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Xylamidine









Xylamidine


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Xylamidine
Xylamidine.png
Clinical data
ATC code
  • none
Identifiers
CAS Number

  • 6443-50-1 ☑Y

PubChem CID
  • 22951
ChemSpider

  • 21486 ☒N
UNII
  • NY0PC84NZK
Chemical and physical data
Formula
C19H24N2O2
Molar mass 312.406 g/mol
3D model (JSmol)
  • Interactive image

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 ☒N☑Y (what is this?)
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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[edit]


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[edit]





  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..mw-parser-output cite.citation{font-style:inherit}.mw-parser-output q{quotes:"""""""'""'"}.mw-parser-output code.cs1-code{color:inherit;background:inherit;border:inherit;padding:inherit}.mw-parser-output .cs1-lock-free a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/6/65/Lock-green.svg/9px-Lock-green.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-limited a,.mw-parser-output .cs1-lock-registration a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/d/d6/Lock-gray-alt-2.svg/9px-Lock-gray-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-lock-subscription a{background:url("//upload.wikimedia.org/wikipedia/commons/thumb/a/aa/Lock-red-alt-2.svg/9px-Lock-red-alt-2.svg.png")no-repeat;background-position:right .1em center}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration{color:#555}.mw-parser-output .cs1-subscription span,.mw-parser-output .cs1-registration span{border-bottom:1px dotted;cursor:help}.mw-parser-output .cs1-hidden-error{display:none;font-size:100%}.mw-parser-output .cs1-visible-error{font-size:100%}.mw-parser-output .cs1-subscription,.mw-parser-output .cs1-registration,.mw-parser-output .cs1-format{font-size:95%}.mw-parser-output .cs1-kern-left,.mw-parser-output .cs1-kern-wl-left{padding-left:0.2em}.mw-parser-output .cs1-kern-right,.mw-parser-output .cs1-kern-wl-right{padding-right:0.2em}


  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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