View source for Harmaline

{{chembox
|   Name = Harmaline
| ImageFileL1 = Harmaline (small).svg
| ImageSizeL1 = 120px
| ImageFileR1=Harmaline_3d_structure.png
| ImageSizeR2 = 120px
|   ImageName = Harmaline
|   IUPACName = 7-methoxy-1-methyl-4,9-dihydro-3''H''-pyrido[3,4-''b'']indole
| Section1 = {{Chembox Identifiers
|   CASNo = 304-21-2
|  PubChem=5280951
|   SMILES =<small>CC1=C2C(=C3C=CC<br />(=CC3=N2)OC)CCN1</small>
  }}
| Section2 = {{Chembox Properties
|   Formula = C<sub>13</sub>H<sub>14</sub>N<sub>2</sub>O<sub></sub>
|   MolarMass = 214.263 g/mol
|   MeltingPt = 232–234 °C<ref name="Aldrich">[http://www.sigmaaldrich.com/catalog/search/ProductDetail/FLUKA/51330 Data from the Sigma Aldrich Catalog (German)]</ref>
  }}
}}
'''Harmaline''' is a [[fluorescent]] [[psychoactive]] [[indole]] [[alkaloid]] from the group of [[harmala]] alkaloids and [[beta-carboline]]s. It is the reduced hydrogenated form of  [[harmine]].

==Occurrence in nature==
Various plants contain harmaline including ''[[Banisteriopsis caapi]]'' (a jungle vine) and ''[[Peganum harmala]]'' (Syrian Rue) as well as the hallucinogenic drink [[ayahuasca]], which is traditionally brewed using ''Banisteriopsis caapi''. Also passionflower (Passiflora incarnata) and tobacco.<ref>http://www.answers.com/topic/passionflower</ref>

==Effects==

[[Image:Harmaline Harmine.jpg|thumb|right|175px|Harmaline and [[harmine]] [[fluoresce]] under [[ultraviolet light]]. These three extractions indicate that the middle one has a higher concentration of the two compounds.]]

Harmaline is a [[central nervous system]] [[stimulant]] and a "reversible [[monoamine oxidase inhibitor|inhibitor]] of [[Monoamine oxidase|MAO]]-A ([[RIMA]])."<ref>{{cite book |author=Massaro, Edward J. |title=Handbook of neurotoxicology |publisher=Humana Press |location=Totowa, NJ |year=2002 |isbn=0-89603-796-7 |url=http://books.google.com/?id=2c2K-epbCDQC&pg=PA237&lpg=PA237&dq=harmaline+antidepressant |page=237}}</ref>  It being a reversible MAO-A inhibitor means that it competes with [[tyramine]] for binding to MAO-A, so foods containing some [[tyramine]] can be safely consumed (wine and aged cheese should probably be avoided for 12 hours prior to consuming harmaline containing plants).  The reversibility means that, instead of binding permanently to MAO-A for weeks until the body replaces the MAO-A enzyme molecules, harmaline binds only transiently, so tyramine can be metabolized as well by competing with harmaline for the binding site on the enzyme.<ref>{{cite journal |author=Youdim MB, Weinstock M |title=Therapeutic applications of selective and non-selective inhibitors of monoamine oxidase A and B that do not cause significant tyramine potentiation |journal=Neurotoxicology |volume=25 |issue=1-2 |pages=243–50 |year=2004 |month=Jan |pmid=14697899 |doi=10.1016/S0161-813X(03)00103-7 }}</ref>  This means that the risk of a hypertensive crisis, a dangerous high blood pressure crisis from eating [[tyramine]]-rich foods such as cheese, is potentially lower with harmaline than with non-reversible MAOI's, especially after 24 hours following ingestion.

