6-Norlysergamide, N,N-diethyl-6-propyl · N,N-Diethylnorlysergamide, 6-propyl · 6-Propylnorlysergamide, N,N-diethyl · 9,10-Didehydro-6-propyl-N,N-diethylergoline-8β-carboxamide · 6-Propyl-nor-LSD
#51 PRO-LAD SYNTHESIS: To a solution of 66 mg (see under for its preparation) in 2 mL freshly distilled DMF under a nitrogen atmosphere, there was added 48 mg anhydrous K2CO3 and 41 mg propyl iodide. When TLC analysis indicated that the nor-LSD had been consumed (9 h) 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, cleared by filtration, and the solvent removed under vacuum. There was 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 N-propyl-nor-LSD (9,10-didehydro-6-propyl-N,N-diethylergoline-8β-carboxamide) as a crystalline product weighing 54 mg (72% yield dry). It had a mp of 87–88 °C.
DOSAGE: 100–200 micrograms, orally
DURATION: 6–8 hrs h
QUALITATIVE COMMENTS: (with 80 μg, orally) “I am aware of some change within a quarter hour, and then nothing more for quite a while. Certainly no visuals, almost like in that I am not really sure that this is even psychedelic—it does not have any of the flavor of . I want to try it at a higher dose some day.”
(with 135 μg, orally) “A strange development into a sort of paranoia place, without any reasonable dialog with my partner. A light-headed experience of a different kind, but we did not find common space. Not too comfortable—emotions are dull. At about mid-experience, considerable visuals came into play, with easy fantasy interlocking with music. Brüchner’s viola quintette in A Viola quintette in A produced extraordinary castle frames within castle walls. Emotions were reknit, food was good, and sleep fine at the 8th or 9th hour. It is not up to (if that is your standard) because it is basically not like LSD.”
(with 175 μg, orally) “This is an intellectually clear material, but it is a funny material. I am certainly at a +++ or at least I was a couple of hours ago. How does one describe PRO-LAD? It’s not-quite-this and not-quite-that sort of stuff. Or, to borrow from Winnie-the-Pooh, ‘It’s not at the bottom, and it’s not at the top (but this is the stair where I always stop)’—oh, never mind. I mean, I’m not sure how to categorize this material. It’s pleasant, it’s fine for fooling around, it’s good for humor, even excellent. It’s very good for clear thinking, although not cosmic-type particularly. It’s a sort of nice, comfortable, middle-American, July-Fourth-Picnic, apple-pie with ice cream sort of psychedelic, the kind that you can wrap up in gold and white striped paper for your youngest aunt, the one who likes to think she’s really a bit wild, you know—the kind of psychedelic that’s a bit much for your Dad or Mom, but it’s just jazzy enough to keep some younger relatives happy with you for a few months. However, I must tell you, kid, if you try to bring this to the Big Town, well… It is pretty much dropped off, now. Ah'm gonna lie mahself on down.”
EXTENSIONS AND COMMENTARY: With success in the preparation of the rather stable intermediate, any number of 6-substituted nor-LSD homologues and analogues can be synthesized. Simply use the appropriate alkyl bromide or alkyl iodide and the desired product will be in hand, after a modest amount of rather sophisticated purification at a micro scale. Several analogues are in the chemical literature, and some of them have been explored in direct comparison to . Here are a few examples:
N-Propynyl-nor-LSD (). Some activity at 160 μg. Active at 500 μg.
N-Butyl-nor-LSD (). Something at 500 μg.
As these substituents get heavier and heavier, the potency of the products drop by an order of magnitude or so, or even more. But here, in this N-substituted family, there is a fantastic research opportunity just waiting to be exploited, an exact parallel to the radio-iodine labeling of as was described in PiHKAL. It is a good guess that this position is one of good metabolic stability. So what about putting on a small group that can be labeled with a reasonably long-lived positron isotope? A specific proposal: N-(2-fluoroethyl)-nor-LSD with an 18F radio-label. The compound should be makable rather quickly (nor-LSD and 18FCH2CH2I in DMF with potassium carbonate) and cleanly purified by centrifugal chromatography, all well within the almost two hour half-life considerations of radio-fluorine. Here is a group that would be (in theory) intrinsic to the central activity of the end product, N-(2-(18F)fluoroethyl)-nor-LSD. The end compound could be synthesized, purified, characterized and sterilized quickly, allowing its brain localization and central dynamics to be determined by PET scanning, with virtually no risk to the subject. Let’s call it .
13 May 2016 · Creative Commons BY-NC-SA ·

About TiHKAL · info

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 align precisely with the printed version. Text appears to have been inserted, deleted, or changed at various points. Where the two are seen to diverge both the Erowid and print versions are given. Sharp-eyed readers are encouraged to report novel discrepancies.
As with PiHKAL, I’ve again attempted to reproduce the typographic style of the printed edition. I’ve again made minor changes to some chemical names in line with current nomenclature practice. Typically the change is little more than expanding a prefix or setting it in italics. The history page has further details.

Cautionary note

“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

Copyright notice

The copyright for Book I of TiHKAL has been reserved in all forms and it may not be distributed. Book II of TiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.

Ordering information

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.
Though 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,
Box 13675
Berkeley, CA 94701

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