Y:��MN�O{X�0�^�ก1� -20 °C �̂�// 5 ��� 3.1.2 0 ��1��2344��Y:��กyU��กl{8Y:�X�� UU��ก��0��2344���P�����4���4P0�6

��ก�8��2|�U 0�ก�� ก)M1X��/P��9��Y�� 4p�U /9 qq�� ก� `���X:l)ก��0��ก���V k/08/��ก q7�./2344��56��9: Cloned enzyme donor immunoassay (CEDIA) `���.78�) กก��Y����XX{5/(�4�4�� (Immunoassay) Y:�.�8l)ก��0�� (Positive) 56�z68�กyU� ก�z8./0{8��y/Y:��MN�O{X�0�^�ก1�

-20 °C �̂�// 15 ���

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50

3.2 ก��'����� ����*!

3.2.1 /̂�2344��Y:�0��ก���V k/08/()8 �̂�// 20 ��� X�Y^�ก��0����/� /56��9: TOXI- LAB THC II `���X:V k/0�/ก��0����������6 �/:k

ก�� '�����+����

1. THC-1 (Fast Blue BB) l4X/k^��� Fast Blue BB 1 V6ก U 250 ml Dichloromethane .41./V6 THC I 2. THC-2 (Diethylamine) 2s�20/k^��� Diethylamine 15-20 ml .41./V6 THC II 56�.�8��6 UV��4��0�^�ก1�(l1/P)�40�ก4:(6� 3. HCL 2s�20ก�6 Hydrochloric 20 ml )�./V6 HCL 56�.�8��6 UV��4��0�^�ก1�(l1/P)�40�ก4:(6� 4. Wash reagent 1 (20 % Acetic acid) l4X 20 ml. Acetic acid ก U 80 ml Distilled water .41./V6 Wash reagent 1 5. Wash reagent 2 (80:20) Heptane / Dighloromethane l4X 20 ml Dichloromethane ก U 80 ml Haptane .41./V6 Wash reagent 2 6. Developing solution l4X 50 ml Haptane ก U 50 ml. Acetone ()� 1 ml Acetic acid .41./V6 Developing solution

O�PY:� 3.1 7M60���������� TOXI- LAB THC II

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51

ก�� '����#� ���������

1.�2s6������� electric warmer 2. �0�:�X pump ��1�.�8��X6 /�ก�/ 18 /�k2��Y 3. �0�:�X�)�6(ก8, Concentration cups .�84�6�)8��ก U�̂�//4���41�0�� ก��'����� ����*!

3.2.1.1 V k/0�/ Hydrolysis �2L/ก���2):��/ ∆9THC-COOH-Glucoronide

�2L/ ∆9THC-COOH

-.412344�� 6 ml ./�)�6(ก8 P�8�Xก U .41�� 4

- �0�X 400 µl V�� Hydrolysis Reagent �V�1�.�8�V8�ก / 0 k�Y�k�z8 5 /�Y: - �0�X 1.5 ml Acetic acid �V�1�.�8�V8�ก / (p8�X:0�ก�/.�823m/(�ก���41/.4)

O�PY:� 3.2 ก���0�:�X0 ��1��2344�� (V k/0�/ก�� Hydrolysis)

3.2.1.2 V k/0�/ Extraction �2L/ก��4ก 6 (�กก q7���ก��ก2344�� - �0�:�X Reservoir()� Spec C 18()8 lable 7���.�8��:�U�8��

- �Y0 ��1��2344��Y:��0�:�Xz8 )�./ Reservoir �XM/�2s6 valve .�80 ��1��2344�� ��6)�X��)yก/8�� - �X���0 ��1��2344����6)�X��/�X6 p�6��� Reservoir ��กX����� ��� Filter ��ก ��ก/ k/.41 Reservoir ก) U6 ��6�X

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52

- �0�X 1.0 ml Wash reagent 1 �X��� Reagent ��6)�X��X6()8Y�k�z8 60 �/�Y: ก1�/���0�X 0.5 ml V�� Wash reagent 2 2)1��.�8 Reagent ��6)�X��/�X6 - )6 Pressure )� ()8p�6��� Spec C 18 disc X�.41./ Concentration cup Y:��0�:�Xz8 ��ก/ k/Y^�.�8(�8�U/ Electric warmer 2��X�N 3 /�Y:

