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Spiperone

HCID 5265
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Basic information

CAS
749-02-0
Standard SMILES
O=C(CCCN1CCC2(CC1)C(=O)NCN2c1ccccc1)c1ccc(F)cc1
InChIKey
DKGZKTPJOSAWFA-UHFFFAOYSA-N
Molecular formula
C23H26FN3O2
Average molar mass
395.5 g/mol
Monoisotopic mass
395.20090529

Overview

Spiperone is an azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively. It has a role as a psychotropic drug, an antipsychotic agent, an alpha-adrenergic antagonist, a serotonergic antagonist and a dopaminergic antagonist. It is a member of piperidines, an azaspiro compound, an organofluorine compound, a tertiary amino compound and an aromatic ketone.

Names & identifiers

Preferred name
Spiperone
IUPAC
8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one
English name
SPIPERONE
Molecular formula
C23H26FN3O2
Molecular weight
395.47

Names & synonyms

spiperone749-02-0SpiropitanSpiroperidolEspiperonaSpiperonum8-[4-(4-fluorophenyl)-4-oxobutyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneR 5147DTXSID50452058-(3-(p-Fluorobenzoyl)propyl)-1-phenyl-1,3,8-triazaspiro(4.5)decan-4-one8-(3-p-Fluorobenzoyl-1-propyl)-4-oxo-1-phenyl-1,3,8-triazaspiro(4,5)decaneR-5147
Show more names
r5147SpiperonLuopenglongSpiperone-d5SpiperoneHClSpiroperidoneSpiperone, 10 mM in DMSO
NSC-1709834X6E73CJ0Q1,3,8-Triazaspiro(4.5)decan-4-one, 8-(4-(4-fluorophenyl)-4-oxobutyl)-1-phenyl-CHEBI:9233DTXCID30252058-(4-(4-Fluorophenyl)-4-oxobutyl)-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-one8-[3-(p-Fluorobenzoyl)propyl]-1-phenyl-1,3,8-triazaspiro[4.5]decan-4-oneSpiroperone

Database identifiers

CAS
749-02-0

Properties

Computed structural propertiesFilling in

XLogP
3
Topological polar surface area
52.7 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
6
Heavy atoms
29
Formal charge
0
Complexity
577

Experimental & physicochemical properties

Solubility50.1 [ug/mL] (The mean of the results at pH 7.4)
Collision Cross Section · 2 items

193.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

199.03 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
190 · 190-193.60C
Boiling point
630.6 · 630.6±55.0 °C(Predicted)
Density
1.1714 · 1.1714 (estimate)
storage temp.
Store at RT
solubility
2 O: · H2O: slightly soluble0.2mg/mL
pka
8.31 · pKa 8.31 (Uncertain);9.09 (Uncertain)
form
solid
color
light yellow
Water Solubility
32 mg/L · 32mg/L(22 ºC)

Safety & regulation

Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.

GHS classification

GHS Classification · 4 items

Warning

H302 (98.5%): Harmful if swallowed [Warning Acute toxicity, oral]

P203, P264, P270, P280, P301+P317, P318, P330, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 68 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Hazard information

Hazard Classes and CategoriesAcute Tox. 4 (98.5%)

Safety data

PPE
Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
wgk
3
rtecs
XX8925000
risk_code
22-63
Signal word
Warning
Symbol(GHS)
GHS07,GHS08
hazard_code
Xn
safety_code
36/37
Storage Class
11 - Combustible Solids
Hazard statements
H302-H361
Hazard Classifications
Acute Tox. 4 OralRepr. 2
Precautionary statements
P201-P301+P312+P330-P308+P313

Chemistry & industry

Pharmacology

MeSH Pharmacological Classification · 2 items

Agents that control agitated psychotic behavior, alleviate acute psychotic states, reduce psychotic symptoms, and exert a quieting effect. They are used in SCHIZOPHRENIA; senile dementia; transient psychosis following surgery; or MYOCARDIAL INFARCTION; etc. These drugs are often referred to as neuroleptics alluding to the tendency to produce neurological side effects, but not all antipsychotics are likely to produce such effects. Many of these drugs may also be effective against nausea, emesis, and pruritus.

