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ዩ䈎䉌ᄢ㤗䈱૶↪䉕⸽᣿䈜䉎䈮䈲䇮ᄢ㤗ᚑಽ䊁䊃䊤䊍 䈠䈖䈪੹࿁䈲䇮ᓸ㊂䉰䊮䊒䊦↪䈱࿕⋧᛽಴䉦䊤䊛䈪
䊄
䊄䊨䉦䊮䊅䊎䊉䊷䊦(THC)
䊎 䈱ઍ⻢‛䈪䈅䉎11-nor-9-
⻢‛ 䈅䉎 䈅䉍 䉰 䊒 ㊂䈏
䈅䉍䇮䉰䊮䊒䊦㊂䈏100 PLએਅ䈪䉅㜞䈇࿁෼₸䈏ᓧ䉌
એਅ 䉅㜞 ࿁෼₸䈏ᓧ䉌
carboxy-'9-carboxylic acid (THCA)䉕ᬌ಴䇮ቯ㊂䈜䉎䈖 䉏䉎MonoSpin䉕↪䈇䈩೨ಣℂ䉕ⴕ䈇䉁䈚䈢䇯ᓧ䉌䉏䈢
䈫䈏ᔅⷐ䈪䈜䇯䈚䈎䈚䇮ዩਛ䈱THCA ฽᦭㊂䈲ppb䉥䊷 ♖⵾䉰䊮䊒䊦䉕LC/MS/MS䈪ಽᨆ䈚䈢䈫䈖䉐䇮⋥✢ᕈ䊶
䉻䊷䈪䈅䉎䈖䈫䈎䉌䇮ૐỚᐲ䊶ૐኈ㊂䈱䉰䊮䊒䊦䉕ౣ⃻ ࿁෼₸䊶ౣ⃻ᕈ䈱ో䈩䈮䈍䈇䈩⦟ᅢ䈭⚿ᨐ䈏ᓧ䉌䉏䉁
⦟䈒ಣℂ䈜䉎䈱䈮ㆡ䈚䈢೨ಣℂᴺ䈏ᦸ䉁䉏䈩䈇䉁䈜䇯 䈚䈢䇯 䋨Y. Yui and S. Ota䋩

HPLC-UV䉕↪䈇䈢䇮MonoSpin C18-CX䈮䉋䉎䉪䊥䊷䊮䉝䉾䊒ലᨐ䈱⹏ଔ

䋼♖⵾೨䋾 䋼♖⵾ᓟ䋾

1. Carboxy-THC (10 ȝg/mL)

1
1
Volts

Volts
0.0

0.0

0 2 4 6 8 10 12 0 2 4 6 8 10 12
Time (min) Time (min)

Conditions; ᭴ㅧᑼ
Column ODS 3 (5 ȝm, 150 㬍 4.6 mm I.D.)
: Inertsil ODS-3 O OH

Eluent: : A) 0.1% HCOOH in H2O

B) 0.1% HCOOH in CH3CN OH
A/B = 60/40 - 10 min - 0/100, v/v
Flow rate: : 1.0 mL/min
Col. Temp.: : 40 ͠
Detection: : UV 214 nm O
Injection Vol.: : 10 ȝL
Sample:
p : ((㫧)-Carboxy-THC
) y 10 ȝg
ȝg/mL (㫧)-11-nor-9-Carboxy-ǻ9-THC
( C COO )
(THC-COOH)
Structures are created using Chemistry 4-D Draw which is provided by ChemInnovation Software, Inc.

MonoSpin 䈫䈲䋿

MonoSpin䉲䊥䊷䉵䈲䇮ဋ৻䈭ㅪ⛯ሹ䉕ᜬ䈧䉲䊥䉦䊝䊉䊥䉴䉕↪䈇䈢䉴䊏䊮䉦䊤䊛䈪䈜䇯ⓨ㓗₸䈱㜞䈇䉲䊥䉦䊝䊉䊥䉴䉕
ᜂ૕䈫䈚䈩↪䈇䈩䈇䉎䈱䈪䇮㆙ᔃᠲ૞䈣䈔䈪ㅢᶧ䈘䈞䉎䈖䈫䈏䈪䈐䉁䈜䇯䈠䈱䈢䉄䇮⍴ᤨ㑆䈱◲ଢ䈭ᠲ૞䈪⹜ᢱ䈱
♖⵾䊶Ớ❗䉕ⴕ䈉䈖䈫䈏䈪䈐䉁䈜䇯䉁䈢䇮䊔䉾䊄䊗䊥䊠䊷䊛䈏ዊ䈘䈒ᶧ䈱䈐䉏䉅⦟䈇䈱䈪䇮⹜ᢱ㊂䈏ዋ䈭䈇႐ว䈮䉅
ㆡ䈚䈩䈇䉁䈜䇯
ᠲ૞ᣇᴺ଀

