Phenethylamines i Have Known and Loved
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#34 2C-N; 2,5-DIMETHOXY-4-NITROPHENETHYLAMINE
SYNTHESIS: A cooled, stirred solution of 1.0 g
2,5-dimethoxyphenethylamine (see the recipe for 2C-H for its
preparation) in 20 mL glacial acetic acid was treated with 3.3 mL 70%
HNO3 in small portions, with the reaction temperature kept down with
periodic cooling. After the addition was completed, the stirring was
continued until there was the spontaneous separation of a yellow
solid. This was 2,5-dimethoxy-4-nitrophenethylamine nitrate (2C-N)
which was obtained after removal by filtration, washing with Et2O and
air drying, as a fluffy yellow solid. This weighed 1.04 g and melted,
with decomposition, in the area of 170-180 °C, depending on the rate
of heating. A solution of 0.8 g of this nitrate salt in 50 mL H2O was
made basic with aqueous NaOH. Extraction with 3x50 mL CH2Cl2, and
removal of the solvent under vacuum gave the free base as a residue.
This was distilled at 130-150 °C at 0.35 mm/Hg to give an orange-red
oil that weighed 0.5 g and set up as crystals. This was dissolved in
3 mL IPA, neutralized with 7 drops of concentrated HCl (the color
lightened considerably at the titration end point) and diluted with 5
mL anhydrous Et2O. There was the formation of the hydrochloride salt
which was a pumpkin-colored crystalline mass. After removal by
filtration, Et2O washing and air drying, these crystals weighed 0.44
g. The mp, 193-195 °C, was not improved by recrystallization from any
of several solvents (MeOH, IPA, CH3CN). The perchlorate salt was a
yellow solid from MeOH, with a mp of 211 °C, with decomposition.
Nitration of 2C-H in a mixture of acetic acid and acetic anhydride
produced the acetamide derivative of 2C-N as yellow crystals with a mp
142.5-143 °C. For the nitrate salt: Anal. (C10H15N3O7) C,H. This was
the form used for all human titrations.
DOSAGE: 100 - 150 mg.
DURATION: 4 - 6 h.
QUALITATIVE COMMENTS: (with 120 mg) This came on very fast--I was
aware of it within a half hour, and it got as far as it would go by an
hour. There are similarities to MDMA, but missing is the benign
anti-stress component. I am light-headed, and there just might be a
little eye wiggling. And then it dropped right off to nothing within
a couple of hours.
(with 150 mg) There may have been some visual changes, I'm not sure.
But the talking was extremely easy. If there were no other things to
use, this would be excellent, but there are other compounds available.
This doesn't have too high a priority.
(with 150 mg) Am I enjoying it? Not exactly, but I am in a good
mood. There is not the light-filled energy that some other materials
can provide. By six hours, pretty much baseline. Strange material,
but okay. Final score: body +3, mind +2, barely.
EXTENSIONS AND COMMENTARY: A most consistent feature with 2C-N was the
fact that in every report, somewhere, there is the note that it
somehow came up just a little short of expectations. From the
esthetic point of view, the pure salt is yellow rather than the usual
white color, so the solutions that are to be consumed are by
definition also yellow colored. From the structural point of view,
the 4-nitro group, like the 4-bromo group of 2C-B, is a dead-end. It
cannot be stretched or compressed or lengthened or shortened. This
unique aspect demands that you have to live with what you have, as
there are no subtle ways of modifying the molecule. With 2C-B, the
end product was a total winner; there was no wish to modify it. With
2C-N the end product is something a little less, and there is no way
to modify it.
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