The Full Wiki

Harmine: Wikis


Note: Many of our articles have direct quotes from sources you can cite, within the Wikipedia article! This article doesn't yet, but we're working on it! See more info or our list of citable articles.


From Wikipedia, the free encyclopedia

Harmine (small).svg
Harmine 3d structure.png
IUPAC name
CAS number 442-51-3
Molecular formula C13H12N2O
Molar mass 212.25 g/mol
Melting point

321 °C (·HCl); 262 °C (·HCl·2H2O)[1]

Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa)
Infobox references

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.[2]



Harmaline and harmine fluoresce under ultraviolet light. These three extractions indicate that the middle one has a higher concentration of the two compounds.

As an 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.[3]

Harmine found in root secretions of Oxalis tuberosa has been found to have insecticidal properties.[4]


"Harmine showed cytotoxicity against HL60 and K562 cell lines. This could explain the cytotoxic effect of P. harmala on these cells."[5]

Adverse effects

Harmine is a reversible and selective inhibitor of MAO-A, which means that it does not induce the "cheese syndrome", which is caused by consuming tyramine-containing foods in combination with some pharmaceutical MAOIs, as tyramine is primarily metabolized by MAO-B.[6] Harmine, and plants containing significant amounts of harmine and other harmala alkaloids are generally not considered safe treatments for depression within the medical community, however this bias is primarily historical and built on previous decades of experience with non-specific pharmaceutical MAOIs that blocked both MAO-A and MAO-B, which are no longer used for this very reason.[7]

Natural sources

Harmine is found in a wide variety of different organisms, most of which are plants. Shulgin[8] 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 Callaeum antifebrile. Callaway, Brito and Neves (2005)[9] 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.

See also


  1. ^ The Merck Index (1996). 12th edition
  2. ^ 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.
  3. ^ Nathalie Ginovart, Jeffrey H. Meyer, Anahita Boovariwala, Doug Hussey, Eugenii A. Rabiner, Sylvain Houle and Alan A. Wilson (2006). "Positron emission tomography quantification of [11C]-harmine binding to monoamine oxidase-A in the human brain". Journal of Cerebral Blood Flow & Metabolism 26: 330–344. doi:10.1038/sj.jcbfm.9600197.  
  4. ^ Pal Bais, Harsh; Sang-Wook Parka, Frank R. Stermitzb, Kathleen M. Halliganb, Jorge M. Vivancoa (18 June 2002). "Exudation of fluorescent b-carbolines from Oxalis tuberosa L. roots" (PDF). Phytochemistry 61: 539–543. doi:10.1016/S0031-9422(02)00235-2. Retrieved 2008-02-02.  
  5. ^ "Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent". Phytochemistry 66: 1581. doi:10.1016/j.phytochem.2005.04.035. Retrieved 2008-01-12.  
  6. ^ McKenna, Callaway, & Grb. "Scientific Investigation of Ayahuasca", Scientific Investigation of Ayahuasca, retrieved 2007-06-03.
  7. ^ Eric Yarnell, Kathy Abascal (April 2001). "Botanical Treatments for Depression". Alternative & Complementary Therapies 7 (3): 138–143. doi:10.1089/10762800151125056.  
  8. ^ Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. Transform Press. ISBN 0963009699.   Pages 713–714
  9. ^ Callaway J. C., Brito G. S. & Neves E. S. (2005). "Phytochemical analyses of Banisteriopsis caapi and Psychotria viridis". Journal of Psychoactive Drugs 37 (2): 145–150. PMID 16149327.  

External links

Got something to say? Make a comment.
Your name
Your email address