§@¬°·sºë¯«¬¡©Êª«½è¡]NPS¡^¤§¤@ªº¦X¦¨¤j³Â¯À¡]SCs¡^¬O§ó·s³t«×³Ì§Öªº¤@Ãþ¡§µ¦¹ºÃÄ¡¨¡CSCs¨ã¦³Ãþ¦ü¤ÑµM¤j³Â¯Àµ²¦X©M¿E°Ê¤j³Â¯À¨üÅéCB1©MCB2µÄÄÜÁ¦£¬·Â´óÂéЧÁ¦´óÓÚ¦¤9-THC¡Aªø´Á§l¹·|P©R{1}¡C±q2004¦~¥X²{ªº²Ä¤@¥Nf¥Ò???Ãþ°_¡]¦pJWH-018¡BJWH-250¡BAM-2201µ¥{2-3}¡^¡Aµo®i¦Ü²Ä¤K¥N??/?Ðü?ÓiÃþ¡]¦pAB-PINACA¡B5F-AB-PINACAµ¥{4-5}¡^¡A¨ì2014¦~¼Ú¬wº¦¸¥X²{¤F??/?Ðü¥ÒàÃþ¡]¦pAMB¡B5F-AMBµ¥{6-9}¡^¡Cªñ´X¦~¡A§Ú°ê¤]³°Äò¥X²{¨Ã±N¨ä¦C¤JºÞ¨î¡]¨£¡m«DÃÄ¥ÎÃþ³Â¾KÃÄ«~©Mºë¯«ÃÄ«~ºÞ¨î«~ºØ¼W¸É¥Ø¿ý¡n¡^¡C ³oÃþ¹êÅç«Ç¬r«~ªö¥Î°©¬[µ²ºc¤W§ïÅÜ×¹¢©x¯à¹Îªº¤è¦¡¥H°kÁצCºÞ¡A¨ä«~ºØ¦h¹F¦ÊºØ¡C¦]«ÜÃø¤Î®ÉÀò¨ú¼Ðã«~©Î¹ï·Ó«~«Ø¥ß§¹¾ãªº¼Æ¾Ú¤ñ¹ïÃЮw¡A¨Ï°ò¼h¤½¦w¬r«~ÀËÅçų©w¤u§@±Á{§xÃø¡A¼vÅT®×¥óªº¦³®Ä°»¿ì¡C¥»¬ã¨s®Ú¾Ú¹êÅç«Ç¨ü²zªº¹ê»Ú®×¨Ò¡A¿ï¾Ü??/?Ðü?ÓiÃþSCs¤¤ªº5F-AB-PINACA¡B AB-FUBINACA¤Î¨ä¹ïÀ³ªº??/?Ðü¥ÒàÃþl¥Íª«5F-AMB¡BAMB-FUBINACA§@¬°¬ã¨s¥Ø¼Ðª«¡]ªí1¡^¡A¨Ï¥ÎGC-MS¡BLC-MS/MS¡BFTIR©MRS¤èªkÀË´ú¤ÀªR¡A¤¬¬Û½TÃÒ¡A¬°Ãþ¦ü®×¥óªºÀËÅç´£¨Ñ¦³®Äªº§Þ³N¤â¬q©M¼Æ¾Ú°Ñ¦Ò¡C ªí1¡@5F-AB-PINACA¡BAB-FUBINACA¤Î¨ä¹ïÀ³l¥Íª«5F-AMB¡BAMB-FUBINACAªº¤Æ¾Çµ²ºc Table 1 Chemical structures of 5F-AB-PINACA or AB-FUBINACA and each individual analogue, the 5F-AMB and AMB-FUBINACA | °©¬[µ²ºc
| ¨ú¥N°ò | | X=H R1=N R2=C5H10F | X=H R1=N R2=C7H6F | | ¡]¹Ï²¤¡^
| ¡]¹Ï²¤¡^ | ¡]¹Ï²¤¡^ | | 5F-AB-PINACA | AB-FUBINACA | | ¡]¹Ï²¤¡^
| ¡]¹Ï²¤¡^ | ¡]¹Ï²¤¡^ | | 5F-AMB | AMB-FUBINACA |