O�PY:� 3.3 V k/0�/ก�� Extraction

3.2.1.3 V k/0�/ Inoculation �2L/ก��/̂�4��Y:�4ก 6z68 (��{1./(l1/ Spec C18) .41)�(l1/ Chromatogram - /̂�(l1/ Toxi gram blank THC II ��U/ Electric warmer 56���^��/8�)� Activate (l1/ Toxi gram blank THC II 2��X�N 30-60 �/�Y: - /̂� Spec C 18 disc .41)�./71��1��V�� Toxi gram blank THC II P�8�X.41 Disc standard - Activate (l1/ Chromatogram Y:�.41 disc ��:�U�8��()8U/(l1/ Electric warmer 56���^��/8�)� 2��X�N 30-60 �/�Y: ก1�/ Develop

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53

3.2.1.4 V k/0�/ Development �2L/ก��(�ก4����ก��กก / - .41 3 ml V�� Developing solution )�./ chromatography jar

- /̂�(l1/ Chromatogram Y:� Activate ()8.41)�./ chromatography jar

- ���/ Dye marker ��)���/Y:�X�p�� 4.5 cm. /̂�(l1/ Chromatogram X�l���U/ Electric warmer 56���^��/8�)�/�/2��X�N 1-2 /�Y: �/ก)��/V�� Acetic acid �X6z2

3.2.1.5 V k/0�/ Detection �2L/ก���8�X4:�P����1�/l)ก��0���������� - �M1X Chromatogram )�./ TOXI DIP THC 1 jar ()8/̂���กX���l���z8V8��V6 /�/2��X�N 30-60 �/�Y:

O�PY:� 3.4 (ก) V k/0�/ก�� Detection O�PY:� 3.4 (V) V k/0�/ก�� Detection

Stage I .41(l1/ Chromatogram )�./ TOXI DIP THC 2 jar 2��X�N 10-15 �/�Y:�/2��ก|(pU4:7XP{ (�X���ก q7�./ Standard ()�./0 ��1�� 4 Xl 4ก U/k^���./ TOXI DIP THC 2 ��Y^�.�8�ก�6(pU4:7XP{) �1�/l)0 ��1���Y:�Uก U Standard

O�PY:� 3.5 (ก) V k/0�/ก�� Detection Stage I O�PY:� 3.5 (V) V k/0�/ก�� Detection Stage I

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54

Stage II .41(l1/ Chromatogram )�./ HCL jar �/2��ก|(pU4:X1� (�X���ก q7�./ Standard ()�./ Sample 4 Xl 4ก U/k^��� HCL ��Y^�.�8�ก�6(pU4:X1�) �1�/l) Sample �Y:�Uก U Standard

O�PY:� 3.6 (ก) V k/0�/ก�� Detection Stage II O�PY:� 3.6 (V) V k/0�/ก�� Detection Stage II

1.2.1.6 V k/0�/ Interpretation �2L/ก��(2)l)ก��0���������� - �1�/l)ก��0�� l)Uก (POSITIVE) V��ก q7� (pU4:V�� 0 ��1��08��0��ก U Standard ()�X:4:�6:�ก /Y k�4�� Stage - �1�/l)ก��0�� l))U (NEGATIVE) V��ก q7� (pU4:V�� 0 ��1��zX10��ก U Standard ()�zX1�2L/4:�6:�ก /Y k�4�� Stage ���� Stage .6 Stage �/���

O�PY:� 3.7 (ก) V k/0�/ก�� Interpretation O�PY:� 3.7 (V) V k/0�/ก�� Interpretation Stage I l)Uก (POSITIVE) V��ก q7� Stage II l)Uก (POSITIVE) V��ก q7�

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55

3.2.2 /̂�2344��Y:�0��ก���V k/08/()8 �̂�// 20 ��� X�Y^�ก��0����/� /56��9: Gas Chromatography/Mass Spectrometry (GC/MS) `���X:V k/0�/ก��0����������6 �/:k

ก�� '�����+����

1.l4X4�� Hexane ()� Ethyl Acetate ./� 0��41/ ( 8 : 2 ) ก�� '����#� ���������

1. �2s6������� GC/MS ��ก/ k/Y^�ก�� Pump Down ()� Bake Out ������� Y�k�z8 2��X�N 10 7 �5X� 2. Y^�ก�� Autotune ������� �P���.�8z68 Condition Y:���X��4X Y:���Y^�ก��0�� ��������01�z2

ก�� '����'����)��'����,&&���

1. -�+�'��ก�� Extraction

1.1 /̂�2344��Y:���4ก 6��Y�k�z8Y:��MN�O{X��8�� �/2344��X:�MN�O{X��Y1�ก U�MN�O{X��8��

1.2 /̂�2344��.41./�)�6�ก):� 2��X�N 5 ml

1.3 �0�X KOH )�./�)�62344�� �̂�// 400 µl ()82s6r��V�1�.�8�V8�ก / /�/ 2 /�Y:

