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Alkaloids of Banisteria Caapi and Prestonia Amazonicum

Alkaloids of Banisteria Caapi and Prestonia Amazonicum

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Alkaloids of Banisteria caapi and Prestonia amazonicum
BY F. A. HOCHSTEIANN D ANITAM . PARADIES
RECEIVEDJU NE 17, 1957
The hallucinogenic plant Banisteria caapi contains, in addition to harmine, the alkaloids harmaline and d-tetrahydroharmine.
Prestonia amazonicum leaves have yielded another psychotomimetic amine, N,N-dimethyltryptamine.
Alkaloids of Banisteria caapi and Prestonia amazonicum
BY F. A. HOCHSTEIANN D ANITAM . PARADIES
RECEIVEDJU NE 17, 1957
The hallucinogenic plant Banisteria caapi contains, in addition to harmine, the alkaloids harmaline and d-tetrahydroharmine.
Prestonia amazonicum leaves have yielded another psychotomimetic amine, N,N-dimethyltryptamine.

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Published by: oolon on Feb 03, 2009
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12/03/2012

 
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Journal of the American Chemical Society is published by the American ChemicalSociety. 1155 Sixteenth Street N.W., Washington, DC 20036
Alkaloids of Banisteria caapi and Prestonia amazonicum
F. A. Hochstein, and Anita M. Paradies
J. Am. Chem. Soc.
,
1957
, 79 (21), 5735-5736 • DOI: 10.1021/ja01578a041
Downloaded from http://pubs.acs.org on November 19, 2008
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The permalinkhttp://dx.doi.org/10.1021/ja01578a041provides access to:Links to articles and content related to this articleCopyright permission to reproduce figures and/or text from this article
 