1¹êÅ糡¤À 1.1»ö¾¹¡B§÷®Æ»P¸Õ¾¯ 5975C-7890A®ð¬Û¦âÃÐ-½èÃлö¡]¬ü°êAglient¤½¥q¡^¡AA&B Qtrap 4500Â÷¤l¨À²G½èÁp¥Î»ö¡]¬ü°êSciex¤½¥q¡^¡ANicolet IN10³ÅùظÅÜ´«¬õ¥~¥úÃлö¡]¬ü°êThermo Fisher¤½¥q¡^¡ADXRxi¦@»EµJÅã·L©Ô°Ò¥úÃлö¡]¬ü°êThermo Fisher¤½¥q¡^¡A¤Q¸U¤À¤§¤@¹q¤l¤Ñ¥¡]¬ü°êMettler Toledo¡^¡AMili-Q¶W¯Â¤ô»ö¡]¬ü°êMilipore¡^¡C SCs¹ï·Óª«½è¡A¥]¬A5F-AB-PINACA¡B5F-AMB¡B AB-FUBINACA ¡BAMB-FUBINACA¡]¤W®üì«ä¼Ðª«¬ì§Þ¦³¤½¥q¡A10 mg, ¡Ö99%¡^¡FµL¤ô¥Ò¾J¡]¦âÃЯ¡ATEDIA¡^¡C 1.2¼Ë«~³B²z ¤À§Oºë½TºÙ¨úSCs¹ï·Ó«~5 mg¡A¥ÎµL¤ô¥Ò¾J©w®e¤_10 mL®e¶q²~¤¤¡A°t¨î¦¨0.5 mg/mLªº²V¦X¹ï·Ó«~·»²G¡A¨ÑGC-MS´ú©w¡F¥Î¶W¯Â¤ôµ}ÄÀ¦Ü0.5¦Ìg/mL¡A¨ÑLC-MS/MS´ú©w¡C¤À§O¨ú¤Ö¶qSCs¹ï·Ó«~¸m¤_¬õ¥~¥úÃлöATRªþ¥óª÷è¥ÛÀË´úµ¡¤f¤W¡A¨ÑFTIR¤ÀªR¡F¥t¤À§O¨ú¤Ö¶qSCs¹ï·Ó«~¸m¤_¬Á¼þ¸ü¬Á¤ù¡A¨ÑRS¤ÀªR¡C 1.3 GC-MS¤ÀªR±ø¥ó ¦âÃЬW¡GHP-5 MS¤ò²ÓºÞ¦âÃЬW¡]30 m¡Ñ0.25 mm¡Ñ0.25¦Ìm¡A¬ü°êAglient¤½¥q¡^¡F¸ü®ð¡G°ª¯Â®ó®ð¡]¯Â«×¤£¤p¤_99.99%¡^¡F¬y¶q¡G1.0 mL/min ¡F¶i¼Ë¤f·Å«×¡G260¢J¡F¶i¼Ë¶q¡G1¦ÌL ¡F¤À¬y¼Ò¦¡¡G20?1¡F¤É·Åµ{§Ç¡Gªì©l·Å«×70¢J¡A«O«ù1 min¡A¥H20¢J/min³t²v¤É·Å¦Ü180¢J¡A¦A¥H10¢J/min³t²v¤É·Å¦Ü275¢J¡A«O«ù10 min¡AÁ`¹B¦æ®É¶¡¬°28 min ¡F¶Ç¿é½u·Å«×¡G280¢J¡FÂ÷¤l·½¡GEI ¡FÅFÀ»¯à¶q¡G70 eV ¡Fªö¶°½d³ò¡G50~500 amu ¡F±½´y¤è¦¡¡Gscan ¡F·»¾¯©µ¿ð¡G3 min¡C 1.4 LC-MS/MS¤ÀªR±ø¥ó 1.4.1 LC³¡¤À ¦âÃЬW¡GPhenomenex Kinetex? C18¬W¡]100 mm¡Ñ3.0 mm¡Ñ2.6¦Ìm¡^¡F¬W·Å¡G40¢J¡F¬y°Ê¬Û¡G§t0.1%¥Ò»Äªº¶W¯Â¤ô¡]A¡^©M§t0.1%¥Ò»Äªº¤A?¡]B¡^¡F±è«×¬~²æ¡G0~1.5 min¡]2% B¡^¡A1.5~6.5 min¡]2%~90% B¡^¡A6.5~9.4 min¡]90%~2% B¡^¡A9.5~12.0 min¡]2% B¡^¡F¬y³t¡G0.4 mL/min ¡F¶i¼Ë¶q¡G1¦ÌL¡C 1.4.2 MS³¡¤À Â÷¤l·½¡G¹q¼QÃú¹qÂ÷·½¡]ESI+¡^¡FÂ÷¤l·½·Å«×¡G550¢J¡F¼QÃú¹qÀ£¡G5500 V ¡FÃú¤Æ¾¹¡G50 psi ¡F»²§U¥[¼ö®ð¡G50 psi ¡F®ðî®ð¡G30 psi ¡F±½´y¼Ò¦¡¡GMS2©MMRM ¡FSCsªº«O¯d®É¶¡¤Î½èÃаѼƨ£ªí2¡C ªí2¡@MRM¼Ò¦¡¤USCs¤Æ¦Xª«ªº«O¯d®É¶¡©MÀu¤Æªº½èÃФÀªR°Ñ¼Æ Table 2 Retention time and optimized mass spectrometric parameters of the tested SCs with MRM analysis | ¤Æ¦Xª«¦WºÙ
| «O¯d®É¶¡/min
| ¥ÀÂ÷¤l/¡]m/z
¡^ | ¤lÂ÷¤l/¡]m/z
¡^ | ¥hÁL¹qÀ£/¡]e
/V¡^ | ¸I¼²¯à/¡]e/V
¡^ | | 5F-AB-PINACA
| 6.76
| 348.9
| 304.2* | 82.0 | 21 | | 233.0 | 82.0 | 32 | | 5F-AMB
| 8.17
| 364.1
| 233.1* | 78.0 | 20 | | 304.3 | 78.0 | 21 | | AB-FUBINACA
| 7.04
| 369.2
| 352.2* | 90.0 | 15 | | 324.2 | 90.0 | 20 | | AMB-FUBINACA
| 8.38
| 384.0
| 324.2* | 72.0 | 20 | | 253.0 | 72.0 | 26 |
ª`¡G*¬°©w¶qÂ÷¤l¡C 1.5 FTIR¤ÀªR±ø¥ó ±½´y½d³ò¡G500~4 000 cm-1 ¡F¤À¿ë²v¡G4 cm-1¡A±½´y¦¸¼Æ¡G32 ¦¸¡A¥ú°é¡G100 ¡FDTGS ÀË´ú¾¹¡C 1.6 RS¤ÀªR±ø¥ó ±½´y½d³ò¡G100~1 800 cm-1 ¡F¿Eµoªiªø¡G532nm¡FÅã·LÃè¡G10 ¿ª«Ãè¡F¿E¥ú¥\²v¡G4 mW¡F»EµJ¤Õ®|¡G25 ¦Ìm slit ¡FÃn¥ú®É¶¡¡G5 s¡C 2 µ²ªG»P°Q½× 2.1 GC-MS¤ÀªRµ²ªG ±N1.2 ¤¤ªº¼Ë«~·»²G«ö·Ó1.3 ©Òzªº»ö¾¹±ø¥ó¶i¦æGC-MS ¤À ªRµo²{¡A5F-AB-PINACA ©M5F-AMBªº«O¯d®É¶¡¤À§O¬°21.27 ©M18.95 min¡A¨âªÌ¹ïÀ³ªº½èÃиH¤ù¥Dn¯S©ºÂ÷¤l®p³£§t¦³m/z 233¡B304¡B145¥B¬Û¹ïÂ׫תñ¦ü¡FAB-FUBINACA©MAMB-FUBIN-ACAªº«O¯d®É¶¡¤À§O¬°24.39©M20.91 min¡A¨âªÌ¹ïÀ³ªº½èÃиH¤ù¥Dn¯S©ºÂ÷¤l®p³£§t¦³m/z 109¡B253¡B324¥B¬Û¹ïÂ׫תñ¦ü¡C¥Ñ¤_®ò¥Ò?°ò??/?Ðü?