1.4 /̂�z2�U./ Dry Block Heater Y:��MN�O{X� 65°C �2L/�)� 1 7 �5X� 1.5 /̂��)�62344����กX�Y�k�z8.�8��y/Y:��MN�O{X��8��

1.6 �0�X Acetic Acid )�./�)�62344�� �̂�// 500 µl ()8/̂�z2 Vortex 2��X�N 15 �/�Y: 1.7 �0�X Hexane ()� Ethyl Acetate `���l4Xก /z8()8./� 0��41/ ( 8 : 2 ) .41)�./�)�62344�� �̂�// 5 ml ()8/̂�z2 Vortex 2��X�N 30 �/�Y: 1.8 /̂��)�62344��z223m/(�ก (Centrifuge ) Y:���X��y 3,000 ��U//�Y:

�2L/�)� 5 /�Y: 2. -�+�'��ก�� Concentration

2.1 /̂��)�62344��Y:�l1�/V k/0�/ก�� Extraction ()8 X�6{641/.47 k/U/ (7 k/ Organic) .41)�./�)�6�ก):� (�)�6.�X1) 2.2 /̂�X� Evaporate .�8(�8�./ Dry Block Heater Y:��MN�O{X�

65°C O��.08(กn4z/50���/ �2L/�)�2��X�N 15 /�Y:

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3. -�+�'��ก��

3.1 �0�X

propanol

2��X�N

3.2 /̂�z2�U./3.3 /̂��)�6��กX�3.4 �V�1�.�8�V8�ก / ()8Screw Cap

ก��'����� ����*!

1. /̂� Vial Y:�.410 ��1��0��Y:�z68�0�:�Xz8 X�.41./ 2. �:��V8�X{)V��0 ��1��0��./ GC/MS 3. 4 ��.�8�������

41/V��- Injection Mode : GC - Front Injector- Constant Column Flow- Column Oven- Column Oven/Ramp Rate : 280.0

O�PY:� 3.8 ก��0 k��1� Method

-�+�'��ก�� Derivatization

�0�X Pentafluoropropionic anhydride �̂�// 50 µl

propanol �̂�// 50 µl 2s6r��)�6()8�V�1�.�8�V8�ก / /̂�z22��X�N 15 �/�Y:

/̂�z2�U./ Dry Block Heater Y:��MN�O{X� 75°C �2L/�)�/̂��)�6��กX�Y�k�z8.�8��y/Y:��MN�O{X��8�� �V�1�.�8�V8�ก / ()8.78 Micro Pipette 6{6.41 Micro-Insert Tube

Screw Cap Vial P�8�X4^��� U/̂�z20��68�������� GC/MSก��'����� ����*!

Y:�.410 ��1��0��Y:�z68�0�:�Xz8 X�.41./ tray V��������� �:��V8�X{)V��0 ��1��0��./ Sample List V��52�(ก�X AS400

4 ��.�8������� GC-MS Run � 05/X 0�0�X method Y:�0 k�z8 ��� 41/V�� GC-450

Injection Mode : GC Liquid Front Injector Port : 250 °C Constant Column Flow : 1.0 ml / min Column Oven/Ramp Rate : 100 (°C) ; 0 (°C/min), Hold time 2 (min)Column Oven/Ramp Rate : 280.0 (°C) ; 15.0 (°C/min), Hold time 6 (min)

Method V��������� Gas Chromatograph ./ก����������0 ��1��0��

56

()� Pentafluoro-1-

()8�V�1�.�8�V8�ก / /̂�z2 Vortex

�2L/�)� 25 /�Y:

Insert Tube Y:���{1./ GC/MS

V��������� CombiPAL AS400 4^��� U�������

), Hold time 2 (min) ), Hold time 6 (min)

./ก����������0 ��1��0��

Page 70: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

41/V�� - Ion Source : - Scan time requested : 0.050 Sec. - Source temperature : 250 °C - Method Specs :

O�PY:� 3.9 ก��0 k��1� Condition 4. Y^�ก����������of Drugs, Poisons, PresticidesPFLEGER, KARL/ WEBER, ARMIN A.

