Xylamidine is a drug which acts as an
antagonist at the
5HT2A receptor
Receptor may refer to:
* Sensory receptor, in physiology, any structure which, on receiving environmental stimuli, produces an informative nerve impulse
*Receptor (biochemistry), in biochemistry, a protein molecule that receives and responds to a ...
, 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
The blood circulatory system is a system of organs that includes the heart, blood vessels, and blood which is circulated throughout the entire body of a human or other vertebrate. It includes the cardiovascular system, or vascular system, tha ...
and
gastrointestinal
The gastrointestinal tract (GI tract, digestive tract, alimentary canal) is the tract or passageway of the digestive system that leads from the mouth to the anus. The GI tract contains all the major organs of the digestive system, in humans and ...
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
Amidines are organic compounds with the functional group RC(NR)NR2, where the R groups can be the same or different. They are the imine derivatives of amides (RC(O)NR2). The simplest amidine is formamidine, HC(=NH)NH2.
Examples of amidines includ ...
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
Lithium aluminium hydride, commonly abbreviated to LAH, is an inorganic compound with the chemical formula Li Al H4. It is a white solid, discovered by Finholt, Bond and Schlesinger in 1947. This compound is used as a reducing agent in organic sy ...
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
5-HT2A antagonists
Phenol ethers
Amidines
Peripherally selective drugs
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