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."
(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."
EXTENSIONS AND COMMENTARY: This is one of the several very potent
compounds in a large series of 5-alkylated analogues of nor-LSD. Most
of them proved to be less potent than LSD, and considerably less
dramatic. The Inderal mentioned in one of the comments is a trade name
for propranolol, an antihypertensive that reduces nervousness.
A comment is appropriate concerning the use of the prefix "nor," as in
the name of this material N-allyl-nor-LSD and of its immediate
precursor, nor-LSD. Its exact meaning is that there is an alkylated
nitrogen atom somewhere that has lost an alkyl group. The original
term is from the German phrase "N-ohne-Radical" meaning N (the
nitrogen) without the radical (meaning the alkyl group). The removing
of the N-methyl group of LSD to form the N-H counterpart is a text
book example of this usage. Unfortunately its use has slopped over to
embrace the removal of an alkyl group from a heteroatom of any
sort. Recently I learned of a metabolite of ibogaine that has lost a
methyl group from the indolic oxygen atom (a methoxy has become a
hydroxy) and the compound was called noribogaine. The correct term, to
retain the use of the parent ibogaine word in its name, would have
been desmethyl ibogaine. The removal of something is usually indicated
with a "de-" or a "des" prefix ahead of the item that has been lost,
as in deoxy (or desoxy) ribonucleic acid, DNA, which is ribonucleic
acid (RNA) missing an oxygen atom.