㆙ᔃ ㆙ᔃ ㆙ᔃ ㆙ᔃ

㆙ᔃ䉼䊠䊷䊑䈮䉴䊏䊮䉦䊤䊛䉕ⵝ⌕䈚䇮
ᐔⴧൻ ๆ⌕ ᵞᵺ ṁ಴ ㆙ᔃജ䉕೑↪䈜䉎䈖䈫䈪ㅢᶧ䈘䈞䉁䈜䇯

䊋䉾䉪䊅䊮䊋䊷䉇䉝䊒䊥䉬䊷䉲䊢䊮ᬌ⚝䈲䈖䈤䉌䈎䉌䊶䊶䊶 http://www.gls.co.jp/hplc.html
 GL Sciences LC Technical Note

MonoSpinC18ͲCX䉕↪䈇䈢೨ಣℂᴺ䈮䈧䈇䈩
MonoSpin䈱䉲䊥䉦䊝䊉䊥䉴䈱⴫㕙䈮䇮䉥䉪䉺䊂䉲䊦ၮ䈍䉋䈶㓁䉟䉥䊮੤឵ၮ䈱2⒳㘃䉕ዉ౉䈚䈢䉦䊤䊛䈪䈜䇯
੹࿁䈱䊜䉸䉾䊄᭴▽ᤨ䈮䈲䇮䉰䊮䊒䊦䊨䊷䊄ᤨ䈮䈍䈇䈩䉰䊮䊒䊦ṁᶧ䉕㉄ᕈ䈫䈜䉎䈖䈫䈪䇮㉄ᕈൻว‛䈪䈅䉎
THCͲCOOH䈱⸃㔌䉕ᛥ೙䈚䇮ಽ㔌೷䈮ㅒ⋧ಽ㈩䈪଻ᜬ䈘䈞䉁䈚䈢䇯

䉰䊮䊒䊦ṁᶧ
0.1%䉩㉄᳓ṁᶧ 490 ȝL
䊙䊃䊥䉾䉪䉴 490 ȝL
1. 䉮䊮䊂䉞䉲䊢䊆䊮䉫
STD⹜ᢱ 10 ȝL 䋨ᐔⴧൻ䋩 ㆙ᔃ*
㆙ᔃ
+) ౝㇱᮡḰ⹜ᢱ 10 ȝL
1000 ȝL 䊜䉺䊉䊷䊦300 ȝL䉕ㅢᶧ(2 min)䈚䈢ᓟ䇮 2 min
0.1%䉩㉄᳓ṁᶧ300 ȝL䉕ㅢᶧ(2 min)

̪⹜ᢱỚᐲ䈲⹜㛎⚿ᨐ䈮⸥タ

2. 䉰䊮䊒䊦䊨䊷䊄 ㆙ᔃ 3. 䉦䊤䊛ᵞᵺ ㆙ᔃ

䉰䊮䊒䊦ṁᶧ200 ȝL䉕ㅢᶧ 2 min 0.1%䉩㉄᳓ṁᶧ300 ȝL䉕ㅢᶧ 2 min

4 ṁ಴
4.
㆙ᔃ
5%䉝䊮䊝䊆䉝-䊜䉺䊉䊷䊦 5. HPLC䈪ಽᨆ
100 ȝL䉕ㅢᶧ 1 min * ㆙ᔃ䈲ో䈩3,000 x g 䈪
ⴕ䈇䉁䈚䈢䇯

ᷝട࿁෼⹜㛎䉕ⴕ䈦䈢ᤨ䈮ᓧ䉌䉏䈢䉪 䊙䊃䉫䊤䊛
ᷝട࿁෼⹜㛎䉕ⴕ䈦䈢ᤨ䈮ᓧ䉌䉏䈢䉪䊨䊙䊃䉫䊤䊛
Conditions;
System : LC800 (GL Sciences)
3.0e4 THCA : 0.5 ng/mL API3000 (AB SCIEX)
I.S.** : 2.5 ng/mL Column : InertSustain C18
2.5e4 (2 ȝm, 100 㬍 2.1 mm I.D.)
Eluent : A) 0.1% HCOOH in H2O
2.0e4
B) 00.1%
1% HCOOH in CH3CN
Intensity, cps