41/V�� MS-300 Ion Source : EI Scan time requested : 0.050 Sec. Source temperature : 250 °C Method Specs : Full Scan mode

Condition V��������� Mass Spectrometer ./ก����������0 ��1��0��

Y^�ก���������� Mass Spectrum V��4��(01)�7/�6 56�.78 Mass Spectralof Drugs, Poisons, Presticides, Pollutants and Their Metabolites 2007 V�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW 2007) �2L/ Database Identification

57

./ก����������0 ��1��0��

Mass Spectral Library MAURER, HANS H./

Database Identification

Page 71: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

58

����� 4

��ก���� ������������ก���� �

��ก��ก���� ����� ������ �������� �������� ��! ��ก�� � " ���#���� 20 ��� &��'ก()� �������� ��!��ก���ก�� *�+�"�"���!� ��ก��' ,ก -�� *�+�.��/ก������ก���0 �����.�ก -������ ��!'�1�/) (NEGATIVE) �#���� 5 ��� ;/!'ก()� �������� ��!��ก���*�+"�� ))��ก�������� ��!',<+�.� ��' ,�����ก.����=�) ��ก�� ก/>�"���,��?���*�� @�) �)#�) �;/!� ก����������' ,���;.������)�"������� *�+�.��/ก������ก���0 �����.�ก -������ ��!'�1�)�ก (POSITIVE) �#���� 15 ��� ก������ก���0 �����.�ก -������ ��!&����?� Cloned Enzyme Donor Immunoassay (CEDIA) S+����./ กก��*����""�&�;� ' �T (Immunoassay) "���� Cut-off '*��ก ) 50 ng/ml ก��;�/�/ก������ @��"��������ก��� 50 ng/mL ."��@� �//) (NEGATIVE) @��"����"�กก��� .�<�'*��ก ) 50 ng/mL ."��@� �/)�ก (POSITIVE) ��ก� ���#�� �������� ��!*�+����ก���0 �����'���)����;/�� "�*#�ก�������<�� �&����?� TOXI- LAB THC II S+�ก����'���!.T������?����"���� Cut-off '*��ก ) 50 ng/mL #�.� )ก��;�/�/ก������&�� �//) (NEGATIVE) 0��ก -�� �!"�;@) �0��� �������"����ก ) Standard ;/!�"�'�1� �'����ก �* �� �� Stage .�<� Stage �� Stage .�+� ��������/ก������ �/)�ก (POSITIVE) 0��ก -�� ;@) �0��� �������������ก ) Standard ;/!"� �'����ก �* �� �� Stage �<� Stage I �!���ก=;@) ��",� ;/! Stage II �!���ก=;@) �"��� �#�� �������� ��!"������<�� �&����?� Gas Chromatography/Mass Spectrometry (GC/MS) ก��;�/�/ก��������'���!.T &���!'*��)ก ) Mass Spectral Library 0�� MPW 2007 S+���� Cut-off 0��ก�������<�� �&����?� GC/MS '*��ก ) 15 ng/mL ก�������/ก������ �//) (NEGATIVE) ; ����������"�,) delta-9-Tetrahydrocannabinol ;/! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol ก�������/ก������ �/)�ก (POSITIVE) ; ���������,) delta-9-Tetrahydrocannabinol ;/! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol .�<�������������.�+� ก��������'���!.T&����?� TOXI- LAB THC II �!��ก��'�/<+��*�+0�� ��' ,���*�+ ก ���ก��ก�� ��!)�;���&��"�&�;ก�" �������!�!*��*�+'�/<+��*�+ &����h�����; ��>/����

Page 72: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

59

��&�'/(� .�<�; �i/���'� 'S���T .�<�*#��=�ก�����ก ) ��'�"�',<+��.�'ก�� �0�� ��' ,���*�+����ก������ �!'�/<+��*�+ �������!� )'����ก ) ��' ,���"���j�� ;/!'ก�� �'."<��ก �*>ก0 �������ก��*#��=�ก�����ก ) ��'�"�

���*�+ 4.1 ก��'�/<+��*�+0�� ��*�+ ก ���ก��ก�� ��!)�;���&��"�&�;ก�" &����?� TOXI- LAB THC II *�+�.��/ก������'�1� �//) (NEGATIVE)

��ก���*�+ 4.1 ก�������/ก��������'���!.T �//) (NEGATIVE) 0��ก -�� ;@) �;/!�!�!*��ก����+�0��� �������"����ก ) Standard ;/!�"�'�1� �'����ก �* �� �� Stage .�<� Stage �� Stage .�+�

Page 73: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

60

���*�+ 4.2 ก��'�/<+��*�+0�� ��*�+ ก ���ก��ก�� ��!)�;���&��"�&�;ก�" &����?� TOXI- LAB THC II *�+�.��/ก������'�1� �/)�ก (POSITIVE)

