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 (5×5 mL) and the pooled extracts dried over anhydrous Na2SO4 which was remove by filtration. The filtrate removed under vacuum leving leaving 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 [α]D +41.8° (c 0.44, EtOH).
DOSAGE: 80–160 micrograms, orally
DURATION: 6–8 h.
QUALITATIVE COMMENTS: (with 50 μg, orally) “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, orally) “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, orally) “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, orally) “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, orally) “I took 160 ug micrograms at 11 a.m. 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, orally) “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, orally) “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 analogues of nor-LSD alkylated on the nitrogen at the six-position. 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.
Hoffman, AJ; Nichols, DE. Synthesis and LSD-like discriminative stimulus properties in a series of N(6)-alkyl norlysergic acid N,N-diethylamide derivatives. J. Med. Chem., 1 Jan 1985, 28 (9), 1252–1255. 583 kB. doi:10.1021/jm00147a022
Watts, VJ; Mailman, RB; Lawler, CP; Neve, KA; Nichols, DE. LSD and structural analogs: Pharmacological evaluation at D1 dopamine receptors. Psychopharmacology, 1 Jan 1995, 118 (4), 401–409. 1367 kB. doi:10.1007/BF02245940
This version of Book II of TiHKAL is based on the Erowid online version created by Bo Lawler with the help of Erowid, from content generously provided in electronic format by the Authors.
The Erowid online version does not always match the printed version—I’ve found over 300 inconsistencies. Text has been inserted, deleted, or changed at various points. Perhaps the Erowid version was created from an earlier (or later) draft? In several places the Erowid version is plainly wrong; elsewhere it’s a tougher call. I don’t claim to have found every discrepancy; in those cases I have found, both the Erowid and print versions are given and marked as such. I would be grateful if any sharp-eyed readers would report any I have missed.
As with PiHKAL • info, I’ve again attempted to reproduce the typographic style of the printed edition. And again, I’ve also made minor changes to some chemical names in line with current nomenclature practice, and in the hope of aligning with more readers’ searches. Typically the change is little more than expanding a prefix and setting it in italics. The errata and changes page has further details.
“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.”
Alexander T. Shulgin
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-commerical reproduction provided that the introductory material, copyright notice, cautionary notice and ordering information remain attached.
TiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of tryptamines. This book belongs in the library of anyone seeking a rational, enlightened and candid perspective on psychedelic drugs.
Although Sasha and Ann have put Book II of TiHKAL in the public domain, available to anyone, I strongly encourage you to buy a copy. We owe them—and there’s still nothing quite like holding a real book in your hands.
TiHKAL (ISBN 0-9630096-9-9) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.Transform Press,