"Ayahuasca-like" effects,obtained with ltalian plants

by Francesco Festi & Giorgio Samorini .

Relación presentada al II· Congreso Internacional per a l'Estudio dels
Estats Modificats de

Consciencia, 3-7 octubre 1994, Llèida (Espania)

Communication presented at the 11· International Congress for the Study of
the modified

States of Consciousness, 3-7 october 1994, Llèida (Espania)

The authors present the results of investigation carried out in the
ayahuasca analogues research field (pharmahuasca), using a species of
Phalaris (Gramineae) native to or naturalized in Italy as source of
tryptamine alkaloids. As a source of ß-carboline alkaloids, the seeds of
Peganum harmala (Zygophyllaceae), a plant living in Mediterranean countries
including Italy, have been used. As a result of some autoexperiments aimed
at reproducing a kind of 'ayahuasca effect', t.he mixing of the acqueous
extract; of young leaves of Phalaris aquatica L. and seeds of P. harmala
proved to be strongly psychoactive; this further confirms the validity of
the model of the action of alkaloids contained in the ayahuasca potions,
which is the basis of the principles of pharmahuasca

With regard to the quantities of psychoactive indolic alkaloids in P.
aquatica and P. arundinacea, great deal of literature exists in the
agronomic and veterinary fields. Genetic, environmental, physiological and
cultural factors which may significantly influence the concentration of
these alkaloids are discussed. Lastly, the results of a series of chemical
analysis carried out on the main European species of the Phalaris genus
will be referred to, up to now unexplored from the point of view of its
psychoactive indolic alkaloid content.

'Efecto ayahuasca' obtenido con plantas italianas.

Los Autores presentan los resultados des indagaciones en el campo de
investigacion de los análogos del ayahuasca (pharmahuasca), utilizando,
como fuente de alcaloides triptamínicos, algunas especies de Phalaris
(Gramineae) originarias o naturalizadas en Italia. Como fuente de
alcaloides ß-carbolinicos, fueron utilizadas las semillas de Peganum
harmala (Zygophyllaceae), una planta que vive en los paises del
Mediterraneo, incluida Italia. Como consecuencia de aigunas
autoexperimentaciones, con el propósito de reproducir una especie de
'efecto ayahuasca', la combinación de extractos acuosos de hojas jovenes de
Phalaris aquatica L. y de semillas de P. harmala resultó fuertemente
psicoactiva; esto confirmo una vez más la validez del modelo de acción de
los alcaloides contenidos en las bebidas de ayahuasca, y que es la base de
los principios de la pharmahuasca.

En lo que se refiere al contenido de alcaloides indolicos psicoáctivos en
P. aquatica y P. arundinacea, existe una vasta Literatura en los sectores
agronomico y veterinario, siendo estas especies ampliamente utilizadas como
forrajes en varias regiones del mundo. Se discuten los factores genéticos,
ambientales, fisiológicos y culturales, que pueden influenciar
significativamente las concentraciones de estos alcaloides. Finalmente, se
presentan resultados de una serie de análisis químicas realizadas en las
principales especies europeas del género Phalaris, aún no exploradas en sus
contenidos de alcaloides indolicos psicoactívos.

The psychoactive alkaloids found in the genus Phalaris, particularly
N,N-dimethyltryptamine (DMT) and 5-methoxy-N,N-dimethyltryptamine
(5-MeO-DMT), are known to be the entheogenic agents in the Amazonian drink
ayahuasca. In this widely used potion the inhibitory action on the
monoamine oxidase by the ß-carbolines (particularly harmine, its main
component) is essential to make the indolakylamines orally active,
otherwise effective only parenterally [MCKENNA, 1992; MCKENNA & TOWERS,
1984; MCKENNA et al. 1984; Ott, 1993; 1994a; 1994b; RIVIER & LINDGREEN,
1972]. Already few years-after the proposal about the interaction between
DMT and ß-carbolines as ayahuasca mechanism of action, there were sporadic
attempts to reproduce this effect by using the only active agents or plants
other than the Amazonian ones [OTT, 1994a; 1994b]. We must mention the
pioneer work of Jeremy Bigwood [1978 in Ott, 1994a], who ingested an
ayahuasca-like preparation constituted by harmine and DMT, obtaining an
action comparable to that of the original ayahuasca. Also the "underground"
publications by "Gracie & Zarkov" [1985; 1986] are very irnportant; they
combined DMT with enriched alkaloids extract of Peganum harmala L., a
Zygophyllaceous plant containing a valuable amount of harrnine and other
ß-carboline alkaloids. The outcomes of these experiments were reported to
be clearly entheogenic, with a threshold of about 20 mg of DMT combined
with 5 g of Peganum harmala seeds. More recently, an increasing attention
has been paid to pharmahuasca or Ayahuasca borealis - as these
preparations, reproducing the "ayahuasca-like effect" with chemical
substances and plants other than those originally used in Amazonia, have
been called.

