Desformylflustrabromine

Desformylflustrabromine

Systematic (IUPAC) name
2-[6-bromo-2-(2-methylbut-3-en-2-yl)-1H-indol-3-yl]-N-methylethanamine
Identifiers
CAS Number	474657-72-2 Y
ATC code	none
PubChem	CID: 637026
ChemSpider	552693 N
Chemical data
Formula	C16H21BrN2
Molecular mass	321.254 g/mol
SMILES C=CC(C)(C)c2nc1cc(Br)ccc1c2CCNC
InChI InChI=1S/C16H21BrN2/c1-5-16(2,3)15-13(8-9-18-4)12-7-6-11(17)10-14(12)19-15/h5-7,10,18-19H,1,8-9H2,2-4H3 N Key:GQHSCJUTJKLZPX-UHFFFAOYSA-N N
NY (what is this?)  (verify)

Desformylflustrabromine (dFBr) is a tryptamine derivative which was first isolated as an active metabolite of the marine bryozoan Flustra foliacea.

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. 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. In the year 2002 it was reported that dFBr was cytotoxic on human colon cancer cell line HCT-116. Desformylflustrabromine has also been found to be a positive allosteric modulator for the α2β2 subtype of neuronal nicotinic acetylcholine receptor. Additionally it relieves the inhibition of both α2β2 and α4β2 Nicotinic Acetylcholine Receptors by β-Amyloid (1–42) Peptide. Thus Desformylflustrabromine can potentially be used in the treatment of Alzheimer's disease. Many of the deconstructed analogs of dFBr are reported to have a potentiating effect on the α4β2 receptors.