A/B = 35/65 - 6 min - 5/95

- 4 min - 5/95 - 0.1 min
1.5e4 - 35/65 - 5 min – 35/65, v/v
Flow rate : 200 ȝL/min
1.0e4
Col. Temp. : 40 ͠
Detection : MS/MS (ESI, Nega, MRM)
Injection Vol. : 5 ȝL
4.07
5000.0

1.35
1.03
0.82 2.02
2.25 2.56
2.32
0.0
1.0 2.0 3.0 4.0 5.0 6.0 7.0 8.0
Time, min

** I.S.䈮䈲䇮㊀᳓⚛ᮡ⼂૕䈪䈅䉎(㫧)-11-nor-9-Carboxy-ǻ9-THC-D9
(THC-COOH-d9)䉕૶↪䈚䉁䈚䈢䇯

Scan Parameters
Precursor Ion Product Ion
Analyte
(m/z) (m/z)
(㫧)-Carboxy-THC 343.0 299.0
(㫧)-Carboxy-THC-d9 352.1 308.1
GL Sciences LC Technical Note

ᬌ㊂✢
4ᣣ㑆ห 䈱ಽᨆ䉕ⴕ䈇䇮䈠䉏䈡䉏䈱⚿ᨐ䈎䉌⋡⊛ᚑಽ䈪䈅䉎THCA䈱ᬌ㊂✢䉕૞ᚑ䈚䈢䈫䈖䉐䇮
4ᣣ㑆ห৻䈱ಽᨆ䉕ⴕ䈇䇮䈠䉏䈡䉏䈱⚿ᨐ䈎䉌⋡⊛ᚑಽ䈪䈅䉎THCA䈱ᬌ㊂✢䉕૞ᚑ䈚䈢䈫䈖䉐䇮
䈇䈝䉏䉅⋧㑐ଥᢙ0.9998䌾1.000䈱⦟ᅢ䈭⋥✢ᕈ䈏␜䈘䉏䉁䈚䈢䇯

1ᣣ⋡ 2ᣣ⋡

3.0
3.0

r2 =0.9999 r2=0.9999
0.9999
A
Analyte

A
Analyte
2.0
2.0
Area / IS Area

Area / IS Area
1.0 1.0

0.0 0.0
0.5 1.0 5.0 10.0 0.5 1.0 5.0 10.0
Analyte Conc. / IS Conc. Analyte Conc. / IS Conc.

3ᣣ⋡ 4ᣣ⋡

3.0 3.0

r2=0.9998 r2=1.000
Analyte Area
Analyte Area / IS Area

2.0 2.0
A / IS Area

1.0 1.0

0.0 0.0
0.5 1.0 5.0 10.0 0.5 1.0 5.0 10.0
Analyte Conc. / IS Conc. Analyte Conc. / IS Conc.

࿁෼₸෸䈶ౣ⃻ᕈ䇮ᱜ⏕ᐲ
4ᣣ㑆䈠䉏䈡䉏䈮䈧䈇䈩䇮࿁෼₸෸䈶ౣ⃻ᕈ䋨C.V.୯䋩䇮ᱜ⏕ᐲ䋨Accuracy䋩䉕᳞䉄䈢䈫䈖䉐䇮䈇䈝䉏䉅᭎䈰
⦟ᅢ䈭⚿ᨐ䈏ᓧ䉌䉏䉁䈚䈢䇯

࿁෼₸䋨%䋩 1ᣣ⋡ 2ᣣ⋡ 3ᣣ⋡ 4ᣣ⋡ ᣣ㑆ᐔဋ

0.5 ng/mL 86.8 94.4 87.0 88.5 89.2
1.0 ng/mL 99.0 100.8 101.4 101.7 100.7
10 ng/mL 88.1 91.1 91.6 92.8 90.9

ౣ⃻ᕈ䋨%䋩 1ᣣ⋡ 2ᣣ⋡ 3ᣣ⋡ 4ᣣ⋡ ᣣ㑆ᐔဋ

0.5 ng/mL 2.67 0.74 2.17 3.20 2.2
1.0 ng/mL 1.00 2.85 2.79 0.57 1.8
10 ng/mL 1.14 1.05 1.79 0.80 1.2

