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Book II of TiHKAL: The Continuation, by Alexander & Ann Shulgin #12: ETH-LAD
#12 ETH-LAD: 6-Norlysergic acid, 6,N,N-triethylamide; 6-Norlysergamide, 6,N,N-triethyl; 6,N,N-Triethyl-6-norlysergamide; N-(6)-Ethylnorlysergic acid, N,N-diethylamide; 9,10-Didehydro-N,N,6-triethylergoline-8β-carboxamide; N-Ethyl-nor-LSD

#12 ETH-LAD SYNTHESIS: A solution of 0.323 g of lysergic acid diethylamide (LSD) in 10 mL CHCl3 was diluted with 70 mL CCl4 and added over the course of 1 h to a refluxing solution of 0.44 g BrCN in 30 mL CCl4 in a nitrogen environment and protected from direct illumination. After the addition was complete, the reaction was held at reflux for an additional 6 h, allowed to cool, and washed with an aqueous solution of tartaric acid. The organic solvents were removed under vacuum, and the residue dissolved in 70 mL CH2Cl2 and washed with 50 mL additional tartaric acid solution. The CH2Cl2 phase was dried with anhydrous Na2SO4, and after removal of the drying agent by filtration, the solvent was removed under vacuum. The residue was cleaned up by passage through 5 g of neutral alumina being eluted with a 9:1 CH2Cl2/MeOH mixture. Centrifugal chromatography with alumina and CH2Cl2, under a nitrogen atmosphere containing ammonia, provided a solid product. After recrystallization from IPA or EtOAc, there was obtained 0.24 g (71%) 6-cyano-nor-LSD (9,10-didehydro-N,N-diethyl-6-cyanoergoline-8β-carboxamide) with a mp of 190–191 °C.

To a solution of 0.33 g 6-cyano-nor-LSD in a mixture of 3 mL acetic acid and 0.6 mL H2O, under a nitrogen atmosphere, there was added 0.6 g powdered zinc and the stirred mixture was heated for 4 h with an external oil bath maintained at 130 °C. The reaction mixture was cooled to ice-bath temperature, diluted with an additional 3 mL H2O, and brought to an alkaline pH with the addition of concentrated NH4OH. This suspension was extracted with CH2Cl2 (5×10 mL), the pooled extracts dried with anhydrous Na2SO4, and the solvent removed (after filtration) under vacuum providing a tan solid. Centrifugal chromatography (with alumina and a 9:1 CHCl3/MeOH elution solvent under an ammonia vapor environment), followed by the removal of the solvent under vacuum, yielded a solid product which was recrystallized from EtOAc/hexanes. There was thus obtained 0.19 g (61%) of tan crystals of nor-LSD (9,10-didehydro-N,N-diethylergoline-8β-carboxamide) with a mp of 196–198 °C (dec).

To a solution of 66 mg nor-LSD in 2 mL freshly distilled DMF under a nitrogen atmosphere, there was added 48 mg anhydrous K2CO3 and 38 mg ethyl iodide. When TLC analysis indicated that the nor-LSD had been consumed (4 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. The residue 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-ethyl-nor-LSD (9,10-didehydro-N,N,6-triethylergoline-8β-carboxamide) as a white crystalline product which weighed 66 mg (61%) after drying. It had a mp of 108–110 °C and an [α]D +40.5° (c 0.46, EtOH).

DOSAGE: 40 to 150 micrograms, orally

DURATION: 8–12 hrs h

QUALITATIVE COMMENTS: (with 20 μgs, orally) “This has a very real effect at this level, whereas I have no response at all from LSD at 20 mikes.”

(with 50 μgs, orally) “This is already coming on in fifteen minutes, and is completely developed in another hour. Very few visual changes or distortions but easy eyes-closed imagery. Pretty much out after ten hours; it was a good, repeatable experiment.”

(with 60 μgs, orally) “In about an hour or so, gentle movements of the house plants were noted. The walkway of the painting above the fireplace changed as if the sunny spots were moving ahead. The visual aspects became more LSD-like after a couple more hours, though in a very gentle way. The spider windowpane looked three-dimensional: at first I thought the windows were double-paned, but they were not. Stones, rocks and glass had a magical look to them, but tree bark looked like tree bark. Occasionally, a dark streak (spot) would go through the visual field and a page of a book would move sharply without effort. These aspects were very pleasant to me.”

(with 75 μgs, orally) “I am up to a ++ within the hour and am feeling lazy. It is very diuretic and certainly not anorexic. Have been dieting strenuously for the past 4 days, but could definitely be interested in food. Also a decongestant. Body feels balanced. Thinking easy. Concepts easy to follow through. Mind and feelings together as should be. Definitely a plus two, no further. I wonder if it would be possible, at any level, to attain that blurring of boundaries that is the plus three at its best? My mind was at all times capable of realistic and down-to-earth thought, this is not a material that will allow you to float two inches off of the floor.”

(with 100 μgs, orally) “It sort of sneaks up on you. Certainly not the push of LSD and, sadly, not the sparkle either. Possible time slowing. Easy sleep and no price to pay the next day.”

(with 150 μgs, orally) “Extraordinary experience, none of the demands of LSD, just a completely together trip. There were hints of tummy discomfort and some chills early in the trial, but they were trivial and quickly passed. Fine music, and fine sex.”

EXTENSIONS AND COMMENTARY: What a remarkable compound. It is a little more potent than LSD, but much less aggressive in the nature of its action. There appears to be little if any of the push, the taking control nature, of LSD and a greatly modified degree of visual distortion. The warmth and humor appears to be there, but all seems more allowing rather than demanding.

I suspect that this material is rather unstable in solution, even as the tartrate in dilute saline, although I cannot guess why that should be. A few months in the dark, at zero degrees and in the absence of air, led to a very real drop in potency, measured by a control assay of a freshly made solution of the same nominal concentration.

What a difference a single atom makes, an ethyl rather than a methyl group at the ring-D nitrogen atom. The absence of any group there (a hydrogen atom rather than the methyl group of LSD or the ethyl group of ETH-LAD) is nor-LSD, the synthetic intermediate mentioned in the preparation recipe above. It has no activity at all even at a half a milligram. The allyl group at this location gives AL-LAD and the propyl group is PRO-LAD, and both of these are active and have their own individual entries.

Updated 30 March 2012 · This work is licensed under a Creative Commons Attribution-NonCommercial-ShareAlike 4.0 International License ·

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 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.

Cautionary Note

“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

Copyright Notice

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.

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.

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,
Box 13675
Berkeley, CA 94701

510 · 934 · 4930 (voice)
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