Ói/¥ÒàÃþSCs¸Hµõ³~®|¬Û¦ü¡A¹ïÀ³ªºµ²ºcÃþ¦üª«¯S©º¸HµõÂ÷¤l´X¥G¤@P¡A¶È¾aCaymanSpectralLibraryÃЮwÀ˯Á¡A¨ä¤Ç°t«×³£¦b95%¥H¤W¡AÃø¥Hã½T§P§O¡C 2.2 LC-MS/MS¤ÀªRµ²ªG ®Ú¾Úªí1©Ò¥Ü¡A4ºØSCs©Ò¨ã¦³ªº¨ûÓiµ²ºc¦bESI+¼Ò¦¡¤U¡A¤@¯Å½èÃйϩö§Î¦¨[M+H]+ã¤À¤lÂ÷¤l®p©M[M+Na]+®p¡A¦P®É¥Ñ¤_5F-AB-PINACA©MAB-FUBINACA¤À¤lµ²ºc¥½ºÝ¨ã¦³®ò°ò¡AÁÙ·|¦s¦b[M+H-NH3]+®p¡C®Ú¾Ú¸Hµõ¾÷¨î¦b¤G¯Å½èÃйϤ¤¡A 5F-AB-PINACAªº[M+H]+®p¡]¹Ï1a¡^¥¢¥hOCH3¡B5F-AMB¡]¹Ï1b¡^ªº[M+H]+®p¥¢¥hNH3¥Í¦¨¦@¦P¸H¤ùm/z 332¡]C18H23FN3O2+¡^¡AÄ~¦ÓÂ_µõ²£¥Í¸H¤ùm/z304¡]C17H23FN3O+¡^¡Bm/z 233¡]C13H14FN2O+¡^¡Bm/z 213¡]C13H13N2O+¡^¡FAB-FUBINACA¡]¹Ï2a¡^©MAMB-FU-BINACA¡]¹Ï2b¡^«ö¤Wz¦P²z¥Í¦¨¸H¤ùm/z 352¡]C20H19FN3O2+¡^¡Bm/z 324¡]C19H19FN3O+¡^¡Bm/z 253¡]C15H10FN2O+¡^¡C¦b¥Ø¼Ðª«©ú½Tªº±¡ªp¤U¡A¥i¥H³q¹L¹ï½èÃбø¥óÀu¤Æ«á¡]ªí2¡^¶i¦æ¤ÀªR½TÃÒ¡A¦pªG¬O¨äµ²ºcÃþ¦üª««h¶·¹ï¨ä¬Û¦üªº¤G¯Å¸H¤ùÂ÷¤lªì¨B±ÀÂ_«á³q¹LTOF¶i¤@¨B½TÃÒ¡C ¡]¹Ï²¤¡^ ¹Ï1¡@5F-AB-PINACA¡]a¡^©M5F-AMB¡]b¡^ªº¤G¯Å½èÃÐ¹Ï Fig.1 MS2 spectrums of 5F-AB-PINACA ¡]a¡^ and 5F-AMB ¡]b¡^ ¡]¹Ï²¤¡^ ¹Ï2¡@AB-FUBINACA¡]a¡^©MAMB-FUBINACA¡]b¡^ªº¤G¯Å½èÃÐ¹Ï Fig.2 MS2 spectrums of AB-FUBINACA ¡]a¡^ and AMB-FUBINACA ¡]b¡^ 2.3 FTIR¤ÀªRµ²ªG ±N1.2¤¤ªº¼Ë«~«ö·Ó1.5©Òzªº»ö¾¹±ø¥ó¶i¦æFTIR¤ÀªRµo²{¡A5F-AB-PINACA©M5F-AMBªº¬õ¥~¥úÃйϦb4000~3000 cm-1«ü¯¾°Ï®t²§©úÅã¡A©ö¤_°Ï¤À¡A¦b1700~500 cm-1«ü¯¾°Ïªº¯S©º§l¦¬®p¸û¬°Â×´I¡FAB-FUBINACA©MAMB-FUBINACAªº¬õ¥~¥úÃйϬ۪ñ¦ü¡AAMB-FUBINACA¦b1732.47 cm-1³Bªº¯S©º§l¦¬®p¨ã¦³¯S²§©Ê¡A¥B¦b1700~500 cm-1«ü¯¾°Ïªº¯S©º§l¦¬®p¤ñAB-FUBINACA§ó¨ã¿ï¾Ü©Ê¡]¨£¹Ï3¡B4¡^¡C¨ä¥Dn¯S©º®pªi¼Æ¦ì¸m¨£ªí3¡C 2.4 RS¤ÀªRµ²ªG ±N1.2¤¤ªº¼Ë«~«ö·Ó1.6©Òzªº»ö¾¹±ø¥ó¶i¦æRS¤ÀªRµo²{¡A5F-AB-PINACA©M5F-AMBªº©Ô°Ò¥úÃЦ첾®p¥Dn¶°¤¤¦b1700~600 cm-1«ü¯¾°Ï¥B¨ã¦³¬Ûªñªº¯S©º®p¡A¦ý5F-AB-PINACA¦b1200~1000 