ᱜ⏕ᐲ䋨%䋩 1ᣣ⋡ 2ᣣ⋡ 3ᣣ⋡ 4ᣣ⋡ ᣣ㑆ᐔဋ

0.5 ng/mL 101.0 105.3 101.0 101.7 102.2
1.0 ng/mL 99.2 97.1 99.5 98.9 98.7
10 ng/mL 99.9 99.9 99.9 100.1 100.1
 GL Sciences LC Technical Note

MonoSpin䉲䊥䊷䉵䈱䊤䉟䊮䊅䉾䊒
㪤㫆㫅㫆㪪㫇㫀㫅㩷㪚㪈㪏 㪤㫆㫅㫆㪪㫇㫀㫅㩷㪪㪘㪯
䉥䉪䉺䊂䉲䊦ၮ䉕⚿ว䈚 ήᭂᕈ
䉥䉪䉺䊂䉲䊦ၮ䉕⚿ว䈚䇮ήᭂᕈ 䊃䊥䊜䉼䊦䉝䊚䊉䊒䊨䊏䊦ၮ䉕⚿
䊥 䉼 䉝 ၮ䉕⚿
Cl
㪤
㪤㫆㫅㫆㫃㫀㫋㪿

㪤
㪤㫆㫅㫆㫃㫀㫋㪿
⋧੕૞↪䉕䉅䈧䉦䊤䊛䈪䈜䇯 +
ว䈚䈢䉦䊤䊛䈪䈜䇯
(CH2)17CH3 ↢૕⹜ᢱ䈭䈬䈎䉌䈱⮎‛᛽಴䉇䇮 (CH2)3 N (CH3)3 ᒝ㒶䉟䉥䊮੤឵૞↪䈫ᒙ䈇ήᭂ
䊕䊒䉼䊄䉰䊮䊒䊦䈱⣕Ⴎ䊶Ớ❗䈮ᦨ ᕈ⋧੕૞↪䉕૬䈞ᜬ䈤䉁䈜䇯
ㆡ䈪䈜䇯 ㉄ᕈ⮎‛䈱᛽಴䈮ᦨㆡ䈪䈜䇯

㪤㫆㫅㫆㪪㫇㫀㫅㩷㪥㪟㪉 㪤㫆㫅㫆㪪㫇㫀㫅㩷㪧㪙㪘
䉝䊚䊉䊒䊨䊏䊦ၮ䉕⚿ว䈚䈢䉦䊤䊛 ቭ⢻ၮ䈮䊐䉢䊆䊦䊖䉡㉄䉕↪䈇

㪤㫆㫅㫆㫃㫀㫋㪿
㪤㫆㫅㫆㫃㫀㫋㪿

䈪䈜
䈪䈜䇯 N 䈢⚿ว․⇣ᕈ䈱㜞䈇䉦䊤䊛䈪䈜䇯
(C 2)3 NH2
(CH 㪟㪠㪣㪠㪚䊝䊷䊄䈮䉋䉎♧㎮䈭䈬䇮ⷫ᳓ᕈ H 䉦䊁䉮䊷䊦䉝䊚䊮䈭䈬䉲䉴ဳ䉳
ൻว‛䈱᛽಴䈮ᦨㆡ䈪䈜䇯 B(OH)2 䉥䊷䊦䉕᦭䈜䉎ൻว‛䈮ኻ䈜䉎䇮
ㆬᛯ⊛䈭᛽಴䈮ᦨㆡ䈪䈜䇯

㪤㫆㫅㫆㪪㫇㫀㫅㩷㪪㪚㪯 㪤㫆㫅㫆㪪㫇㫀㫅㩷㪫㫀㪦
䊒䊨䊏䊦䊔䊮䉷䊮䉴䊦䊖䊮㉄䉕
ੑ㉄ൻ䉼䉺䊮䉕䉮䊷䊁䉞䊮䉫䈚䈢

㪤㫆㫅㫆㫃㫀㫋㪿
㪤㫆㫅㫆㫃㫀㫀㫋㪿

ᵋ ⚿ว䈚䈢䉦䊤䊛䈪䈜䇯
䉦䊤䊛䈪䈜䇯
(CH2)3 SO3 ᒝ㓁䉟䉥䊮੤឵૞↪䈫ήᭂᕈ⋧ TiO2 䊥䊮㉄ၮ䉕᦭䈜䉎ൻว‛䈱᛽಴
੕૞↪䉕૬䈞ᜬ䈤䉁䈜䇯
䈮ᦨㆡ䈪䈜䇯
Ⴎၮᕈ⮎‛䈱᛽಴䈮ᦨㆡ䈪䈜䇯

