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Category:Alkaloids found in Nicotiana
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| isbn = 0-9630096-9-9
| isbn = 0-9630096-9-9
}} Pages 713&ndash;714</ref>
}} Pages 713&ndash;714</ref>
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.
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. Lemon Balm contains Harmine. <ref>{{cite journal | title = Harmala Alkaloids as Bee Signaling Chemicals | author = Natalie Harrington | volume = 1 | issue = 1 | year = 2012 | journal = Journal of Student Research | url = http://www.jofsr.com/index.php/path/article/view/30 | pages = 23–32}}</ref>


In addition to ''[[Banisteriopsis caapi|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)<ref>{{Cite journal
In addition to ''[[Banisteriopsis caapi|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)<ref>{{Cite journal

Revision as of 07:18, 25 August 2013

Harmine
Names
IUPAC names
7-MeO-1-Me-9H
-pyrido[3,4-b]-indole
Identifiers
3D model (JSmol)
ChEBI
ChEMBL
ChemSpider
DrugBank
ECHA InfoCard 100.006.485 Edit this at Wikidata
KEGG
UNII
  • InChI=1S/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3 checkY
    Key: BXNJHAXVSOCGBA-UHFFFAOYSA-N checkY
  • InChI=1/C13H12N2O/c1-8-13-11(5-6-14-8)10-4-3-9(16-2)7-12(10)15-13/h3-7,15H,1-2H3
    Key: BXNJHAXVSOCGBA-UHFFFAOYAR
  • n3ccc2c1c(cc(OC)cc1)nc2c3C
Properties
C13H12N2O
Molar mass 212.25 g/mol
Melting point 321 °C (·HCl); 262 °C (·HCl·2H2O)[1]
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
checkY verify (what is checkY☒N ?)

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 (also known as "yage" or "ayahuasca"). Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a RIMA. Harmine selectively binds to MAO-A but does not inhibit the variant MAO-B.[2]

Uses

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

Monoamines include neurotransmitters (serotonin, dopamine), hormones (melatonin, epinephrine, norepinephrine) and psychedelic drugs (psilocybin, DMT and mescaline). By slowing the breakdown of neurotransmitters, monoamine oxidase inhibitors (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 has been found to increase EAAT2 glutamate pump expression in central nervous system, therefore reducing glutamate toxicity.[5]

Anticancer

"Harmine showed cytotoxicity against HL60 and K562 cell lines. This could explain the cytotoxic effect of P. harmala on these cells."[6]

Adverse effects

Harmine, and plants containing significant amounts of harmine and other harmala alkaloids are generally not considered safe treatments for depression within the medical community. This bias however is primarily built on previous decades of experience with pharmaceutical non-specific MAOIs that block both MAO-A and MAO-B.[7] Inhibiting MAO-A or MAO-B (in high enough doses) while consuming foods rich in tyramine, e.g. cheese, can cause tyramine, ordinarily metabolized by these enzymes, to accumulate to dangerous levels. This can cause a potentially fatal hypertensive crisis. Because harmine reversibly and selectively inhibits MAO-A and does not degrade MAO-B, MAO-B remains free to metabolize tyramine in the digestive tract. Consequently, the harmala alkaloids (including harmine) are unlikely to elicit tyramine-mediated hypertensive crisis, and a special diet does not need to be so strictly adhered to. Nonetheless, due to the reduction of the levels of tyramine degrading compounds in the gut, it is still not advisable to eat excessively large amounts of tyramine-rich food products.[8] The reversibility and MAO-A selectivity of harmala alkaloids do not, however, prevent potentially fatal interactions with common medications such as antihistamines, most antidepressants, many stimulants, common migraine medications, some herbs, decongestants, expectorants, and common cough and cold medications.

It has recently been shown in the Journal of Photochemistry and Photobiology B: Biology that beta-carboline MAO inhibitors, such as harmine, bind with DNA and also exhibit anti-tumor properties. Harmine has been shown to bind one hundred times more effectively than its close analogue harmaline. The consequences of this are currently not well understood.[9]

Rapid discontinuation of MAO inhibitors can cause serious withdrawal syndrome [disambiguation needed].

Overdosage

Oral or intravenous harmine doses ranging from 30–300 mg have caused agitation, bradycardia or tachycardia, blurred vision, hypotension, paresthesias and hallucinations. Serum or plasma harmine concentrations may be measured as a confirmation of diagnosis. The plasma elimination half-life is on the order of 1–3 hours.[10]

Natural sources

Harmine is found in a wide variety of different organisms, most of which are plants. Shulgin[11] 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. Lemon Balm contains Harmine. [12]

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)[13] 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

References

  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 (3): 330–344. doi:10.1038/sj.jcbfm.9600197. PMID 16079787.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  4. ^ Pal Bais, Harsh (18 June 2002). "Exudation of fluorescent b-carbolines from Oxalis tuberosa L. roots" (PDF). Phytochemistry. 61 (5): 539–543. doi:10.1016/S0031-9422(02)00235-2. Retrieved 2008-02-02. {{cite journal}}: Unknown parameter |coauthors= ignored (|author= suggested) (help)
  5. ^ Li Y, Sattler R, Yang EJ, Nunes A, Ayukawa Y, Akhtar S, Ji G, Zhang PW, Rothstein JD. (18 June 2011). "Harmine, a natural beta-carboline alkaloid, upregulates astroglial glutamate transporter expression". Neuropharmacology. 60 (7–8): 1168–75. doi:10.1016/j.neuropharm.2010.10.016. PMID 21034752.{{cite journal}}: CS1 maint: multiple names: authors list (link)
  6. ^ Jahaniani, F; Ebrahimi, SA; Rahbar-Roshandel, N; Mahmoudian, M. "Xanthomicrol is the main cytotoxic component of Dracocephalum kotschyii and a potential anti-cancer agent". Phytochemistry. 66 (13): 1581–92. doi:10.1016/j.phytochem.2005.04.035. PMID 15949825. Retrieved 2008-01-12. {{cite journal}}: Cite has empty unknown parameter: |coauthors= (help)
  7. ^ Eric Yarnell, Kathy Abascal (2001). "Botanical Treatments for Depression". Alternative & Complementary Therapies. 7 (3): 138–143. doi:10.1089/10762800151125056. {{cite journal}}: Unknown parameter |month= ignored (help)
  8. ^ McKenna, Callaway, & Grb. "Scientific Investigation of Ayahuasca", Scientific Investigation of Ayahuasca, retrieved 2007-06-03.
  9. ^ [1]
  10. ^ R. Baselt, Disposition of Toxic Drugs and Chemicals in Man, 8th edition, Biomedical Publications, Foster City, CA, 2008, pp. 727-728.
  11. ^ Shulgin, Alexander and Shulgin, Ann (1997). TiHKAL: The Continuation. Transform Press. ISBN 0-9630096-9-9.{{cite book}}: CS1 maint: multiple names: authors list (link) Pages 713–714
  12. ^ Natalie Harrington (2012). "Harmala Alkaloids as Bee Signaling Chemicals". Journal of Student Research. 1 (1): 23–32.
  13. ^ 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. doi:10.1080/02791072.2005.10399795. PMID 16149327.

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