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Seeds and roots contain MAO-inhibiting beta-carboline alkaloids, mostly harmine, as well as harmaline, harmalol, harmane, peganine, isopeganine, dipegene, vasicinone and deoxyvasicinone.
The whole plant is toxic but the amount of alkaloids is far more important in the seed (3-4%) than in the root, the stem (0,36%) and the leaves (0,52%). The amount of alkaloids increases suddenly in summer, when the fruit ripes, in that time the seed is harvested.
Chemical structure of the alkaloids.
Beta-carbolines are a subclass of indoles; some beta-carbolines induce visual hallucinations, among them harmine and harmaline.
The indole structure derived from tryptophane combines a indole and a pyridine core.
Harmine: 7-methoxy-1-methyl-b-carboline, C13H12N2O (mol. wt. 212.25)
Harmaline: methoxy-harmalol and dihydroharmine, 3,4-dihydro-7-methoxy-1-methyl-b-carboline, C13H14N2O (mol. wt. 214.26). Builts 2/3 of the totality of the seeds alkaloids. twice more toxic than harmine.
Harmalol: C12 H12 N20 (= Harmol)
Harmane: C12 H10 N2
The unusual harmala alkaloids, harmine and harmaline are psychoactive derivatives of B-carboline, When administered to man, the harmala alkaloids are serotonin antagonists, CNS stimulants, hallucinogens and extremely potent, short term MAO inhibitors.
The harmala alkaloids may be extracted from the seeds and roots of P. harmala- and purified as crystalline bases.Hasenratz described this process in 1927.
The harmala alkaloids are especially potent short-term MAO inhibitors. They temporarily prevent biogenic amines from binding to the active site of the MAO molecule and undergoing deamination. Amine synthesis continues but inactivation is blocked. The result is an accumulation of physiologically active amines - dopamine epinephrine, norepinphrine, and serotonin - within the tissues and at the synapses. MAO inhibitors increase the action of these neurotransmitters at their receptors, which may account for some of the hallucingenic effects characteristic of the harmala alkaloids. For 3 to 6 hours, the harmala alkaloids interfere with the protective enzyme MAO, before their action is reversed and MAO activity restored.
Metabolisme of the alkaloids: sulfo- and glycuroconjunction in the liver, elimination through bile and urine
Other components of the plant are:
- amino-acids: phenylalanine, valine, proline, threonine, histidine, glutamic acid and hydrocarbonates.
- flavonoïds, cumarins, volatile bases, tanins, sterols/triterpens
- pigment: the external integument of the seed contains a red pigment known as "Turkey red".
- fluorescent compound
Egyptian studies found that extract is markedly fungicidal and bactericidal, due to harmine mostly.
After ingestion of seeds, the alcaloïds are absorbed in few minutes by the gastro-intestinal system.
The ingestion of more than one teaspoon of seeds provokes intoxication symptoms.
The alcaloïdes reach the target organs, especially the CNS and the heart.
The physical symptoms are:
- digestive troubles, bradycardia
- neurological troubles: euphoria, visual hallucinations, then
- trembling of whole body up to convulsions.
- in severe cases, paralyse, depression of the CNS, dyspneoa
- hypothermia and arterial hypotension
- kidneys: cases of death of children in a state of anuria and uremia have been reported.
Case from literature: february 18th 1984, at 7am, A.N. 27y, swallows on empty stomach a teaspoon of crushed seeds blended with honey. In the followings minutes appear awful headaches, paresthesia, neurosensorial troubles like hypoacousis and amaurosis followed by visual hallucinations (flames). At 11am, the neurological and cardiovascular examination are normalised; only remain stupefaction and vivid reflexes.
At 2pm, the patient arrives in the Emergency Center in Tunis. She presents a severe asthenia, diffuse abdominal pain, headaches, but no other symptoms. ECG, bloodtests (liver, kidneys) are normal.
After 30 hours, all symptoms have disappeared.(3), (4)