In this context, the experiments carried out by Jonathan Ott and recently
published are very interesting. The author reports about the ingestion of
varying amounts of Peganum harmala seeds extract together with pure
indoalkylamines or extracts of Psychotria viridis RUIZ & PAVON (Rubiaceae),
Desmanthus illinoensis (Michaux) MACM. (Legumitiosae) or Acacia
phlebophylla F. VON MÜLLER (Leguminosae). 4 g of Peganum seeds and an
equivalent amount of 30 mg of DMT are reported to be clearly psychoactive;
the same results can be achieved by using MAO inhibitors contained in
pharmaceutical preparations [Ott, 1993; 1994a., 1994b]. Parallel
experiments also proved the possibility of reproducing the "ayahuasca-like
effect" with MAO inhibitors in combination with 5-MeO-DMT [CALLAWAY, 1993;
CALLAWAY, 1992 in Ott, 1994a; LEUNER & SCHLICHTUNGEN, 1989] and DET [Ott,
1994a].

The "psychonautic" exploration of the genus Phalaris as a source of
indolalkylamines in the Ayahuasca borealis has a shorter history, up to now
tied to the "underground" circle. The Entheogen Review published in 1992 a
note, written under the pseudonym of "Johny Appleseed" describing a simple
method to extract the alkaloids from Peganum harmala and other plants
[APPLESEED, 1992., 1993a; 1993b]. At the end of the next year the review
claimed the full entheogenic activity of Phalaris arundinacea (var. "Turkey
Red" and "Yugoslavian Fresh Cut") extract smoked with inert matter
[DEKORNE, 1993b. 1994a. 1994c]. At the same time, positive outcomes were
reported, referred to some experiments with the ingestion of Peganum
extract (125 rng) and Phalaris arundinacea (var. "Turkey Red" extract
(30-50 mg) [APPLESEED, 1993a; 1993b; DEKORNE, 1993a; 1993b; 1994a; 1994b;
1994c].

In the present work we are communicating some results of the researches
that we have been carrying out about the genus Phalaris, including some
auto-experiments of pharmahuasca obtained with an Italian strain of
Phalaris aquatica.

Botany and chemistry of the genus Phalaris L.

The genus Phalaris belonging to the family Graminaceae (also called Poaceae
or Gramineae), includes, according to the most recent revisions, about 15
to 20 species (depending on the concept of species adopted by the authors)
[ANDERSON, 1961; BALDINI, 1993; PRAT, 1960]. Some specific or subspecific
entities are widespread in the temperate and subtropical areas of both
hemispheres; however, the determination of the natural distribution of the
genus is difficult, since many species have been introduced in some parts
of the world as forage or ornamental plants [HITCHCOCK, 1950; VOSE, 1959;
HEATH & HUGHES, 1961; TUTIN in TUTIN et al., 1980; GÖHL, 1982; WALTERS et
al, 1984; MARTEN, 1985; WASSON & DALLWITZ, 1992]. Undoubtedly, the
Mediterranean and Macaronesian phytogeographical regions have the maximum
of taxonomic variability and can be considered as the differentiation
centre for the genus. In fact, at least 13 entities are known in Europe
[BALDINI, 1993; MEUSEL et al., 1965; TUTIN in TUTIN et al., 1980; WALTERS
et al., 1984]:

*P. arundinacea L., sometimes segregated from the genus Phalaris as
Typhoides MOENCH, Digraphis TRIN., Baldingera Dumort. or Phalaroides
RAUSCH. It is widespread in wet places, particularly on the riversides and
along the canals, also outside the strictly Mediterranean region and almost
in every state of the European continent. Besides the type, the variety
picta L. is also

cultivated as an ornarmental plant: it differs trom,the variety arundinacea
through the white or yellowish stripped leaves.

   * P. caesia NEES is very similar to the above mentioned species, also
     having non-winged keels of the glumes and panicle lobate at maturity.
     It occurs in South-western Europe (Portugal, Spain and-Southem France)
     as well as in tropical and Southern Africa.
   * P. rotgesii (HUSNOT) BALDINI is also similar to P. arundinacea, of
     which it is considered a variety by some authors. It has a very
     restricted distribution, occurring only in Corsica and Sardinia.
   * P. aquatica L. (= P. nodosa MURRAY; P. tuberosa L.; P. bulbosa Auct.
     non L.; P. commutata ROEM. & SCHULT.) is naturally widespread in the
     Mediterranean areas of Europe. It is also widely introduced as forage
     in many parts of the globe, where it is often adventive or
     naturalized.
   * P. stenoptera HACK. is sometimes treated as an infraspecific taxa of
     P. aquatica, of which it may constitute a modified form. It probably
     originated in Northern Africa (Morocco) but it is present, adventive
     or naturalized, also in many parts of Europe, Australia and America,
     because of its use as forage.
   * P. truncata Guss. ex BERTOL., comes from the Mediterranean region. It
     has been used as animal food very rarely and only around the
     Mediterranean basin.
   * P. canariensis L, Most authors think it originally came from the
     Canary Islands and Northwestern Africa, However, it is widely
     cultivated as an ornamental plant or for the seeds (as bird food) and
     so it is present almost everywhere in Europe with adventive or
     naturalized status. This wide, but probably secondary distribution,
     has led some authors (such as BALDINI [1993]) to think that the
     species originally came from some areas of the Mediterranean region.
   * P. minor RETZ. grows wildly in most European countries on the
     Mediterranean Sea. It is sometimes found casual or naturalized, owing
     to its growing as forage or, not frequently, as an ornamental plant.
   * P. brachystachys LINK in SCHRADER grows in the Mediterranean and
     Macaronesian regions, where it has sometimes been used as fodder. It
     is therefore found also casual, but very rarely outside its natural
     distribution area.
   * P. paradoxa L. has, more or less, the same distribution area as the
     above mentioned species. It is seldom grown as ornamental.
   * P. coerulescens DESF. is also distributed in the Mediterranean and
     Macaronesian regions, where it seems to have little or no economical
     value.
   * P. maderensis (MENEZ) MENEZ has a very restricted distribution, being
     known only from Madeira and the Canary Islands.
   * P. hirtiglumis (TRABUT) BALDINI (=P. bulbosa L. var. hirtiglumis
     TRABUT) comes originally from North Africa but recently has been
     reported also in Italy and Southern France.