��ก���*�+ 4.2 ก�������/ก��������'���!.T �/)�ก (POSITIVE) 0��ก -�� ;@) �;/!�!�!*��ก����+�0��� �������������ก ) Standard ;/!"� �'����ก �* �� �� Stage �<� Stage I �!���ก=;@) ��",� ;/! Stage II �!���ก=;@) �"��� '"<+�*#�ก��������'���!.T' �(�;/�� .�ก����ก��'ก();���&��"�&�;ก�"0���/ก������������ �.��#�;���&��"�&�;ก�"*�+����0 ����� Stage II ����ก/ )���)����#��� TOXI DIP

THC 2 ��ก�� ��.�+� ;/����� ก(��'*�� ���* );���&��"�&�;ก�"���/�)� ">�

'"<+��#�� �������� ��!"������ �����'*���� GC/MS &���#� ��/!/��"���j��

delta-9-Tetrahydrocannabinol ;/!11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol "�'��"/����� ��!0���� � " ��*�+�"�"���!� ��ก��' ,ก -�� ; ���/ก��*�/��� � Chromatogram ;/! Mass Spectrum ���*�+ 4.3 ;/! ���*�+ 4.5

Page 74: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.3 Chromatogram 100 ng/ml &����?� Gas Chromatography/Mass Spectrometry ��ก���*�+ 4 .Tetrahydrocannabinol "� Mass Spectrum 0�� ��*�+���ก ) KARL/ WEBER, ARMIN A.delta-9-Tetrahydrocannabinolpentafluoro-1-propanol ���m/z 377, 417, 460 ;/! 461 MCounts

Chromatogram ;/! Mass Spectrum 0�� delta-9-TetrahydrocannabinolGas Chromatography/Mass Spectrometry (GC/MS)

.3 ; ���/ก�������� '���!.T&��ก���#� ��"���j�� "� Spiked /���� �������� ��! *�+���"'0�"0�� 10

0�� ��*�+���ก ) Library of Drugs 0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW 2007) &����� Full Scan mode S+� Mass Spectrum

etrahydrocannabinol *�+ Derivatization ���� pentafluoropropionic

���'�1� Tetrahydrocannabinol isom-1 PFP &��"� Mass Spectrum 461 "� Probability '*��ก ) 98.93 ;/!���" ��0�� Abundance

61

etrahydrocannabinol *�+���"'0�"0��

�#� ��"���j�� delta-9-100 ng/ml ;/��'*��)

MAURER, HANS H./ PFLEGER, Mass Spectrum 0�� ��

entafluoropropionic anhydride ;/! Mass Spectrum ./ ก�<� Abundance ��!"�v 20

Page 75: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.4 Library Search a Spectrum &����?� Gas Chromatography/Mass Spectrometry ��ก���*�+ 4.4 0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.Scan mode S+� Mass Spectrumpentafluoropropionic anhydride

1 PFP (Formula : C24H

Probability '*��ก ) 98.89

Library Search a Spectrum 0�� delta-9-Tetrahydrocannabinol *�+���"'0�"0�� Gas Chromatography/Mass Spectrometry (GC/MS)

4 ; ���/ก��'*��) Mass Spectrum 0�� ��*�+���ก ) MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW 2007)

Mass Spectrum 0�� ��delta-9-Tetrahydrocannabinol *�+anhydride ;/! pentafluoro-1-propanol ���'�1� Tetrahydrocannabinol

H29F5O3)&��"� Mass Spectrum ./ ก�<� m/z 377, ;/!Retention Time (RT) �����#�;.���*�+ 12.669 ��*�

62

*�+���"'0�"0�� 100 ng/ml

0�� ��*�+���ก ) Library of Drugs MPW 2007) &����� Full

*�+ Derivatization ���� Tetrahydrocannabinol isom-

, 417, 460 ;/! 461 "� ��*�

Page 76: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.5 Chromatogram binol *�+���"'0�"0�� 50 ng/ml ��ก���*�+ 4.5 delta-9-Tetrahydrocannabinol'*��) Mass Spectrum 0�� ��*�+���ก ) KARL/ WEBER, ARMIN A.11-Nor-9-Carboxy-delta-9anhydride ;/! pentafluoro

Spectrum ./ ก�<� m/z 445Abundance ��!"�v 7.5

Chromatogram ;/! Mass Spectrum 0�� 11-Nor-9-Carboxy-deltang/ml &����?� Gas Chromatography/Mass Spectrometry

5 ; ���/ก��������'���!.T&��ก���#� ��"���j�� binol "� Spiked /���� �������� ��! *�+���"'0�"0��

