Chemistry:Xylamidine

Short description: Chemical compound

Xylamidine

Clinical data
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 N
UNII	NY0PC84NZK
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
NY (what is this?)  (verify)

Xylamidine is a drug which acts as an antagonist at the 5HT_2A receptor, and to a lesser extent at the 5HT_1A receptor. It does not cross the blood–brain barrier, which makes it useful for blocking peripheral serotonergic responses like cardiovascular and gastrointestinal effects, without producing the central effects of 5HT_2A blockade such as sedation, or interfering with the central actions of 5HT_2A agonists.

Synthesis

Xylamidine is an amidine which serves as a serotonin inhibitor. This agent is prepared by alkylation of 3-methoxyphenol (m-methoxyphenol) with α-chloropropionitrile, KI and potassium carbonate in MEK 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 HCl, the synthesis is completed. Alternately, one can react primary amine # with m-tolylacetamidine under acid catalysis to produce xylamidine.