㹙㈨ᩱ㹛 රᗜ┴࠾ࡅࡿ᳜≀⣔㐪ἲࢻࣛࢵࢢ〇ရ୰ࡢ ྜᡂ࢝ࣥࢼࣅࣀࢻศᯒ⤖ᯝࡘ࠸࡚ ㉥ᯇᡂᇶ㸨 ୕ᶫ㝯ኵ Analysis of Synthetic Cannabinoids in Illegal Herbal Incense Blends in Hyogo Prefecture, Japan Shigeki AKAMATSU㸨 and Takao MITSUHASHI Life Science Division, Public Health Science Research Center, Hyogo Prefectural Institute of Public Health and Consumer Sciences,2-1-29, Arata-cho, Hyogo-ku, Kobe 652-0032, Japan A simple method was described for determination of synthetic cannabinoids in illegal herbal incense blends by gas chromatography mass spectrometry (GC/MS) and liquid chromatography mass spectrometry (LC/MS). The method was applied to illegal products being purchased in February of 2013 in Japan. The synthetic cannabinoids, which are controlled as “Designated Substances (Shitei-Yakubutsu)” in Japan, were detected in two products. One was XLR-11, and the other was both XLR-11 and UR-144. Ϩ ࡣࡌࡵ ϩ ᮦᩱ᪉ἲ ㏆ᖺ㸪 ࠕ⬺ἲࣁ࣮ࣈࠖࡢᦤྲྀࡀཎᅉᛮࢃࢀࡿᩆᛴᦙ㏦ ࡸ⮬ື㌴ᨾ➼ࡀᛴቑࡋ㸪┴ෆ࡛ࡶᗣ⿕ᐖࡀሗ࿌ࡉࢀ ࡚࠸ࡿ㸬 ࠕ⬺ἲࣁ࣮ࣈࠖࡣ㸪࠸ࢃࡺࡿ㐪ἲࢻࣛࢵࢢࡢ୍✀ 1 ヨ⸆ ᖹᡂ 25 ᖺ 2 ᭶⚄ᡞᕷෆࡢᗑ⯒ࡽ㉎ධࡋࡓ᳜≀⣔ 㐪ἲࢻࣛࢵࢢ 10 〇ရࢆ⏝࠸ࡓ㸬 ࡛㸪⇱᳜≀㯞⸆ࡸぬࡏ࠸㢮ఝࡋࡓᗁぬࡸ⯆ዧస 2 ヨ⸆ ⏝ࢆ㉳ࡇࡍ≀㉁ࢆῧຍࡋࡓࡶࡢ࡛࠶ࡿ㸬 ཌປ┬ࡣ㸪2007 ᖺࡽࠕᣦᐃ⸆≀ࠖไᗘࢆ㛤ጞࡋ㸪㐪 ࣓ࢱࣀ࣮ࣝ࠾ࡼࡧࢭࢺࢽࢺࣜࣝࡣ㸪ග⣧⸆ᕤᴗओ ἲࢻࣛࢵࢢࡢつไࢆᙉࡋ࡚࠸ࡿࡀ㸪ᡂศࡢᵓ㐀ࢆ୍㒊 〇 HPLC ⏝ࢆ⏝࠸㸪㓑㓟ࣥࣔࢽ࣒࢘ࡣ㸪ග⣧⸆ᕤᴗ ኚ࠼ࡓࡶࡢࡀฟ⌧ࡋ㸪༑ศ࡞ຠᯝࡀᚓࡽࢀ࡚࠸࡞࠸㸬 ओ〇ヨ⸆≉⣭ࢆ⏝࠸ࡓ㸬 ࡾࢃࡅ㯞ᵝࡢస⏝ࢆ♧ࡍྜᡂ࢝ࣥࢼࣅࣀࢻࡣ㸪ከࡃ ≀㉁ྠᐃࡣ㸪Cayman Chemical ♫〇ࡢࡶࡢࢆᶆ‽ ࡢᵓ㐀㢮ఝయࡀᏑᅾࡋ㸪᳜≀⣔㐪ἲࢻࣛࢵࢢ〇ရ࡛ ရࡋ࡚⏝࠸ࡓ㸬ྛᶆ‽ရࡣ㸪࣓ࢱࣀ࣮ࣝ⁐ゎࡋ㸪250 ࡢ᳨ฟࡀከ࠸㸬 Ǎg/mL ㄪᩚࡋࡓࡶࡢࢆᶆ‽ཎᾮࡋ࡚-20 Υ࡛ಖ⟶ ᙜࢭࣥࢱ࣮࠾࠸࡚ࡶ㸪2013 ᖺ 2 ᭶⸆ົㄢࡢ㈙࠸ ࡋ㸪⏝ᕼ㔘ࡋ࡚ᶆ‽⁐ᾮࡋࡓ㸬 ୖࡆㄪᰝࡢ୍⎔ࡋ࡚㸪᳜≀⣔㐪ἲࢻࣛࢵࢢ〇ရࢆศᯒ ࡋ㸪ࡑࡢ୍㒊ࡽᣦᐃ⸆≀ࢆ᳨ฟࡋࡓࡢ࡛ሗ࿌ࡍࡿ㸬 3 ヨ㦂⁐ᾮࡢㄪ〇 ヨᩱ㸦⇱᳜≀⣽∦㸧ࢆࣁࢸࢵࢡ♫〇ࣇ࣮࣐ࣥ࢞ ᗣ⛉Ꮫ㒊 㸨ูๅㄳồඛ㸸ࠛ652-0032 ⚄ᡞᕷරᗜ༊Ⲩ⏣⏫ 2-1-29 රᗜ┴❧ᗣ⏕ά⛉Ꮫ◊✲ᡤ ᗣ⛉Ꮫ◊✲ࢭࣥࢱ࣮ ᗣ⛉Ꮫ㒊 ㉥ᯇᡂᇶ － 52 － ࢵࢩ࣮࡛ࣕ⢊○ࡋࠊࡑࡢ⣙ 20 mg ࢆ⢭ᐦ㔞ࡾ㸪࣓ࢱࣀ ࣮ࣝ 1.0 mL ࢆຍ࠼࡚㉸㡢Ἴୗ 10 ศ㛫ᢳฟࢆ⾜ࡗࡓ㸬 㐲ᚰศ㞳ᚋ㸪ୖΎࢆ 0.45 Ǎm ࣓ࣥࣈࣛࣥࣇࣝࢱ࣮࡛ࢁ රᗜ┴❧ᗣ⏕ά⛉Ꮫ◊✲ᡤᗣ⛉Ꮫ◊✲ࢭࣥࢱ࣮◊✲ሗ࿌ ➨ ྕ 㐣ࡋࡓࡶࡢࢆヨ㦂ཎᾮࡋ㸪㐺ᐅᕼ㔘ࡋ࡚GC/MS࠾ࡼࡧ LC/MS࡛ ᐃࡋࡓ㸬 4 ศᯒ᮲௳ ㏻▱1)‽ࡌ࡚ヨ㦂ࢆᐇࡋࡓ㸬 4.1 GC/MS ⨨ࡣ㸪Agilent♫〇6890Nᆺ࢞ࢫࢡ࣐ࣟࢺࢢࣛࣇ࠾ࡼ ࡧ5673 inertᆺ㉁㔞ศᯒィࢆ⏝࠸࡚㸪௨ୗࡢศᯒ᮲௳࡛ XLR-11 ⾜ࡗࡓ㸬 UR-144 ศᯒ࣒࢝ࣛ㸸Agilent♫〇HP-5MS㸦0.25 mm i.d.30 m㸪⭷ཌ0.25 Ǎm㸧 㸪࣮࢞ࢻ࣒࢝ࣛ㸸Restek♫〇 Siltek ࢞ Fig.1 Chemical structures of synthetic cannabinoids ࣮ࢻ࣒࢝ࣛ㸦0.25 mm i.d.0.5 m㸧 㸪࣒࢝ࣛ ᗘ㸸80 Υ detected in the present study. 