8-(3-(4-Fluorophenoxy)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one
Basic information
- CAS
510-74-7- Standard SMILES
O=C1NCN(c2ccccc2)C12CCN(CCCOc1ccc(F)cc1)CC2- InChIKey
FJUKDAZEABGEIH-UHFFFAOYSA-N- Molecular formula
- C22H26FN3O2
- Average molar mass
- 383.5 g/mol
- Monoisotopic mass
- 383.20090524
Overview
Spiramide is an azaspiro compound that consists of 1,3,8-triazaspiro[4.5]decan-4-one having a phenyl group attached to N-1 and a 3-(4-fluorophenoxy)propyl attached to N-8. Selective 5-HT antagonist, which binds to 5-HT2 sites as potently as spiperone but has lower affinity for 5-HT2C receptors. Also a high affinity D2 receptor antagonist (Ki = 3 nM). Lacks the disruptive effect of spiperone on animal behaviour. It has a role as a serotonergic antagonist and a dopaminergic antagonist. It is a member of piperidines, an aromatic ether, an azaspiro compound, an organofluorine compound and a tertiary amino compound.
Names & identifiers
- Preferred name
- 8-(3-(4-Fluorophenoxy)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one
- IUPAC
- 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
- English name
- AMI-193
- Molecular formula
- C22H26FN3O2
- Molecular weight
- 383.46
Names & synonyms
Spiramide510-74-7EspiramidaSpiramidum8-[3-(4-Fluorophenoxy)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneR 5808R-5808471LF4O004CHEBI:642078-(3-(4-fluorophenoxy)propyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one8-(3-(4-Fluorophenoxy)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-oneRefChem:184726
Show more names
AMI-193, 10 mM in DMSO8-[3-(4-FLUOROPHENOXY)PROPYL]-1-PHENYL-1,3,8-TRIAZASPIRO[4.5]-DECANONE1-Phenyl-8-[3-(4-fluorophenoxy)propyl]-1,3,8-triazaspiro[4.5]decane-4-one1,3,8-Triazaspiro[4.5]decan-4-one, 8-[3-(4-fluorophenoxy)propyl]-1-phenyl-
8-(3-(4-Fluorophenoxy) propyl)-1-phenyl-1,3,8-triazaspiro(4, 5)decan-4-oneAMI-193Spiramide [INN]DTXSID6042579CHEMBL79834FluroxyspiramineNCGC00024633-02AMI 193;AMI-193;AMI193
Database identifiers
- CAS
510-74-7
Properties
Computed structural properties
- XLogP
- 3.4
- Topological polar surface area
- 44.8 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 5
- Rotatable bonds
- 6
- Heavy atoms
- 28
- Formal charge
- 0
- Complexity
- 510
Physicochemical properties
- Melting point
- 176 · 176 - 179°C
- storage temp.
- Store at RT
- solubility
- DMSO (Slightly), Methanol (Slightly)
- form
- White solid.
- color
- Off-White to Pale Yellow
- FDA UNII
- 471 LF4O004 · 471LF4O004
Chemistry & industry
Applications
UsesAMI-193 is a selective 5-HT2A and D2DR receptor antagonist. Endoplasmic reticulum (ER) stress inducer; Also, it is derived from 4-Fluorophenol (F595325), which is a fluorinated phenolic compound with various applications as an starting reagent for the synthesis of pharmaceutical goods.
Additional notes
DefinitionChEBI: An azaspiro compound that consists of 1,3,8-triazaspiro[4.5]decan-4-one having a phenyl group attached to N-1 and a 3-(4-fluorophenoxy)propyl attached to N-8. Selective 5-HT antagonist, which binds to 5-HT2 sites as potently as spipero e but has lower affinity for 5-HT2C receptors. Also a high affinity D2 receptor antagonist (Ki = 3 nM). Lacks the disruptive effect of spiperone on animal behaviour.
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