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#10 B
BUSCALINE; 4-(n)-BUTOXY-3,5-DIMETHOXYPHENETHYLAMINE
SYNTHESIS: A
solution of 5.8 g of
homosyringonitrile (see under E for
preparation), 100 mg
decyltriethylammonium iodide, and 11 g n-butyl
bromide in 50 mL
anhydrous acetone was treated with 6.9 g finely
powdered
anhydrous K2CO3 and held at reflux for 10 h. An additional 6
g of n-butyl
bromide was added to the mixture, and the refluxing
continued for another 48 h. The mixture was filtered, the solids
washed with
acetone, and the
solvent from the combined filtrate and
washes removed under vacuum. The residue was suspended in acidified
H2O, and extracted with 3x175 mL
CH2Cl2. The pooled extracts were
washed with 2x50 mL 5%
NaOH, once with dilute HCl, and then stripped
of
solvent under vacuum giving 13.2 g of a deep yellow oil. This was
distilled at 132-145 °C at 0.2 mm/
Hg to yield 5.0 g of
4-(n)-butyloxy-3,5-dimethoxyphenylacetonitrile as a pale yellow oil
which set up to
crystals spontaneously. The mp was 42-43 °C. Anal.
(
C14H19NO3) C H N.
A
solution of AH was prepared by the cautious addition of 0.67 mL of
100% H2SO4 to 25 mL of 1.0 M LAH in THF, which was being vigorously
stirred under He at ice bath tem
perature. A total of 4.9 g of
4-(n)-butyloxy-3,5-dimethoxyphenylacetonitrile was added as a solid
over the course of 10 min. Stirring was continued for another 5 min,
then the reaction mixture was brought to reflux on the steam bath for
another 45 min. After cooling again to room tem
perature, IPA was
added to destroy the excess
hydride (about 5 mL) followed by 10 mL of
15%
NaOH which was sufficient to make the
aluminum salts loose, white,
and filterable. The reaction mixture was filtered, the filter cake
washed with IPA, and the mother liquor and washes combined and the
solvent removed under vacuum to yield an amber oil. This residue was
treated with dilute H2SO4 which generated copious solids. Heating
this suspension effected
solution, and after cooling, all was washed
with 3x50 mL
CH2Cl2. The aqueous
phase was made basic with aqueous
NaOH, and the product extracted with 2x100 mL
CH2Cl2. The extracts
were
evaporated to a residue under vacuum, and this was
distilled at
128-138 °C at 0.5 mm/
Hg yielding 3.8 g of a colorless oil. This was
dissolved in 40 mL IPA, neutralized with concentrated HCl (about 55
drops required) and, with vigorous stirring, 80 mL of
anhydrous Et2O
was added which produced fine white plates. After standing for
several h, the product was filtered, washed with 20% IPA in
Et2O, and
finally with
Et2O. Air drying yielded 3.9 g of
4-(n)-butyloxy-3,5-dimethoxyphenethylamine hydrochloride (B) with a mp
of 152-153 °C. An
analytical sample melted at 155-157 °C. Anal.
(
C14H24ClNO3) C,H,N.
DOSAGE: greater than 150 mg.
DURATION: several hours.
QUALITATIVE COMMENTS: (with 120 mg) There is a strange taste, not
really bitter, it does not linger. The slight change of baseline has
certainly disappeared by the eighth hour. No noticeable changes in
either the visual or the auditory area.
(with 150 mg) Throughout the experiment it was my impression that
whatever effects were being felt, they were more in body than mind.
The body load never mellowed out, as it would have with mescaline,
after the first hour or two. Mental effects didn't develop in any
interesting way. I was aware of brief heart
arrhythmia. Tummy was
uncomfortable, off and on, and there was light
diarrhea. Even as late
as the fifth hour, my feet were cold, and the whole thing left me with
a slightly uncomfortable, 'Why did I bother?' feeling.
EXTENSIONS AND COMMENTARY: There is a jingle heard occasionally in
chemical circles, concerning the
homologues of
methyl. It goes,
"There's
ethyl and
propyl, but butyl is futile." And to a large
measure this is true with the 4-position
homologues of mescaline.
This butyl compound, B or
Buscaline, had originally been patented in
England in 1930 without any physical or
pharmacological description,
and the few physical studies that had involved it (
lipophilic this and
serotonin that) suggested that it was less active than mescaline.
In principle, the 5-, the 6-, the 7- and the on-up
homologues might be
called
amylescaline (possibly
pentescaline?),
hexescaline,
heptescaline (possibly
septescaline), and God-knows-what-scaline.
They would certainly be easily makeable, but there would be little
value that could be anticipated from nibbling them. In keeping with
the name B (for butoxy), these would be known as A (for amyloxy, as
the use of a P could confuse pentoxy with propoxy), as H (for
hexyloxy, but careful; this letter has been used occasionally for
DMPEA, which is Homo
piperonylamine), and as S (the H for
heptyloxy has
been consumed by the hexyloxy, so let's shift from the Greek hepta to
the Latin
septum for the number seven). It seems most likely that the
toxic symptoms that might well come along with these
phenethylamines
would discourage the use of the dosage needed to affect the higher
centers of the brain. The same generally negative feeling applies to
the
amphetamine counterparts 3C-B, 3C-A, 3C-H and 3C-S.
A brief reiteration of the 2C-3C
nomenclature, to avoid a possible
misunderstanding. The drug
2C-B is so named in that it is the
two-
carbon chain
analogue of the three-carbon chain compound DOB. The
drug 3C-B is so named because it is the three-
carbon chain
analogue of
the two-
carbon chain compound
Buscaline, or more simply, B. There is
no logical connection whatsoever, either structural or
pharmacological, between
2C-B and 3C-B.
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