Desformylflustrabromine

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Desformylflustrabromine
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Systematic (IUPAC) name
2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine
Identifiers
ATC code none
PubChem CID 637026
Chemical data
Formula C16H21BrN2
Molar mass 321.254 g/mol[[Script error: No such module "String".]]
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Desformylflustrabromine (dFBr) is a tryptamine derivative which was first isolated as an active metabolite of the marine bryozoan Flustra foliacea.[1]

Bioactivity

dFBr has been identified as a novel positive allosteric modulator of neuronal nicotinic acetylcholine receptor with sub-type specificity for heteromeric receptor with no effect on homomeric sub-type.[2] A recent study has been published which describes the synthesis of water-soluble salts of dFBr and its action has been confirmed as selective potentiator of α4β2 nicotinic acetylcholine receptor responses by using two-electrode voltage clamp whole cell recordings.[3] In the year 2002 it was reported that dFBr was cytotoxic on human colon cancer cell line HCT-116. [4]

References

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  1. Peters, L.; Wright, A. D.; Kehraus, S.; Gündisch, D.; Tilotta, M. C.; König, G. M. Planta Medica. 2004, 70, 883.
  2. Sala F, Mulet J, Reddy KP, Bernal JA, Wikman P, Valor LM, Peters L, König GM, Criado M, Sala S. Potentiation of human alpha4beta2 neuronal nicotinic receptors by a Flustra foliacea metabolite. Neuroscience Letters. 2005 Jan 10;373(2):144-9. PMID 15567570
  3. Jin-Sung Kim, Anshul Pandya, Maegan Weltzin, Brian W. Edmonds, Marvin K. Schulte, and Richard A. Glennon. Synthesis of desformylflustrabromine and its evaluation as an alpha4beta2 and alpha7 nACh receptor modulator. Bioorganic and Medicinal Chemistry Letters. 2007 Sep 1;17(17):4855-60. doi:10.1016/j.bmcl.2007.06.047
  4. Lysek N, Rachor E, Lindel T. Isolation and structure elucidation of deformylflustrabromine from the North Sea bryozoan Flustra foliacea. Zeitschrift zur Naturforschung [C]. 2002 Nov-Dec;57(11-12):1056-61. PMID 12562094