B. caapi

Banisteriopsis caapi The primary hallucinogenic constituents of B. caapi are the jS-carbolines. These include harmaline, tetrahydroharmine, harmol, harmic acid methyl ester, harmic amide, acetyl norharmine, harmine A/-oxide, harmalinic acid, and ketotetrahydronorharmine (figure 9.8). B. rusbyana also contains DMT, as well as A/-methyltryptamine, 5-methoxy-N,/V-dimethyltryptamine, and 5-hydroxy-N,/V-dimethyltryptamine (bufotenin). /V-methyltetrahydro-jS-carboline is found in trace amounts. 

DMT elevates pulse rate and blood pressure. In one study, heart rate elevated from around 70 beats per minute at baseline to 100 beats per minute at the highest dose (0.4 mg/kg, IV). Neurophysiological effects Harmane produces excitation in the nucleus accumbens in nanomolar concentrations, but depression in micromolar concentrations (Ergene and Schoener 1993). Harmine and B. caapi extract decrease the acoustic startle, which is reversed to some degree by DMT (Freedland and Mansbach 1999). j3-carbolines may have antioxidant effects through inhibiting oxidative enzymes in the microsomal system (Tse et al. 1991). 

Hochstein and Paradies (1957) suggest that, in addition, the alkaloids harmaline and d-tetrahydroharmine, discovered in B. caapi, "may have substantial psychotomimetic activity in their own right."... 

Ayahuasqueros often indude at least one additive toyagS infusions to enhance states of mind brought about by B. caapi, inebrians and quitensis. In Colombia, Daturas and dosely related species of Brugmansia are sometimes used they undoubtedly give this drink added kick but are dangerous. Often tobacco appears other additives are listed by Schultes and Hofmann ... 

The main additives are Psychotria carthaginensis, P. viridis, Tetrapterys methystica and Banisteriopsis rusbyana. Leaves and stems of the last, known as oco-yagi or chagrapanga, don t contain the /3-carboline alkaloids produced by B. caapi and inebrians instead, they have a large amount of N,N-DMT, 5-methoxy-N,N-DMT, 5-hydroxy-N,N-DMT andN-/3 -methyltetrahydro-/3 -carboline. The other added species contain DMT-type compounds, rendered orally active by the harmala compounds in ayahuasca. 

The structure of harmine was known by this time (Fischer 1899 Perkin Robinson 1919A Perkin Robinson 19193), and the compound had been synthesized in 1927 (Manske etaL 1927 Spath Lederer 1930A Spath Lederer 19303). In 1957, Hochstein and Paradies isolated from Peruvian B. caapi harmine as well as harmaline and i leptaflorine or tetrahydroharmine (Hochstein Paradies 1957). These compounds were also found in an ayahuasca potion from Peril, and harmaline and (sf-leptaflorine (TetraHydroHarmine) were proposed to be psychotropic compounds in this ayahuasca potion. In 1969, the stable P-carboline alkaloid harmine was found in quantities similar to fresh material in Spruce s original type collection of Banisteriopsis caapi from 1852 (Schultes etaL 1969) Rivier and Lindgren found the same three p-carbolines as major alkaloids of Banisteriopsis caapi (Rivier Lindgren... 

Use activity H. are used in pharmacological research, they may have significance in the development of alcoholism, and are considered to be metabolites of tryptamine. Plasma levels of barman in heroin-depen-dent and methadone-substituted patients are elevated by ca. 200%. H. have hallucinogenic and narcotic activities. Extracts of the above-mentioned plants are thus used by traditional healers in central Asia. South American Indians and mestizos use the macerated bark of B. caapi as a hallucinogenic drink (ayahuasca= liana of the soul, also Yaje, Caapi), the effects begin with nervousness, sweating, nausea, and then intoxication states (visions in brilliant colors), dream-like... 

H-Oxide [57498-78-9]. Harmine -oxide C13H12N2O2 M 228.250 Alkaloid from B. caapi (Malphigiaceae). Needles (MeOH). Mp 226-227° dec. 

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