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HA DOB Report[1]

HA DOB Report[1]

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Published by Harry Manass

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Published by: Harry Manass on Nov 16, 2010
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12/06/2012

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HA-DOB
4-bromo-2,5-dimethoxyhomoamphetamine hydrochloride
4-(4-bromo-2,5-dimethoxyphenyl)butan-2-amine hydrochloride
OCH
3
OCH
3
BrCH
3
NH
2
 
SYNTHESIS:"4-[4-Bromo-2,5-dimethoxyphenyl]-butan-2-one".
In a 250 mL flask on an oil bath and magnetic stirring was added 100 mL of 96% ethanol and 4 gof sodium hydroxide (94 mmol). Heating was applied to the oil bath and with stirring the sodiumhydroxide soon dissolved. When the temperature of the solution reached 50 °C there was added13 mL of ethyl acetoacetate (94 mmol).After 10 min there was slowly added also 20 g of “crude4-bromo-2,5-dimethoxybenzyl chloride”
1
(75 mmol) and the reflux condenser immediately set onthe flask. The temperature of the oil bath was raised in order to maintain reflux for 1 h and 20min. The suspension was vacuum filtered while still warm in order to remove the sodium chloride precipitate which was washed with 2×10 mL of ethanol. The filtrate was put back in the 250 mLflask, neutralized with 3 mL 30% hydrochloric acid and the solvent removed with the aid of vacuum until the volume of 50 mL was reached (marked on the flask earlier). Then 70 mL of 25%hydrochloric acid was added and the mixture heated at reflux on the oil bath with intensivemagnetic stirring for 8 h when all CO
2
evolution ceased. The evolution of CO
2
gas was monitoredwith a bubbler or a balloon set on the condenser exit. The product was extracted with 40 mLtoluene, washed with 40 mL 5% sodium bicarbonate and 2×30 mL brine. The toluene wasstripped off and the resulting dark oil diluted with 50 mL ethanol. The resulting solution wasadded to the solution of 10 g sodium bisulphite in 20 mL water and 20 mL ethanol. The formed precipitate was vacuum filtered after 30 min of stirring and washed with 15 mL water and 2×15mL ethanol but after air drying there was only 4.25 g of the bisulphite adduct left (14%).
2
Thefiltrate was therefore diluted with an equal volume of water and the formed oil separated, the restextracted with 2×7 mL methylenechloride, the combined organic fractions washed with 2×25 mLwater and the solvent evaporated. There remained 14.1 g of a dark oil. This crude product wasused without further purification or analysis.
1
 
Later, it was found by
1
H NMR spectroscopy to consist of about 51% 4-bromo-2,5-dimethoxybenzyl chloride,36% 6-bromo-2,5-dimethoxybenzyl chloride and about 13% diarylmethylenic side products. But since this wasnot known at the time of synthesis, the product was used without further purification.
2
The ketone made from the small amount of the bisulphite adduct was pure enough to crystallize. During theHA-DOC synthesis, it was found that the bisulphite method can efficiently be used, but 2 eq. of NaHSO
3
must be used and the slow reaction left stirring for at least 24 h. The so purified ketone for HA-DOC crystallized incold. The HA-DOC synthesis also highlighted that the yield of the benzylation/decarboxylation/bisulphite purification step is probably low. So the ketone used in the HA-DOB synthesis was seriously impure – thus thelow yield after the reduction of the “oxime”.
 
 
OCH
3
OCH
3
BrClOCH
3
OCH
3
BrCH
3
O
+ CH
3
COCH
2
COOEt, NaOH/ EtOH- NaCl+ H
2
O / HCl, EtOH- CO
2
, EtOH
OOEtOCH
3
OCH
3
Br CH
3
O
 
"4-[4-Bromo-2,5-dimethoxyphenyl]-butan-2-one oxime".
 In a 250 mL flask there was added 3.20 g of hydroxylamine hydrochloride (45 mmol), 15 mLwater and while stirring was slowly added also 2.40 g of anhydrous sodium carbonate (22.5mmol). Then the solution of 10g “4-[4-bromo-2,5-dimethoxyphenyl]-butan-2-one” in 50 mLof methanol was added and the mixture stirred at reflux for 2 h. After the reaction mixturecooled, 50 mL of water was slowly added and a viscous oil precipitated. This refused tocrystallize in the freezer thus the supernatant was decanted, the viscous oil washed with somewater, dissolved in 15 mL methylenechloride washed with 2×25 mL water and the solventstripped off. There remained 10.23g of the oily product.
OCH
3
OCH
3
BrCH
3
NOHOCH
3
OCH
3
BrCH
3
O
+ H
2
 NOH / MeOH ,H
2
O
 
