A.A. Shulgin - TiHKAL [ENG].pdf

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TiHKAL: The Continuation, by Alexander and Ann Shulgin
Tryptamines i Have Known
And Loved:
The Chemistry Continues
By Alexander and Ann Shulgin
trypt-amine \ 'trip-ta-,men \ n. [tryptophan fr. tryptic, fr. trypsin, fr. Gk. tryein, to
wear down (from its occurence in pancreatic juice as a proteolytic enzyme) + amine
fr. NL ammonia] 1: A naturally occurring compound found in both the animal and
plant kingdoms. It is an endogenous component of the human brain. 2: Any of a
series of compounds containing the tryptamine skeleton, and modified by chemical
constituents at appropriate positions in the molecule.
INDEX TO THE TRYPTAMINES
#
SUBSTANCE
CHEMICAL NAME
1
AL-LAD
6-Allyl-N,N-diethyl-NL
2
DBT
N,N-Dibutyl-T
 
141576079.003.png
3
DET
N,N-Diethyl-T
4
N,N-Diisopropyl-T
5
5-Methyoxy- alpha -methyl-T
6
DMT
N,N-Dimethyl-T
7
2, alpha -Dimethyl-T
8
alpha ,N-Dimethyl-T
9
DPT
N,N-Dipropyl-T
10
N-Ethyl-N-isopropyl-T
11
alpha -Ethyl-T
12
6,N,N-Triethyl-NL
13
3,4-Dihydro-7-methoxy-1-methyl-C
14
7-Methyoxy-1-methyl-C
15
N,N-Dibutyl-4-hydroxy-T
16
N,N-Diethyl-4-hydroxy-T
17
N,N-Diisopropyl-4-hydroxy-T
18
N,N-Dimethyl-4-hydroxy-T
19
N,N-Dimethyl-5-hydroxy-T
20
N,N-Dipropyl-4-hydroxy-T
21
N-Ethyl-4-hydroxy-N-methyl-T
22
4-Hydroxy-N-isopropyl-N-methyl-T
23
4-Hydroxy-N-methyl-N-propyl-T
24
4-Hydroxy-N,N-tetramethylene-T
25
A complexly substituted-T
26
LSD
N,N-Diethyl-L
27
MBT
N-Butyl-N-methyl-T
28
N,N-Diisopropyl-4,5-methylenedioxy-T
29
N,N-Diisopropyl-5,6-methylenedioxy-T
30
N,N-Dimethyl-4,5-methylenedioxy-T
31
N,N-Dimethyl-5,6-methylenedioxy-T
32
N-Isopropyl-N-methyl-5,6-methylenedioxy-T
33
N,N-Diethyl-2-methyl-T
34
2,N,N-Trimethyl-T
35
N-Acetyl-5-methoxy-T
36
N,N-Diethyl-5-methoxy-T
37
N,N-Diisopropyl-5-methoxy-T
38
5-Methoxy-N,N-dimethyl-T
39
N-Isopropyl-4-methoxy-N-methyl-T
40
N-Isopropyl-5-methoxy-N-methyl-T
41
5,6-Dimethoxy-N-isopropyl-N-methyl-T
141576079.004.png
42
5-Methoxy-N-methyl-T
43
5-Methoxy-N,N-tetramethylene-T
44
6-Methoxy-1-methyl-1,2,3,4-tetrahydro-C
45
5-Methoxy-2,N,N-trimethyl-T
46
N,N-Dimethyl-5-methylthio-T
47
N-Isopropyl-N-methyl-T
48
alpha -Methyl-T
49
NET
N-Ethyl-T
50
NMT
N-Methyl-T
51
6-Propyl-NL
52
N,N-Tetramethylene-T
53
T
Tryptamine
54
7-Methoxy-1-methyl-1,2,3,4-tetrahydro-C
55
alpha ,N-Dimethyl-5-methoxy-T
141576079.005.png
#1. AL-LAD
6-NORLYSERGIC ACID, 6-ALLYL-N,N-DIETHYLAMIDE; 6-NORLYSERGAMIDE, 6-ALLYL-
N,N-DIETHYL; N,N-DIETHYLNORLYSERGAMIDE, 6-ALLYL; N-(6)-ALLYLNORLYSERGIC
ACID, N,N-DIETHYLAMIDE; 9,10-DIDEHYDRO-6-ALLYL-N,N-DIETHYLERGOLINE-8b-
CARBOXAMIDE
SYNTHESIS: To a solution of 66 mg nor-LSD (see under
ETH-LAD for its preparation) in 2 mL freshly distilled DMF
under a nitrogen atmosphere, there was added 48 mg
anhydrous K2CO3 and 30 mg allyl bromide. When TLC
analysis indicated that the nor-LSD had been consumed
(30 min) all volatiles were removed under a hard vacuum.
The residue was solubilized in CHCl3 (5x5 mL) and the
pooled extracts dried over anhydrous Na2SO4 which was
remove by filtration. The filtrate removed under vacuum
leving a residual white solid. This was separated into two
components by centrifugal chromatography (alumina,
CH2Cl2, nitrogen and ammonia atmosphere), the first of
which was the major product. After removal of the solvent,
this was dissolved in hot benzene, filtered and cooled. The
addition of hexane prompted crystallization of AL-LAD (N-
allyl-nor-LSD) as a white crystalline product weighing 66
mg, yield 88%. It had a mp of 88-90°C and an [a]D + 41.8