0�� ��*�+���ก ) Library of Drugs 0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW 2007) &����� Full Scan mode S+� Mass Spectrum

9-Tetrahydrocannabinol *�+ Derivatization ���� entafluoro-1-propanol ���'�1� Tetrahydrocannabinol-M 2

445, 459,607 ;/! 622 "� Probability '*��ก ) 95.5 MCounts

63

delta-9-Tetrahydrocanna Chromatography/Mass Spectrometry (GC/MS)

&��ก���#� ��"���j�� 11-Nor-9-Carboxy-*�+���"'0�"0�� 50 ng/ml ;/��

MAURER, HANS H./ PFLEGER, Mass Spectrum 0�� ��

���� pentafluoropropionic

M 2 PFP &��"� Mass 5.14 ;/!���" ��0��

Page 77: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.6 Library Search a Spectrum ���"'0�"0�� 50 ng/ml &����?� ��ก���*�+ 4.6 0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.Scan mode S+� Mass SpectrumDerivatization ���� pentafluoropropio

drocannabinol-M 2 PFP (Formula : C

;/! 622 "� Probability '*��ก )

4.6 Library Search a Spectrum 0�� 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol&����?� Gas Chromatography/Mass Spectrometry (GC/MS

6 ; ���/ก��'*��) Mass Spectrum 0�� ��*�+���ก ) MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW 2007)

Mass Spectrum 0�� �� 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinolentafluoropropionic anhydride;/! pentafluoro-1-propanol

M 2 PFP (Formula : C27H28F10O5)&��"� Mass Spectrum ./ ก�<� '*��ก ) 95.14 ;/! Retention Time (RT) �����#�;.���*�+

64

etrahydrocannabinol *�+(GC/MS)

0�� ��*�+���ก ) Library of Drugs MPW 2007) &����� Full

etrahydrocannabinol *�+ propanol ���'�1� Tetrahy

./ ก�<� m/z 445, 459,607 *�+ 13.884

Page 78: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.7 Calibration Curve ;/! 1,000 ng/ml &����?� Gas Chromatography/Mass ��ก���*�+ 4.7 ��"���j�� delta-9-Tetrahydrocannabinol50, 100, 250 ;/! 1,000 anhydride ;/! pentafluoro

y = +2.6140 e+4x + 3.8590e+5 �#����,<��*�+���,��#�"������ก����'���!.T'������"�v���

Calibration Curve 0�� delta-9-Tetrahydrocannabinol *�+���"'0�"0��Gas Chromatography/Mass Spectrometry (GC/MS)

7 ; �� Calibration Curve 0�� delta-9-Tetrahydrocannabinoletrahydrocannabinol "� Spiked /���� �������� ��!

000 ng/ml ;/���#��� ก � ;/!Derivatization ���� entafluoro-1-propanol ���������"'�1�' ����� (Linear regression) r2 = 0.998

y = +2.6140 e+4x + 3.8590e+5

�#����,<��*�+���,��0�� ��"���j�� "� ����ก��i"���j�� S+���?� �#�"������ก����'���!.T'������"�v���

65

*�+���"'0�"0�� 10, 50, 100, 250 )

etrahydrocannabinol &��ก���#�/���� �������� ��! *�+���"'0�"0�� 10,

���� pentafluoropropionic

Linear regression) r2 = 0.998 ;/!

�0�� ��"���j�� "� ����ก��i"���j�� S+���?� GC/MS ��� �"��@

Page 79: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.8 Calibration Curve 10, 50 ;/! 100 ng/ml &����?� ��ก���*�+ 4.8cannabinol &��ก���#� ��"���j��/���� �������� ��! *�+���"'0�"0������ pentafluoropropionic

regression) r2 = 0.999 ;/!

Calibration Curve 0�� 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol&����?� Gas Chromatography/Mass Spectrometry (GC/MS

8 ; �� Calibration Curve 0�� 11-Nor-9-Carboxy&��ก���#� ��"���j�� 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol

*�+���"'0�"0�� 10, 50 ;/! 100 ng/ml ;/���#��� ก �;/!entafluoropropionic anhydride ;/! pentafluoro-1-propanol ���������"'�1�' �����

;/! y = +6930.1650x y 2.5830e+4

66

etrahydrocannabinol *�+���"'0�"0�� (GC/MS)

arboxy-delta-9-Tetrahydro

etrahydrocannabinol "� Spiked ;/���#��� ก �;/! Derivatization

���������"'�1�' ����� (Linear

Page 80: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.9 Chromatogram Chromatography/Mass Spectrometry ��ก���*�+ 4.9����ก���0 �����.�ก -������ ��!&����?� #�.� )� � ���������*�+ 20 ���� �/ก�� ����'�1� )�ก ����ก���0 �����'���)����;/! Pentafluoro-1-propanol

