Xylamidine

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Xylamidine
Xylamidine.png
Systematic (IUPAC) name
N'-[2-(3-methoxyphenoxy)propyl]-2-(3-methylphenyl)ethanimidamide
Identifiers
CAS Number 6443-50-1 YesY
ATC code none
PubChem CID: 22951
ChemSpider 21486 N
UNII NY0PC84NZK YesY
Chemical data
Formula C19H24N2O2
Molecular mass 312.406 g/mol
  • CC1=CC(=CC=C1)CC(=NCC(C)OC2=CC=CC(=C2)OC)N
  • 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
 NYesY (what is this?)  (verify)

Xylamidine is a drug which acts as an antagonist at the 5HT2A receptor, and to a lesser extent at the 5HT1A receptor. It does not cross the blood–brain barrier, which makes it useful for blocking peripheral serotonergic responses like cardiovascular[1][2] and gastrointestinal effects,[3] without producing the central effects of 5HT2A blockade such as sedation, or interfering with the central actions of 5HT2A agonists.[4]

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 aluminum 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.

References

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