Beta-Carboline
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{{Refimprove|date=December 2007}}
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|ImageFile=Beta-carboline (small).svg
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|IUPACName=9H-pyrido[3,4-b]indole
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|Section1= {{Chembox Identifiers
| CASNo=244-63-3
| PubChem=64961
| SMILES=C1=CC=C2C(=C1)C3=C(N2)C=NC=C3
| MeSHName=norharman
}}
|Section2= {{Chembox Properties
| Formula=C<sub>11</sub>H<sub>8</sub>N<sub>2</sub>
| MolarMass=168.19462
| Appearance=
| Density=
| MeltingPt=
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|Section3= {{Chembox Hazards
| MainHazards=
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{{lowercase}}
β-'''Carboline''' (9''H''-[[pyridine|pyrido]][3,4-''b''][[indole]]) is an [[organic compound|organic]] [[amine]] that is the prototype of a class of [[Chemical compound|compounds]] known as β-''carbolines''.
==Pharmacology==
β-carboline [[alkaloid]]s are widespread in [[plants]] and [[animal]]s, and frequently act as [[monoamine oxidase inhibitor]]s (MAOI). As components of the liana ''[[Banisteriopsis caapi]]'', the β-carbolines [[harmine]], [[harmaline]], and [[tetrahydroharmine]] play a pivotal role in the pharmacology of the [[psychedelic]] brew [[ayahuasca]]. Some β-carbolines, notably [[tryptoline]] and [[pinoline]], are formed naturally in the human body. The latter is implicated along with [[melatonin]] in the role of the [[pineal gland]] in regulating the sleep-wake cycle.{{Fact|date=July 2008}}
United States [[Patent]] Number 5591738 describes a method for treating various chemical dependencies via the administration of 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>
==Structure==
The structure of β-carboline is similar to that of [[tryptamine]], with the [[ethylamine]] chain re-connected to the [[indole]] ring via an extra [[carbon]] atom, to produce a three-ringed structure. Indeed, biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines. Different levels of [[saturation (chemistry)|saturation]] are possible in the third ring, which is indicated here in the [[structural formula]] by colouring the optionally double bonds red and blue:
[[Image:betacarbolines.png|center|200px|Substituted beta-carbolines (structural formula)]]
==Examples of β-carbolines==
Some of the more important β-carbolines are tabulated by structure below.
{| class="wikitable"
!Short Name
|bgcolor=#FF0000|<center>Red Bond</center>
|bgcolor=#0000FF|<center>Blue Bond</center>
!R1
!R6
!R7
!Structure
|-
| β-Carboline || style="width:50px"|<center>×</center> || style="width:50px"|<center>×</center> ||style="width:75px"|<center>H</center> ||style="width:75px"|<center>H</center> ||style="width:75px"|<center>H</center> ||style="width:125px"|<center>[[Image:Beta-carboline (small).svg|align=right|β-Carboline]]</center>
|-
| [[Tryptoline]] || || ||<center>H</center> ||<center>H</center> ||<center>H</center> ||<center>[[Image:Tryptoline (small).svg|align=right|Tryptoline]]</center>
|-
| [[Pinoline]] || || ||<center>H</center> ||<center>[[Methoxy|OCH<sub>3</sub>]]</center> ||<center>H</center> ||<center>[[Image:Pinoline (small).svg|align=right|Pinoline]]</center>
|-
| [[Harmane]] || <center>×</center> || <center>×</center> || <center>[[Methyl|CH<sub>3</sub>]]</center> ||<center>H</center> ||<center>H</center> ||<center>[[Image:Harmane (small).svg|align=right|Harmane]]</center>
|-
| [[Harmine]] || <center>×</center> || <center>×</center> || <center>[[Methyl|CH<sub>3</sub>]]</center> ||<center>H</center> ||<center>[[Methoxy|OCH<sub>3</sub>]]</center> ||<center>[[Image:Harmine (small).svg|align=right|Harmine]]</center>
|-
| [[Harmaline]] || <center>×</center> || || <center>[[Methyl|CH<sub>3</sub>]]</center> ||<center>H</center> ||<center>[[Methoxy|OCH<sub>3</sub>]]</center> ||<center>[[Image:Harmaline (small).svg|align=right|Harmaline]]</center>
|-
| [[Tetrahydroharmine]] || || || <center>[[Methyl|CH<sub>3</sub>]]</center> ||<center>H</center><center>H</center> ||<center>[[Methoxy|OCH<sub>3</sub>]]</center> ||<center>[[Image:Tetrahydroharmine (small).svg|align=right|Tetrahydroharmine]]</center>
|}
== Occurrence in nature ==
{{Citecheck|date=December 2007}}
"There are presently 64 known .beta.-carboline alkaloids dispersed throughout at least eight plant families."<ref name="fpo">[http://www.freepatentsonline.com/5591738.html Method of treating chemical dependency using .beta.-carboline alkaloids, derivatives and salts thereof]</ref> The seeds of ''[[Peganum harmala]]'' (Syrian Rue) are a good source of beta-carbolines, since they contain about 2-6% alkaloids, most of which is harmaline.<ref>[http://www.amazing-nature.com/-i-43.html www.amazing-nature.com]</ref>{{Rs|date=December 2007}}
== See also ==
* [[Harmala alkaloid]]
* [[Tryptamine]]
== External links ==
* [http://www.erowid.org/library/books_online/tihkal/tihkal44.shtml TiHKAL #44]
* [http://www.erowid.org/library/books_online/tihkal TiHKAL] in general
* {{MeshName|Beta-Carbolines}}
* [http://www.biopsychiatry.com/coffee-maoi.htm Beta-carbolines in Coffee]
* [http://www.ncbi.nlm.nih.gov/sites/entrez?cmd=Retrieve&db=PubMed&list_uids=16183262&dopt=AbstractPlus Antidepressant-like effect of harmane and other beta-carbolines in the mouse forced swim test]
==References==
{{Reflist}}
[[Category:Amines]]
[[Category:Entheogens]]
[[pl:Beta-karbolina]]