Xylamidine

Xylamidine
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
Molar mass 312.406 g/mol
 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

  1. ↑ Fuller, RW; Kurz, KD; Mason, NR; Cohen, ML (1986). "Antagonism of a peripheral vascular but not an apparently central serotonergic response by xylamidine and BW 501C67". European Journal of Pharmacology 125 (1): 71–7. doi:10.1016/0014-2999(86)90084-1. PMID 3732393.
  2. ↑ Dedeoğlu, A; Fisher, LA (1991). "Central and peripheral injections of the 5-HT2 agonist, 1-(2,5-dimethoxy-4-iodophenyl)-2-aminopropane, modify cardiovascular function through different mechanisms". The Journal of Pharmacology and Experimental Therapeutics 259 (3): 1027–34. PMID 1762059.
  3. ↑ Baker, BJ; Duggan, JP; Barber, DJ; Booth, DA (1988). "Effects of dl-fenfluramine and xylamidine on gastric emptying of maintenance diet in freely feeding rats". European Journal of Pharmacology 150 (1–2): 137–42. doi:10.1016/0014-2999(88)90759-5. PMID 3402534.
  4. ↑ Dave, KD; Quinn, JL; Harvey, JA; Aloyo, VJ (2004). "Role of central 5-HT2 receptors in mediating head bobs and body shakes in the rabbit". Pharmacology, Biochemistry, and Behavior 77 (3): 623–9. doi:10.1016/j.pbb.2003.12.017. PMID 15006475.


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