㸦1 minಖᣢ㸧㸫5 Υ/min㸫190 Υ㸦15 minಖᣢ㸧㸫 10 Υ/min㸫310 Υ㸦10 minಖᣢ㸧 㸪࢟ࣕࣜ࢞ࢫ㸦࣊ Table 1 Determination of synthetic cannabinoids in herbal ࣒ࣜ࢘㸧ᅽຊࣉࣟࢢ࣒ࣛ㸸40 psi㸦1 min㸧Ѝ16.8 psiᐃ incense blends by LC/MS. ᅽ࣮ࣔࢻ㸪ὀධ㔞㸸1 ǍL㸦ࢫࣉࣜࢵࢺࣞࢫ㸧 㸪ὀධཱྀ ࢚ࢿࣝࢠ࣮㸸70 eV㸪ࢫ࢟ࣕࣥ⠊ᅖ㸸m/z 50-550. Sample name Compound Content (%) a) 4.2 LC/MS A XLR-11 8.1 ± 0.0 B XLR-11 UR-144 10.4 ± 1.6 0.53 ± 0.03 ᗘ㸸250 Υ㸪࢜ࣥἲ㸸㟁Ꮚ࢜ࣥ㸦EI㸧 㸪࢜ࣥ ᾮయࢡ࣐ࣟࢺࢢࣛࣇࡣAgilent♫〇1200ᆺ㸪㉁㔞ศᯒ ィࡣAgilent♫〇㣕⾜㛫㸦TOF㸧ᆺ6210ࢆ⏝࠸ࡓ㸬ศ a) ᯒ᮲௳ࡣ௨ୗࡢ࠾ࡾ࡛࠶ࡿ㸬 ศᯒ࣒࢝ࣛ㸸Agilent♫〇Poroshell 120 EC-18㸦3.0 The mean value ± S.D, n=3. 50 mm㸪⢏Ꮚᚄ2.7 Ǎm㸧 㸪࣮࢞ࢻ࣒࢝ࣛ㸸GLࢧ࢚ࣥࢫ ࠶ࡗࡓ㸬ࡉࡽ㸪Uchiyamaࡽࡢሗ࿌2)ྠᵝ㸪XLR-11 ♫〇Inertsil ODS-3㸦3.010 mm㸪⢏Ꮚᚄ3.0 Ǎm㸧 㸪⛣ ࠾ࡼࡧUR-144ࡢྛࢧࣈࣆ࣮ࢡࡀぢࡽࢀࡓ㸬ࢧࣈࣆ࣮ࢡ ࡣ㸪GC/MSศᯒ⏕ᡂࡋࡓศゎ≀⪃࠼ࡽࢀ㸪ࡑࢀࡒ ື┦A㸸10 mM㓑㓟ࣥࣔࢽ࣒࢘㸪⛣ື┦B㸸ࢭࢺࢽ ࢀࡢ࣐ࢫࢫ࣌ࢡࢺࣝࡣ㸪๓⪅ࡢࡶࡢࡣm/z 247㸪ࡲࡓᚋ ࢺࣜࣝ㸪ࢢࣛࢪ࢚ࣥࢺ᮲௳㸸Bᾮ㸹10 %㸫50 %㸦3 min㸧 㸫95 %㸦10 min㸪5 minಖᣢ㸧 㸪ὶ㏿㸸0.5 mL/min㸪࢝ ⪅࡛ࡣm/z 229ࡢᙉᗘࡀࡁ࠸࠸࠺≉㛗ࡀ࠶ࡗࡓ㸬࡞ ࣒ࣛ ᗘ㸸40 Υ㸪ὀධ㔞㸸2 ǍL㸪࢜ࣥ㸸࢚ࣞࢡࢺ ࠾㸪ᡃࠎࡢ᮲௳࡛ࡣࢧࣈࣆ࣮ࢡࡢ᪉ࡀ࣓ࣥࣆ࣮ࢡࡼࡾ ࣟࢫࣉ࣮ࣞ࢜ࣥ㸦࣏ࢪࢸࣈ࣮ࣔࢻ㸧 㸪࢟ࣕࣆ࣮ࣛࣜ ࡶࡁ࡞ࣆ࣮ࢡ࡞ࡗࡓ㸬 㟁ᅽ㸸4000 V㸪ࣇࣛࢢ࣓ࣥࢱ࣮㟁ᅽ㸸100 V࠾ࡼࡧ250 V㸪 ୍᪉㸪LC/MSศᯒ࡛ࡣ㸪࣒࢝ࣛ㛗ࡀ▷ࡃ㸪⢏Ꮚᚄࢆᑠ 㸪ࢫ࢟ࣕࣥ⠊ᅖ㸸m/z ⇱࢞ࢫ㸸N2㸦10 L/min㸪350 Υ㸧 ࡉ࠸ࡶࡢࢆ⏝ࡋࡓࡓࡵ㸪 ᐃ㛫ࡣ15ศࡋࡓ㸬㏻▱ 50-950㸪ࣜࣇࣞࣥࢫ࣐ࢫ㸸121.0509࠾ࡼࡧ922.0098. ἲ㸦75ศ㸧ẚ▷㛫࡛࠶ࡾ㸪⁐፹⏝㔞ࡶ๐ῶ࡛ࡁ ࡓ㸬ᅇᡃࠎࡀLC/MSࡋ࡚⏝࠸ࡓTOF-MSࡣ㸪⢭ᐦ㉁ 㔞ࡀᚓࡽࢀࡿࡇࡽ㸪≀㉁ࡢ᥎ᐃ᭷⏝࡛࠶ࡿ㸬ண Ϫ ⤖ᯝ࠾ࡼࡧ⪃ᐹ ࡉࢀࡿῧຍ≀㉁ࡢ㹙M㸩H㹛㸩ࡢ⢭ᐦ㉁㔞ࡢ⌮ㄽ್ࢆࢹ࣮ GC/MS࠾ࡼࡧLC/MSࡼࡿศᯒࡢ⤖ᯝ㸪10〇ရ୰2 ࢱ࣮࣋ࢫⓏ㘓ࡋ㸪 ᐃࢆ⾜ࡗࡓ㸬Fig.3ࡣࠊ〇ရBࡢ 〇ရࡽᣦᐃ⸆≀㸦〇ရA㸸XLR-11㸪〇ရB㸸XLR-11 LC/MSࡢTICࢆ♧ࡋࡓ㸬GC/MSྠᵝTIC࠾࠸࡚ࡶ ࠾ࡼࡧUR-144㸧ࡀ᳨ฟࡉࢀࡓ㸦Fig.1㸪Table 1㸧 㸬 ࣆ࣮ࢡࡢ☜ㄆࡣྍ⬟࡛࠶ࡗࡓ㸬ᚓࡽࢀࡓ࣐ࢫࢫ࣌ࢡࢺࣝ GC/MSศᯒ࡛ࡣ㸪 ᐃ㛫ࡣ60ศẚ㍑ⓗ㛗࠸ࡀ㸪 ࡽ㸪⢭ᐦ㉁㔞ࡢᐇ ್ࡣᶆ‽ရ࠾ࡼࡧ㹙M㸩H㹛㸩ࡢ⌮ ㄽ್࣑࣐ࣜࢫ୍࡛ࣞ࣋ࣝ⮴ࡋࡓ㸬 ࢝ࢳࣀࣥ⣔⸆≀➼ࡢಖᣢ㛫ࡢ▷࠸ྜ≀ࡢศ㞳ࡀྍ⬟ ࡞ࡿࡼ࠺㸪 ࣒࢝ࣛ᪼ ᮲௳ࡣ㏻▱࠾ࡾタᐃࡋࡓ㸬 Fig.2GC/MS࢜ࣥࢡ࣐ࣟࢺࢢ࣒ࣛ㸦TIC㸧ࡢ୍ ࡲࡓ㸪XLR-11࠾ࡼࡧUR-144ࡢࣆ࣮ࢡࡣ༢୍ࡢࣆ࣮ࢡ ࡛࠶ࡾ㸪ࢧࣈࣆ࣮ࢡࡣぢࡽࢀ࡞ࡗࡓࡓࡵ㸪ᐃ㔞ࡣ ࡋ࡚〇ရBࡢࡶࡢࢆ♧ࡋࡓ㸬ᣦᐃ⸆≀ࡀ㧗⃰ᗘῧຍ LC/MSࡢ ᐃ್࡛⾜ࡗࡓ㸦Table 1㸧 㸬ࡋࡋ㸪㐪ἲࢻࣛ ࡉࢀ࡚࠸ࡓࡓࡵ㸪 TIC࠾࠸࡚ࡶࣆ࣮ࢡࡢ☜ㄆࡀᐜ࡛᫆ ࢵࢢࡢᛶ㉁ୖ㸪ῧຍ⃰ᗘࡤࡽࡘࡁࡀ࠶ࡿ᥎ᐃࡉࢀࡿ － 53 － A AA 44 45 46 47 48 49 0 10 20 296 311 144㻌 6.0E+06 m/z C 314 329 m/z 40 50 B 144 0.0E+00 1.0E+07 232 144 0.0E+00 3.0E+06 214㻌 A 0.0E+00 30 Time (min) Abundance 4.0E+06 Abundance D C 3.5E+07 0.0E+00 Abundance B Abundance Abundance 7.0E+07 60 214 229 296 311 spectra of the illegal products (Sample m/z 232 247 D name B in Table 1) by GC/MS. The inset 314 329 144 0.0E+00 Fig.2 Total ion chromatogram and four EI mass m/z shows part of the same data with expanded x- and