Structure via PubChem · Public domain (PubChem)
xylamidine
Sign in to saveXylamidine is a drug which acts as an antagonist of the serotonin 5-HT2A and 5-HT2C receptors, and to a lesser extent of the serotonin 5-HT1A receptor. The drug does not cross the blood–brain barrier and hence is peripherally selective, which makes it useful for blocking peripheral serotonergic responses like cardiovascular and gastrointestinal effects, without producing the central effects of 5-HT2A receptor blockade such as sedation, or interfering with the central actions of 5-HT2A receptor agonists.
Chemical data
- Formula
- C19H24N2O2
- Molecular weight
- 312.4 g/mol
- IUPAC name
- N'-[2-(3-methoxyphenoxy)propyl]-2-(3-methylphenyl)ethanimidamide
- SMILES
- CC1=CC(=CC=C1)CC(=NCC(C)OC2=CC=CC(=C2)OC)N
- InChIKey
- JRYTUFKIORWTNI-UHFFFAOYSA-N
- XLogP
- 3.3
- Polar surface area
- 56.8 Ų
- H-bond donors
- 1
- H-bond acceptors
- 3
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 2
- Molecule type
- Small molecule
via ChEMBL · EBI
Research
76 papers- Effects of xylamidine on peripheral 5-hydroxytryptamine-induced anorexia.Pharmacology, biochemistry, and behavior · 1989
- Xylamidine tosylate: differential antagonism of the hypothermic effects of N,N-dimethyltryptamine, bufotenine, and 5-methoxytryptamine.Archives internationales de pharmacodynamie et de therapie · 1972
- Antagonism of a peripheral vascular but not an apparently central serotonergic response by xylamidine and BW 501C67.European journal of pharmacology · 1986
- Effects of dl-fenfluramine and xylamidine on gastric emptying of maintenance diet in freely feeding rats.European journal of pharmacology · 1988
- Studies on the role of 5-HT receptors in satiation and the effect of d-fenfluramine in the runway test.European journal of pharmacology · 1990
via PubMed
Wikidata facts
- Subclass of
- chemical compound
- Has part
- carbon
- Mass
- 312.184
Show 4 more facts
- chemical formula
- C₁₉H₂₄N₂O₂
- canonical SMILES
- CC1=CC(=CC=C1)CC(=NCC(C)OC2=CC=CC(=C2)OC)N
- isomeric SMILES
- CC1=CC=CC(=C1)C/C(=N/CC(C)OC2=CC=CC(=C2)OC)/N
- subject has role
- serotonin antagonist
Sources (2)
via Wikidata · CC0
~2 min read
Encyclopedic overview
4 sectionsContents
- Chemistry
- Synthesis
- See also
- References
Xylamidine is a drug which acts as an antagonist of the serotonin 5-HT2A and 5-HT2C receptors, and to a lesser extent of the serotonin 5-HT1A receptor. The drug does not cross the blood–brain barrier and hence is peripherally selective, which makes it useful for blocking peripheral serotonergic responses like cardiovascular and gastrointestinal effects, without producing the central effects of 5-HT2A receptor blockade such as sedation, or interfering with the central actions of 5-HT2A receptor agonists.
Xylamidine and analogues were patented for use in combination with serotonin 5-HT2A receptor agonists like serotonergic psychedelics in 2023.
Excerpted from Wikipedia’s “xylamidine” article, available under the CC BY-SA 4.0 licence.