Drugs that bind to but do not activate DOPAMINE RECEPTORS, thereby blocking the actions of dopamine or exogenous agonists. Many drugs used in the treatment of psychotic disorders (ANTIPSYCHOTIC AGENTS) are dopamine antagonists, although their therapeutic effects may be due to long-term adjustments of the brain rather than to the acute effects of blocking dopamine receptors. Dopamine antagonists have been used for several other clinical purposes including as ANTIEMETICS, in the treatment of Tourette syndrome, and for hiccup. Dopamine receptor blockade is associated with NEUROLEPTIC MALIGNANT SYNDROME.

Applications · 3 items

UsesSpiperone is an antipsychotic.

Usesantibacterial

General DescriptionSpiperone is a butyrophenone antipsychotic agent. It induces calcium-dependent chloride secretion in the airway and functions as a potential therapeutic target for cystic fibrosis.

Upstream & downstream products

Upstream raw materials

Formamide4-Chloro-4'-fluorobutyrophenone

Downstream products

N-(p-Nitrophenethyl)spiperone

Related reactions

13 records
New reaction record
HRID 5142 reaction equation
HRID 5142As reactantuspto-grants-1993_09
HRID 258269 reaction equation
HRID 258269As reactantuspto-grants-1993_11
HRID 327593 reaction equation
HRID 327593As reactantuspto-grants-1993_12
HRID 487568 reaction equation
HRID 487568As reactantuspto-grants-1994_03
HRID 1031135 reaction equation
HRID 1031135As reactantuspto-grants-1992_04
HRID 1034421 reaction equation
HRID 1034421As reactantuspto-grants-1994_05
HRID 1196914 reaction equation
HRID 1196914As reactantuspto-grants-1992_05
HRID 1586781 reaction equation
HRID 1586781As reactantuspto-grants-1993_06
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Compound notes

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PubChem CID
5265
DTXSID
DTXSID5045205
ChEMBL
CHEMBL267930
ChEBI
CHEBI:9233
UNII
4X6E73CJ0Q
EC Number
212-024-0
Nikkaji
J3.320K
InChI
1S/C23H26FN3O2/c24-19-10-8-18(9-11-19)21(28)7-4-14-26-15-12-23(13-16-26)22(29)25-17-27(23)20-5-2-1-3-6-20/h1-3,5-6,8-11H,4,7,12-17H2,(H,25,29)
InChIKey
DKGZKTPJOSAWFA-UHFFFAOYSA-N
SMILES
Fc1ccc(cc1)C(=O)CCCN2CCC3(CC2)N(CNC3=O)c4ccccc4
FDA UNII
4 X6E73CJ0Q · 4X6E73CJ0Q
UNSPSC Code
12352200 · 12352200
NACRES
77 · NA.77
Symbol(GHS)
7 · GHS07,GHS08
Signal word
Warning
Hazard statements
302 · H302-H361
Precautionary statements
201 · P201-P301+P312+P330-P308+P313
PPE
3 · Eyeshields, Gloves, type P3 (EN 143) respirator cartridges
Hazard Codes
Xn
Risk Statements
22 · 22-63
Safety Statements
36 · 36/37
WGK Germany
3 · 3
RTECS
8925000 · XX8925000
Storage Class
11 · 11 - Combustible Solids
Hazard Classifications
4 OralRepr · Acute Tox. 4 OralRepr. 2

Additional notes

DefinitionChEBI: An azaspiro compound that is 1,3,8-triazaspiro[4.5]decane which is substituted at positions 1, 4, and 8 by phenyl, oxo, and 4-(p-fluorophenyl)-4-oxobutyl groups, respectively.