Most of the above-mentioned species have been used as forage, sometimes
also with satisfactory results and promising developing prospects. However,
P. arundinacea and P. aquatica are the species most widely utilized for
such a purpose, owing to their good agronomical features [BERG, 1978. HEATH
& HUGHES 1961; MARTEN, 1985; VOSE, 1959]. The first one has been cultivated
in Europe since 1749 and in America since 1885; nowadays its growing is
particularly widespread in the temperate areas of the American continent
and Australia, both in the pastures and for the control of grassed
waterways or stream banks, because of its fast growth it prevents soil
erosion. As a matter of fact just the U.S.A. and Canada are presently the
most important seed producers in the world and in these countries more than
20 cultivars have been selected [ibid.]. On the contrary, the cultivation
area of P. aquatica emphasizes its adaptation to the rainy
mediterranean/subtropical climates. In fact, apart from its native
countries, it is also widely used as a forage in Australia, North- and
South-Africa, in the Southern states of the U.S.A. and in South America
[BALTENSBERGER & KALTON, 1958; 1959; HEATH & HUGHES, 1961; HITCHCOCK, 1950;
HOVELAND & ANTHONY, 1971; MARTEN, 1985; VOSE, 1959].

Already during the first years of the intensive utilization [GALLAGHER et
al., 1966a; LEE & KUCHEL, 1953; LEE et al., 1956; McDONALD, 1942] both
species, particularly the P. aquatica, showed to be associated, under
certain environmental conditions and only in ruminants (sheep and cattle),
with a typical complex of neurological disorders, commonly grouped under
the term "phalaris staggers". The peracute syndrome or "sudden death",
formerly included in the toxicosis complex, is now considered apart, owing
to the etiology, almost certainly not tied to tryptamine alkaloids [BOURKE
& CARRIGAN, 1992; BOURKE et al., 1988; BOURKE et al., 1992; GALLAGHER et
al., 1964. 1966a; 1966b; KERR, 1972; MOORE et al., 1961; ORAM 1970].
Nowadays most authors prefer to use the term "phalaris staggers" referring
to the formerly separate acute and chronic syndromes, that seem to differ
only for the duration of the exposure to the toxic agents [BOURKE et al.,
1987; 1988; 1990; BRAUND, 1986; CULVENOR et al., 1964; CULVENOR, 1987; DE
LAHUNTA, 1983; EAST & HIGGINS, 1988., GAGGINO et al , 1963a, 1963b., 1965.,
GALLAGHER et al., 1964; 1966a; 1966b., 1967a. 1967b; HARTLEY & KATER, 1965;
HARTLEY, 1978; LEAN et al., 1989; LEE & KUCHEL, 1953a., 1953b., LEE et al.,
1956; 1957a; 1957b; MCDONALD, 1942; MOORE et al., 1961; NICHOLSON, 1989;
NICHOLSON et al., 1989; RENDIG et al., 1976; SIMPSON et al., 1969; ULVUND,
1985; WRIGHT et al., 1981]. The prodroms emphasize the neurological
character of the disease: gait abnormalities, rigidity of the legs and then
ataxia or weakness of the fore-limbs, muscular spasms, head nodding,
depressed placing reflexes, convulsions, nystagmus, hyper-excitability,
mydriasis, tachypnea, arrhythmic tachycardia. Death may occur by heart
failure, few hours after the intake of toxic forage in the acute syndrome,
until 5 months later in the chronic one [ibid]. In the latter case,
postmortem examination gives evidence of irreversible degenerative lesion
in the central nervous system. Macroscopically there are characteristic
greyish-green deposits of pigments, particularly evident in the region of
the geniculate bodies of the thalamus, in the ventral portion of the
medulla oblongata at the level of the cerebellar peduncle and in the dorsal
root ganglia.The same deposits are also found in the renal medulla and
sometimes in the liver. The granular brown intracytoplasmatic pigments
observed in the central nervous system and mainly accumulated in the
lysosomes, are believed to be derived from the tryptamine alkaloids by
oxidative deamination to aldehydes and self-condensation to melanin
polymers. Microscopic degenerations, such as astrocytosis and secondary
demyelination, followed the accumulation of the pigments in the cytoplasm,
with a final apparent death and lysis of the nerve cell body [BOURKE et
al., 1990. EAST & HIGGINS, 1988. FERNANDEZ DE LUCO et al. 1990; GALLAGHER
et al., 1964; 1966a; 1966b; HARTLEY & KATER, 1965. JOLLY & HARTLEY, 1977;
LEAN et al., 1989; NICHOLSON, 1989; ULVUND, 1985; VAN HALDEREN et al.,
1990].