(c 0.44, EtOH).
DOSAGE : 80 - 160 micrograms
DURATION : 6 - 8 h.
QUALITATIVE COMMENTS : (with 50 µg) "I am aware in twenty minutes, and am into a
stoned place, not too LSD like, in another hour. I would very much like to push higher, but that
is not in the cards today and I must acknowledge recovery by hour eight."
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(with 80 µg) "I had a mild effect, although the doors to my repressed feelings somehow really
become opened up. There was nothing transcendental here, but there were moments where I
felt a conscious separation from the world about me. None of the profound meanings that I had
hoped to have explained were explained."
(with 150 µg) "I felt it in less than a quarter hour, and was shooting up past a +++ in another
quarter hour. Fast. Just like LSD but without the vaguely sinister push. A little time slowing,
randy, no body disturbance. Dropping at six hours and totally tired and going to sleep at twelve
hours. I will repeat."
(with 150 µg) "Simply beautiful. Erotic and music absorption after second hour. Clear thinking
with superb imagery and good interpretation. Easy, gentle sleeping. Next day -- serene, clear-
thinking peacefulness. One of the best materials ever."
(with 160 µg) "I took 160 ug at 11 AM on an empty stomach and lay down to listen to a hypnotic
relaxing tape, with eye shades and headphones. The onset was very gradual over two or three
hours. There was some visual distortion similar to LSD, but mild. I decided that this was about
as intense as it was going to get, so I lay down in the living room with the others. The
experience continued to intensify over the next hour in intermittent waves. I had to verify that I
was actually in a physical room rather than in the music I was hearing. There was never any
fear or panic, but I chose to retreat to a private place for the next couple of hours. Soon I
started to feel worse and I tried to gain some insight and relief from my negative attitude. I
prayed, and I cried, and I began to feel calmer and had more positive thoughts as to how to
deal with the others, but I was still afraid to go out into the group. I was afraid that my
hopelessness would bother them but I eventually went back out at about the five hour point and
the rest of the day was spent pleasantly and smoothly. I took 2.5 g of L-tryptophan to sleep,
and I slept well, waking twice."
(with 160 µg) "I pretreated myself with 40 milligrams of inderal 40 minutes beforehand, took the
AL-LAD, and went to bed with eye-shades and ear-phones. There was a very slow onset. The
effects were best described as very short bursts of loss of contact with my body, which became
increasingly intense and frequent as things progressed. It became really trippy, like acid. There
were no visuals with my eyes closed, but when I removed my eye-shades the floors were
melting, and the wall patterns and the wood ceiling really flowed. My body felt very blob-like,
and I had to get help from my sitter to get up so I could pee. I was very affected by music.
There was a very long down-ramp, with physical excitation appearing to linger longer than
psychic excitation. Pretty much out of it by 12 hours and I felt well the next day."
(with 200 µg) "This was taken on the tail end (seventh hour) of an MDMA experience. I felt it
quickly, but it never got to a super level. Complicated erotic, good talking, looked pretty stoned,
and yet I still had cognitive integrity."

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