在1996年聯合國國際藥物管制計畫(United Nations International Drug Control Programme, UNDCP) 提出安非他命類興奮劑(amphetamine-type stimulants)可能成為二十一世紀時最主要毒品的警訊。因此本次以七種2C系列的新興苯乙胺類毒品，包含2,5-dimethoxy-4-bromophenethylamine (2C-B)、2,5-dimethoxy-4-chlorophenethylamine (2C-C)、2,5-dimethoxy-4-iodo-
phenethylamine(2C-I)、2,5-dimethoxy-4-ethylthiophenethylamine(2C-T-2)
、2,5-dimethoxy-4-propylthiophenethylamine (2C-T-7)、2,5-dimethoxy-4-
methylphenethylamine(2C-D)、2,5-dimethoxy-4-ethylphenethylamine(2C-E)來進行研究探討，建立其儀器檢量線、方法檢量線、定性(量)極限、平均回收率、日內(間)變異等系統化的分析方法開發，共計完成501張EI質譜，並確立最佳分析條件。
在進行GC/MS分析前，運用三氟醋酸酐(TFAA)、五氟丙酸酐(PFPA)、七氟丁酸酐(HFBA)分別予以醯化衍生後再行分析，所得結果在儀器檢量線方面其線性範圍皆在25~2000ng/mL，線性相關係數經TFAA、PFPA及HFBA衍生後之2C-Series分別落於0.999~0.993、0.997~0.986及0.998~0.991間；各項藥物之平均回收率以2C-T-7(TFAA)回收率98%為最高，最差為2C-B(HFBA)的79%。方法檢量線方面其線性範圍皆在50~2000ng/mL，線性相關係數經TFAA、PFPA及HFBA衍生後之2C-Series分別落於0.995~0.991、0.999~0.984及0.999~0.989之間；定量極限(LOQ)與偵測極限(LOD)方面，TFAA及PFPA部份LOQ以2C-T-2及2C-T-7最低，分別為30及40ng/mL，HFBA部份LOQ以2C-D、2C-T-2及2C-T-7最低為40ng/mL;在LOD部份TFAA以2C-D，2C-E，2C-T-2及2C-T-7為30ng/mL最低，PFPA以2C-T-2及2C-T-7為40ng/mL最低，HFBA以2C-T-2為30ng/mL最低；分析方法在日內變異方面其變異量除極少部份(2C-D(TAFF衍生)100ng/mL:10.34%、2C-D(HFBA衍生)100ng/mL:10.15%及2C-B(HFBA衍生)100ng/mL:11.65%)外，餘均低於10%，而日間變異方面則全數均低於10%。
案內7種藥物中2C-B,2C-C及2C-I屬同類型藥物，2C-T-2及2C-T-7屬同類型藥物，2C-D及2C-E屬同類型藥物，當該藥物紅外光譜在指紋區密切吻合(其它範圍也相同)，將對鑑定產生此一光譜的物質提供了強大的見證，大多數單鍵在指紋區有吸收帶，因為彼此的能量相近，相鄰各鍵會有強烈的交互作用。因為此一複雜性，所以此區的光譜很少能解釋清楚，但相對的，由於複雜性而有唯一性，所以對鑑定工作非常有幫助。
現今有機合成技術、生化科技甚至利用電腦進行模擬等科學技術的進步下，許多藥物可以人工合成的方式製造生產。本研究將提供查緝單位查獲可疑藥物時，可立即正確的鑑定其成份，及時掌握濫用狀況，並在緝獲嫌犯時有標準的分析方法可供使用，不至造成鑑定結果受到質疑，甚至出現鑑定能力不足之窘境。

In 1996, The United Nations International Drug Control Programme, UNDCP proposed a signal that amphetamine-type stimulants might be the most main drug in the 21st century. Therefore, we have gone through 7 kinds of phenethylamine series drugs including 2,5-dimethoxy-4-bromophenethylamine (2C-B), 2,5-dimethoxy-
4-Chloro-phenethylamine (2C-C), 2,5-dimethoxy-4-iodophenethylamine(2C-I), 2,5-dimethoxy-4-ethylthiophenethylamine(2C-T-2), 2,5-dimethoxy-4-
propylthiophenethylamine(2C-T-7), 2,5-dimethoxy-4-methylphenethylamine(2C-D) and 2,5-dimethoxy-4-ethylphenethylamine(2C-E) for researching and establishing the analysis systems of instrument calibration, method calibration, LOD(LOQ), the recoveries calculated, the within-day/between-day CVs resulting. We completed 501 electron impact(EI) and built up the best conditions for analysis.

