Methallylescaline · 3,5-Dimethoxy-4-methallyloxyphenethylamine
SYNTHESIS: To a solution of 5.8 g of homosyringonitrile (see under 2CO3. The suspension was kept at reflux by a heating mantle, with effective stirring. After 6 h an additional 4.0 mL of methallyl chloride was added, and the refluxing was continued for an additional 36 h. The solvent and excess methallyl chloride was removed under vacuum and the residue was added to 400 mL H2O. This solution was extracted with 3×75 mL CH2Cl2. The extracts were pooled, washed with 2×50 mL 5% NaOH, and the solvent removed to provide a dark brown oil. This was distilled at 120–130 °C at 0.4 mm/Hg to provide 6.1 g of 3,5-dimethoxy-4-methyallyloxyphenylacetonitrile as a lemon-colored viscous oil. Anal. (C14H17NO3) C,H.
A suspension of 4.2 g LAH in 160 mL anhydrous THF under He was stirred, cooled to 0 °C, and treated with 2.95 mL of 100% H2SO4 added dropwise. This was followed by the addition of 6.0 g of 3,5-dimethoxy-4-methallyloxyphenylacetonitrile dissolved in 10 mL anhydrous THF, at a slow rate with vigorous stirring. The reaction mixture was held at reflux on the steam bath for 0.5 h, brought back to room temperature, and the excess hydride destroyed with IPA. Sufficient 15% NaOH was added to convert the formed solids to a loose, granular texture, and the entire mixture filtered and washed with THF. The filtrate and washings were pooled, the solvent removed under vacuum, and the residue added to 500 mL dilute HCl. This solution was washed with 2×50 mL CH2Cl2, made basic with aqueous NaOH, and extracted with 3×75 mL CH2Cl2. The extracts were pooled, the solvent removed under vacuum, and the residual pale amber oil distilled at 120–130 °C at 0.3 mm/Hg to provide 1.5 g of a white oil. This was dissolved in 8.0 mL of IPA and neutralized with 25 drops of concentrated HCl. The addition of 40 mL of anhydrous Et2O with stirring produced, after a few moments delay, a spontaneous crystallization of 3,5-dimethoxy-4-methallyloxyphenethylamine hydrochloride (MAL) as fine white needles. After standing overnight these were removed by filtration, washed with an IPA/Et2O mixture, then with Et2O, and allowed to air dry to constant weight. The product weighed 1.1 g, and had a mp of 153–154 °C. Anal. (C14H22ClNO3) C,H.
DOSAGE: 40–65 mg.
DURATION: 12–16 h.
QUALITATIVE COMMENTS: (with 45 mg) “Too much overload. I am surrounded with unreality. I do not choose to repeat the experiment.”
(with 45 mg) “I am basically favorably impressed. I believe the initial discomfort would be alleviated by taking two 30 milligram doses separated by an hour.”
(with 45 mg) “Much too much too much. There are shades of what might become amnesia. I am losing immediate contact. I will not repeat.”
(with 50 mg) “A good level. I found myself totally caught up in the visual theater. Although I had trouble sleeping, I would willingly repeat the experiment at the same level.”
(with 60 mg) “Extremely restless. Am very impressed with all the activity. But if I repeated it would be at a lower dose.”
(with 60 mg) “Friendly territory. There is much kaleidoscopic ‘neon’ colors. Eyes closed very active. Eyes open there is considerable visual distortions seen in melted wax. Faces are distorted (friendly) but the sinister is not far away.”
(with 65 mg) “Completely involved—good psychedelic state—visual entertainment with alternation (i.e., depth and movement) at the retinal level—detail in watercolors. Later in the experience (the 8 hour point) easy childhood memory recall.”
(with 65 mg) “Beautiful. To a +2 by the 1st hr and continued climbing. Intense +3 within 2 hrs. Quite strong body. Diuretic. Fantasy, imagery, erotic. Way up, good connections between parts of self. Slight slowing of pulse in 7th to 8th hour. Excellent solid sleep with strong, clear, balancing dreams. But not until after 12 hrs.”
EXTENSIONS AND COMMENTARY: This testimony can be accurately described as a mixed bag!
This base, MAL, lies as a hybrid of two other compounds,
Speaking of generalization, I am glad that there are always exceptions. Some years ago, I had a most difficult experience with a strain of marijuana that was known by the name of DRED. The only word that I can use to describe my response to it is to say that I felt I had been poisoned. From this I warned myself to beware (and to believe in) whatever common name a drug might have been given. Fortunately, MAL did not live up to its name (at least for me), although some of the experimental subjects might disagree!
One additional compound was suggested by these parallels. Each of these three drugs can be viewed as having a negative something hanging out a-ways from the molecular center. With
The name methallylescaline actually is completely unsound. There is no union of a methallyl with an
13 May 2016 · · Isomer Design
About PiHKAL · info
This version of Book II of PiHKAL is based on the Erowid online version, originally transcribed by Simson Garfinkle and converted into HTML by Lamont Granquist. I drew also on “Tyrone Slothrop’s” (Unfinished) Review of PIHKAL to enumerate the many analogues mentioned in PiHKAL but not described at length. Many, many others have since been added.
I have tried here to expunge any artifacts introduced by the earlier transcriptions and restore the typographic niceties found in the printed edition. I’ve also 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.
“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.”
The copyright for Book I of PiHKAL has been reserved in all forms and it may not be distributed. Book II of PiHKAL may be distributed for non-commercial reproduction provided that the introductory information, copyright notice, cautionary notice and ordering information remain attached.
PiHKAL is the extraordinary record of the authors’ years exploring the chemistry and transformational power of phenethylamines. 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 PiHKAL 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.
PiHKAL (ISBN 0-9630096-0-5) is available for US$24.50 (plus $10 domestic first-class shipping) from Transform Press.Transform Press,
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