Harmine
From Wikipedia, the free encyclopedia
| Harmine | |
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| Systematic name | 7-MeO-1-Me-9H-pyrido[3,4-b]-indole |
| Chemical formula | C13H12N2O |
| Molecular mass | 212.25 g/mol |
| Melting point | 321 °C (·HCl) |
| 262 °C (·HCl·2H2O)[1] | |
| CAS number | [442-51-3] |
| SMILES | CC1=NC=CC2=C1NC3=C2C=CC(=C3)OC |
| Disclaimer and references | |
Harmine is an alkaloid belonging to the Beta-carboline family of compounds. It occurs in a number of different plants, most notably the Middle Eastern plant harmal or syrian rue (Peganum harmala) and the South American vine Banisteriopsis caapi ('yage', 'ayahuasca'). Harmine is a reversible monoamine oxidase inhibitor (MAO inhibitor or MAOI) and CNS stimulant.
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[edit] Uses
As a MAO inhibitor, harmine inhibits the breakdown of monoamines by enzymes called monoamine oxidases. Monoamines include neurotransmitters (serotonin, dopamine), hormones (melatonin) and drugs, including many hallucinogens (psilocybin, dimethyltryptamine (DMT), mescaline). By slowing the breakdown of neurotransmitters, MAOIs can help to replenish the body's supply of these chemicals, and many MAOIs are used as antidepressants. Harmine has not been the subject of much clinical research in the treatment of depression, which could be due in part to its restricted legal status in many countries, as well as the existence of synthetic MAOIs with fewer side effects.
P. harmala and B. caapi are both traditionally used for their psychoactive effects. B. caapi has a tradition of use in conjunction with plants containing the drug DMT. Traditionally, B. caapi is consumed as a drink, with or without the DMT-bearing plants (see Ayahuasca). Ordinarily, DMT is not active when taken orally, but users report very different effects when DMT is present in such beverages. Harmine and substances containing it have been used in conjunction with many other drugs by modern experimenters. Many hallucinogens appear to exhibit increased potency when used in this way.
[edit] Adverse effects
It is important to note that unlike synthetic reversible MAOIs such as moclobemide, harmine is still capable of interacting adversely with monoamines found in everyday foods such as cheese and yeast extracts. Individuals should not attempt to self-medicate themselves for depression using harmine. One specific example is tyramine, an amine present in a variety of foods, but with higher concentrations in hard cheeses and aged/canned meats (tyramine is formed from the gradual breakdown of some proteins). Normally, it is oxidized quickly in the body and is harmless. However, when the MAO enzymes are inhibited, tyramine concentrations can rapidly increase and become toxic. Tyramine mimics dopamine and norepinephrine structure and toxicity includes hypertensive crisis and possibly heart failure.
[edit] Natural sources
Harmine is found in a wide variety of different organisms, most of which are plants. Shulgin (1997)[2] lists about thirty different species known to contain harmine, including seven species of butterfly in the Nymphalidae family. The harmine-containing plants listed include tobacco, two species of passion flower/passion fruit, and numerous others.
In addition to B. caapi, at least three members of the Malpighiaceae contain harmine, including two more Banisteriopsis species and the plant Cabi paraensis. Callaway, Brito and Neves (2005)[3] found harmine levels of 0.31-8.43% in B. caapi samples.
The Zygophyllacae family, which harmal belongs to, contains at least two other harmine-bearing plants: Peganum nigellastrum and Zygophyllum fabago.
[edit] References
- ^ The Merck Index (1996). 12th edition
- ^ Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. pp. 713-14
- ^ Callaway JC, Brito GS & Neves ES (2005). Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis. Journal of Psychoactive Drugs 37(2): 145-150.
