Harmala, alkaloids

Harderian gland porphyrins in, 4, 382 Harderoporphyrin, 4, 382 Harmala alkaloids, 4, 529 Harmaline... 

Raymond-Hamet has made a special study of the vascular action of the harmala alkaloids and certain of their proximate derivatives, including their influence on the pressor and other effects of adrenaline in comparison with that of yobyrine and ketoyobyrine (pp. 505-6). 

Other examples of syntheses under physiological conditions will be found under arecaidine, lobelia, papaverine, cusparia bark alkaloids, harmala alkaloids, rutascarpine and yohimbine. 

The nomenclature used to describe the fused benzene-pyrrole-pyridine system of the compounds under discussion has been repeatedly modified, and the compounds have been numbered in an astonishing variety of ways since Perkin and Robinson introduced the name carboline for the ring system, which was encountered for the first time in the harmala alkaloids. In the earliest version of carboline nomenclature, the parent compound of the series, whose trivial name was norharman, was referred to as 4-carboline and numbered as in 1. Harmine (2) then became ll-methoxy-3-methyl-4-carboline. 

Naranjo, C. (1979) Psychotropic properties of the harmala alkaloids. In Ethnopharmacologic Search for Psychoactive Drugs, edited by D. H. Efron, B. Holmstedt, and N. S. Kline, pp. 385-391. Raven Press, New York. 

Yage Banisteriopsis caapi Woody vine Harmala alkaloids Di methy Itry pta mine... 

There are two major types of hallucinogenic alkaloids in yage. These are DMT and the harmala alkaloids (or j8-carbolines). 

Also, harmala alkaloids create effects on monoamine turnover. Postnatal rats administered harmaline (shortly before birth) have elevations in brain levels of the norepinephrine metabolite 3-methoxy-4-hydroxy-phenylglycol (MHPG), but decreases in the dopamine and serotonin metabolites 3,4-dihydroxyphenylacetic acid (DOPAC) and 5-hydroxyindole acetic acid (5-HIAA) (Okonmah et al. 

Harmala alkaloids are inhibitors of brain MAO. Harmane inhibits MAOA in the submicromolar range (5 X 10-7 M) and MAOB in the micromolar range (5 x 10-6 M) (Glover et al. 1982). Harmine inhibits MAOA, but also has additional unspecified monoamine modulatory effects (Meneguz et al. 1994 Fernandez de Arriba et al. 1994). Harmaline or its metabolites may also stimulate aldehyde reductase or catechol 0-methyltransferase (COMT) (Okonmah et al. 1988). 

Autonomic effects Harmala alkaloids, as well as isolated harmine and harmaline, produce a dose-dependent hypothermia (Abdel-Fattah et al. 1995). This effect is serotonin-dependent, and partly mediated by 5-HTlA receptors. 

Cardiovascular effects Harmala alkaloids have cardiovascular effects (Aarons et al. 1977). Harmine, harmaline, and harmalol decrease heart rate, but increase pulse pressure, peak aortic flow, and myocardial contractile force in dogs. Harmine reduces systemic arterial blood pressure and peripheral vascular resistance. Vascular resistance effects are not mediated by jS-adrenergic or histamine HI receptors. 

Harmala alkaloids are potent inhibitors of monoamine oxidase (Callaway and Grob 1998). Thus, if combined with other antidepressants, such as selective serotonin reuptake inhibitors, there is potential for serious side effects. Harmaline or its metabolites also cross the placental barrier (Okonmah et al. 1988). 

Aarons DH, Rossi GV, Orzechowski RF. (1977). Cardiovascular actions of three harmala alkaloids harmine, harmaline, and harmalol. J Pharm Sci. 66(9) 1244-48. 

Abdel-Fattah AF, Matsumoto K, Gammaz FIA, Watanabe H. (1995). Flypothermic effect of harmala alkaloid in rats involvement of serotonergic mechanism. Pharmacol Biochem Behav. 52(2) 421-26. Abraham FID. (1983). Visual phenomenology of the LSD flashback. Arch Gen Psychiatry. 40(8) 884-89. 