Harmaline is shown to act as an [[acetylcholinesterase]] inhibitor.<ref>{{cite journal |author=Zheng XY, Zhang ZJ, Chou GX, Wu T, Cheng XM, Wang CH, Wang ZT. |title=Acetylcholinesterase inhibitive activity-guided isolation of two new alkaloids from seeds of Peganum nigellastrum Bunge by an in vitro TLC- bioautographic assay |journal=Arch Pharm Res. |volume=32 |issue=9 |pages=1245-51 |year=2009 |month=Sep |url=http://www.springerlink.com/content/2561160164458518/ |doi=10.1007/s12272-009-1910-x }}</ref>Harmaline also stimulates [[striatum|striatal]] dopamine release in rat at very high dose levels.<ref>{{cite journal |author=M. J. Schwarza, P. J. Houghtona, S. Roseb, P. Jennerb and A. D. Leesc |title=Activities of extract and constituents of Banisteriopsis caapi relevant to parkinsonism |journal=Pharmacology Biochemistry and Behavior |volume=75 |issue=3 |pages=627-33 |year=2003 |month=June |url=http://www.sciencedirect.com/science?_ob=ArticleURL&_udi=B6T0N-48V972J-3&_user=10&_coverDate=06%2F30%2F2003&_rdoc=1&_fmt=high&_orig=search&_sort=d&_docanchor=&view=c&_searchStrId=1428794180&_rerunOrigin=google&_acct=C000050221&_version=1&_urlVersion=0&_userid=10&md5=c86ea82a1fedc0f2bc6e029e5f7bb880 |doi=10.1016/S0091-3057(03)00129-1 }}</ref>
Depending upon the dosage, harmaline induces temporary [[oneirophrenia]] and [[ataxia]]. Harmaline, on the higher end of its safe dosage range, has hallucinogenic properties, but it differentiates itself significantly from the "classical" [[hallucinogen]]s in its [[pharmacology]]. Since harmaline is a reversible [[monoamine oxidase inhibitor]], it could increase the effect of some drugs problematically.  Harmaline causes no known physical or psychological dependence.

United States [[Patent]] Number 5591738 describes a method for treating various chemical dependencies via the administration of harmaline and or other beta-carbolines.<ref name=fpo>[http://www.freepatentsonline.com/5591738.html Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof]</ref> 

[[Claudio Naranjo]] has studied potential applications of harmal alkaloids in [[psychotherapy]].

Harmaline has also been shown to induce "vasorelaxant effects" in "isolated rat [[aorta]]."<ref>{{cite journal |author=Berrougui H, Martin-Cordero C, Khalil A, Hmamouchi M, Ettaib A, Marhuenda E, Herrera MD |title=Vasorelaxant effects of harmine and harmaline extracted from Peganum harmala L. seeds in isolated rat aorta |journal=Pharmacol Res. |volume=54 |issue=2 |pages=150–7 |month=Aug|year=2006 |doi=10.1016/j.phrs.2006.04.001 |pmid=16750635 }}</ref>

Harmaline has both protective and toxic effects on [[neuron]]s.<ref name=fpo/>

Harmaline is known to act as a [[histamine N-methyltransferase]] inhibitor.

==History==
In the year 1841 harmaline was isolated from ''[[Peganum harmala]]'' by [[Goegel]].<ref name=fpo/>  It was first synthesized in 1930 by [[Hasenfratz]].<ref name=fpo/>

==External links==
* [http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml TIHKAL, #13]
* [http://tihkal.info/read.php?domain=tk&id=13 Harmaline entry in TiHKAL • info]

*{{cite journal |author=Evans AT, Croft SL |title=Antileishmanial activity of harmaline and other tryptamine derivatives |journal=Phytotherapy Research |volume=1 |issue=1 |pages=25–7 |year=2006 |doi=10.1002/ptr.2650010106 }}
*[http://www.aapspharmaceutica.com/search/view.asp?ID=78110 Study Indicating that Harmaline is a Free Radical Scavenger]

==References==
{{reflist}}

{{Adrenergics}}
{{Dopaminergics}}
{{Histaminergics}}
{{Serotonergics}}

[[Category:Antidepressants]]
[[Category:Aromatic compounds]]
[[Category:Beta-Carbolines]]
[[Category:Entheogens]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Phenol ethers]]

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