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#11 BEATRICE
N-METHYL-DOM; 2,5-DIMETHOXY-4,N-DIMETHYLAMPHETAMINE
SYNTHESIS: A fused sample of 5.0 g of white,
crystalline free base
2,5-dimethoxy-4-methylamphetamine, DOM, was treated with 10 mL ethyl
formate, and held at reflux on the steam bath for several h. Removal
of the
solvent gave 5.5 g of a white solid, which could be
re
crystallized from 15 mL MeOH to give 3.8 g of fine white crystals of
2,5-dimethoxy-N-
formyl-4-
methylamphetamine. An
analytical sample from
ethyl formate gave granular white
crystals.
To a stirred suspension of 4.0 g LAH in 250 mL
anhydrous Et2O at
reflux and under an inert
atmosphere, there was added, by the shunted
Soxhlet technique, 4.2 g of
2,5-dimethoxy-N-
formyl-4-
methylamphetamine
as rapidly as its solubility in hot
Et2O would allow. The mixture was
held at reflux for 24 h and then stirred at room tem
perature for
several additional days. The excess
hydride was destroyed with the
addition of dilute H2SO4 (20 g in 500 mL water) followed by the
additional dilute H2SO4 needed to effect a clear
solution. The
Et2O
was separated, and the aqueous
phase extracted with 100 mL
Et2O and
then with 2x250 mL
CH2Cl2. Following the addition of 100 g
potassium
sodium tartrate, the mixture was made basic with 25%
NaOH. The clear
aqueous
phase was extracted with 3x250 mL
CH2Cl2 These extracts were
pooled, and the
solvent removed under vacuum. The
residual amber oil
was
dissolved in 400 mL
anhydrous Et2O, and saturated with hydrogen
chloride gas. The white
crystals that formed were removed by
filtration, washed with
Et2O, and air dried to constant weight. There
was obtained 4.2 g of product with a mp of 131.5-133.5 °C. This
product was recrys-tallized from 175 mL boiling
ethyl acetate to give
3.5 g
2,5-dimethoxy-4,N-di-
methylamphetamine hydrochloride (BEATRICE)
as pale pink
crystals with a mp of 136-137 °C. A sample obtained from
a preparation that employed the
methyl sulfate methylation of the
benzaldehyde adduct of DOM had a mp of 125-126 °C and presented a
different infra-red
spectrum. It was, following re
crystallization
from
ethyl acetate, identical to the higher melting form in all
respects.
DOSAGE: above 30 mg.
DURATION: 6 - 10 h.
QUALITATIVE COMMENTS: (with 20 mg) There was a gentle and demanding
rise from the one to the three hour point that put me into an
extremely open, erotic, and responsive place. I had to find a
familiar spot to orient myself, and the kitchen served that need. As
the experience went on, it showed more and more of a stimulant
response, with tremor, restlessness, and a bit of trouble sleeping.
But there was no
anorexia! An OK experience.
(with 30 mg) There is a real physical aspect to this, and I am not
completely happy with it. There is
diarrhea, and I am restless, and
continuously aware of the fact that my body has had an impact from
something. The last few hours were spent in talking, and I found
myself still awake some 24 hours after the start of the experiment.
The mental was not up there to a +++, and yet the physical disruption
was all that I might care to weather, and exceeds any mental reward.
When I did sleep, my dreams were OK, but not rich. Why go higher?
EXTENSIONS AND COMMENTARY: This is another example of the N-
methyl
homologues of the
psychedelics. None of them seem to produce stuff of
elegance. It is clear that the adding of an N-
methyl group onto DOM
certainly cuts down the activity by a factor of ten-fold, and even
then results in something that is not completely good. Three
milligrams of DOM is a winner, but even ten times this, thirty
milligrams of N-
methyl-DOM, is somewhat fuzzy. In the rabbit
hyperthermia studies, this compound was some 25 times less active than
DOM, so even animal tests say this is way down there in value. This
particular measure suggests that the active level in man might be 75
milligrams. Well, maybe, but I am not at all comfortable in trying it
at that level. In fact I do not intend to explore this any further
whatsoever, unless there is a compelling reason, and I see no such
reason. For the moment, let us leave this one to others, who might be
more adventurous but less discriminating.
In browsing through my notes I discovered that I had made another
N-
substitution product of DOM. Efforts to fuse free-base DOM with the
ethyl cyclopropane carboxylate failed, but the reaction between it and
the acid
chloride in
pyridine gave the corresponding amide, with a mp
of 156-157 °C from MeOH. Anal. (
C16H23NO3) C,H,N. This reduced
smoothly to the corresponding
amine,
N-
cyclopropyl-
2,5-dimethoxy-4-methylamphetamine which formed a
hydrochloride salt melting at 153-156 °C. I can't remember the
reasoning that led to this line of synthesis, but it must not have
been too exciting, as I never tasted the stuff.
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