㪤㫆㫅㫆㪪㫇㫀㫅㩷㪘㫄㫀㪻㪼 㪤㫆㫅㫆㪪㫇㫀㫅㩷㪚㪙㪘
䉝䊚䊄ၮ䉕⚿ว䈚䈢䉺䉟䊒䈪䈜䇯 䉦䊦䊗䉨䉲䊦ၮ䉕䉲䊥䉦䊝䊉䊥䉴
㪤㫆㫅㫆㫃㫀㫋㪿
㪤㫆㫅㫆㫃㫀㫋㪿

O HILIC䊝䊷䊄䈮䉋䉍䇮♧㎮䉕ᆎ䉄 O 䈮⚿ว䈚䈢䉺䉟䊒䈪䈜䇯ᒙ㓁䉟䉥
䈫䈚䈢᏷ᐢ䈇ⷫ᳓ᕈൻว‛䈱 䊮੤឵૞↪䈮䉋䉍䇮Ⴎၮᕈൻว‛
NH2 ᛽಴䈮ㆡ䈚䈩䈇䉁䈜
᛽಴䈮ㆡ䈚䈩䈇䉁䈜䇯 OH 䈱᛽಴䈮ㆡ䈚䈩䈇䉁䈜䇯

㪤㫆㫅㫆㪪㫇㫀㫅㩷㪚㪈㪏㪄㪚㪯 䋨੹࿁૶↪䈚䉁䈚䈢䋩 㪤㫆㫅㫆㪪㫇㫀㫅㩷㪫㫉㫐㫇㫊㫀㫅

㪚㪈㪏䈫㪪㪚㪯䈱ਔᣇ䈱ቭ⢻ၮ䉕⚿
䉺䊮䊌䉪⾰ᶖൻ㉂⚛䈪䈅䉎䊃䊥䊒
㪤㫆㫅㫆㫃㫀㫋㪿
㪤㫆㫅㫆㫃㫀㫋㪿

(CH2)17CH3 ว䈚䈢䉺䉟䊒䈪䈜䇯ⴊᷡ䉇ዩਛ䈱
䉲䊮䉕࿕ቯൻ䈚䈢䉦䊤䊛䈪䈜䇯
Ⴎၮᕈ⮎‛䈱೨ಣℂ䈮䈍䈇䈩䇮 Trypsin
ᵋ 䉺䊮䊌䉪⾰䈱ㄦㅦᶖൻ䈏น⢻䈮
(CH2)3 SO3 㪚㪈㪏䉇㪪㪚㪯䈱න૕䈫Ყ䈼䈩㜞䈇䉪
䈭䉍䉁䈜䇯
䊥䊷䊮䉝䉾䊒ലᨐ䈏ᦼᓙ䈪䈐䉁䈜䇯

૶↪䈚䈢೨ಣℂ䉦䊤䊛䋻 MonoSpin C18-CX 50/pk

Cat.No. 5010-21731

p C18-CX
MonoSpin 100/pk
p
Cat.No. 5010-21732

䉳䊷䉣䊦䉰䉟䉣䊮䉴䈪䈲䇮ಽᨆ䊉䉡䊊䉡䈫䈐䉄䈖䉁䉇䈎䈭䊐䉤䊨䊷䉅䈍ઃ䈔䈚䈢䉲䉴䊁䊛ឭ᩺䉕ⴕ䈦䈩䈍䉍䉁䈜䇯
䈍ㄭ䈒䈱༡ᬺᚲ䉇 䉦䉴䉺䊙䊷䉰䊘䊷䊃䉶䊮䉺䊷 䉁䈪䈍᳇シ䈮䈍໧䈇ว䉒䈞䈒䈣䈘䈇䇯

䊖䊷䊛䊕䊷䉳䈲䈖䈤䉌䈎䉌䊶䊶䊶
http://www.gls.co.jp/hplc.html
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