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#102 MDBU
N-BUTYL-MDA; 3,4-METHYLENEDIOXY-N-BUTYLAMPHETAMINE
SYNTHESIS: A total of 30 mL
butylamine was introduced under the
surface of 33 mL concentrated HCl, and the mixture stripped of
volatiles under vacuum. The resulting glassy solid was
dissolved in
160 mL MeOH and treated with 7.2 g
3,4-methylenedioxyphenylacetone
(see under
MDMA for its preparation). To this there was added 50%
NaOH dropwise until the
pH was at about 6 as determined by the use of
external dampened universal
pH paper. The
solution was vigorously
stirred and 2.8 g
sodium cyanoborohydride was added. Concentrated HCl
was added as needed, to keep the
pH constant at about 6. The addition
required about two days, during which time the reaction mixture first
became quite cottage-cheese like, and then finally thinned out again.
All was dumped into 1 L H2O acidified with HCl, and extracted with
3x100 mL
CH2Cl2. These extracts were combined, extracted with 2x100
mL dilute H2SO4, which was combined with the aqueous fraction above.
This latter mixture was made basic with 25%
NaOH, and extracted with
3x150 mL
CH2Cl2. Evaporation of the
solvent yielded 4.0 g of an amber
oil which, on
distillation at 90-100 °C at 0.15 mm/
Hg, yielded 3.2 g
of a white clear oil. This was
dissolved in 20 mL IPA, neutralized
with 30 drops of concentrated HCl, and the spontaneously formed
crystals were diluted with sufficient
anhydrous Et2O to allow easy
filtration. After
Et2O washing and air drying, there was obtained 2.8
g of
3,4-methylenedioxy-N-butyl
amphetamine hydrochloride (MDBU) as
white
crystals with a mp of 200-200.5 °C. Anal. (
C14H22ClNO2) N.
DOSAGE: greater than 40 mg.
DURATION: unknown.
EXTENSIONS AND COMMENTARY: Straight chain
homologues on the
nitrogen
atom of
MDA longer than two
carbons are probably not active. This
butyl compound provoked no interest, and although the longer chain
counterparts were made by the general
sodium cyanoborohydride method
(see under MDBZ), they were not tasted. All mouse assays that
compared this
homologous series showed a consistent decrease in action
(
anesthetic potency and motor activity) as the alkyl chain on the
nitrogen atoms was lengthened.
This
synthetic procedure, using the
hydrochloride salt of the
amine
and
sodium cyanoborohydride in
methanol, seems to be quite general for
ketone compounds related to
3,4-methylenedioxyphenylacetone. Not only
were most of the MD-group of compounds discussed here made in this
manner, but the use of
phenylacetone (
phenyl-2-propanone, P-2-P)
itself appears to be equally effective. The reaction of
butylamine
hydrochloride in
methanol, with
phenyl-2-propanone and
sodium
cyanoborohydride at
pH of 6, after
distillation at 70-75 °C at 0.3
mm/
Hg, produced N-butyl
amphetamine hydrochloride (23.4 g from 16.3 g
P-2-P). And, in the same manner with
ethylamine hydrochloride there
was produced N-
ethylamphetamine (22.4 g from 22.1 g P-2-P) and with
methylamine hydrochloride there was produced N-
methylamphetamine
hydrochloride (24.6 g from 26.8 g P-2-P). The reaction with simple
ammonia (as
ammonium acetate) gives consistently poor yields in these
reactions.
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