Dopamine → Morphine

HRID 537750

反応式

HRID 537750 の反応式
NCCC1C=CC(O)=CC=1.NCCC1C=CC(O)=C(O)C=1.COC1C=CC2N=CC=C([C@H](O)[C@@H]3N4C[C@H](C=C)C(CC4)C3)C=2C=1.[CH3:46][N:47]1[CH:56]([CH2:57][C:58]2[CH:59]=[CH:60][C:61]([O:65]C)=[C:62]([OH:64])[CH:63]=2)[C:55]2[CH:54]=[C:53](O)[C:52]([O:68]C)=[CH:51][C:50]=2[CH2:49][CH2:48]1.CN1[C@@H]2CC3C=CC(OC)=C4O[C@H]5[C@@H](O)C=C[C@@H]2[C@]5(C=34)CC1>>[CH:59]1[C:58]2[CH2:57][C@H:56]3[N:47]([CH2:48][CH2:49][C@@:50]45[C@H:55]3[CH:54]=[CH:53][C@H:52]([OH:68])[C@@H:51]4[O:64][C:62]([C:63]=25)=[C:61]([OH:65])[CH:60]=1)[CH3:46]

参加物

6

反応物 5

HCID 681Dopamine5 回HCID 5610Tyramine3 回HCID 5953(S)-[(2R,5R)-5-ethenyl-1-azabicyclo[2.2.2]octan-2-yl]-(6-methoxyquinolin-4-yl)methanol2 回HCID 102331-((3-Hydroxy-4-methoxyphenyl)methyl)-6-methoxy-2-methyl-1,2,3,4-tetrahydroisoquinolin-7-olHCID 5284371Codeine

生成物 1

HCID 5288826Morphine

実験手順

To examine the tyramine to dopamine step, dopamine (DA) levels in ganglia and hemolymph were examined before and after tyramine addition followed by CYP2D6 inhibition by quinidine. Tyramine injection significantly increased ganglionic (4.98±0.27 μg/g to 9.17±1.21 μg/g wet weight; P<0.01) and hemolymph (10.13±1.24 μg/mL to 16.47±1.28 μg/mL, P<0.05) DA levels (FIGS. 19 and 20). The ganglionic and hemolymph DA level increases were blocked by quinidine exposure, demonstrating that the CYP2D6 enzyme was mediating this step. Ganglia were also exposed to THP, reticuline, DA, or codeine. Each resulted in significantly enhanced morphine levels, a phenomenon that was also significantly blocked by quinidine exposure, again demonstrating a role for CYP2D6 in the second part of the morphine biosynthetic pathway (FIGS. 15 and 20).

出典と根拠

ORDレコード
ord-2ec5527aa42a48c2a66b77c8f7d0e87c
出典データセット
uspto-grants-2014_10
特許番号
US08865696B2

関連ノート

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