Structure via PubChem · Public domain (PubChem)
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.
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.