Pipamperone

HCID 4830CAS 1893-33-0

Basic information

Standard SMILES
NC(=O)C1(N2CCCCC2)CCN(CCCC(=O)c2ccc(F)cc2)CC1
InChIKey
AXKPFOAXAHJUAG-UHFFFAOYSA-N
Molecular formula
C21H30FN3O2
Average molar mass
375.5 g/mol
Monoisotopic mass
375.23220537

Names & identifiers

Preferred name
Pipamperone
IUPAC
1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide
English name
Pipamperone dihydrochloride approx. 99
Molecular formula
C21H30FN3O2
Molecular weight
375.48

Names & synonyms

Pipamperone1893-33-0FloropipamideDipiperonePipamperonaPipamperonumR 3345NSC-7591781'-(3-(p-Fluorobenzoyl)propyl)-(1,4'-bipiperidine)-4'-carboxamideR-3345p-Fluoro-gamma-(4-piperidino-4-carbamoylpiperidino)butyrophenone5402501F0W
Show more names
FPAPiperonylD02622PropitanDipiperonDipiperalpiperonilMCN-JR-3345
DTXSID8048369CHEBI:78549(1,4'-Bipiperidine)-4'-carboxamide, 1'-(4-(4-fluorophenyl)-4-oxobutyl)-[1,4'-Bipiperidine]-4'-carboxamide, 1'-[4-(4-fluorophenyl)-4-oxobutyl]-1-[4-(4-fluorophenyl)-4-oxobutyl]-4-piperidin-1-ylpiperidine-4-carboxamide1-(4-(4-fluorophenyl)-4-oxobutyl)-4-piperidin-1-ylpiperidine-4-carboxamideRefChem:863377DTXCID8028343

Database identifiers

CAS
1893-33-0
PubChem CID
4830
DTXSID
DTXSID8048369
ChEMBL
CHEMBL440294
ChEBI
CHEBI:78549
UNII
5402501F0W
EC Number
606-172-9
Nikkaji
J7.805K

Properties

Computed structural properties

XLogP
2
Topological polar surface area
66.6 Ų
Hydrogen bond donors
1
Hydrogen bond acceptors
5
Rotatable bonds
7
Heavy atoms
27

Experimental & physicochemical properties

LogP2.02
Solubilitysoluble in methanol
Melting Point>254
Kovats Retention Index3090;3070;3070
Collision Cross Section · 3 items

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

194.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

194.65 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards];191.8 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Physicochemical properties

Melting point
126 °C · 126°C(lit.)
Boiling point
563.7 · 563.7±50.0 °C(Predicted)
Density
1.1017 · 1.1017 (estimate)
storage temp.
-20 °C · Store at -20°C
solubility
2 O: · H2O: ~50 mg/mL
form
powder

Safety & regulation

GHS classification

GHS Classification · 5 items

Danger

H301 (75%): Toxic if swallowed [Danger Acute toxicity, oral];H302+H312+H332 (25%): Harmful if swallowed, in contact with skin or if inhaled [Warning Acute toxicity, oral; acute toxicity, dermal; acute toxicity, inhalation];H302 (25%): Harmful if swallowed [Warning Acute toxicity, oral];H312 (25%): Harmful in contact with skin [Warning Acute toxicity, dermal];H315 (25%): Causes skin irritation [Warning Skin corrosion/irritation];H332 (25%): Harmful if inhaled [Warning Acute toxicity, inhalation];H335 (25%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation];H411 (50%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]

P261, P264, P270, P271, P273, P280, P301+P316, P301+P317, P302+P352, P304+P340, P317, P319, P321, P330, P332+P317, P362+P364, P391, P403+P233, P405, and P501 (click each P-code to see the statement)

Aggregated GHS information provided per 4 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.;Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown. For more detailed information, please visit ECHA C&L website.

Hazard information

Regulatory InformationStatus: Active Update: 02-12-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18516
Hazard Classes and CategoriesAcute Tox. 3 (75%);Acute Tox. 4 (25%);Acute Tox. 4 (25%);Skin Irrit. 2 (25%);Acute Tox. 4 (25%);STOT SE 3 (25%);Aquatic Chronic 2 (50%)

Regulatory information

Regulatory InformationStatus: Active Update: 02-12-2016 https://echa.europa.eu/registration-dossier/-/registered-dossier/18516

Safety data

wgk
1
rtecs
DW1060000
ridadr
UN 2811 6.1/PG III
hs_code
2933.39.3100
risk_code
22
Signal word
Danger

Chemistry & industry

Pharmacology

ATC Code · 3 items

N05AD05

N - Nervous system;N05 - Psycholeptics;N05A - Antipsychotics;N05AD - Butyrophenone derivatives;N05AD05 - Pipamperone

QN - Nervous system;QN05 - Psycholeptics;QN05A - Antipsychotics;QN05AD - Butyrophenone derivatives;QN05AD05 - Pipamperone

Pharmacodynamics · 1 item

Pipamperone is an antipsychotic medication that has sedative effects, which may be beneficial in the management of agitation and disordered sleep. Pipamperone, showing antidopaminergic and anti-serotonergic properties, has been noted for its anti- agitation effects and for its ability to normalize sleep rhythms in psychiatric patients. One study showed that pipamperone increased the expression of D4 (dopaminergic) receptors, explaining its helpfulness in decreasing positive psychotic symptoms, such as delusions and hallucinations.

Mechanism of Action · 1 item

Pipamperone binds mainly to 5-HT2A receptors, with a nearly equal affinity to D4 receptors and a moderate affinity for 5-HT2C, D2, D3, 1- and 2B-adrenoceptors. This drug is a selective 5-HT2A, D1 and D4 antagonist. Extrapyramidal adverse effects also appear to be limited in pipamperone treatment compared to traditional antipsychotic medications due to its high receptor selectivity. Pipamperone has a 15-fold higher affinity for D4 than D2 receptors. It has been suggested that D4 receptors may play a role in the modulation of GABAergic neuronal activity by dopamine.

Biological Half-Life17-26h
Metabolism/MetabolitesPipamperone is metabolised in the liver.
MeSH Pharmacological Classification · 2 items

Drugs that bind to but do not activate serotonin receptors, thereby blocking the actions of serotonin or SEROTONIN RECEPTOR AGONISTS.

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.

Uses & manufacturing

UsesUse (kg; approx.) in Germany (2009): >2500;Consumption (g per capita; approx.) in Germany (2009): 0.0305;Calculated removal (%): 2.3
Use ClassificationPharmaceuticals

Applications

UsesAntipsychotic.

Suppliers44 total

南通飞宇生物科技有限公司0513-68819626 15152877458 · [email protected]
Career Henan Chemica Co+86-0371-86658258 +86-13203830695 · [email protected]
成都超九八生物科技有限公司13348960310 13348960310 · [email protected]
上海钰博生物科技有限公司021-60514606 18321282235 · [email protected]
上海麦克林生化科技股份有限公司021-50706066 15221275939 · [email protected]
Additional notes · 1 item

DefinitionChEBI: A member of the class of bipiperidines that is 1,4'-bipiperidine which is substituted at the 1' and 4' positions by 4-(p-fluorophenyl)-4-oxobutyl and carboxamide groups, respectively. A first generation antipsychotic, its properties are gener lly similar to those of haloperidol.

Related reactions

1 records

Linked notes

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