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Umespirone
Sign in to saveUmespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties. It behaves as a 5-HT1A receptor partial agonist (Ki = 15 nM), D2 receptor partial agonist (Ki = 23 nM), and α1-adrenoceptor receptor antagonist (Ki = 14 nM), and also has weak affinity for the sigma receptor (Ki = 558 nM). Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.
In the Vinony graph
Vinony's link graph records 581 inbound references to Umespirone, and connects out to propranolol, fluphenazine and zuclopenthixol.
Vinony files it under 1-(2-Pyrimidinyl)piperazines, 2-Methoxyphenyl compounds and Azapirones.
Vinony links it to 5 Wikipedia language editions.
Chemical data
- Formula
- C28H40N4O5
- Molecular weight
- 512.6 g/mol
- IUPAC name
- 3-butyl-7-[4-[4-(2-methoxyphenyl)piperazin-1-yl]butyl]-9,9-dimethyl-3,7-diazabicyclo[3.3.1]nonane-2,4,6,8-tetrone
- SMILES
- CCCCN1C(=O)C2C(=O)N(C(=O)C(C1=O)C2(C)C)CCCCN3CCN(CC3)C4=CC=CC=C4OC
- InChIKey
- BXNRTMZZILHVNJ-UHFFFAOYSA-N
- XLogP
- 3.4
- Polar surface area
- 90.5 Ų
- H-bond donors
- 0
- H-bond acceptors
- 7
- Formal charge
- 0
via PubChem
Wikidata facts
- Subclass of
- chemical compound
- Mass
- 512.29987
Show 2 more facts
- chemical formula
- C₂₈H₄₀N₄O₅
- canonical SMILES
- CCCCN1C(=O)C2C(=O)N(C(=O)C(C1=O)C2(C)C)CCCCN3CCN(CC3)C4=CC=CC=C4OC
Sources (2)
via Wikidata · CC0
~1 min read
Encyclopedic overview
3 sectionsContents
- Synthesis
- See also
- References
Umespirone (KC-9172) is a drug of the azapirone class which possesses anxiolytic and antipsychotic properties. It behaves as a 5-HT1A receptor partial agonist (Ki = 15 nM), D2 receptor partial agonist (Ki = 23 nM), and α1-adrenoceptor receptor antagonist (Ki = 14 nM), and also has weak affinity for the sigma receptor (Ki = 558 nM). Unlike many other anxiolytics and antipsychotics, umespirone produces minimal sedation, cognitive/memory impairment, catalepsy, and extrapyramidal symptoms.
==Synthesis== center|700px|thumb|class=skin-invert-image|Synthesis: Patent:
Excerpted from Wikipedia’s “Umespirone” article, available under the CC BY-SA 4.0 licence.