The symptomatologic complex and the experimental administration of indole
alkaloids to ruminants seem to support a direct action on the
serotoninergic system by the Phalaris compounds (mainly indolalkylamines,
even though it is not possible to exclude a synergic action by the
ß-carbolines), [BOURKE et al., 1988; BOURKE et al., 1990] rather than a
monoamine oxidase inhibition with consequent increase of the endogenous
cathecolamines [GALLAGHER et al., 1966a; 1966b]. In this context, it is
worth remembering that DMT and 5-MeO-DMT are not orally active in human
beings and in general in non-ruminant animals, because of their
inactivation in the digestive tract by the monoamine oxidase. The
absorbtion of physiologically active amount of indole alkaloids in sheep
and cattle would be therefore possible only in the rumen where evidendy the
inactivating process does not occur.

The economical importance of "phalaris staggers" and the more general
negative influence of the indole alkaloids on the forage quality [ARNOLD &
HILL, 1972; AUDETTE et al., 1970; BERRY & HOVELAND, 1956; BLOOD et al.,
1983. BRINK, 1964; CARLSON et al,, 1968; 1972; GALLAGHER et al., 1966a;
1966b; 1967; JORDAN & MARTEN 1975; KENNEDY et al., 1986; KERR, 1972;
MARTEN, 1973; 1981; MARTEN & JORDAN, 1974; MARTEN et al., 1976; 1981;
NICHOLSON, 1989; NICHOLSON et al., 1989, O'DONOVAN et al., 1967; ODRIOZOLA
et al., 1991; PARMAR 1975; PARMAR & BRINK 1976, ROE & MOTTERSHEAD, 1962;
ROGLER, 1944; SIMONS, 1970; SIMONS & MARTEN 1971; VAN ARSDELL

et al., 1954; WILLIAMS et al., 1970; WITENBERG et al., 1992; WOODS5 1973;
WOODS & CLARK 1974]

have been led up to a large number of chemical studies about the two main
forage species in the genus Phalaris. From the work of WILKINSON [1958],
who first reported in 1958 the presence of hordenine and
5-methoxy-N,N-dimethyltriptamin.e (5-MeO-DMT) in P. arundinacea, many other
researches have been done [APPLESEED, 1993b; AUDETTE et al., 1969; 1970;
BALL & HOVELAND, 1978; BARNES et al., 1971; BERG, 1978; JOHNSEN, 1978;
COULMAN et al., 1976; COULMAN et al., 1977; CULVENOR et al., 1964; DONKER
et al., 1976; DUYNISVELD et al., 1990; FRAHN & O'KEEFE, 1971; FRAHN in
KENNEDY et al., 1986; FRELICH & MARTEN, 1972; FRELICH, 1973; FRELICH 1972;
GANDER et al., 1975; HAGMAN et al., 1975. HOVIN & MARTEN, 1975; JORDAN &
MARTIN, 1976; KENDALL & SHERWOOD, 1975., MAJAK & BOSE, 1977; MAJAK et al.,
1978; 1979; MARTEN, 1981; MARTEN et al., 1973; 1974; 1976; 1981; McCOMB et
al., 1969; MOORE et al., 1966; 1967; MULVENA & SLAYTOR, 1982; 1983; MULVENA
et al., 1983; ORAM & WILLIAMS, 1967; ORAM in KENNEDY et al.,1986; ORAM,
1970; STREM & MARUM, 1989. STREM, 1987; PARMAR, 1975; PARMAR & BRINK, 1976;
RENDIG et al., 1970; 1976; SIMONS & MARTEN, 1971. SIMONS in BARKER & HOVIN,
1974; SIMONS, 1970; ULVUND, 1985; VIJAYANAGAR et al. 1975 (cf. also ;
SHANNON & LEYSHON, 1971); WELCH, 1971; WILLIAMS et al., 1971; WILLIAMS,
1972; WOODS & CLARK, 1971a; 1971b; WOODS et al., 1979]. The alkaloids until
now found in P. arundinacea and P. aquatica are:

   * N-methyltryptamine (NW)
   * 5-methoxy-N-methyltryptamine (5-MeO-DMT)
   * N,N-dimethyltryptamine (DMT)
   * 5-methoxy-N,N-dimethyltryptamine (5-MeO-DMT)
   * 5-hydroxy-N,N-dimethyltryptamine (Bufotenine, 5-OH-DMT)
   * 5-methyl-tryptamine
   * 5-methoxy-tryptamine
   * 2-methyl-1,2,3,4-tetrahydro-8-carboline (MTHC), not found in P.
     aquatica
   * 2-meth 1-6-methox -1 2 3 4-tetrahydro-ß-carboline (MMTHC
   * 2-methyl-6-methoxy-1,2,3,4-tetrahydro-ß-carboline (MMTHC)
   * 2,9-dimethyl-6-methoxy-1,2,3,4-tetrahydro-ß-carboline (DMTHC)
   * Gramine
   * 7-methoxy-gramine
   * 5,7-dimethoxy-gramine
   * Hordenine