Callaway JC, Raymon LP, Fleam WL, McKenna DJ, Grob CS, Brito GS, Mash DC. (1996). Quantitation of N,N-dimethyltryptamine and harmala alkaloids... 

The harmala alkaloids harmaline (368 X = NH) and harmi.ne (369 X = NH) are active reversible inhibitors of monoamine oxidase (MAO). Benzo[ Jthiophene analogs of harmaline (368 X = S) and harmine (369 X = S), when tested in vitro as inhibitors of rat liver MAO, showed that (368 X = S) was 50 times more potent than harmaline, but (369 X = NH or S) were equivalent in potency. The replacement of the indolic nitrogen by sulfur greatly increased the lipid solubility of the molecule, which was reflected in the physiological disposition of the two analogs. 

Effects Competitive acetylcholine inhibitor at receptor site (postganglionic junction). Does not prevent acetylcholine liberation. Hallucinogen, similar to scopolamine, but producing more excitement and less stupor. Potentiates other psychotropics, including opium, cannabis, harmala alkaloids, mescaline. 

Note Notes on other harmala alkaloids Different harmala alkaloids vary in potency. The equivalent of 10 mg harine is 50 mg harmaline, 35 mg tetrahydraharman, 25 mg harmalol or harmol, 4 mg methoxyharmalan. Harmal alkaloids are synergistic (mutually potentiating) and are therefore most effective when combined in an appropriate balance. Tropines (belladonna alkaloids) also potentiate harmals. Harmol and harmalol (phenols) in overdoses can cause... 

Effects Smoked, very mild, short-lasting marijuana-like high. Tea, tranquilizer and sedative. Harmala alkaloids are hallucinogens. 

Contraindications Other materials in crude alkaloid reduction may cause nausea. Harmala alkaloids are short-term MAO inhibitors. 

Effects Trembling within a few minutes followed by perspiration and physical stimulation for 10-15 minutes, then calm with mental clouding, hallucinations, increased color, blue-violet shades, size changes, and improvide night vision. Harmala alkaloids are short-term MAO inhibitors. 

The most commonly used MAO inhibitors include hydrazines, such as iproniazid, Marsilid, Marplan, Niamid, Nardil, Catron also nonhydrazines such as propargylamines, cyclopropylamines, aminopyrazine derivatives, indolealkylamines, and carbolines. MAO-inhibiting materials discussed in this book include yohimbine various tryptamines, especially 5-MeO-DMT and the alpha-methyltryptamines and the various harmala alkaloids. The latter are especially potent inhibitors, but, like yohimibine and the tryptamines, are short-lasting in action (30 minutes to several hours). Some of the commercial MAO inhibitors listed above are effective for several days to several weeks. 

Syrian rue is the only botanical source of harmala alkaloids other than ayahuasca that is known to have been used as a mild-alterer. It has lately been linked to the "Drink of the Immortals once known as "Soma. ... 

At least one harmala alkaloid is present in the pineal gland of both humans and several animals. This compound is more abundant in the pineal glands of highly advanced yogis, according to some reports, which has led to speculation that its presence may impart power to the "third eye in midforehead, where the pineal gland lies. 

At a 1977 conference in San Francisco, Bo Holmstedt, a pioneer in research on harmala alkaloids from the Karolinska Institutet in Sweden, suggested that similar substrates and enzymes are in the pineal gland for endogenous production of DMT, 5-methoxy-DMT and the N-methyl analogues of harmine and harmaline. Brimblecombe and Pinder, in their Hallucinogenic Agents (p. 116), discuss possible metabolism routes by... 

As with DMT, theories have again been advanced that schizophrenia is associated with increased production of harmala alkaloids. As Shulgin has remarked, consensus among researchers now is that this approach is "a red-herring. ... 

Ayahuasca, yagi and harmala alkaloids prompt a wide range of experiences, which reflect dosage to a considerable degree and the influence of psychoactive additives. Descriptions vary from no psychoactive effects to effects rivaling those of LSD or psilocybin. 

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