4-(4-Bromo-2,5-dimethoxyphenyl)butan-2-amine hydrochloride.
In a 1 L two neck flask was added 100 mL 96% ethanol, 10 mL water, 4 g aluminium foil in small pieces (cut in a mixer), 4 mL 2% aqueous HgCl
2
and stirred intensively. To one neck a refluxcondenser was set and to the other a dropping funnel with a solution of the above crude oxime in 20mL ethanol and 20 mL 85% formic acid. After stirring for 15 min the aluminium apparentlyamalgamated and the solution of the oxime was slowly being added drop-wise at such a rate that thereaction mixture was mildly refluxing. After 15 min most of the aluminium got consumed andanother portion of 4 g was added. The mixture was stirred for additional 2 h. The alumina slurry wasvacuum filtered with some difficulty and washed with 2×20 mL ethanol. The clear filtrate wasconcentrated to about 45 mL volume, 20 mL 10M NaOH(aq) was added, extracted with 3×20 mLtoluene. The joined extracts were washed with 3×40 mL water (an emulsion formed and was brokenwith adding some brine) and back extracted with 20 mL 2M and 2×10 mL 1M hydrochloric acid.The aqueous extract was evaporated using vacuum, adding 20 mL isopropanol and againevaporating under vacuum. There remained a slightly grey to pinkish paste which was triturated inacetone and filtered to give a grey powder. This was dissolved in dichloromethane and filtered toremove some insoluble material. After evaporating the filtrate there remained 2 g of an off-white powder, HA-DOB×HCl containing an NMR visible impurity that was assumed to be 4-(2-bromo-2,5-dimethoxyphenyl)butan-2-amine hydrochloride (up to 10 mol%): mp 193-198°C; IR (KBr disc)2940, 1603, 1499, 1387, 1211, 1057, 1029 cm
-1
. Free base
1
H NMR (CDCl3)
δ
1.10 (d,
 J 
= 6.3 Hz,3H, CH
3
), 1.33 (broad, 2H, NH
2
), 1.48-1.67 (m, 2H, CH
2
), 2.62 (t,
 J 
= 7.9 Hz, 2H, CH
2
), 2.89 (m,1H, CH), 3.78 (s, 3H, CH
3
O), 3.84 (s, 3H, CH
3
O), 6.74 (s, 1H, ArH), 7.01 (s, 1H, ArH). 
 
OCH
3
OCH
3
BrCH
3
NOHOCH
3
OCH
3
BrCH
3
NH
2
+ Al / EtOH , H
2
O, HCOOH
 
DOSAGE: 60 – 120 mg
(threshold 10 - 15 mg)
 DURATION: 8 - 12 h60 mg (male; 80 kg):
I drank the solution of 60mg HA-DOB in water at 11AM. The taste isdisgusting but not more than most other compounds. It slowly started after one hour and took further half hour to become intense. I have not eaten breakfast and expected I would not feelhungry during the experiment instead I got really hungry. I could not eat just anything. Iwanted something good so I went cooking. This was quite an adventure in itself since I wasquite tripping already. But it was worth it, the food tasted delicious. I was alone, but had acouple of phone calls during the experience and communication and “faking” was relativelyeasy even during the peak. This day I had to do some work, some translation of a certain text.I tried and the first paragraphs I did just fine, the second was a bit harder and when I came atthe third I just closed the file. It was too annoying. I like this compound. I’m aboveeverything, like a string in resonance with my own inner universe. Externalities don’t bother me much, or at least not as much as they should. At 2:30PM I went to rest a bit on the bed.Behind the closed eyes patterns soon emerged, but they are less marked than the influence onthe mood and thoughts so that they don’t really entertain me. I could not rest for long and feltlike the peak is about to end. I went on doing some lab work. I almost thought that it is quitesimilar to its regioisomer 4C-DOB, but now I see that there is a big difference in the length of action. At 4PM there was still activity, but now stabilized to a lower level. I haven’t evennoticed the time passing. Two or three hours later it was nearly over, but it was not untilmidnight that I could say for sure that I’m at baseline.
90 mg (male; 80 kg):
I drank the disgusting aqueous solution at about 1PM on an islandtogether with Lucy who took 80mg. I had no watch, but it seamed to me that it passed wayover an hour, or perhaps even two hours, before the effects became apparent. Perhaps it was because I eat dinner an hour earlier. The effects, though clearly psychedelic, were notdramatic at all, which I believe had to do with the strong sunlight and the absence of other humans. There were little visuals, but the stones, the sea and the whole natural ambient initself had become so familiarly similar to what us two experienced a couple of years earlier while tripping on psilocybin containing mushrooms on this same spot. This time was however much less intense. I got a kind of a feeling that the psychedelic experience is nothing else butan enhanced state of the mind we already had while still children, a mind mode enabling usfast absorption and analysis of language, experiences and other data in order to learn fast for the life in adulthood. A couple of hours later we went walking trough a beautiful canyon of adry stream into the interior of the island. I had a narcissistic urge to share my thoughts andchat about various things. We saw a snake and I wanted to observe it but Lucy got scared sorushed forward. We passed by several already decomposed carcasses of a dead sheep and one

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