HO Me Me

COOH
CHO H
NH2 NH2 OGlu OGlu
+ H
O OH
N O Me Me
N MeO2C MeO2C
H H

Tryptamine Loganine Geraniol

Tryptophane Secologanine

7
5

2 3 NH 18
N
H H H
15 OGlu
20
21
H
O
MeO2C 17

7
5

2 3 NH
N 21
H 20
15

H
18

N(4) + C(21)
17

C(17) + C(20)
C(2) + C(3) C(2) + C(3) 7
C(2) + C(3) N(4) + C(21)
5

C(15) C(16)
7 7 7
5 5 5

3 NH 2 3 NH N 2 3 NH 18
C(2)N + C(16)
5

N 5 N 21
20
18
N 2
21 N 17 H 3 21 N 2
21 3
H H 15
20
H 3 15
20 7 7
15 15 20 20
21 15
H H H 2
16 15
16
17
18 N 17
2
18
20 H 18 N 16
17 21 17
17
18 H

7
5
7
7 5
5
3 NH 18
N 2 3 N N 2
7
N 2 3 N 17 H 5
3
H
21
H 15
20 5 N
20 15
15
H
21
21 N 15
H 18
H
O N 2 3 7
21
20

18 20 17 20
21
15 17
17
16 2
17 N 16
18
H
18

5
5

21
N N 5
3 3 21
7 3 7
7 20
N 18 5
5 N 21
20
18
7 20 18
21
16 2 16 20 3 N 15
2
16
N 2 15 N N 2 21 7
3
N 15 H H H 18 H 17 15
H 17 15
20
2
17

17
16 N 16
17 H
18