cm-1«ü¯¾°Ï¦ì²¾®p§óÂ×´I¡A¦b§CÀW°Ï161.93©M146.36 cm-1³BÂù®p¨ã¦³¯S²§©Ê¡A¦Ó5F-AMBªº±j®z®p§ó©úÅã¡A¦b°ªÀW°Ï1732.59©M1666.05 cm-1ªº¨â³B®p¨ã¦³¯S²§©Ê¡FAB-FUBINACA©MAMB-FUBINACAªº©Ô°Ò¥úÃЮt²§©Ê»P5F-AB-PINACA©M5F-AMBªñ¦ü¡AAB-FUBINACA¦b§CÀW°Ï159.99 cm-1³B¦ì²¾®p©MAMB-FUBINACA¦b°ªÀW°Ï1732.08©M1664.47cm-1ªº¨â³B®p¥i¥H§@¬°°Ï¤À¨âªÌ§P§O¨Ì¾Ú¡]¨£¹Ï5¡B6¡^¡C¨ä¥Dn¦ì²¾®pÀW²v¨£ªí4¡C ¡]¹Ï²¤¡^ ¹Ï3¡@5F-AB-PINACA¡]a¡^©M5F-AMB¡]b¡^ªº¬õ¥~¥úÃÐ¹Ï Fig.3 FTIR spectra of 5F-AB-PINACA ¡]a¡^ and 5F-AMB ¡]b¡^ ¡]¹Ï²¤¡^ ¹Ï4¡@AB-FUBINACA¡]a¡^©MAMB-FUBINACA¡]b¡^ªº¬õ¥~¥úÃÐ¹Ï Fig.4 FTIR spectra of AB-FUBINACA ¡]a¡^ and AMB-FUBINACA ¡]b¡^ ªí3¡@5F-AB-PINACA¡B5F-AMB¡BAB-FUBINACA ¡BAMB-FUBINACAªº¬õ¥~¯S©º§l¦¬®pªi¼Æ Table 3 Characteristic absorption peaks of 5F-AB-PINACA, 5F-AMB, AB-FUBINACA, AMB-FUBINACA | ¦WºÙ | ¬õ¥~¯S©º§l¦¬®pªi¼Æ/cm-1 | | 5F-AB-
PINACA | 3374.05,3288.31,2943.15,1674.71,1528.72,1490.99,1371.75,1320.25,
1303.18,1215.13,1168.77,1059.01,1020.74,957.16,750.82,648.65 | | 5F-AMB
| 3412.58,2965.81,1730.27,1666.56,1524.26,1491.27,1335.40,1308.22,
1205.84,1170.03,1151.63,996.64,919.01,815.83,754.77,670.50 | | AB-FUB
INACA | 3366.02,1644.57,1512.74,1488.97,1433.57,1300.40,1226.22,1171.15,
1104.27,1010.57,752.04 | | AMB-FU
BINACA | 3403.13,2957.26,1732.47,1662.77,1524.33,1488.76,1317.08,1253.16,
1166.98,1003.11,816.96,781.46,752.76,616.28 |
