Beta-Carboline 608186 225261627 2008-07-12T19:26:37Z SmackBot 433328 Date the maintenance tags or general fixes {{Refimprove|date=December 2007}} {{Chembox new |ImageFile=Beta-carboline (small).svg |ImageSize= |IUPACName=9H-pyrido[3,4-b]indole |OtherNames= |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= | BoilingPt= | Solubility= }} |Section3= {{Chembox Hazards | MainHazards= | FlashPt= | Autoignition= }} }} {{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>&times;</center> || style="width:50px"|<center>&times;</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]] || &nbsp; ||&nbsp; ||<center>H</center> ||<center>H</center> ||<center>H</center> ||<center>[[Image:Tryptoline (small).svg|align=right‎|Tryptoline]]</center> |- | [[Pinoline]] ||&nbsp; ||&nbsp; ||<center>H</center> ||<center>[[Methoxy|OCH<sub>3</sub>]]</center> ||<center>H</center> ||<center>[[Image:Pinoline (small).svg|align=right‎|Pinoline]]</center> |- | [[Harmane]] || <center>&times;</center> || <center>&times;</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>&times;</center> || <center>&times;</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>&times;</center> ||&nbsp; || <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]] ||&nbsp; ||&nbsp; || <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]]