| 词条 | Beta-Carboline | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
| 释义 |
| Name = β-Carboline | verifiedrevid = 443419704 | ImageFile=beta-Carboline.svg | ImageSize= | ImageFile2=Β-Carboline.png | ImageSize2= | ImageAlt2=Chemical structure of β-carboline | IUPACName=9H-β-carboline | OtherNames={{ubl|Norharmane | Norharman | 9H-pyrido[3,4-b]indole}} |Section1={{Chembox Identifiers | IUPHAR_ligand = 8222 | InChIKey = AIFRHYZBTHREPW-UHFFFAOYAG | ChEMBL_Ref = {{ebicite|correct|EBI}} | ChEMBL = 275224 | StdInChI_Ref = {{stdinchicite|correct|chemspider}} | StdInChI = 1S/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H | StdInChIKey_Ref = {{stdinchicite|correct|chemspider}} | StdInChIKey = AIFRHYZBTHREPW-UHFFFAOYSA-N | CASNo_Ref = {{cascite|correct|CAS}} | CASNo=244-63-3 | PubChem=64961 | ChEBI_Ref = {{ebicite|correct|EBI}} | ChEBI = 109895 | SMILES=c1ccc3c(c1)[nH]c2cnccc23 | InChI=1/C11H8N2/c1-2-4-10-8(3-1)9-5-6-12-7-11(9)13-10/h1-7,13H | MeSHName=norharman | ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}} | ChemSpiderID=58486 |Section2={{Chembox Properties | Formula=C11H8N2 | MolarMass=168.20 g/mol | Appearance= | Density= | MeltingPt= | BoilingPt= | Solubility= |Section3={{Chembox Hazards | MainHazards= | FlashPt= | AutoignitionPt = }} β-Carboline (9H-pyrido[3,4-b]indole), also known as norharmane, is a nitrogen containing heterocycle. It is also the prototype of a class of compounds known as β-carbolines. Pharmacologyβ-Carboline alkaloids are widespread in plants and animals, and frequently act as benzodiazepine inverse agonists. As components of the liana Banisteriopsis caapi, the β-carbolines harmine, harmaline, and tetrahydroharmine play a pivotal role in the pharmacology of the indigenous psychedelic drug ayahuasca by preventing the breakdown of dimethyltryptamine in the gut by reversibly inhibiting monoamine oxidase, thus making it psychoactive upon oral administration. Some β-carbolines, notably tryptoline and pinoline, may be formed naturally in the human body. The latter is possibly implicated along with melatonin in the role of the pineal gland in regulating the sleep-wake cycle.{{Citation needed|date=July 2008}} β-carboline is a benzodiazepine receptor inverse agonist and can therefore have convulsive, anxiogenic and memory enhancing effects.[1] 9-Methyl-β-carbolines appear to induce DNA damage when exposed to ultra-violet light.[2] Structureβ-Carboline belongs to the group of indole alkaloids and consist of pyridine ring that is fused to an indole skeleton.[3] 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. The biosynthesis of β-carbolines is believed to follow this route from analogous tryptamines.[4] Different levels of saturation are possible in the third ring, which is indicated here in the structural formula by colouring the optionally double bonds red and blue: Examples of β-carbolinesSome of the more important β-carbolines are tabulated by structure below.
