Pimavanserin

Base Information

• Chemical Name: Pimavanserin
• CAS No.: 706779-91-1
• Molecular Formula: C25H34FN3O2
• Molecular Weight: 427.562
• Hs Code.: 29339900
• European Community (EC) Number: 810-275-6
• UNII: JZ963P0DIK
• DSSTox Substance ID: DTXSID90990906
• Wikipedia: Pimavanserin
• Wikidata: Q7194603
• NCI Thesaurus Code: C76444
• RXCUI: 1791685
• Pharos Ligand ID: 8AH6H4VNJSA6
• Metabolomics Workbench ID: 149444
• ChEMBL ID: CHEMBL2111101
• Mol file: 706779-91-1.mol

Synonyms:ACP 103;ACP-103;ACP103;bis(1-(4-fluorobenzyl)-1-(1-methylpiperidin-4-yl)-3-(4-(2-methylpropoxy)benzyl)urea) (2R,3R)-2,3-dihydroxybutanedioate;N-(4-fluorophenylmethyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl)carbamide;Nuplazid;Pimavanserin;pimavanserin tartrate;urea, n-((4-fluorophenyl)methyl)-n-(1-methyl-4-piperidinyl)-n'-((4-(2-methylpropoxy)phenyl)methyl)-, (2R,3R)-2,3-dihydroxybutanedioate (2:1)

Chemical Property of Pimavanserin

Chemical Property:

• Appearance/Colour: Pale Yellow to Pale Orange Solid
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 100-103 oC
• Refractive Index: 1.576
• Boiling Point: 604.222 °C at 760 mmHg
• PKA: 13.52±0.46(Predicted)
• Flash Point: 319.222 °C
• PSA: 44.81000
• Density: 1.15 g/cm³
• LogP: 4.99530
• Storage Temp.: Refrigerator
• Solubility.: Methanol (Slightly)
• XLogP3: 4.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 8
• Exact Mass: 427.26350550
• Heavy Atom Count: 31
• Complexity: 523

Purity/Quality:

99.0% MIN ^*data from raw suppliers

Pimavanserin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Safety Statements: 24/25

MSDS Files:

SDS file from LookChem

Useful:

• Drug Classes: Antipsychotic Agents
• Canonical SMILES: CC(C)COC1=CC=C(C=C1)CNC(=O)N(CC2=CC=C(C=C2)F)C3CCN(CC3)C
• Recent ClinicalTrials: Pimavanserin for the Treatment of Irritability Associated With Autism Spectrum Disorder
• Recent EU Clinical Trials: A Phase 2, Randomized, Double-blind, Placebo-controlled Study to Evaluate the Efficacy and Safety of Pimavanserin for the Treatment of Irritability Associated With Autism Spectrum Disorder
• Uses: Drug used in the treatment of Parkinson disease psychosis. Drug used in the treatment of Parkinson’s disease psychosis. Drug used in the treatment of Parkinson’s disease and psychosis.
• Description: Pimavanserin is an inverse agonist of the serotonin (5-HT) receptor subtype 5-HT2A (IC50 = 1.86 nM; Ki = 0.5 nM). It is selective for 5-HT2A over a panel of 65 ion channels, enzymes, and receptors (Kis = >100 nM). Pimavanserin reduces head-twitch behavior and prepulse inhibition deficits induced by the 5-HT2A receptor agonist DOI in rats at doses of 3 mg/kg, p.o. and 1-10 mg/kg, s.c., respectively. It also exhibits antipsychotic-like activity, reducing hyperactivity induced by (+)-MK-801 in mice. Pimavanserin acts synergistically with haloperidol or risperidone to suppress (+)-MK-801-induced hyperactivity and attenuates haloperidol- and risperidone-induced catalepsy in rats. Formulations containing pimavanserin have been used for the treatment of psychosis in Parkinson''s disease.

Technology Process of Pimavanserin

There total 94 articles about Pimavanserin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine (359878-47-0) + di(succinimido) carbonate (74124-79-1) + 1-[4-(2-methylpropyloxy)phenyl]methanamine (4734-09-2) → N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1)

Guidance literature:

N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine; di(succinimido) carbonate; With 4-methyl-morpholine; In dichloromethane; at -5 - 25 ℃; for 5h;

1-[4-(2-methylpropyloxy)phenyl]methanamine; In dichloromethane; at 25 ℃; for 10h; Solvent; Temperature; Time;

Reference yield: 94.2%

1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)thiourea → N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1)

Guidance literature:

With silver carbonate; In acetonitrile; at 20 ℃; for 24h; Reagent/catalyst; Green chemistry;

DOI:10.14233/ajchem.2019.21808

Reference yield: 92.0%

N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine (359878-47-0) + N-(4-isobutoxybenzyl)carbamic acid phenyl ester → N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1)

Guidance literature:

With potassium carbonate; In toluene; at 90 ℃; for 24h; Reagent/catalyst; Temperature;

upstream raw materials:

1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene

N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine

4-hydroxy-benzaldehyde

4-isobutoxybenzaldehyde

Downstream raw materials:

N-(4-fluorobenzyl)-N-(1-methylpiperidin-4-yl)-N'-(4-(2-methylpropyloxy)phenylmethyl)carbamide phosphate

2C₂₅H₃₄FN₃O₂*0.5C₄H₆O₆

Pimavanserin tartrate

1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea L-hemitartrate

Refernces

• 1、 -. "A PHARMACEUTICAL INTERMEDIATE". . . Retrieved 2020/12/07.
• 2、 -. "PROCESS FOR THE MANUFACTURING OF PIMAVANSERIN". . . Retrieved 2020/05/28.