Library of Drugs 0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.2007) &����� Full Scan mode

�<� m/z 445, 459,607 ;/! *�+ 10.266 ��*� ;/!���" ��

Chromatogram ;/! Mass Spectrum 0��� ������������ ��!Chromatography/Mass Spectrometry (GC/MS)

9 ; ���/ก��������'���!.T &��ก���#�� ������������ ��!�0 �����.�ก -������ ��!&����?� Cloned enzyme donor immunoassay (CEDIA)

20 �� ��!"�/ ก�v! �'0���'0�" '�<+����กก��*�+�� � " �����*����)���/ก�� ����'�1� )�ก (POSITIVE) ������'*��ก ) 162 ng/ml ��ก� ���#�

'���)����;/�� �� ก �;/! Derivatization ���� Pentafluoropropionic anhydride

propanol ������'���!.T&����?� GC/MS '*��) Mass SpectrumMAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.mode ���'�1� Tetrahydrocannabinol-M 2 PFP &��"�

;/! 622 "� Probability '*��ก ) 98.74 ;/! Retention Time (RT)���" ��0�� Abundance ��!"�v 13 MCounts

67

�� ��! &����?� Gas

� ������������ ��!"�*#�ก��immunoassay (CEDIA)

ก��*�+�� � " �����*����)����ก� ���#�� �������� ��!*�+

Pentafluoropropionic anhydride Mass Spectrum 0�� ��*�+��� ก )

MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A. (MPW &��"� Mass Spectrum ./ ก

Time (RT) �����#�;.���

Page 81: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

���*�+ 4.10 Library Search a Spectrum Spectrometry (GC/MS) '"<+�ก��'����)'*��)ก ) Library of Drugs 0��(MPW 2007) &����� Full Scan

�#�;.���*�+ 10.266��*�

4.10 Library Search a Spectrum 0��� ����������*�+ 20 &����?� Gas Chromatography/Mass

'"<+�ก��'����)'*��) Mass Spectrum ��ก���*�+ 4.10 0��� ������������ ��!*�+���0�� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.

Full Scan mode "� Probability '*��ก ) 98.74 ;/! Retention

68

Chromatography/Mass

0��� ������������ ��!*�+��� MAURER, HANS H./ PFLEGER, KARL/ WEBER, ARMIN A.

Retention Time (RT) ����

Page 82: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

69

56กก689:;<=:>?@A9BCDB GC/MS E6F68GH8?5?DAB86IJKJ6L8DF6M:N=H686=9OP 4.1

�����*�+ 4.1 �/ก��������'���!.T.����"�vก -������ ��!&����?� Gas Chromatography/Mass Spectrometry (GC/MS)

� ����������*�+

��ก���������� ��������������� GC/MS delta-9-Tetrahydrocannabinol

(ng/mL) 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol

(ng/mL) 1 0 ng/mL 0 ng/mL 2 0 ng/mL 0 ng/mL 3 0 ng/mL 0 ng/mL 4 0 ng/mL 0 ng/mL 5 0 ng/mL 0 ng/mL 6 0.30 ng/mL 3.56 ng/mL 7 0.32 ng/mL 1.82 ng/mL 8 0.99 ng/mL 1.71 ng/mL 9 0.48 ng/mL 6.31 ng/mL

10 1.12 ng/mL 6.42 ng/mL

11 38.96 ng/mL 160.61 ng/mL

12 26.77 ng/mL 85.16 ng/mL

13 41.81 ng/mL 113.89 ng/mL

14 53.18 ng/mL 96.27 ng/mL

15 44.98 ng/mL 209.63 ng/mL

16 74.56 ng/mL 160.06 ng/mL

17 87.39 ng/mL 345.75 ng/mL

18 89.48 ng/mL 575.19 ng/mL

19 23.41 ng/mL 97.16 ng/mL

20 62.72 ng/mL 499.52 ng/mL

Page 83: C C C Ü - Silpakorn University · ก ˘ ˇˆ˙ ˝˛ ˚ "ก ˙ ! ˆ delta 9-Tetrahydrocannabinol 2 ! 11-Nor-9-Carboxy-delta-9-Tetrahydrocannabinol 7 ˚ 899!:; ˇ Gas

70

'"<+��#�� ������*>ก� ������"�'����)'*��)ก )�/ก����'���!.T��*>กz ��?����� ������*�+ 4.2