Some of the above-mentioned compounds, such as N-methyl-tryptamine,
5-methyltryptamine, 7-methoxy-gramine etc. are contained in the two species
only in trace amount and they seem to be present exclusively in particular
growing stages, probably as a part of the biosynthetical pathways of other
indole alkaloids [MULVENA et al., 1983]. The ß-carbolines are also found in
the two Phalaris in very low concentration, at most 5% of the indole
alkaloids total amount, that is 0.0003% of the dry weight [AUDETTE et al.,
1969; 1970; FRAHN & O'KEEFE, 1971; GANDER et al., 1976. VIJAYANAGAR et al.,
1975]. Such an unfavorable ratio of B-carbolines/indolalkylamines makes
improbable (but maybe not impossible, particularly for some strains) the
occurrence of the pharmacological conditions for carrying out an
"ayahuasca-like effect" with only the Phalaris plants.

On the other hand the concentration of the other indole alkaloids, among
which the psychoactive DMT and 5-MeO-DMT, is very variable. This
variability, referred to both the absolute amount and the mutual
relationship between the alkaloids, is influenced by many and often
interacting factors.

In the first place, the capacity of producing indolalkylamines is
genetically fixed. Many P. aquatica and P. arundinacea cultivars, under the
same environmental conditions, differ considerably for quantity and type of
alkaloids produced [BARKER & HOVIN, 1974. BROWN, 1961; COULMAN, 1977.
COULMAN et al., 1976; DUYNISVELD et al., 1990. GANDER et al., 1975; HOVIN &
MARTEN, 1975; MARTEN et al., 1976; MARUM et al., 1979; ORAM, 1970; ORAM &
WILLIAMS, 1967; STREM, 1987; SACHS & COULMAN, 1983; SIMONS, 1970; WOODS &
CLAM, 1971a; 1971b]. This means that it is possible, as has been widely
verified in the crop science, to select strains with low (and, obviously,
high) alkaloids content. A genetical model has also been proposed [MARUM et
al., 1979] which, even though it does not completely explain the
relationships between the different classes of chemical compounds (probably
affected by other factors), is valid according to the researches carried
out in this field. The model proposes two dominant alleles controlling the
phenotype T (synthesizing mainly DMT, MMT and MTHC) and M (containing
5-MeO-DMT. 5-MeO-MMT and MMTHC). Tne phenotype G, containing almost only
gramine, would be produced when both the alleles are homozygous recessive.
With regard to the biosynthesis, the double recessive mmtt would synthesize
gramine from tryptophan through 3-aminomethylindole and
3methyl-aminomethylindole; the genotypes m recessive/T dominant (mmT) would
use the pathway tryptophan à tryptamine à MMT à DMT and MTHC (with a
possible secondary pathway from DMT to MTHC); the genotypes t recessive/M
dominant (Mtt) and M dominant/t dominant could use the pathway tryptophan à
5-methoxy-tryptophan à 5-methoxy-tryptamine à triptamine à 5-MeOMMT (à
derivation to MMTHC) à 5-MeO-DMT (à derivation to DMTHC) [ibid.; cf. also
BAXTER & SLAYTOR, 1972a; 1972b; LEETE, 1967; MACK, 1974; MACK & SLAYTOR,
1974; 1976; 1978; 1979; 1988; SPENSER, 1970]

The greatest amount of indole alkaloids is found in the plant parts where
the chlorophyllous activity is considerable [BALL & HOVELAND, 1978; FRELICH
1973; HAGMAN et al., 1975; MARTEN, 1981; SIMONS & MARTEN, 1973; WELCH 1971;
WOODS et al., 1979]. The highest concentration is therefore contained in
the leaf blades, particularly in the upper third of the seedling; on the
contrary culm, panicle, quiescent leaves, leaf sheaths and hypogean parts
show a low to very low content of indolalkylamines [ibid.; PARMAR, 1975;
PARMAR & BRINK 1976]. The total alkaloids concentration decreases with
plant maturity [SIMONS & MARTEN 1973; MARTEN et al., 1976; PARMAR & BRINK
1976]; in some cases the decrease can be more than 50% during the progress
from a vegetative stage to anthesis [FRELICH, 1973; FRELICH & MARTEN, 1972;
SIMONS, 1970], even though for the latter maturity degree it is worth
taking into account the larger weight of cuims and panicles on the total
biomass. In general, the total alkaloids and particularly the substituted
tryptamines, are more concentrated in the first regrowth, after the cutting
or grazing, than in the first growth just after the sowing, decreasing then
in the following regrowths [BALL & HOVELAND, 1978; BARNES et al., 1969;
1971; COULMAN et al., 1977; DUYNISVELD et al., 1990; HAGMAN et al., 1975;
McCOMB et al., 1969; PARMAR & BRINK, 1976; WILLIAMS, 1972; WOODS et al.,
1979]. It is worth noting that,'whereas the above-mentioned trend and
distribution in plant parts is generally valid for indole alkaloids
(although with characteristic behaviours of the separate compounds), the
non-indole alkaloid hordenine is normally more concentrated in the leaf
sheath than in the blade and it follows a different trend during the
maturity stages and the regrowths [COULMAN et al., 1977; DUYNISVELD et al.,
1990; WOODS et al., 1979].

The availability of soil nitrogen increases the alkaloids concentration,
particularly in cultivars with high alkaloids content, during the first
growing stages and in plants growing in full sunlight [FRELICH 1973;
FRELICH & MARTEN, 1972; MARTEN, 1981; MARTEN et al., 1974; MOORE et al.,
1966; 1967; PARMAR 1975; PARMAR & BRINK 1976; SIMONS, 1970; WELCH, 1971].
In these conditions, the addition of 120 kg/ha of nitrogen to a mixture of
nitrogen-deficient peat and mineral soil produces an average total
alkaloids increase of 50 % [MARTEN et al., 1974; MARTEN, 1984; SIMONS,
1970]. In soil, but not in nutrient solution cultivations, the
concentration of indole alkaloids depends also from the source of nitrogen;
in fact, the increase is greater in plants supplied with ammonium nitrogen
compared to the nitric source [FRELICH, 1973; FRELICH & MARTEN, 1972;
MARTEN, 1981; MARTEN et al., 1974; PALMAR, 1975; PALMAR & BRINK, 1976;
WELCH, 1971].

The photoperiod has little influence on the production of alkaloids
[FRELICH, 1973; FRELICH & MARTEN, 1972; MARTEN & FRELICH, 1977; MOORE et
al., 1966; 1967; WILLIAMS 1972] that is instead sensible to the shading.
Samples of P. arundinacea growing with 20 % of the full sunlight can
contain an amount of DMT about twice compared to the control, 5-MeO-DMT may
increase up to a factor 25 [ibid.]. Regarding to the circadian
oscillations, the DMT seems to show a maximum in the first hours of the
morning, at least in the shaded plants, whereas the 5-MeO-DMT reaches a
concentration peak in the late morning [WILLIAMS, 1972].

Plants growing after a moisture stress may contain up to three times the
concentration of alkaloids found in regularly watered sarnples. The highest
increase of the tryptamine alkaloids is shown at the first reduction of the
leaves turgor: the most affected alkaloid seems to be the 5-MeODMT.
Moreover, the first regrowth of the stressed plants contains more DMT and
less 5-MeO-DMT than the regrowth of the non-stressed ones [MARTEN, 1981;
WILLIAMS, 1972; cf. BALL & HOVELAND, 1978]. The influence of frost is very
similar, even though in this case the DMT appears to be the most affected
indole alkaloid. The highest increase for an exposure to -2·C during the
night, is found in seedling of P. aquatica growing at high nitrogen level
in the soil and with day/night temperature of respectively 21 and 16 ·C
[WILLIAMS 1972]. There is, in conclusion, a little increase of the
alkaloids in plants growing at high compared to low temperature but in
general the effects of this factor are weak [FRELICH, 1973; FRELICH &
MARTEN, 1972; MARTEN, 1981 , MARTEN & FRELICH 1977; MOORE et al., 1966;
1967; ORAM, 1970].

The almost satisfactory knowledge about the chemistry of P. aquatica and P.
arundinacea demonstrates the wide interest to these species and the large
number of researches dedicated to them. The situation is quite different,
however, for the rest of the genus Phalaris. The only chemical study which
analyzed the indole alkaloids in some species other than P. aquatica and P.
arundinacea was, as far as we know, a research conducted by ORAM in 1970.
The author studied 33 strains of 14 different entities but without
specifying their identity. On this topic, the only results reported by Oram
are the following:

   * no species was entirely free of tryptamine alkaloids;
   * the three species with chromosome number 2n= 12 (probably P.
     brachystachys, P. canariensis and P. truncata) had low alkaloids
     level; and P. canariensis always showed lower levels than any P.
     aquatica ecotype;
   * variation in the alkaloid content was found between strains within P.
     minor and P. arundinacea.

Recentely, ODRIOZOLA and others (1991) did not find by thin layer
chromatography any 5MEO-DMT in toxic samples of P. angusta NEES ex TRIN.,
an American species. However, the authors reported an unidentified
chromatographic spot producing the same color reaction as 5-MeO-DMT to
Erlich's reagent, but having a different Rf value; this compound could be
DMT. As a confirmation that all or the most species within the genus
Phalaris contain indolalkylamines, it has been reported that it is possible
to produce livestock intoxications also for P. angusta NEES ex TRIN.
angusta [ODRIOZOLA et al., 1991 ], P. brachystachys LINK in SCHRADER
[FERNANDEX DE Luco et al., 1990a; 1990b], P. caroliniana WALT. [NICHOLSON,
1989; NICHOLSON et al., 1989], P. minor L. [KELLERMAN et al., 1988;
NICHOLSON, 1989; SCHNEIDER, 1978 (unpub. data) in VAN HALDEREN et al.,
1990; VAN HALDEREN et al., 1990], and for the hybrid P. aquatica X
arundinacea (also known as Ronphagrass) [VAN DER MERWE, 1959; RUELKE &
MCCALL, 1961].

