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#99 MAL


[3D .mol structure]
SYNTHESIS: To a solution of 5.8 g of homosyringonitrile (see under ESCALINE for its preparation) in 50 mL of acetone containing 100 mg of decyltriethylammonium iodide there was added 7.8 mL methallyl chloride followed by 6.9 g of finely powdered anhydrous K2CO3. 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 3x75 mL CH2Cl2. The extracts were pooled, washed with 2x50 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-methallyloxy-phenylacetonitrile 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 2x50 mL CH2Cl2, made basic with aqueous NaOH, and extracted with 3x75 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 sur-rounded 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, AL and CPM. It is an olefin (as is AL) which means that it has a place of unsaturation in its structure. And it is an isostere of CPM which means that the carbon atoms are all in the same location, but just the connecting electrons (called the chemical bonds) are in different places. Actually there is yet a third compound in this same picture, called PROPYNYL. And yet, although all of them have extremely close structural similarities, there are such great differences in action that one does not dare to generalize. CPM leads largely to fantasy, MAL largely to visual imagery, AL is twice as potent as either of these but it doesn't show either effect, and PROPYNYL is almost without any action at all.

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 AL and MAL, this is the olefin double bond. With CPM this is a very strained three-member ring. What about an oxygen? The reaction between homosyringonitrile and methoxyethyl chloride produced the precursor to such a product (3,5-dimethoxy-4-(2-methoxyethoxy)-phenethylamine) but the yield was so bad that the project was abandoned. This same grouping has successfully been put into the 4-position of the sulfur-containing analog, and the result (2C-T-13) has proved to be quite a potent and interesting material. Maybe someday hang a sulfur atom out there at the end of that chain.

The name methallylescaline actually is completely unsound. There is no union of a methallyl with an escaline. What is really there is not an escaline at all, but rather a mescaline with a 2-propene attached to the methyl of the methoxy on the 4-position. There is no way of naming the thing in that manner, so the only logical solution is to take off the methyl entirely, and then put the methallyl on in its place. The name of this would then be 4-methylallyldesmethylmescaline. That would have received the abbreviation MAD which would have been even more difficult to deal with. MAL is preferable.

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