6-NORLYSERGIC ACID, 6-ALLYL-N,N-DIETHYLAMIDE; 6-NORLYSERGAMIDE,
6-ALLYL-N,N-DIETHYL; N,N-DIETHYLNORLYSERGAMIDE, 6-ALLYL; N-(6)-ALLYLNORLYSERGIC
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
(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
(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
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.
The first half of the book is kept under strict copyright, however part 2 has been officially released for non-commercial use by the authors under the conditions described below. Each compound from part two will be separately hardlinked and noded. Unlike the hardlinks in the PiHKAL node, I have chosen to hardlink the common abbreviation or common name rather than the long chemical name. I believe this is friendlier to E2 noders and the search box. I mean, honestly, who is going to look for melatonin under n-acetyl-5-methoxy-tryptamine?
The Copyright for Part 1 of TiHKAL has been reserved in all forms and it may not be distributed. Part 2 of TiHKAL may be distributed for non-commercial reproduction provided that this notice, the cautionary notice and the ordering information are retained.
Cautionary Note - Please read before proceeding
I would like to take a moment to reiterate that at the present time restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings..... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herein, without being familiar with that drug's action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law.
If you are seriously interested in the chemistry contained in these files, you can order the books TIHKAL: The Continuation, and PIHKAL: A Chemical Love Story by Ann and Alexander Shulgin. These books are available from:
P.O. Box 13675
Berkeley, CA 94712
Call or write to get ordering information.