Harmala alkaloid
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223328667
2008-07-03T16:19:23Z
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[[Image:Peganum harmala1.jpg|thumb|250px|''Peganum harmala'', commonly known as Syrian Rue]]
The [[MAOI]] (Monoamine oxidase inhibitor) [[alkaloid]]s found in [[seed]]s of ''[[Peganum harmala]]'' (also known as ''[[Harmal]]'' or ''[[Syrian Rue]]'')- [[harmine]], [[harmaline]], and [[tetrahydroharmine]]- are collectively known as ''harmala alkaloids''.
The harmala alkaloids are of great interest for their complicated relation to phyto-indole entheogens used in Amazonian shamanism.
The harmala alkaloid harmine - once known as '''Telepathine''' and '''Banisterine''' - is a naturally occurring [[beta-carboline]] [[alkaloid]] that is structurally related to [[harmaline]]. The Shulgins suggest harmaline is a breakdown product of harmine [http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml]. Harmine and harmaline are reversible [[MAOI]]s. They can stimulate the [[central nervous system]] by inhibiting the metabolism of monoamines compounds- such as serotonin.
The harmala alkaloids occur in ''[[harmal]]'' in concentrations of roughly 3%, though tests have documented anywhere from 2-7%, as natural sources tend to vary widely in chemical makeup. Harmala alkaloids are also found in the ''[[Banisteriopsis caapi]]'' vine, the key plant ingredient in the sacramental beverage [[Ayahuasca]], in concentrations that range between 0.31-8.43% for harmine, 0.03-0.83% for harmaline and 0.05-2.94% for tetrahydroharmine [THH].<ref>Callaway JC, Brito GS & Neves ES (2005). [[Phytochemical]] analyses of Banisteriopsis caapi and Psychotria viridis Journal of Psychoactive Drugs 37(2): 145-150.</ref>
Many other psychoactive plants are often added to Ayahuasca to achieve visionary consciousness, including leaves from "[[Psychotria viridis]]", a source of [[Dimethyltryptamine|DMT]], The harmala alkaloids serve to potentiate these brewed compounds by preventing their breakdown in the digestive tract.
The harmala alkaloids are also psychoactive on their own if the dosage is sufficient, perhaps due to endogenous sources of DMT in the human brain.
Harmala alkaloids are also found in many other plants, such as [[tobacco]] and [[passion flower]].
==Telepathine==
'''Telepathine''' was originally thought to be the active chemical constituent of ''[[Banisteriopsis caapi]]'', a key plant ingredient in the preparation of Ayahuasca; a sacremental beverage from the Amazon. This isolated chemical was so named because of the reported effects of Ayahuasca among the indigenous users, including: collective contact with and/or visions of jaguars, snakes, and jeweled birds, and ancestral spirits; the ability to see future events; and as the name suggests, [[telepathy|telepathic]] communication among tribal members. It was assumed to be a newly discovered chemical at the time, however, it was soon realized that Telepathine was already more widely known as "[[harmine]]" from its previous discovery in ''[[Peganum harmala]]'' (Syrian Rue).
==Uses==
As mentioned above, some harmala alkaloids can be used as an [[MAOI]] ('''M'''ono'''A'''mine '''O'''xidase '''I'''nhibitor) to facilitate the ingestion of [[Dimethyltryptamine|DMT]] and other tryptamines; while not generally used as a hallucinogen alone, there are reports of such use.<ref>Shulgin, Alexander. [http://www.erowid.org/library/books_online/tihkal/tihkal13.shtml "#13 Harmaline"], Erowid Online Texts: TiHKAL #13 HARMALINE, retrieved November 26, 2006.</ref> In high doses, it acts as purgative. Harmala alkaloids from ''Banisteriopsis caapi'' have been used to treat [[Parkinson's disease]].
Additionally, harmaline is used as a model for [[Essential Tremor]] (ET) when injected to animals. Rats being treated with harmaline exhibit severe tremors after 5-7 minutes.