Occurrence in nature{{Cite check|date=December 2007|section}}Eight plant families are known to express 64 different kinds of β-carboline alkaloids. By dry weight, the seeds of Peganum harmala (Syrian Rue) contain between 0.16%[5] and 5.9%[6] β-carboline alkaloids. As a result of the presence of β-carbolines in the cuticle of scorpions, their skin is known to fluoresce when exposed to certain wavelengths of ultraviolet light such as that produced by a blacklight.[7] A group of β-carboline derivatives, termed eudistomins were extracted from ascidians (marine tunicates of the family Ascidiacea), like Ritterella sigillinoides,[8] Lissoclinum fragile [9] or Pseudodistoma aureum.[10] Nostocarboline was isolated from freshwater cyanobacterium. See also
References1. ^{{cite journal |vauthors=Venault P, Chapouthier G | title = From the behavioral pharmacology of beta-carbolines to seizures, anxiety, and memory | journal = ScientificWorldJournal | volume = 7 | issue = | pages = 204–23 | year = 2007 | pmid = 17334612 | pmc = 5901106 | doi = 10.1100/tsw.2007.48 }} 2. ^{{cite journal |vauthors=Vignoni M, Rasse-Suriani FA, Butzbach K, Erra-Balsells R, Epe B, Cabrerizo FM | title = Mechanisms of DNA damage by photoexcited 9-methyl-β-carbolines | journal = Org Biomol Chem | year = 2013 | pmid = 23842892 | doi = 10.1039/c3ob40344k | volume=11 | issue = 32 | pages=5300–9}} 3. ^The Encyclopedia of Psychoactive Plants: Ethnopharmacology and its Applications. Ratsch, Christian. Park Street Press c. 2005 4. ^{{cite journal | doi = 10.3762/bjoc.7.164 | title = Manganese dioxide mediated one-pot synthesis of methyl 9H-pyrido[3,4-b]indole-1-carboxylate: Concise synthesis of alangiobussinine | year = 2011 | last1 = Baiget | first1 = Jessica | last2 = Llona-Minguez | first2 = Sabin | last3 = Lang | first3 = Stuart | last4 = MacKay | first4 = Simon P | last5 = Suckling | first5 = Colin J | last6 = Sutcliffe | first6 = Oliver B | journal = Beilstein Journal of Organic Chemistry | volume = 7 | pages = 1407–11 | pmid = 22043251 | pmc = 3201054}} 5. ^{{cite journal |vauthors=Hemmateenejad B, Abbaspour A, Maghami H, Miri R, Panjehshahin MR |title=Partial least squares-based multivariate spectral calibration method for simultaneous determination of beta-carboline derivatives in Peganum harmala seed extracts |journal=Anal Chim Acta |volume=575 |issue=2 |pages=290–9 |date=Aug 2006 |pmid=17723604 |doi=10.1016/j.aca.2006.05.093 }} 6. ^{{ cite journal |vauthors=Herraiz T, González D, Ancín-Azpilicueta C, Arán VJ, Guillén H |title=beta-Carboline alkaloids in Peganum harmala and inhibition of human monoamine oxidase (MAO)|journal=Food Chem. Toxicol. |volume=48 |issue=3 |pages=839–43 |year=2010 |pmid=20036304 |doi=10.1016/j.fct.2009.12.019 |hdl=10261/77694}} 7. ^{{cite journal |vauthors=Stachel SJ, Stockwell SA, van Vranken DL | title = The fluorescence of scorpions and cataractogenesis | journal = Chem. Biol. | volume = 6 | issue = 8 | pages = 531–9 |date=August 1999 | pmid = 10421760 | doi = 10.1016/S1074-5521(99)80085-4 }} 8. ^{{cite journal |vauthors=Lake RJ, Blunt JW, Munro MH | title = Eudistomins from the New Zealand ascidian Ritterella sigillinoides | journal = Aust. J. Chem. | volume = 42 | issue = 7 | pages = 1201–1206 | year = 1989 | doi = 10.1071/CH9891201 }} 9. ^{{cite journal |vauthors=Badre A, Boulanger A, Abou-Mansour E, Banaigs B, Combaut G, Francisco C | title = Eudistomin U and isoeudistomin U, new alkaloids from the Caribbean ascidian Lissoclinum fragile | journal = J. Nat. Prod. | volume = 57 | issue = 4 | pages = 528–533 |date=April 1994 | doi = 10.1021/np50106a016 }} 10. ^{{cite journal |vauthors=Davis RA, Carroll AR, Quinn RJ | title = Eudistomin V, a new β-carboline from the Australian ascidian Pseudodistoma aureum | journal = J. Nat. Prod. | volume = 61 | issue = 7 | pages = 959–960 |date=June 1998 | doi = 10.1021/np9800452 | pmid = 9677285 }} External links
7 : Anxiolytics|Convulsants|Beta-Carbolines|Entheogens|Monoamine oxidase inhibitors|GABAA receptor negative allosteric modulators|Indole alkaloids |
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