According to such inforriation, in the. summer 1993 we made some paper
chromatographies regarding 10 samples from 5 species of cultivated
Phalaris: P.aquatica L., P.canariensis L., P.coerulescens DESF., P.paradoxa
L. and P.Iruncala L. The seeds of P.aquatica, paradoxa and coerulescens
came from wild or naturalized places respectively in the province of
Bologna, Livorno and Pisa (Central Italy). Other seeds of P. coerulescens
and P. truncata came from the Botanical Garden of Bordeaux (France),
whereas the ones of P.canariensis came from a commercial strain (Benary,
Ziergröser, Germany). The seedlings were collected about 20-30 days after
their germination. All the samples were found to contain indolalkylamines
even though, lacking the chemical standards, the separate compounds were
not identified [FESTI & SAMORINI, 1994]. During these preliminary
researches we also undertook a semi-quantitative analysis on the total
alkaloids extract of the wild P. aqualica strain, we will refer to as AQ1.
The seeds, collected near Bologna, were cultivated in Rovereto (North
Italy, latitude 46· north ca.). The total alkaloids fraction from the
distal two thirds of the first regrow after the cutting, previously
fertilized with ammonium sulfate, was extracted in accordance with the
simple method described by "John Appleseed" in Entheogen Review [APPLESEED,
1992]. The weighing of the oily residue led us to estimate the alkaloids
content to be greater than 1% on dry weight.

These preliminary data has urged us to undertake, in 1994, a more specific
research which aims at a chemical characterization of the European Phalaris
and which is still going on. Seeds of P.aquatica L., P. arundinacea L., P.
brachystachys LINK in SCHRADER, P.Canariensis L., P. coerulescens DESF., P.
minor RETZ., P. paradoxa L., P. stenoptera HACK. and P. truncata L., from
different European botanical gardens or from authors' collections, were
grown on commercial standard soil in Rovereto. One or two samples (first
growth and regrowth after cutting) for each species were collected and sent
to the chemist Fabio Calligaris, working at the University Institute of
Chemistry in Turin, to whom we are grateful, for his precious
collaboration. Some qualitative results of this analysis, mainly carried
out by means of high pressure liquid chromatography (HPLC), will be
presented here, while for the complete results and the experimental methods
a specific publication will follow. Since the quantitative researches and
the checks about the extraction method are still lacking, the following
data must be considered absolutely preliminary, although they could give an
idea on the species variability.

All the seven species analyzed so far contain DMT as the main alkaloid:
however, P. brachystachys and P. minor seem to contain only this
indolalkylamine, the former in high concentration, the latter in trace
amount. Bufotenine,- or 5-OH-DMT, is found in very low quantity in all the
other species. MMT is present in P. paradoxa. P. truncata and P. aquatica
even though only in the last species it reaches significant concentrations.
Also 5-MeO-DMT shows a scattered distribution among the analyzed samples,
being present only in P. truncata, P. canariensis and P. aquatica. These
data, in any case not definitive, seem to be only partially in accordance
with the few above mentioned researches on the Phalaris other than P.
aquatica and P. arundinacea. Therefore, we need the results of a wider
spectrum of samples in order to go deeper into the topic. For the time
being we can emphasize the importance of analysing separately the presence
of every single indolalkyiamine in the plants. As a matter of fact, the
total alkaloids content is not sufficient to understand the possible
pharmacological activity as well as the variability and the chemiotaxonomic
relationships among the Phalaris species.

Pharmahuasca with Phalaris aquatica and Peganum harmala

Occasionally P. aquatica has been pointed out as a possible source of
entheogenic indolalkylamines [DEKORNE, 1993b; 1994a; 1994c; FESTI &
ALIOTTA, 1990; OTT 1993; 1994a; SAMORINI, 1992] but until now and as far as
we know, there are no published data about its use in

pharmahuasca experiments.

On these grounds, we have paid particular attention to an Italian wild
strain of P. aquatica, that we found interesting in the preliminary
chemical analysis. This strain was first observed growing near Bologna and
named AQ1 by Giorgio Samorini. From a morphological point of view its
characters are included in the variability limits of the species [cf.
BALDINI, 1993], apart from the panicle tending to be a little longer at the
plant maturity. However, its habitat is quite particular: AQ1 is in fact
widespread on the calanchi, that is big furrows dug by the eroding water on
clay hill soils, in general showing a very typical and interesting flora.
As we have not pursued, until now, any systematic investigation about
different Italian strains of P. aquatica, it is possible that the high
alkaloids content of AQ1 is shared with other P. aquatica populations in
Italy. On the other hand, the bibliographical data seem to show that there
is not a correlation between alkaloids content of Phalaris wild strains and
their geographical origin [ORAM & WILLIAMS, 1967; ORAM 1970].

Seeds of AQ1 collected in its original habitat near Bologna, were sown in a
field in Rovereto during the first spring months; the plants, regularly
watered, were fertilized after the first cutting with ammonium sulfate in
an amount equivalent to 200 kg/ha.

