N
N
H
H
N
N
H
H
R
Ergoline
D-Lysergic acid (R = CO 2 H)
Found in ergot fungus
Ergine (R = CONH 2 )
Occurs in various species of
vines of the Convolvulaceae
LSD [R = CON(C 2 H 5 ) 2 ]
A psychedelic drug.
Lysergic acid diethylamide, molecular formula C 20 H 25 N 3 O, also known as
LSD or LSD-25, is a semi-synthetic psychedelic drug, synthesized from the
natural precursor lysergic acid found in ergot, a grain fungus. It is a
colourless, odourless and mildly bitter compound. LSD produces altered
experience of senses, emotions, memories, time and awareness for 8 to 14 h.
Moreover, LSD may cause visual effects, e.g. moving geometric patterns,
‘trails’ behind moving objects and brilliant colours.
b-carbolines Alkaloids that possess a 9H-pyrid-[3,4-b]-indole skeleton
are called b-carboline alkaloids, and are found in several plants and
animals. The structure of b-carboline is similar to that of tryptamine, with
the ethylamine chain re-connected to the indole ring via an extra carbon
atom, to produce a three-membered ring structure. The biosynthesis of
b-carboline alkaloids follows a similar pathway to tryptamine. The
b-carbolines, e.g. harmine, harmaline and tetrahydroharmine, play an
important role in the pharmacology of the psychedelic brew ayahuasca.
Some b-carbolines, notably tryptoline and pinoline, are formed naturally in
the human body.
N
N
H
R'
R
N
H
R'
R''
R
N H
β-Carboline R = R' = H
Harmine R = Me, R' = OMe
1
2
3
4
5
6
7 8
Pinoline R = R'' = H, R' = OMe
Tetrahydroharmine R = Me, R'' = OMe
1
2
3
4
5
6
7 8
The major sources of b-carboline alkaloids with their medicinal or pharmacological properties are summarized below.
b-carboline alkaloids
Natural sources
Medicinal or pharmacological
properties
Harmine and harmaline Seeds of ‘harmal’ (Peganum CNS stimulant, acts by inhibiting
harmala) and
the metabolism of serotonin and
Banisteriopsis caapi
other monoamines
6.2 ALKALOIDS
299
N
H
H
N
N
H
H
R
Ergoline
D-Lysergic acid (R = CO 2 H)
Found in ergot fungus
Ergine (R = CONH 2 )
Occurs in various species of
vines of the Convolvulaceae
LSD [R = CON(C 2 H 5 ) 2 ]
A psychedelic drug.
Lysergic acid diethylamide, molecular formula C 20 H 25 N 3 O, also known as
LSD or LSD-25, is a semi-synthetic psychedelic drug, synthesized from the
natural precursor lysergic acid found in ergot, a grain fungus. It is a
colourless, odourless and mildly bitter compound. LSD produces altered
experience of senses, emotions, memories, time and awareness for 8 to 14 h.
Moreover, LSD may cause visual effects, e.g. moving geometric patterns,
‘trails’ behind moving objects and brilliant colours.
b-carbolines Alkaloids that possess a 9H-pyrid-[3,4-b]-indole skeleton
are called b-carboline alkaloids, and are found in several plants and
animals. The structure of b-carboline is similar to that of tryptamine, with
the ethylamine chain re-connected to the indole ring via an extra carbon
atom, to produce a three-membered ring structure. The biosynthesis of
b-carboline alkaloids follows a similar pathway to tryptamine. The
b-carbolines, e.g. harmine, harmaline and tetrahydroharmine, play an
important role in the pharmacology of the psychedelic brew ayahuasca.
Some b-carbolines, notably tryptoline and pinoline, are formed naturally in
the human body.
N
N
H
R'
R
N
H
R'
R''
R
N H
β-Carboline R = R' = H
Harmine R = Me, R' = OMe
1
2
3
4
5
6
7 8
Pinoline R = R'' = H, R' = OMe
Tetrahydroharmine R = Me, R'' = OMe
1
2
3
4
5
6
7 8
The major sources of b-carboline alkaloids with their medicinal or pharmacological properties are summarized below.
b-carboline alkaloids
Natural sources
Medicinal or pharmacological
properties
Harmine and harmaline Seeds of ‘harmal’ (Peganum CNS stimulant, acts by inhibiting
harmala) and
the metabolism of serotonin and
Banisteriopsis caapi
other monoamines
6.2 ALKALOIDS
299