¡]¹Ï²¤¡^ ¹Ï5¡@5F-AB-PINACA¡]a¡^©M5F-AMB¡]b¡^ªº©Ô°Ò¥úÃÐ¹Ï Fig.5 Raman spectra of 5F-AB-PINACA ¡]a¡^ and 5F-AMB ¡]b¡^ ¡]¹Ï²¤¡^ ¹Ï6¡@AB-FUBINACA¡]a¡^©MAMB-FUBINACA¡]b¡^ªº©Ô°Ò¥úÃÐ¹Ï Fig.6 Raman spectra of AB-FUBINACA ¡]a¡^ and AMB-FUBINACA ¡]b¡^ ªí4¡@5F-AB-PINACA¡B5F-AMB¡BAB-FUBINACA ¡BAMB-FUBINACAªº©Ô°Ò¥Dn¦ì²¾ÀW²v Table 4 Raman shift frequencies of 5F-AB-PINACA, 5F-AMB, AB-FUBINACA, AMB-FUBINACA | ¦WºÙ | ©Ô°Ò¥Dn¦ì²¾ÀW²v/cm-1 | | 5F-AB-PINA
CA1
| 644.65,1572.68,1491.68,1476.11,1405.12,1383.12,1356.16,1320.
42,1264.85,1153.64,1134.83,1092.52,1002.73,886.82,787.62,761
.50,621.65,
290.99,161.93,146.36 | | 5F-AMB
| 1732.59,1668.05,1619.42,1575.22,1528.03,1471.87,1408.66,1361
.61,1239.96,1210.98,1005.69,919.76,778.17,751.54,148.88 | | AB-FUBINAC
A
| 1647.21,1571.01,1528.03,1474.53,1403.92,1356.86,1267.94,1226
.40,1159.32,1001.58,884.12,852.70,829.93,766.80,337.25,159.9
9 | | AMB-FUBINA
CA | 1732.08,1664.47,1616.50,1575.79,1526.39,1469.48,1401.75,1359
.73,1220.87,1002.82,902.16,853.46,763.63,621.56,168.63 |
3µ²½× ¥»¤åªö¥ÎGC-MS¡BLC-MS/MS¡BFTIR©MRSªk¹ï5F-AB-PINACA¡B5F-AMB¡BAB-FUBINACA¡BAMB-FUBINACA¥|ºØ·s«¬¦X¦¨¤j³Â¯À¶i¦æÀË´ú¤ÀªR¡A¥Ñ¤_¨ä¨ã¦³¬Û¦Pªº°©¬[©MÃþ¦üªº¤À¤lµ²ºc¡A¨CºØ¥Ø¼Ðª«¨ä¹ïÀ³ªºl¥Íª«¦bGC-MS¡BLC-MS/MSÀË´ú¤U¡A¸g¸Hµõ«á©Ò§Î¦¨ªº¯S©º¸H¤ù®p°ª«×¬Û¦ü¡F¦bFTIR¡BRSÀË´ú¤U¡A¥Ñ¤_×¹¢©x¯à¹Î¦ùÁY®¶°Êªº®t²§¡A¨ä¬õ¥~§l¦¬¯S©º®p©M©Ô°Ò¦ì²¾ÀW²vªº¯S²§©Ê¸û¬°©úÅã¡A¨ã¦³¸û¦nªº¿ï¾Ü©Ê¡C¦]¦¹³q¹L¦âÃнèÃЧ޳N©M¥úÃЧ޳Nªº¦@¦P¹B¥Î¡B¬Û¤¬½TÃÒ¡A¯à°÷¬°¸ÓÃþª«½èªº±ÀÂ_¡Bų©w´£¨Ñ¤èªk©M¼Æ¾Ú°Ñ¦Ò¡C ¡D¡D¡D¡D¡D¡D
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