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5-MeO-DALT
Entry from a forthcoming book
by Alexander & Ann Shulgin
Aug 2004
#xxx 5-METHOXY-DALT; TRYPTAMINE, n,n-DIALLYL-5-METHOXY; N,N-DIALLYL-5-METHOXYTRYPTAMINE; INDOLE, 3-[2-(DIALLYLAMINO)ETHYL]-5-METHOXY; 3-[2-(DIALLYLAMINO)ETHYL]-5-METHOXYINDOLE

SYNTHESIS : To a solution of 2.08 g. 5-methoxytryptamine (11 mM) in 25 mL tetrahydrofuran, there was added 5.2 mL diisopropylethylamine and 2.7 mL allyl iodide (30 mM). The slightly exothermic reaction became cloudy in about a minute, and was allowed to stir at ambient temperature for 12 h. The lower phase had become quite solid and chunky. The upper phase was decanted from the solids, which were then rinsed with 2x10 mL portions of ether. The combined decantation and ether washes were stripped of solvent on the rotary evaporator to yield a white solid residue with a brown oil contamination. This was dissolved in dilute aq. HCl, washed with 2x50 mL methylene chloride (which removed the color), made basic with dilute aq. NaOH, and extracted with 2x50 mL methylene chloride. The extracts were pooled and taken to dryness on the rotary evaporator to give 0.67 g of a tan oil that crystallized. This was distilled at the KugelRohr to give a colorless fraction with b.p. 165-175 degrees C at 40 microns which weighed 0.53 g. and set up immediately as a white crystalline mass with a m.p. 98-101 degrees C. This was dissolved in 10 mL warm isopropanol and treated with 14 drops of conc. HCl. With scratching and stirring, crystals began to form slowly. With vigorous stirring, 10 mL of anh. ether were added dropwise, producing a heavy crystalline mass. This was removed by filtration, washed with ether, and air dried to constant weight. There was thus obtained 0.51 g 5-MeO-DALT hydrochloride with a m.p. of 163-164 degrees C. The infra-red spectrum of the free base contained the following major peaks (cm-1): 796, 923, 939, 1009, 1033, 1061, 1115. For the hydrochloride salt (cm-1): 809, 829, 837, 946, 1002, 1083, 1180. The GCMS indicated a purity >99% with the following fragments (m/z): 110 (diallylaminomethylene fragmen, 100%) 117 (26%), 145 (35%), 160 (5-methoxyindolemethylene fragment, 60%), 174 (8%), 229 (2%) and 270 (parent, 4%).

The solids that remained after the above decantation and ether washing were thoroughly ground up under 10 mL methylene chloride and removed by filtration to give 2.73 g. of fine white crystals of 5-methoxy-N,N,N-triallyltryptammonium iodide. The infra-red spectrum contained the following major peaks (cm-1): 818, 860, 952, 998, 1085, 1188. To a solution of 1.1 g. phenyl mercaptan (10 mM) in 20 mL acetone there was added 0.4 g. 50% W/W aq. NaOH followed by 2.2 g of this quaternary salt, and the mixture was held at reflux on the steam-bath for 18 hrs. After removal of the volatiles on the rotary evaporator, the residue brown solids were suspended in 75 mL water which was made acidic by the addition of aqueous HCl. This was washed with 3x40 mL methylene chloride (the washings were saved), made basic with 5% aq. NaOH and extracted with 3x40 mL methylene chloride. The combined extracts were stripped of solvent on the rotary evaporator yielding .12 g of crude 5-MeO-DALT as a light brown oil that crystallized. The methylene chloride washings (saved above) was extracted with dilute H2SO4 (leaving the diphenyldisulfide reaction product in the organic phase), made basic, extracted with methylene chloride which, on being stripped of solvents on the rotary evaporator, yielded an additional 0.37 g. additional crude 5-MeO-DALT. These two lots were combined and distilled at the KugelRohr to give 0.32 g. of a fraction boiling at 155-165 degrees C at 20 microns. This was converted to the hydrochloride salt as described above, yielding 0.30 g of 5-MeO-DALT HCl. GCMS analysis showed this the be 95% pure with a 5% contamination with the mono-deallylated base 5-MeO-NALT. The fragmentation pattern of this base (m/z) was: 70 (allylaminomethylene, 50%), 160, 161 (5-methoxyindolemethylene, 40%, 100%), 230 (parent, 10%).

DOSAGE : 12 - 20 mg. orally

DURATION : 2 - 4 h

QUALITATIVE COMMENTS (from various sources) : (with 10 mg. orally) "I am looking at everything through someone's open friendly eyes, not mine. I would like to go through life like this if others saw me as OK. I am 10 feet tall, my pulse is 72 but uneven, and light-headed is a better describer of where I am than psychedelicized."

(with 16 mg. orally) "The music was fabulous, as was the sex and neither of us had a problem with orgasm. But there was a total lack of imagery -- less than I would normally have to the music when unstoned, so there might have been an actual suppression. I was pretty much baseline by the third hour."

(with 20 mg. orally) "It's coming on strongly in 15 minutes, and at the half hour point I am at a +++ with eyes closed -- but nothing with them open! No hang-over."

EXTENSIONS AND COMMENTARY : The rapid onset and rapid drop-off of 5-MeO-DALT is remarkable. With oral administration, it is common to be aware of the effects in less than 15 minutes and to be fully there at the half-hour point. This implies absorption into the blood stream directly from the stomach and rapid metabolic destruction. To my total suprise, this compound is not in the scientific literature, at least as searched by Chem. Abstracts. Its synthesis and its pharmacology have never been published.

There are a number of modifications of the two double bonds on there on the nitrogen alkyl groups that would be interesting to explore. If they were changed from double bonds to triple bonds, one would have 5-methoxy-N,N-dipropargyltryptamine, or 5- MeO-DPRT. I have made a little bit of it but it was quite impure and difficult to clean up. The complexity of the GCMS patterns suggested that there might be some chemistry going on between the two propargyl groups.

Another direction possible for modifying the structure would be to relocate the oxygen in indole ring over to the 4- position. 4-Methoxytryptamine is commercially available, and it should be directly substitutable for the 5-methoxytryptamine used in this synthetic process giving rise to 4-MeO-DALT. Yet further out, what about starting the 4-benzyloxytryptamine and walking the same path? The product could be easily stripped of the benzyl ether by the usual catalytic hydrogenation, giving rise to the diallyl analogue of psilocin, 4-HO-DALT. I would wager a ten dollar bet that the acetate ester of this material, 4-AcO-DALT would be in the brain within minutes of swallowing the pill.

There are a lot of interesting extensions, but all of them would call for careful chemistry. And, of course, the essential care of tasting new things in very small increasing doses. Some of these could be extremely potent.