SYNTHESIS: A solution of 3.6 g syringaldehyde (3,5-dimethoxy-4- hydroxybenzaldehyde) in 50 mL MeOH was combined with a solution of 3.7 g 85% KOH in 75 mL warm MeOH. This clear solution suddenly set up to crystals of the potassium salt, too thick to stir satisfactorily. To this suspension there was added 7.4 g ethyl iodide (a large excess) and the mixture was held at reflux temperature with a heating mantle. The solids eventually loosened and redissolved, giving a clear amber-colored smooth-boiling solution. Refluxing was maintained for 2 days, then all volatiles were removed under vacuum. The residue was dissolved in 400 mL H2O, made strongly basic with 25% NaOH, and extracted with 4×100 mL CH2Cl2. The pooled extracts were washed with saturated brine, and the solvent removed under vacuum to give 3.3 g of a pale amber oil which set up as crystals of 3,5-dimethoxy-4-ethoxybenzaldehyde with a mp of 47-48 °C. A small sample recrystallized from methanol had a mp of 48-49 °C.
A solution of 3.3 g 3,5-dimethoxy-4-ethoxybenzaldehyde in 25 mL nitroethane was treated with 0.5 g anhydrous ammonium acetate and heated on the steam bath for 36 h. The solvent/reagent was removed under vacuum giving a thick yellow-orange oil that was dissolved in two volumes hot MeOH. As this cooled, crystals appeared spontaneously, and after cooling in ice for a short time, these were removed by filtration and washed sparingly with cold MeOH, Air drying to constant weight provided 2.2 g 1-(3,5-dimethoxy-4-ethoxyphenyl)-2-nitropropene with a mp of 84-85 °C. The mother liquors, on standing overnight, deposited large chunks of crystalline material which was isolated by decantation, ground up under a small amount of methanol, then recrystallized from 60% EtOH. A second crop of 0.7 g of the nitrostyrene was thus obtained, as canary-yellow crystals with a mp of 83-85 °C.

A solution of 2.7 g 1-(3,5-dimethoxy-4-ethoxyphenyl)-2-nitropropene in 20 mL anhydrous THF was added to a suspension of 2.0 g LAH in 150 mL warm THF. The mixture was held at reflux for 48 h. After stirring at room temperature for another 48 h, the excess hydride was destroyed by the addition of 2.0 mL H2O in 10 mL THF, followed by 2.0 mL 15% NaOH and then an additional 6.0 mL H2O. The inorganic salts were removed by filtration, and the filter cake washed with THF. The combined mother liquor and washings were stripped of solvent under vacuum leaving a yellow oil with some inorganic salts still in it. This was dissolved in 300 mL CH2Cl2, washed with dilute NaOH, and extracted with 3×150 mL 1 N HCl. The pooled extracts were washed once with CH2Cl2 made basic with 25% NaOH, and extracted with 3×100 mL CH2Cl2. The combined organics were washed with saturated brine, and the solvent removed under vacuum to yield about 2 mL of a colorless oil. This was dissolved in 10 mL IPA, neutralized with concentrated HCl (10 drops were required), and diluted with 125 mL anhydrous Et2O. The slight cloudiness gradually became the formation of fine white crystals. After standing at room temperature for 2 h, these were removed, Et2O washed, and air dried. There was thus obtained 1.9 g of 3,5-dimethoxy-4-ethoxyamphetamine hydrochloride (3C-E) as brilliant white crystals.

DOSAGE: 30 – 60 mg.

DURATION: 8 – 12 h.

QUALITATIVE COMMENTS: (with 40 mg) It developed into a strange and indefinable something. It is unworldly. I am very much in control, but with an undertone of unreality that is a little reminiscent of high doses of LSD. If there were a great deal of sensory input, I might not see it. And if I were in complete sensory quiet I would miss it, too. But just where I am, I can see it. Eerie state of awareness. And by the 8th hour I am sober, with no residue except for some slight teeth clenching, and pretty much disbelieving the whole thing.

(with 60 mg) Visuals very strong, insistent. Body discomfort remained very heavy for first hour. Sense of implacable imposition of something toxic for a while. I felt at the mercy of uncomfortable physical effects–faint or pre-nausea, heavy feeling of tremor (although tremor actually relatively light) and general dis-ease, un-ease, non-ease. Kept lying down so as to be as comfortable as possible. Fantasy began to be quite strong. At first, no eyes closed images, and certainly anti-erotic. 2nd hour on, bright colors, distinct shapes–jewel-like–with eyes closed. Suddenly it became clearly not anti-erotic. That was the end of my bad place, and I shot immediately up to a +++. Complex fantasy which takes over–hard to know what is real, what is fantasy. Continual erotic. Image of glass-walled apartment building in mid-desert. Exquisite sensitivity. Down by ? midnight. Next morning, faint flickering lights on looking out windows.

EXTENSIONS AND COMMENTARY: This is an interesting closing of the circle. Although mescaline launched the entire show, the first half could be called the amphetamine period, with variations made on all aspects of the molecule except for that three-carbon chain. And it was found that the 4-substitution position was of paramount importance in both the potency and the quality of action of a compound. Then, looking at the long-ignored chain, lengthening it by the addition of a carbon atom eliminated all psychedelic effects and gave materials with reduced action. The action present was that of an antidepressant. But removing a carbon atom? This returned the search to the world of mescaline, but with the knowledge of the strong influence of the 4-position substituent. The two-carbon side-chain world was rediscovered, principally with 2C-B and 2C-D, and the 4-ethoxy-analogue of mescaline, E. This second half of the show could be called the phenethylamine period. And with compounds such as 3C-E which is, quite simply, Escaline (or E) reextended again to a 3-carbon chain amphetamine, there is a kind of satisfying closure. A fascinating compound, but for most subjects a little too heavy on the body.

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