The first harvest, carried out 15 days after the sowing, could contain
cyanogenetic compounds, even though in little concentration [GAGGINO et
al., 1965], and so it was not used for the ingestion experiments. From a
part of these young leaf blades the total alkaloids were extracted using
the Entheogen Review method [APPLESEED, 1992]. About 100 mg of extract
smoked with tobacco produced a clearly entheogenic experience. On the
contrary, the effects of the smoke from dried young plants were scarcely
perceptible and only perceived by one subject. However, it is worth
remembering that the drying at room temperature or in a dryer at 40· C
reduces the total alkaloids concentration by up to 50 % [CULVENOR et al.,
1964. MARTEN, 1974 in DONKER et al., 1976; DONKER et al., 1976]. To this
reduction we should add the partial destruction of the indole alkaloids
owing to the direct burning. In this way, the amount of DMT or 5-MeO-DMT
inhaled during the first mouthfuls is not enough to produce entheogenic
effects but it succeeds in inducing tolerance, so blocking the possible
action of the smoke subsequently inhaled. However, eliminating the causes
of the alkaloids loss, P. aquatica becomes completely active also by
pulmonary way. In fact, some subjects reported a clearly entheogenic
experience after inhalation of different amounts of the vapour emitted by
heated (without combustion) fresh plant. It must be mentioned that the
samples used in these experiments were cut from the second regrowth: this
could be interpreted as further evidence for the AQ1 potency, since, in
accordance with the bibliographical data, the alkaloids level decreases
with the maturity [vide supra].

The upper part of the first regrowth (about 1.5 kg) was boiled in water
acidified with citric acid to pH 4 for about half an hour. the water was
enough to cover completely the vegetal material. After filtration, the
residue was extracted once again with the same procedure. The resulting
liquid was then reduced to a quarter by means of light heating. Seeds of
Peganum harmala were separately extracted using the same method.

Lacking quantitative analysis about the strain AQ1 and even though we knew
the wide variability of the P. aquatica alkaloids content, we bad to refer
only to the bibliographical data in estimating the approximate
indolalkylamines amount to ingest during the experiments. This is the
reason why the first experiment produced in one of us an effect that we
could define as an alkaloids overdose. A P. harmala extract quantity
corresponding to 4.5 g of seeds was first ingested on an empty stomach; the
AQ1 extract supposed to correspond to 40 mp, of indole alkaloids, but
probably greater for at least a factor 5, and equivalent to about 400 g of
fresh Phalaris aquatica was ingested 20 minutes later. A first peak,
clearly entheogenic but fully controllable, became evident about 30 minutes
later, followed by an apparent sensation of diminishing effects. In this
first phase neither nausea nor any other physical symptoms or feeling to be
intoxicated appeared. One hour and a half after the ingestion of P.
aquatica the effects quickly became acute again leading, for one of us, to
a complete loss of consciousness 40 minutes later. During this unconscious
phase, that was resolved only 13 hours after the ingestion of P. harmala,
we observed symptoms of adrenergic activation with strong mydriasis,
muscular hypertonicity (particularly in the nape and the back), muscular
clonus, tremors, exaggerated reflexes. These physical symptoms became less
intense about 8 hours after the ingestion even though clonic movements and
atavistic motor reflexes of clearly psychogenic origin still persisted.
During the following days neither hangover nor other after-effects were
observed, apart from the obvious tiredness the day after the experience.
However, the oneiric activity was disturbed for the whole of the following
week; this may be considered in accordance with the hypotheses proposed by
CALLAWAY [1988] about the interaction between endogenous ß-carbolines and
indolalkylamines as a possible base for the oneirogenic mechanism.

Starting from the results of this first attempt, in a second experiment a
Peganum harmala extract amount corresponding to about 2.5 g of seeds was
ingested followed, after 20 minutes, by

a quantity of AQ1 extract approximately corrisponding to 60 g of fresh
Phalaris (that is less than 1/5 compared to the first experiment). After 5
minutes a frankly entheogenic experience began, with a peak after one hour
and completely cleared up after 6 hours. The plateau was characterized by
alternate phases of partial evanescence and rush of the effects.

In conclusion, verified the expected psychoactivity of P. aquatica either
by pulmonar absorbtion or in the pharmahuasca combined with Peganum
harmala, the results of these few, preliminar experiments need some
considerations.

First of all, the oral psychoactivity of the P. aquatica integral aqueous
extract is obviously different from those of the single compounds DMT or
5-MeO-DMT and maybe also from those of the total alkaloids extract from the
plant. Moreover, in spite of the title of this communication where we use
the word "ayahuasca-like effect", the pharmahuasca P. aquatica/P. harmala
seems to be a lot different from the Ayahuasca australis: the sometimes
aggressive and often up-down subjective effects of the former are in
contrast with the meditative and often almost oneiric characteristic of the
latter. The reasons for this difference are probably due to the distinct
chemistry of the two preparations. It is possible that some pharmahuasca
characters are linked to the interaction between DMT and 5-MeO-DMT
considering that the latter substance is not contained in the classic
additive Psychotria viridis RIAZ & PAVON [cf. OTT, 1993; 1994a]. We cannot
exclude, however, that other compounds present in the Phalaris, little or
not active themselves, could play an important role in the global
pharmacology of these species.

[Bibliography Not Included!]