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Revision as of 07:47, 14 November 2024

BW-501C67
Clinical data
Other namesBW-501; BW-501C; α-Anilino-N-2-(3-chlorophenoxy)-propylacetamidine
Drug classPeripherally selective serotonin receptor antagonist
Identifiers
  • 2-anilino-N'-[3-(2-chlorophenoxy)propyl]ethanimidamide
PubChem CID
ChemSpider
Chemical and physical data
FormulaC17H20ClN3O
Molar mass317.82 g·mol−1
3D model (JSmol)
  • C1=CC=C(C=C1)NCC(=NCCCOC2=CC=CC=C2Cl)N
  • InChI=1S/C17H20ClN3O/c18-15-9-4-5-10-16(15)22-12-6-11-20-17(19)13-21-14-7-2-1-3-8-14/h1-5,7-10,21H,6,11-13H2,(H2,19,20)
  • Key:IKCBXYTYVXLXIR-UHFFFAOYSA-N

BW-501C67 is a peripherally selective serotonin 5-HT2A and 5-HT2C receptor antagonist which is used in scientific research.[1][2][3][4][5][6] It shows selectivity for the serotonin 5-HT2 receptors over the α1-adrenergic receptor.[1]

The drug antagonizes peripheral but not central effects of serotonin receptor agonists like serotonin.[2][3][7][6] As examples, it has been found to antagonize the sympathomimetic effects of serotonin in animals, including vasoconstriction and pressor effects, but does not block centrally mediated effects like increased corticosterone secretion or myoclonus.[3][7][8][6]

BW-501C67 and analogues were patented for use in combination with serotonin 5-HT2A receptor agonists like serotonergic psychedelics in 2023.[9]

See also

References

  1. ^ a b Middlemiss DN, Hibert M, Fozard JR (1986). "Chapter 5. Drugs Acting at Central 5-Hydroxytryptamine Receptors". Annual Reports in Medicinal Chemistry. Vol. 21. Elsevier. p. 41–50. doi:10.1016/s0065-7743(08)61115-x. ISBN 978-0-12-040521-3.
  2. ^ a b Sharp T, Boothman L, Raley J, Quérée P (December 2007). "Important messages in the 'post': recent discoveries in 5-HT neurone feedback control". Trends in Pharmacological Sciences. 28 (12): 629–636. doi:10.1016/j.tips.2007.10.009. PMID 17996955.
  3. ^ a b c Green AR (December 1984). "5-HT-mediated behavior. Animal studies". Neuropharmacology. 23 (12B): 1521–1528. doi:10.1016/0028-3908(84)90096-0. PMID 6152026.
  4. ^ Ramage AG (November 2001). "Central cardiovascular regulation and 5-hydroxytryptamine receptors". Brain Research Bulletin. 56 (5): 425–439. doi:10.1016/s0361-9230(01)00612-8. PMID 11750788.
  5. ^ Chaouloff F, Layeillon C, Baudrie V (January 1993). "5-HT1C/5-HT2 receptor blockade prevents 1-(2,5-dimethoxy-4-iodophenyl)2-aminopropane-, but not stress-induced increases in brain tryptophan". European Journal of Pharmacology. 231 (1): 77–82. doi:10.1016/0014-2999(93)90686-c. PMID 8095238.
  6. ^ a b c Fuller RW, Kurz KD, Mason NR, Cohen ML (June 1986). "Antagonism of a peripheral vascular but not an apparently central serotonergic response by xylamidine and BW 501C67". European Journal of Pharmacology. 125 (1): 71–77. doi:10.1016/0014-2999(86)90084-1. PMID 3732393.
  7. ^ a b Cook DA (1984). "The pharmacology of cerebral vasospasm". Pharmacology. 29 (1): 1–16. doi:10.1159/000137986. PMID 6379682.
  8. ^ Fuller RW (1996). "Serotonin receptors involved in regulation of pituitary-adrenocortical function in rats". Behavioural Brain Research. 73 (1–2): 215–219. doi:10.1016/0166-4328(96)00099-x. PMID 8788505.
  9. ^ WO 2023028086, Kruegel AC, "Combinations of peripheral 5-HT2A receptor antagonists and central 5-HT2A receptor agonists", published 2 March 2023, assigned to Gilgamesh Pharmaceuticals, Inc. 
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