�����*�+ 4.2 �/ก��������'���!.T.�ก -������ ��!&����?� Cloned Enzyme Donor Immunoassay (CEDIA), TOXI- LAB THC II ;/! Gas Chromatography/Mass Spectrometry

� ������ ����*�+

��ก�������������

���� CEDIA

(��� Cut-off = 50 ng/ml)

���� TOXI- LAB

THC II

���� GC/MS

(��� Cut-off =

15 ng/ml)

�+,���-

1 45 NEGATIVE NEGATIVE NEGATIVE � ����������*�+1-5 ��ก�� � " ��*�+�"�"���!� ��ก��' ,ก -��

2 48 NEGATIVE NEGATIVE NEGATIVE 3 44 NEGATIVE NEGATIVE NEGATIVE 4 40 NEGATIVE NEGATIVE NEGATIVE 5 46 NEGATIVE NEGATIVE NEGATIVE 6 59 POSITIVE NEGATIVE NEGATIVE � ����������*�+

6-20 ��ก�� � " ��*�+"���!� ��ก��' ,ก -��

7 65 POSITIVE NEGATIVE NEGATIVE 8 56 POSITIVE NEGATIVE NEGATIVE 9 58 POSITIVE NEGATIVE NEGATIVE

10 54 POSITIVE NEGATIVE NEGATIVE 11 76 POSITIVE POSITIVE POSITIVE 12 62 POSITIVE POSITIVE POSITIVE 13 74 POSITIVE POSITIVE POSITIVE 14 78 POSITIVE POSITIVE POSITIVE 15 85 POSITIVE POSITIVE POSITIVE 16 109 POSITIVE POSITIVE POSITIVE 17 116 POSITIVE POSITIVE POSITIVE 18 121 POSITIVE POSITIVE POSITIVE 19 61 POSITIVE POSITIVE POSITIVE *�� ��! �

'0���� 20 162 POSITIVE POSITIVE POSITIVE *�� ��! �

'0���'0�"

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������ก)�

Clinical Applications of Mass Spectrometry. (2010). !Methods in molecular biology' Volume

603: 137-144.

Clinical Chemistry. (1988). !Adulterants Causing False Negatives in Illicit Drug Testing.'

Clinical Chemistry. no. 34: 2333-2336.

___________. (2009). !Drug Monitoring and Toxicology.' no. 55: 2180-2189.

Dixit V., Dixit VM. (1991). !Solid-phase extraction of 11-nor-delta-9-tetrahydrocannabinol-9

carboxylic acid from human urine with gas chromatographic-mass spectrometric

confirmation.' J Chromatogr. 14, 567 (June): 81-91.

Dugan, S., Bogema S., Schwartz RW, Lappas NT. (1994). !Stability of drugs of abuse in urine

samples stored at -20 degrees.' C. J Anal Toxicol 18, 7 (Nov-Dec):391-6.

Forensic science centre, South Australia Police Forensic Services. (2007). !Quantification of

THC and 11-nor-9-carboxy-THC in blood by GC/MS.' Australia.

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Frazee III, C. Clinton, Michael Kiscoan, and Uttam Garg. (2010). !Quantitation of total 11-Nor-

9-Carboxy-Delta 9-Tetrahydrocannabinol in urine and blood using gas

chromatography-mass spectrometry (GC-MS). Methods Mol Biol. no. 603: 137-44.

Goldberger, BA., and EJ Cone. (1994). !Confirmatory tests for drugs in the workplace by gas

chromatography-mass spectrometry.' J Chromatogr A. 15, 674 (July): 73-86.

Hawks, Richard L., and C. Nora Chiang. (1986). !Urine testing for drugs of abuse. National

Institute on Drug Abuse Research Monograph: 73.

Interference of Common Household Chemicals in Immunoassay Methods for Drugs of

Abuse Clinical Chemistry 35:648-651 (1989)

Kim, Seon Yeong. et al. (2013). !Method development for simultaneous determination of

amphetamine type stimulants and cannabinoids in urine using GCEMS.'

Microchemical Journal 110 (September): 326E333.

Schwilke, Eugene W. et al. (2002). !Tetrahydrocannabinol (THC), 11-Hydroxy-THC, and 11-

Nor-9-carboxy-THC plasma pharmacokinetics during and after continuous high-dose

oral THC.' Federal government guidelines (by NIDA-The National Institute on Drug

Abuse and SAMHSA- The Substance Abuse and Mental Health Services

Association).

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Always Test Clean. (2014.) False positive drug test information. Accessed July 21. Available

from http://alwaystestclean.com/atc/false-positive-drug-test-facts/

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