Biosynthesis of Morphine

HO

O
HO
N
H

CH3

HO

O
HO
HO

N
H

CH3

HO

HO

CH3

NH2

NH2

CO2H

OH
Decarboxylation
&
Hydroxylation

CO2H

OH
Oxidative Deamination
&
Decarboxylation

NH2

O
H

HO
OH
Dopamine

OH

NH2

O
H

HO
OH
- H2O

OH

HO
HO

HO

O
HO

HO

NH
H

MeO

HO
HO

NH
H

HO

N CH3

HO

H
HO
MeO
(S)-Reticuline

MeO
HO

N CH3
H

HO
MeO

(S)-Reticuline
Undergoes Epimerization to (R)-Reticuline

MeO

MeO
HO

N CH3
H

HO
MeO

NAD

HO
HO
MeO

N CH3

MeO
HO

MeO
N CH3
HO
NADH

HO

HO

MeO

MeO

N CH3
H

(R)-Reticuline

Undergoes Phenolic Coupling

MeO
O
O
MeO

N CH3
H

MeO
O
MeO

H
N CH3

O
H

Undergoes Rearomatization

MeO
HO
MeO
N CH3

O
H

Undergoes Reduction

MeO
HO
MeO
N CH3

HO
H

Undergoes Cyclisation with loss of H2O

MeO
O
MeO
N CH3
H
Undergoes Demethylation

MeO
O
HO
N CH3
H

MeO
O
O
N CH3
H
H
Codeinone
Undergoes Reduction

MeO
O
HO
N CH3
H
H
Codeine
Undergoes Demethylation

HO
O
HO
N CH3
H
H
Morphine

Heroin is Diacetyl Morphine

AcO
O
AcO
N CH3
H
H