We acylated and derived TFAA , PFPA and HFBA separately before analyzing GC/MS. The instrument calibration achieved a linear range of 25~2000ng/mL, the 2C-Series of r2 derived by TFAA, PFPA and HFBA are around 0.999~0.993, 0.997~0.986 and 0.998~0.991, the highest recoveries calculated of all drugs is 2C-T-7(TFAA) 98%, the lowest is 2C-B(HFBA) 79%. The method calibration achieved a linear range of 50~2000ng/mL, the 2C-Series of r2 derived by TFAA, PFPA and HFBA are around 0.995~0.991, 0.999~0.984 and 0.999~0.989, the highest recoveries calculated of all drugs is 2C-T-7(TFAA) 98%. In LOQ, 2C-T-2(30ng/mL) and 2C-T-7(40ng/mL) are two of the lowest for TFAA and PFPA, 2C-D, 2C-T-2 and 2C-T-7 are two of the lowest(40ng/mL) for HFBA. In LOD, 2C-D,2C-E, 2C-T-2 and 2C-T-7 are three of the lowest(30ng/mL) for TFAA. 2C-T-2 and 2C-T-7 are two of the lowest(40ng/mL) for PFPA. 2C-T-2 is the lowest(30ng/mL) for HFBA. The within-day and between-day CVs resulting mostly below 10% except 2C-D(derived by TAFF)100ng/mL:10.34179%, 2C-D(derived by HFBA)100ng/mL:10.15201% and 2C-B(derived by HFBA)100ng/mL:11.64905%). The within-day CVs resulting all below 10%

In this study, 2C-B,2C-C and 2C-I are belong to same type, 2C-T-2and 2C-T-7 are belong to another, 2C-D and 2C-E are belong the other type of drugs. The spectrum substance will result powerful evidence for identification when all infrared spectrum are match(also match other range) perfectly at fingerprint. The energy is similar between each other and those neighboring area would have strongly effect, therefore largely single bond would have absorption at fingerprint. Also because of the complexity, it’s not easy to explain the spectrum at this area but owns its unique for improving identification.

Today, lots drugs could made by synthesized under science and technology
(organic synthesis technology, biochemistry science and computer modeling…ext.)
keep making progress. This study will contribute investigation organizations that identify ingredient fast and correctly, control the abuses condition immediately, and also contribute the standard analysis methods while hunting down suspect and finding suspicious drugs, avoid the identification result and ability will be questioned.

目錄
中文摘要．．．．．．．．．．．．．．．．．．．．．．．．．．．．．Ⅰ
Abstract ．．．．．．．．．．．．．．．．．．．．．．．．．．．．．Ⅲ
目錄．．．．．．．．．．．．．．．．．．．．．．．．．．．．．．．Ⅴ
圖目錄．．．．．．．．．．．．．．．．．．．．．．．．．．．．．．Ⅶ
表目錄．．．．．．．．．．．．．．．．．．．．．．．．．．．．．．Ⅸ
第一章 緒論．．．．．．．．．．．．．．．．．．．．．．．．．．．．1
1.1研究動機．．．．．．．．．．．．．．．．．．．．．．．．．．．1
1.2研究目的．．．．．．．．．．．．．．．．．．．．．．．．．．．2
第二章 文獻探討．．．．．．．．．．．．．．．．．．．．．．．．．．3
2.1藥物簡介及其濫用現況．．．．．．．．．．．．．．．．．．．．．3
2.2氣相層析質譜分析法．．．．．．．．．．．．．．．．．．．．．．9
2.3紅外光譜分析法．．．．．．．．．．．．．．．．．．．．．．．．12
2.3.1穿透式吸收 ．．．．．．．．．．．．．．．．．．．．．．．．14
2.3.2 反射式吸收．．．．．．．．．．．．．．．．．．．．．．．．14
2.3.2.1 鏡面反射 ．．．．．．．．．．．．．．．．．．．．．．．15
2.3.2.2 漫反射 ．．．．．．．．．．．．．．．．．．．．．．．．15
2.3.2.3 衰減式全反射 ．．．．．．．．．．．．．．．．．．．．．16
第三章 實驗器材設備．．．．．．．．．．．．．．．．．．．．．．．．19
3.1藥品與材料．．．．．．．．．．．．．．．．．．．．．．．．．．19
3.2儀器設備．．．．．．．．．．．．．．．．．．．．．．．．．．．19
3.2.1 Hewlett-Packard氣相層析質譜儀 ．．．．．．．．．．．．．．．19
3.2.2 SHIMADZU氣相層析質譜儀．．．．．．．．．．．．．．．．．20
3.2.3 Perkin Elmer傅立葉紅外光譜儀．．．．．．．．．．．．．．．．20
第四章 實驗方法．．．．．．．．．．．．．．．．．．．．．．．．．．21
4.1空白尿液萃取及衍生．．．．．．．．．．．．．．．．．．．．．．21
4.2定量與定性離子選擇．．．．．．．．．．．．．．．．．．．．．．23
4.3儀器檢量線．．．．．．．．．．．．．．．．．．．．．．．．．．23
4.4方法檢量線．．．．．．．．．．．．．．．．．．．．．．．．．．24
4.5回收率評估．．．．．．．．．．．．．．．．．．．．．．．．．．24
4.6定量極限與偵測極限．．．．．．．．．．．．．．．．．．．．．．25
4.7穩定度評估．．．．．．．．．．．．．．．．．．．．．．．．．．26
4.8未知樣品之分析．．．．．．．．．．．．．．．．．．．．．．．．27
4.9紅外光譜分析法．．．．．．．．．．．．．．．．．．．．．．．．28
4.9.1穿透式吸收 ．．．．．．．．．．．．．．．．．．．．．．．．28
4.9.2混合樣品分析 ．．．．．．．．．．．．．．．．．．．．．．．28
第五章 結果與討論．．．．．．．．．．．．．．．．．．．．．．．．．29
5.1氣相層析質譜分析結果．．．．．．．．．．．．．．．．．．．．．29
5.1.1合成藥品成份之確認 ．．．．．．．．．．．．．．．．．．．．29
5.1.2衍生試劑探討 ．．．．．．．．．．．．．．．．．．．．．．．33
5.1.3儀器檢量線 ．．．．．．．．．．．．．．．．．．．．．．．．42
5.1.4方法檢量線 ．．．．．．．．．．．．．．．．．．．．．．．．47
5.1.5萃取回收率 ．．．．．．．．．．．．．．．．．．．．．．．．52
5.1.6偵測極限與定量極限 ．．．．．．．．．．．．．．．．．．．．55
5.1.7穩定度評估 ．．．．．．．．．．．．．．．．．．．．．．．．58
5.1.8綜合分析 ．．．．．．．．．．．．．．．．．．．．．．．．．61
5.1.9未知樣品分析 ．．．．．．．．．．．．．．．．．．．．．．． 68
5.2 紅外光譜分析結果 ．．．．．．．．．．．．．．．．．．．．．．70
5.2.1 2C-B樣品分析結果．．．．．．．．．．．．．．．．．．．．．70
5.2.2 2C-C樣品分析結果．．．．．．．．．．．．．．．．．．．．．73
5.2.3 2C-I樣品分析結果．．．．．．．．．．．．．．．．．．．．．75
5.2.4 2C-D樣品分析結果．．．．．．．．．．．．．．．．．．．．．77
5.2.5 2C-E樣品分析結果．．．．．．．．．．．．．．．．．．．．．79
5.2.6 2C-T-2樣品分析結果．．．．．．．．．．．．．．．．．．．．81
5.2.7 2C-T-7樣品分析結果．．．．．．．．．．．．．．．．．．．．83
5.2.8 2C-Series紅外光譜細部比較．．．．．．．．．．．．．．．．．85
5.2.9混合樣品之分析探討 ．．．．．．．．．．．．．．．．．．．．89
第六章 結論．．．．．．．．．．．．．．．．．．．．．．．．．．．．95
第七章 參考文獻．．．．．．．．．．．．．．．．．．．．．．．．．．97







