Harmine

Chembox new
Name = Harmine
ImageFile = Harmine.png ImageName = Harmine
IUPACName = 7-MeO-1-Me-9H
-pyrido [3,4-b] -indole
Section1 = Chembox Identifiers
CASNo = 442-51-3
SMILES = CC1=NC=CC2=C1NC3
=C2C=CC(=C3)OC
Section2 = Chembox Properties
Formula = C₁₃H₁₂N₂O
MolarMass = 212.25 g/mol
MeltingPt = 321 °C (·HCl); 262 °C (·HCl·2H₂O) [The Merck Index (1996). 12th edition]

Harmine is a fluorescent harmala 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. It inhibits MAO-A but has no effect on MAO-B. [ [http://www.ihop-net.org/UniPub/iHOP/pm/7997187.html?pmid=7938567 Abstract Gerardy J, "Effect of moclobemide on rat brain monoamine oxidase A and B: comparison with harmaline and clorgyline.", Department of Pharmacology, University of Liège, Sart Tilman, Belgium.] ]

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.

Harmine is also a useful fluorescent pH indicator. As the pH of its local environment increases, the fluorescence emission of harmine decreases.

With the radioisotope carbon-11 harmine is used in positron emission tomography neuroimaging to examine its binding to MAO-A. [Cite journal
author = Nathalie Ginovart, Jeffrey H. Meyer, Anahita Boovariwala, Doug Hussey, Eugenii A. Rabiner, Sylvain Houle and Alan A. Wilson
title = Positron emission tomography quantification of ¹¹C-harmine binding to monoamine oxidase-A in the human brain
journal = Journal of Cerebral Blood Flow & Metabolism
year = 2006
volume = 26
pages = 330–344
doi = 10.1038/sj.jcbfm.9600197]

"Harmine" found in root secretions of "Oxalis tuberosa" has been found to have insecticidal properties. [cite journal
title=Exudation of fluorescent b-carbolines from "Oxalis tuberosa" L. roots
journal = Phytochemistry
date=18 June 2002
first=Harsh
last=Pal Bais
coauthors=Sang-Wook Parka, Frank R. Stermitzb, Kathleen M. Halliganb, Jorge M. Vivancoa
volume=61
pages=539–543
url=http://lamar.colostate.edu/~jvivanco/papers/Phytochem/2002Harsh.pdf
accessdate=2008-02-02
doi=10.1016/S0031-9422(02)00235-2]

Anticancer

"Harmine showed cytotoxicity against HL60 and K562 cell lines. This could explain the cytotoxic effect of P. harmala on these cells." [ cite journal|title=Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent|journal=Phytochemistry |date=|first=|last=|coauthors=|volume=66|issue=|pages=1581|id= |url=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6TH7-4GC1RHC-5&_user=10&_rdoc=1&_fmt=&_orig=search&_sort=d&view=c&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=7a0868781e73d21bfd439c89db8177bc|format=|accessdate=2008-01-12|doi=10.1016/j.phytochem.2005.04.035|author=Jahaniani, F ]

Adverse effects

It is important to note that unlike synthetic pharmaceutical MAOIs such as phenelzine, harmine is reversible and selective meaning it does not have nearly as high a risk for the "cheese syndrome" caused by consuming tyramine-containing foods, which is a risk associated with pharmaceutical MAOIs sometimes (mistakenly) applied to all MAO inhibitors. [McKenna, Callaway, & Grb. [http://psychoactiveherbs.com/catalog/article_info.php?articles_id=9 "Scientific Investigation of Ayahuasca"] , Scientific Investigation of Ayahuasca, retrieved 2007-06-03.] Harmine, and plants containing significant amounts of harmine and other harmala alkaloids are generally not considered safe treatments for depression within the medical community. [cite journal
author = Eric Yarnell, Kathy Abascal
year = 2001
month = April
title = Botanical Treatments for Depression
journal = Alternative & Complementary Therapies
volume = 7
issue = 3
pages = 138–143
doi = 10.1089/10762800151125056
url = http://www.liebertonline.com/doi/abs/10.1089/10762800151125056]

Natural sources

Harmine is found in a wide variety of different organisms, most of which are plants. Shulgins [Cite book
author = Shulgin, Alexander and Shulgin, Ann
year = 1997
title =
publisher = Transform Press
isbn = 0963009699 Pages 713–714] list 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 "Callaeum antifebrile". Callaway, Brito and Neves (2005) [Cite journal
author = Callaway J. C., Brito G. S. & Neves E. S.
year = 2005
title = Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis
journal = Journal of Psychoactive Drugs
volume = 37
issue = 2
pages = 145–150
pmid = 16149327] found harmine levels of 0.31-8.43% in "B. caapi" samples.

The Zygophyllaceae family, which harmal belongs to, contains at least two other harmine-bearing plants: "Peganum nigellastrum" and "Zygophyllum fabago".

ee also

*Monoamine oxidase inhibitor

References

External links

* [http://lamar.colostate.edu/~jvivanco/papers/Phytochem/2002Harsh.pdf "Harmine" found in "Oxalis tuberosa"]