Convolutindole A: Difference between revisions

Browse history interactively

← Previous edit

Content deleted Content added

VisualWikitext

@@ Line 1: / Line 1: @@
+{{More citations needed|date=July 2023}}
 {{chembox
+| Verifiedfields = changed
 | Watchedfields = changed
-| verifiedrevid = 385692945
+| verifiedrevid = 445343109
-|   Name = Convolutindole A
+| Name = Convolutindole A
-|   ImageFile = Convolutindole A.svg
+| ImageFile = Convolutindole A.svg
-|   ImageSize = 200px
+| ImageSize =
-|   ImageName =
+| ImageName =
+| ImageFile1 = Convolutindole A 3D ball.png
-|   IUPACName = 2,4,6-Tribromo-1,7-dimethoxy-''N'',''N''-dimethyltryptamine
+| ImageAlt1 = Ball-and-stick model of convolutindole A
-| Section1 = {{Chembox Identifiers
+| PIN = ''N'',''N''-Dimethyl-2-(2,4,6-tribromo-1,7-dimethoxy-1''H''-indol-3-yl)ethan-1-amine
-|   CASNo = 443356-86-3
+|Section1={{Chembox Identifiers
-|    CASNo_Ref = {{cascite|correct|CAS}}
-|   SMILES =
+| CASNo = 443356-86-3
+| CASNo_Ref = {{cascite|correct|CAS}}
-  }}
+| UNII_Ref = {{fdacite|correct|FDA}}
-| Section2 = {{Chembox Properties
+| UNII = D37997A5KB
-|   Formula = C<sub>14</sub>H<sub>17</sub>Br<sub>3</sub>N<sub>2</sub>O<sub>2</sub>
+| PubChem = 5324072
-|   MolarMass =
+| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}
-|   Density =
+| ChemSpiderID = 4481610
-|   MeltingPt = 61.5-62.5 °C
+| SMILES = CN(C)CCc2c1c(c(OC)c(Br)cc1Br)n(OC)c2Br
-|   BoilingPt =
+| StdInChI_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChI = 1S/C14H17Br3N2O2/c1-18(2)6-5-8-11-9(15)7-10(16)13(20-3)12(11)19(21-4)14(8)17/h7H,5-6H2,1-4H3
+| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}
+| StdInChIKey = KPTXBOJWIDAMOS-UHFFFAOYSA-N
   }}
+|Section2={{Chembox Properties
+| C=14
+| H=17
+| Br=3
+| N=2
+| O=2
+| Density =
+| MeltingPtC = 61.5 to 62.5
+| MeltingPt_notes =
+| BoilingPt =
+ }}
 }}
-'''Convolutindole A''' ('''2,4,6-tribromo-1,7-dimethoxy-N,N-dimethyltryptamine''') is a [[bromide|brominated]] [[indole]] [[alkaloid]] that was first identified in 2001 in ''[[Amathia (genus)|Amathia]] [[Amathia convoluta|convoluta]]'', a marine [[bryozoan]]. Bryozoans are aquatic [[invertebrates]] that grow in colonies and superficially resemble [[coral]]s.
+'''Convolutindole A''' ('''2,4,6-tribromo-1,7-dimethoxy-''N'',''N''-dimethyltryptamine''') is a [[bromine|brominated]] [[tryptamine]] [[alkaloid]] that was first identified in 2001 in ''Amathia convoluta'', a marine [[bryozoan]]. Bryozoans are aquatic [[invertebrate]]s that grow in colonies and may resemble [[coral]]s.
 ==Chemistry==
-Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy [[analog (chemistry)|analog]] of [[dimethyltryptamine|DMT]], a [[hallucinogen]] that occurs naturally in many plants and animals. Other brominated derivatives of DMT include [[5-Bromo-DMT|5-bromo-DMT]] and [[5,6-Dibromo-DMT|5,6-dibromo-DMT]], both of which also occur in marine invertebrates.
+Convolutamine A is the 2,4,6-tribromo-1,7-dimethoxy derivative of [[N,N-Dimethyltryptamine|DMT]], a [[hallucinogen]] that occurs naturally in many plants and animals. Convolutamine A is chemically related to [[5-Bromo-DMT|5-bromo-DMT]] which also occurs in many marine [[invertebrates]].
-The researchers who discovered the chemical drew specific attention to the methoxy group at the indole 1-position (attached to the nitrogen atom in the pentagonal ring) as being an unknown occurrence in the marine world until recently. 1-methoxyindoles also occur in the [[Brassicaceae]], the plant family that [[cabbage]] and [[Mustard plant|mustard]] belong to.
+Until the discovery of convolutindole A, the 1-methoxyindole [[Moiety (chemistry)|moiety]] was unknown in the marine world. 1-Methoxyindoles, such as [[lespedamine]], were previously only known to occur in plants of the [[Fabaceae|bean]] and [[Brassicaceae|mustard]] families.
 ==Biological activity==
-The chemical was tested for its ability to kill [[nematodes]], a type of parasitic worm. It was found to be more effective in this regard than [[levamisole]], a commercial drug used to kill parasitic worms (and in the treatment of [[colon cancer]]).
+This chemical was tested for its ability to kill [[parasitic]] [[nematode]]s. It was found to be more effective than [[levamisole]] - a synthetic drug used to kill parasitic worms and to treat [[colon cancer]]. {{CN|date=July 2023}}
 ==References==
-{{Citation style|date=September 2007}}
 <references/>
 *Narkowicz, C. K.; Blackman, A. J., (June 2001). ''Abstracts of Papers''; 10th International Symposium on Marine Natural Products: Nago, Okinawa, Abstract OR1.
+*{{Cite journal | last1 = Narkowicz | first1 = C. K. | last2 = Blackman | first2 = A. J. | last3 = Lacey | first3 = E. | last4 = Gill | first4 = J. H. | last5 = Heiland | first5 = K. | title = Convolutindole a and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine BryozoanAmathia convoluta | doi = 10.1021/np010574x | journal = Journal of Natural Products | volume = 65 | issue = 6 | pages = 938–941 | year = 2002 | pmid =  12088445}}
+{{Tryptamines}}
-*Narkowicz, C. K. et al., (2002). Convolutindole A and Convolutamine H, New Nematocidal Brominated Alkaloids from the Marine Bryozoan ''Amathia convoluta''. ''Journal of Natural Products'' 65(6) pp 938–941.
-[[Category:Natural tryptamine alkaloids]]
+[[Category:Tryptamine alkaloids]]
 [[Category:Halogen-containing alkaloids]]
-[[Category:Organobromides]]
+[[Category:Bromoarenes]]
-[[Category:Phenol ethers]]
+[[Category:Indole ethers at the benzene ring]]
+[[Category:Hydroxylamines]]