BW-723C86

BW-723C86
Identifiers
  • 1-[5-(2-Thienylmethoxy)-1H-indol-3-yl]-2-propanamine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC16H18N2OS
Molar mass286.39 g·mol−1
3D model (JSmol)
  • c2c1c([nH]cc1CC(C)N)ccc2OCc3cccs3
  • InChI=1S/C16H18N2OS/c1-11(17)7-12-9-18-16-5-4-13(8-15(12)16)19-10-14-3-2-6-20-14/h2-6,8-9,11,18H,7,10,17H2,1H3 ☒N
  • Key:ALFGDCNSEBJYSP-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

BW-723C86 is a tryptamine derivative drug which acts as a 5-HT2B receptor agonist. It has anxiolytic effects in animal studies,[1][2] and is also used for investigating the function of the 5-HT2B receptor in a range of other tissues.[3][4][5]

BW-723C86 is actually a mixed 5-HT2B/5-HT2C agonist, and while it has good selectivity over 5-HT2A and other serotonin receptor subtypes, it is around only 3 times as selective for 2B compared to 2C and so is much less selective than most research ligands, but no superior 5-HT2B agonist was available until the potent and selective 5-HT2B activity of 6-APB was discovered in 2012.[6] Highly selective 5-HT2C antagonists are available however, and so a combination of BW-723C86 with a selective 5-HT2C antagonist allows 5-HT2B mediated responses to be studied in isolation.

An in vitro study including assay on normal (healthy) human melanocytes found that BW-723C86 causes skin whitening.[7] The mechanism of action of BW-723C86 is decreasing the expression of MITF which in turn, decreases the expression of the melanin main synthesizing enzymes: tyrosinase, TRP-1 and TRP-2.[notes 1] BW-723C86 is not cytotoxic to melanocytes and, unlike many skin whitening agents, does not directly inhibit the activity of tyrosinase.[notes 2]

  1. ^ Kennett GA, Bright F, Trail B, Baxter GS, Blackburn TP (April 1996). "Effects of the 5-HT2B receptor agonist, BW 723C86, on three rat models of anxiety". British Journal of Pharmacology. 117 (7): 1443–8. doi:10.1111/j.1476-5381.1996.tb15304.x. PMC 1909458. PMID 8730737.
  2. ^ Kennett GA, Trail B, Bright F (December 1998). "Anxiolytic-like actions of BW 723C86 in the rat Vogel conflict test are 5-HT2B receptor mediated". Neuropharmacology. 37 (12): 1603–10. doi:10.1016/S0028-3908(98)00115-4. PMID 9886683. S2CID 7310462.
  3. ^ Knowles ID, Ramage AG (January 2000). "Evidence that activation of central 5-HT(2B) receptors causes renal sympathoexcitation in anaesthetized rats". British Journal of Pharmacology. 129 (1): 177–83. doi:10.1038/sj.bjp.0703011. PMC 1621132. PMID 10694218.
  4. ^ Günther S, Maroteaux L, Schwarzacher SW (August 2006). "Endogenous 5-HT2B receptor activation regulates neonatal respiratory activity in vitro" (PDF). Journal of Neurobiology. 66 (9): 949–61. doi:10.1002/neu.20253. PMID 16758492. S2CID 26716284.
  5. ^ Ryan BK, Anwyl R, Rowan MJ (August 2008). "5-HT2 receptor-mediated reversal of the inhibition of hippocampal long-term potentiation by acute inescapable stress". Neuropharmacology. 55 (2): 175–82. doi:10.1016/j.neuropharm.2008.05.006. PMID 18538800. S2CID 17626074.
  6. ^ Iversen L, Gibbons S, Treble R, Setola V, Huang XP, Roth BL (January 2013). "Neurochemical profiles of some novel psychoactive substances". European Journal of Pharmacology. 700 (1–3): 147–51. doi:10.1016/j.ejphar.2012.12.006. PMC 3582025. PMID 23261499.
  7. ^ a b c Oh EJ, Park JI, Lee JE, Myung CH, Kim SY, Chang SE, Hwang JS (April 2016). "A Novel Role of Serotonin Receptor 2B Agonist as an Anti-Melanogenesis Agent". International Journal of Molecular Sciences. 17 (4): 546. doi:10.3390/ijms17040546. PMC 4849002. PMID 27077852.


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