Nov. 5, 19575735
LKALOIDS
F
Banisteria
caapi
AND
Prestonia amazonicum
[CONTRIBUTION FROM
THE
RESEARCH
ABORATORIES
F CHAS.
PFIZER
AND
CO.,
INC.]
Alkaloids
of
Banisteria caapi
and
Prestonia amazonicum
BY
F.
A. HOCHSTEIN
ND
ANITA
M.
PARADIES
RECEIVED
UNE
17,
1957
The hallucinogenic plant
Banisteria
caapi
contains, in addition to harmine, the alkaloids harmaline
and
d-tetrahydrohar-mine.
Prestonia
amazonicum
leaves have yielded another psychotomimetic amine, N,N-dimethyltryptamine.
The plant
Banisteria caapi
Spruce has been ex-amined repeatedly by workers who were attractedby the hallucinogenic activity of this drug.
p2
Three names, telepathine, yageine (yajeine) andbanisterine were assigned to the alkaloids isolatedby early workers. Several subsequent investiga-tors agree that harmine is the sole alkaloid of
B.
caapi,
though Oryekhov3 reported that harmalinealso is present. The properties reported for ya-geine,2v4 owever, are quite unlike those of harmineor harmaline. Undoubtedly, some
of
these incon-sistencies resulted from errors in botanical identi-fication and confusion
of
the common names
of
theseveral species
of
plants used in northern SouthAmerica as hallucinogens.2We have recently had occasion to examine thisplant anew.6The availability
of
modern investigational tech-niques, especially paper chromatography, has en-abled us to extend the earlier work. In our hands,
Banisteria
caapi
“Ayahuasca” has yielded harmine(I) as
its
major alkaloid. We have found in addi-tion, lesser quantities of harmaline (3,4-dihydro-harmine), and a third alkaloid, previously undescribed. The new alkaloid, colorless crystals, m.p.198-200°,
[Q]D
+32O, was isolated in quantitiesinadequate for degradative study. The ultra-violet absorption spectrum clearly indicated it tobe a 6-methoxyindole, and the analyses suggestedthat
it
was
N,N-dimethyl-6-methoxytryptamine.
The optical activity observation was discountedand the substituted tryptamine was accordinglysynthesized, but found to be different. The slightdifference between the ultraviolet spectra
of
thenew alkaloid and
6-methoxy-N,N-dimethyltryp-
(1)
(a) T.
A.
Henry, “The Plant Alkalolds.” 4th Ed., Blaklston
Co.,
Philadelphia-Toronto, 1949, p. 488, lists a reasonably completebibliography
on
this subject through 1939; (b) H. H. Pennes and P. H.Hoch,
Am.
J.
Psychiatry,
118,
887 (1957), have reported
on
the psy-chotomimetic effect
of
harmine in man.(2)
W.
B. Mors and P. Zaltzman, Boletim do Insituto de QuimicaAgricola (Brazil)
No.
34,
p.
17 (19541, covers the botanical questionthoroughly,
as
wellasother aspects.(3)
A.
P. Oryekhov, Byull-Nauch.
lsslcdooatcl
Khim-Farm.
Insl.,
3 (1930);
C.
A.,
86,
5699 (1932).(4)
A.
M.
Barriga Villalba,
J.
Sot.
Chcm.
Id,
4,
205T (1925).
(5)
We are Indebted to
Mr.
D.
H.
Allen
for
a supply
of
the plantmaterial studied here. Both the
Banisleria
caapi
“Ayahuasca”and the Hacmdictyon amasonicum (Prcstonia amasouicum), “Yage,”were collected on the Nap0 River, near Iquitos,
Peru.
The botanicalfdentilicatloo was made by
Dr.
R.
Ferreyra,
of
the
Unlversity
of
SaoMarcos, Llma. It might
he
noted that both
01
the
trivial
names,or
varlants
of
them, have prevfously been
quoted
81
refdng
to
Banisleria
caafii.
See
ref.
1
and 2.
tamine suggested that our compound was an
a,&
disubstituted indole. Tetrahydroharmine ap-peared to be the only likely alternate structure,though it seemed improbable that the reportedm.p. (199-200’) of the synthetic material wouldbe the same as that of our dextrorotatory alkaloid.Careful comparison of the isolated alkaloid withracemic
1.2,3,4-tetrahydroharmine
eaves no doubtthat the two compounds differ only in the opticalactivity of the naturally occurring material.The presence
of
these three alkaloids, differingonly in their state of oxidation in the same plant isof biogenetic interest. In view of the low degreeof psychotomimetic activity reported for harmine,
b
and the effectiveness ascribed to
Banisteria
caapi
extracts, it seems likely that the harmaline or
d-
tetrahydroharmine may have substantial psychoto-mimetic activity in their own right.A second plant, “Yage,”
Preston& amazonicum(Haemadictyon amazonicum
Spruce) was madeavailable to us as an aqueous extract of the leaves.The natives of the area of collection commonlyconsume a mixed extract
of
the
B.
caapi
vine and
P. amazonicum
leaves, in the belief that the lattersuppresses the more unpleasant hallucinations as-sociated with pure
B.
caapi
extracts. This plantis reported to be the source
of
the alkaloid“yageine,’’4 m.p. 206”,
CIdHSN30,
though othersattributed it to
B. caapi2
This
P. amazonicum
extract yielded substantial amounts of anotherpsychotomimetic amine, N,N-dimethyltryptamine,an alkaloid which has been identified recently as acomponent of the seeds of certain
Piptadenia
species.6 Its psychotomimetic effect in man has alsobeen demonstrated by recent work.?
No
otheralkaloids were detected in this plant extract.
ADDED
N
PROOF.-R. R. Paris,
F.
Percheron,
J.
Maniland R. Goutarel,
Bull.
SOL.
Chim.,
France,
780
(1957),
havereported that the alkaloid leptaflorine is the racemic form
of
tetrahydroharmine.
Experimental
Extraction of
Crude
Alkaloids
of
Banister&
caapi.-
Fifteen hundred grams of the ground vine of
Banisteria
caapi
was stirred under reflux with
3
liters of methanol forfive hours, filtered and washed with methanol. The ex-traction was twice repeated in the same manner, and thecombined extracts were then concentrated to dryness
in
vacuo
to
yield
120
g. of total extracted solids.This crude extract was suspended in
1
liter of
5%
ammo-nium hydroxide, and extracted with four 400-ml. portionsof chloroform. Centrifuging was necessary to break thestable emulsions. The combined chloroform extracts werethen dried over sodium sulfate, and concentrated
in
vacuo
to yield
15
g. of crude alkaloids
(A).
A
partially crystallinesolid
(20
9.)
was filtered from the aqueous phase, dried andextracted overnight in a Soxhlet with chloroform to yieldan additional
9
g. of crude alkaloids
(B).
(6)
M.
S.
Flsh,
N.
M.
Johnson
End
E.
C.
Hornlng, THIS
JOURNAL,
71,
6892 (1956).
(7)
St. Sfara,
Brpcrieutia,
XII,
441 (1956).

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