Tryptamines
N
NH 2
H
Tryptamine
Moschamine, moschamindole,
psilocybin and serotonin
Ergolines
N
N
H
H
Ergoline
Ergine, ergotamine and
lysergic acid
b-carbolines
N
N
H
β-Carboline
Emetine, harmine and reserpine
Indolizidine
N
Indolizidine
Swainsonine and castanospermine
Isoquinoline
(Tyrosine derived)
N
Isoquinoline
Codeine, berberine, morphine,
papaverine, sanguinarine and
thebaine
Macrocyclic spermines
and spermidines
N
N
N
O
H
H
H
Spermine
Celabenzine
Norlupinane
(Lysine derived)
N
Norlupinane
Cytisine and lupanine
Phenethylamine
(Phenylalanine derived)
NH 2
Phenylethylamine
Ephedrine and mescaline
Purine
N
N
N
N
H
Purine
Caffeine, theobromine
and theophylline
Pyridine and
N
N
H
Pyridine Piperidine
Arecoline, coniine, nicotine,
(Nicotinic acid derived)
piperine, sparteine and trigonelline
Class/structural types
Generic structure
Examples
290
CH6 NATURAL PRODUCT CHEMISTRY
N
NH 2
H
Tryptamine
Moschamine, moschamindole,
psilocybin and serotonin
Ergolines
N
N
H
H
Ergoline
Ergine, ergotamine and
lysergic acid
b-carbolines
N
N
H
β-Carboline
Emetine, harmine and reserpine
Indolizidine
N
Indolizidine
Swainsonine and castanospermine
Isoquinoline
(Tyrosine derived)
N
Isoquinoline
Codeine, berberine, morphine,
papaverine, sanguinarine and
thebaine
Macrocyclic spermines
and spermidines
N
N
N
O
H
H
H
Spermine
Celabenzine
Norlupinane
(Lysine derived)
N
Norlupinane
Cytisine and lupanine
Phenethylamine
(Phenylalanine derived)
NH 2
Phenylethylamine
Ephedrine and mescaline
Purine
N
N
N
N
H
Purine
Caffeine, theobromine
and theophylline
Pyridine and
N
N
H
Pyridine Piperidine
Arecoline, coniine, nicotine,
(Nicotinic acid derived)
piperine, sparteine and trigonelline
Class/structural types
Generic structure
Examples
290
CH6 NATURAL PRODUCT CHEMISTRY