It is important to note that unlike synthetic pharmaceutical MAOIs such as [[phenelzine]], harmine is [[MAOI#Reversibility|reversible]] and [[MAOI#Selectivity|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 [[monoamine oxidase A]] inhibitors, but not [[monoamine oxidase|monoamine oxidase B]] inhibitors.<ref>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.</ref>
===Anticancer===
"Harmine showed [[cytotoxicity]] against [[HL60]] and [[K562]] cell lines. This could explain the cytotoxic effect of ''[[Peganum harmala|P. harmala]]'' on these cells."<ref> {{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= |doi= 10.1016/j.phytochem.2005.04.035|format=|accessdate=2008-01-12|author=Jahaniani, F }}</ref>
==Chemical Forms==
*'''[[Harmine]]''': '''C'''<sub>13</sub>'''H'''<sub>12</sub>'''N'''<sub>2</sub>'''O'''
::7-Methoxy-1-methyl-9H-pyrido[3,4-b]indole
[[Image:Harmine.png|thumb|150px|none|<center>Harmine</center>]]
Harmine is a reversible inhibitor of MAO-A ([[RIMA]]).
*'''[[Harmaline]]''': '''C'''<sub>13</sub>'''H'''<sub>14</sub>'''N'''<sub>2</sub>'''O'''
::4,9-Dihydro-7-methoxy-1-methyl-3H-pyrido[3,4-b]indole
[[Image:Harmaline.png|thumb|150px|none|<center>Harmaline</center>]]
Harmaline is a reversible inhibitor of MAO-A (RIMA).<ref>[http://books.google.com/books?id=2c2K-epbCDQC&pg=PA237&lpg=PA237&dq=harmaline+antidepressant&source=web&ots=IrcpVr4R_H&sig=5FvlysKKEN7Hb4_YjfgoZM8rsTg Edward J. Massaro, Handbook of Neurotoxicology]</ref>
*'''Harmalol''':<ref>{{cite web|url=http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?cid=5353656 |title=CID 5353656 -- PubChem Compound Summary |accessdate=2008-01-18 |date=2008-01-18 |publisher=[[PubChem]] }}</ref> '''C'''<sub>12</sub>'''H'''<sub>12</sub>'''N'''<sub>2</sub>'''O'''
::1-methyl-2,3,4,9-tetrahydropyrido[3,4-b]indol-7-one
*'''Tetrahydroharmine''': '''C'''<sub>13</sub>'''H'''<sub>16</sub>'''N'''<sub>2</sub>'''O'''
::7-Methoxy-1,2,3,4-Tetrahydro-Harmine
[[Image:THH.png|thumb|150px|none|<center>Tetrahydroharmine</center>]]
*'''Harman''': '''C'''<sub>12</sub>'''H'''<sub>10</sub>'''N'''<sub>2</sub>
::1-methyl-9H-b-carboline
[[Image:Harman.png|thumb|150px|none|<center>Harman</center>]]
*'''Harmine acid''': methylester:
::Methyl-7-methoxy-b-carboline-1-carboxylate
*'''Harmilinic acid''':
::7-methoxy-3,4-dihydro-b-carboline1-carboxylic acid
*'''Harmanamide''':
::1-carbamoyl-7-methoxy-b-carboline
*'''Acethylnorharnine''':
::1-acethyl-7-methoxy-b-carboline
==See also==
*[[Beta-carboline]]
*[[Monoamine oxidase inhibitor]]
*[[RIMA]]
*[[Time Machines]] (album by the band [[coil]] featuring a track dedicated to "telepathine", in addition to [[psilocybin]], [[5-MeO-DMT]], and [[2,5-dimethoxy-4-ethylamphetamine|DOET]])
==References==
<references/>
{{Antidepressants}}
[[Category:Psychedelic tryptamines]]
[[Category:Monoamine oxidase inhibitors]]
[[Category:Ayahuasca]]
[[de:Harmalin]]
[[pl:Harmina]]
[[ru:Гармала]]
[[fr:Harmane]]