BW-501C67 explained

Width:

250px

Class:

Peripherally selective serotonin receptor antagonist

Cas Supplemental:

68518-39-8 (hydrochloride)

Pubchem:

172196

Chemspiderid:

150502

Synonyms:

BW-501; BW-501C; α-Anilino-N-2-(3-chlorophenoxy)-propylacetamidine

Iupac Name:

2-anilino-N-[3-(2-chlorophenoxy)propyl]ethanimidamide| C=17 | H=20 | Cl=1 | N=3 | O=1| SMILES = C1=CC=C(C=C1)NCC(=NCCCOC2=CC=CC=C2Cl)N| StdInChI = 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)| StdInChIKey = IKCBXYTYVXLXIR-UHFFFAOYSA-N}}

BW-501C67 is a peripherally selective serotonin 5-HT_2A and 5-HT_2C 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.

The drug antagonizes peripheral but not central effects of serotonin receptor agonists like serotonin.^[7] 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.^[8]

BW-501C67 and analogues were patented for use in combination with serotonin 5-HT_2A receptor agonists like serotonergic psychedelics in 2023.^[9]

See also

• Xylamidine
• AL-34662
• VU0530244

References

Notes and References

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