圖目錄
圖1.氣相層析質譜圖(A)2C-B,(B)2C-C,(C)2C-D,(D)2C-E,(E)2C-I,(F)2C-T-2,(G)2C-T-7．32
圖2.1 2C-D質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生 34
圖2.2 2C-E質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．35
圖2.3 2C-C質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．36
圖2.4 2C-B質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．37
圖2.5 2C-I 質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．38
圖2.6 2C-T-2質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．． 39
圖2.7 2C-T-7質譜圖(A)未衍生、(B)TFAA衍生、(C)PFPA衍生與(D)HFBA衍生．． 40
圖3.1 2C-Series經TFAA衍生後之儀器檢量線 ．．．．．．．．．．．．．43
圖3.2 2C-Series經PFPA衍生後之儀器檢量線．．．．．．．．．．．．．．44
圖3.3 2C-Series經HFBA衍生後之儀器檢量線 ．．．．．．．．．．．．．45
圖4.1 2C-Series經TFAA衍生後之尿液分析方法檢量線 ．．．．．．．．．48
圖4.2 2C-Series經PFPA衍生後之尿液分析方法檢量線．．．．．．．．．．49
圖4.3 2C-Series經HFBA衍生後之尿液分析方法檢量線 ．．．．．．．．．50
圖5.1 2C-B紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．．71
圖5.2 2C-B重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．．72
圖6.1 2C-C紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．．73
圖6.2 2C-C重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．．74
圖7.1 2C-I紅外光譜圖．．．．．．．．．．．．．．．．．．．．．．．．75
圖7.2 2C-I重複試驗紅外光譜圖．．．．．．．．．．．．．．．．．．．．76
圖8.1 2C-D紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．．77
圖8.2 2C-D重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．．78
圖9.1 2C-E紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．．79
圖9.2 2C-E重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．．80
圖10.1 2C-T-2紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．81
圖10.2 2C-T-2重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．82
圖11.1 2C-T-7紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．83
圖11.2 2C-T-7重複試驗紅外光譜圖 ．．．．．．．．．．．．．．．．．．84
圖12.1以(a)2C-B,(b)2C-C及(c)2C-I為例，比較圖5.1~7.1．．．．．．．．．85
圖12.2以(a)2C-D,(b)2C-E為例，比較圖8.1及9.1．．．．．．．．．．．．86
圖12.3以(a)2C-T-2,(b)2C-T-7為例，比較圖10.1及11.1 ．．．．．．．．．87
圖12.4以(a)2C-B,(b)2C-D,(c)2C-T-2為例，比較各紅外光譜之不同處．．．．88
圖13.1(a) 2C-C MIX 2C-B IN KBr(b)2C-C IN KBr (c)2C-B IN KBr．．．．．．90
圖13.2(a) 2C-C IN KBr (b) 2C-C MIX 2C-B IN KBr 扣減2C-B 後之紅外光譜圖 ．90
圖14.1(a)2C-C MIX Ketamine IN KBr(b) 2C-C IN KBr (c) Ketamine IN KBr．．92
圖14.2(a) 2C-C IN KBr (b) 2C-C MIX Ketamine IN KBr扣減Ketamine後之紅外光譜圖 ．．．．．．．．．．．．．．．．．．．．．．．．．．．．92
圖15.1(a)2C-C MIX Ketamine and Dextrose IN KBr(b) 2C-C IN KBr (c) Ketamine IN KBr (d) Dextrose IN KBr．．．．．．．．．．．．．．．．．．．94
圖15.2(a) 2C-C IN KBr (b) 2C-C MIX Ketamine and Dextrose IN KBr扣減Ketamine and Dextrose 後之紅外光譜圖 ．．．．．．．．．．．．．94










表目錄
表1. 2C-Series藥物之定量（性）離子與滯留時間．．．．．．．．．．．．32
表2. 2C-Series藥物未衍生化及經衍生化後滯留時間．．．．．．．．．．．41
表3. 2C-Series藥物經衍生化後之定量（性）離子．．．．．．．．．．．．41
表4. 2C-Series藥物經衍生化後以GC/MS分析之儀器檢量線 ．．．．．．．46
表5. 2C-Series藥物經衍生化後以GC/MS分析之方法檢量線 ．．．．．．．51
表6. 2C-Series萃取回收率之評估．．．．．．．．．．．．．．．．．．．53
表7. 2C-Series經TFAA衍生後之定量極線(LOQ)及偵測極限(LOD) ．．．．55
表8. 2C-Series經PFPA衍生後之定量極線(LOQ)及偵測極限(LOD)．．．．．56
表9. 2C-Series經HFBA衍生後之定量極線(LOQ)及偵測極限(LOD) ．．．．57
表10.2C-Series經TFAA衍生後之日內變異及日間變異．．．．．．．．．．58
表11.2C-Series經PFPA衍生後之日內變異及日間變異．．．．．．．．．．59
表12 2C-Series經HFBA衍生後之日內變異及日間變異 ．．．．．．．．．60
表13.2C-D經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．61
表14.2C-E經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．62
表15.2C-C經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．63
表16.2C-B經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．64
表17.2C-I經不同試劑衍生化後所得之分析數據 ．．．．．．．．．．．．．．．65
表18.2C-T-2經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．66
表19.2C-T-7經不同試劑衍生化後所得之分析數據．．．．．．．．．．．．．．．67
表20.未知樣品分析結果．．．．．．．．．．．．．．．．．．．．．．．69
表21.2C-B吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．．71
表22.2C-C吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．．74
表23.2C-I吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．．76
表24.2C-D吸收峰及其對應的官能基 ．．．．．．．．．．．．．．．．．78
表25.2C-E吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．．80
表26.2C-T-2吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．82
表27.2C-T-7吸收峰及其對應的官能基．．．．．．．．．．．．．．．．．84

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