Xylamidine

Xylamidine is a drug which acts as an antagonist of the serotonin 5-HT_2A and 5-HT_2C receptors,^[1][2] and to a lesser extent of the serotonin 5-HT_1A receptor. The drug does not cross the blood–brain barrier and hence is peripherally selective, which makes it useful for blocking peripheral serotonergic responses like cardiovascular^[3][4] and gastrointestinal effects,^[5] without producing the central effects of 5-HT_2A receptor blockade such as sedation, or interfering with the central actions of 5-HT_2A receptor agonists.^[6]

Xylamidine

Clinical data
Drug class	Peripherally selective serotonin receptor antagonist
ATC code	None
Identifiers
IUPAC name N'-[2-(3-methoxyphenoxy)propyl]-2-(3-methylphenyl)ethanimidamide
CAS Number	6443-50-1 Y
PubChem CID	22951
ChemSpider	21486 Y
UNII	NY0PC84NZK
CompTox Dashboard (EPA)	DTXSID90863843
Chemical and physical data
Formula	C19H24N2O2
Molar mass	312.413 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC(=CC=C1)CC(=NCC(C)OC2=CC=CC(=C2)OC)N
InChI InChI=1S/C19H24N2O2/c1-14-6-4-7-16(10-14)11-19(20)21-13-15(2)23-18-9-5-8-17(12-18)22-3/h4-10,12,15H,11,13H2,1-3H3,(H2,20,21) N Key:JRYTUFKIORWTNI-UHFFFAOYSA-N N
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Xylamidine and analogues were patented for use in combination with serotonin 5-HT_2A receptor agonists like serotonergic psychedelics in 2023.^[7]

Chemistry

Synthesis

Xylamidine is an amidine. It is prepared by alkylation of 3-methoxyphenol (m-methoxyphenol) with α-chloropropionitrile, potassium iodide, and potassium carbonate in butanone to give #, which is in turn reduced with lithium aluminium hydride to give the primary amine #. When # is treated with m-tolylacetonitrile in the presence of anhydrous hydrochloric acid, the synthesis is completed. Alternately, one can react primary amine # with m-tolylacetamidine under acid catalysis to produce xylamidine.

See also

• BW-501C67
• AL-34662
• VU0530244