y-axes. (A), UR-144; (B), UR-144 degradant; (C), XLR-11; (D), XLR-11 degradant. Fig.2. (A) 9.420 min (D) 100 V 10.659 min (B) (E) 100 V㻌 (C) Fig.3 Total ion chromatogram (A), extracted ion chromatograms (B, C) and mass spectra (D,E) of the illegal products (Sample name B in Table 1) by LC/MS. ࡇ㸪࠾ࡼࡧࢧࣥࣉࣜࣥࢢࡀᑡ㔞࡛࠶ࡿࡇ➼ࡽ㸪 ࡉࢀࡓ2✀㢮ࡢᣦᐃ⸆≀ࡘ࠸࡚ࡶ㸪㈙࠸ୖࡆⅬ࡛ࡣ ᐃ್ࡣཧ⪃್ࡋࡓ㸬 つไ┤ᚋࡢ≀㉁࡛࠶ࡾ㸪ᚋࡶつไࢆ㏨ࢀࡿࡓࡵ㸪᪂つ 㢮ఝ≀㉁ࡀฟ⌧ࡍࡿྍ⬟ᛶࡀ࠶ࡿ㸬ཌ⏕ປാ┬ࡣ㸪2013 ϫ ⤖ ㄽ ᖺ2᭶ࡽ㢮ఝᵓ㐀ࢆࡶࡘ≀㉁ࢆࡲࡵ࡚つไࡍࡿࠕໟ ྜᡂ࢝ࣥࢼࣅࣀࢻࢆࡣࡌࡵ㸪ᣦᐃ⸆≀ไᗘࡼࡾ㸪 ┴࠾࠸࡚ࡶᅜෆእࡢ㐪ἲࢻࣛࢵࢢὶ㏻≧ἣࢆ㋃ࡲ࠼ࡓ ≉ᐃࡢ≀㉁ࢆつไࡋ࡚ࡶ㸪ᵓ㐀ࡢ୍㒊␗࡞ࡿูࡢ≀㉁ࡀ ⥅⥆ⓗ࡞ᐇែㄪᰝࡣྍḞ࡛࠶ࡿ㸬 ᣓᣦᐃࠖࢆᑟධࡋ㸦3᭶⾜㸧 㸪ᑐ⟇ࢆࡗ࡚࠸ࡿࡀ㸪ᮏ Ⓩሙࡋ㸪 ࠕ࠸ࡓࡕࡈࡗࡇࠖࡢ≧ែࡀ⥆࠸࡚࠸ࡿ㸬ᅇ᳨ฟ － 54 － රᗜ┴❧ᗣ⏕ά⛉Ꮫ◊✲ᡤᗣ⛉Ꮫ◊✲ࢭࣥࢱ࣮◊✲ሗ࿌ ➨ ྕ ㅰ ㎡ ▱㸸ᣦᐃ⸆≀ࡢศᯒἲࡘ࠸࡚㸬ᖹᡂ19ᖺ5᭶21᪥㸪 ⸆㣗┘㯞Ⓨ0521002ྕ (2007) ᮏㄪᰝࡢ㐙⾜࠶ࡓࡾ㸪ᚚ༠ຊ࠸ࡓࡔࡁࡲࡋࡓᗣ⚟ 2) Uchiyama, N., Kawamura, M., Kikura-Hanajiri,R. ♴㒊ᗣᒁ⸆ົㄢ࡞ࡽࡧ㜰ᗓ❧බ⾗⾨⏕◊✲ᡤ⾨⏕ and Goda, Y. : URB-754 : A new class of designer Ꮫ㒊⸆ᣦᑟㄢࡢ㛵ಀ⪅ࡢ᪉ࠎ῝ㅰ࠸ࡓࡋࡲࡍ㸬 drug and 12 synthetic cannabinoids detected in illegal products. Forensic Sci. Int., 227, 21-32 (2013) ᩥ ⊩ [ᖹᡂ26ᖺ3᭶25᪥ཷ⌮] 1) ཌ⏕ປാ┬་⸆㣗ရᒁ┘どᣦᑟ࣭㯞⸆ᑐ⟇ㄢ㛗㏻ － 55 －
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