Ammonia → Benzoic Acid

HRID 1005266노트

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HRID 1005266 반응식
[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10][C:11]([C:13]3[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=3)=[O:12])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2.[CH3:23][N:24]1[CH:28]2[CH:29]([C:41]([OH:43])=[O:42])[CH:30]([O:32][C:33]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:34])[CH2:31][CH:25]1[CH2:26][CH2:27]2.[CH3:44][O:45][C:46]([C@H:48]1[C@@H:55]([O:56][C:57]([C:59]2[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=2)=[O:58])[CH2:54][C@H:52]2[NH:53][C@@H:49]1[CH2:50][CH2:51]2)=[O:47].N>O.CO.C(OCC)(=O)C.C(N(CC)CC)C.C(Cl)(Cl)Cl>[CH3:1][N:2]1[C@H:6]2[C@@H:7]([C:19]([O:21][CH3:22])=[O:20])[C@@H:8]([O:10][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[O:12])[CH2:9][C@@H:3]1[CH2:4][CH2:5]2.[CH3:23][N:24]1[CH:28]2[CH:29]([C:41]([OH:43])=[O:42])[CH:30]([O:32][C:33]([C:35]3[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=3)=[O:34])[CH2:31][CH:25]1[CH2:26][CH2:27]2.[C:57]([OH:58])(=[O:56])[C:59]1[CH:64]=[CH:63][CH:62]=[CH:61][CH:60]=1.[CH3:44][O:45][C:46]([C@H:48]1[C@@H:55]([O:56][C:57]([C:59]2[CH:60]=[CH:61][CH:62]=[CH:63][CH:64]=2)=[O:58])[CH2:54][C@H:52]2[NH:53][C@@H:49]1[CH2:50][CH2:51]2)=[O:47]

참가 물질

13

반응물 4

HCID 222AmmoniaHCID 23403-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 446220CocaineHCID 644007(-)-Norcocaine

생성물 4

HCID 243Benzoic AcidHCID 23403-(Benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acidHCID 446220CocaineHCID 644007(-)-Norcocaine

시약·촉매·용매 5

HCID 887Methanol용매2회HCID 962Water용매HCID 6212Chloroform용매HCID 8471Triethylamine용매HCID 8857Ethyl Acetate용매

실험 절차

Plasma samples were aliquoted and non-radioactive cocaine, benzoyl ecgonine, and norcocaine were added in order to assist in the UV visualization of the compounds. Samples were then applied to silica TLC plates which were developed in two solvent systems: methanol, chloroform, and triethylamine (3:1:0.1); and ethyl acetate, methanol, water, and concentrated ammonia (85:10:3:1). Metabolites were identified by reference to control compounds run on the same plates. The bands were scraped off the plates and 3H-containing compounds were detected through scintillation counting. From the counts obtained the amount of cocaine, benzoyl ecgonine, benzoic acid, and norcocaine as percent of total counts was determined. The total radioactivity in the plasma was determined by scintillation counting of whole plasma. Benzoic acid is detected as a metabolite when cocaine degrades into ecgonine methyl ester and benzoic acid, and so is equimolar to the ecgonine methyl ester metabolite.

출처 및 근거

ORD 기록
ord-24eeb9bd112f40fea8eb05bb0b8694aa
출처 데이터셋
uspto-grants-2000_04
특허 번호
US06054127

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