|Chemical and physical data|
|Molar mass||312.406 g/mol|
|3D model (Jmol)||Interactive image|
|(what is this?)|
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 and gastrointestinal effects, without producing the central effects of 5HT2A blockade such as sedation, or interfering with the central actions of 5HT2A agonists.
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.
- 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.
- 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.
- 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.
- 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.