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Dopamine → Morphine

HRID 537750
Notes
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Reaction equation

HRID 537750 reaction equation
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]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 5

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

Product 1

HCID 5288826
Morphine

Procedure

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).

Sources & evidence

ORD record
ord-2ec5527aa42a48c2a66b77c8f7d0e87c
Source dataset
uspto-grants-2014_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08865696B2

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes