Pimavanserin

Base Information

• Chemical Name: Pimavanserin
• CAS No.: 706782-28-7
• Molecular Formula: 0C₄H₆O₆*C₂₅H₃₄FN₃O₂
• Molecular Weight: 502.606
• Hs Code.: 29299090
• 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: 706782-28-7.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:

• PSA: 204.68000
• LogP: 7.86800
• 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% ^*data from raw suppliers

PimavanserinTartrate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

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
• Description: Pimavanserin, developed by San Diego-based Acadia Pharmaceuticals, is a selective and potent serotonin 2A (5-HT2A) receptor inverse agonist. The USFDA approved this once-daily drug to treat the delusions and hallucinations associated with psychosis as a function of Parkinson’s disease. Pimavanserin has a unique mechanism of action relative to other antipsychotics, behaving as a selective inverse agonist of the serotonin 5-HT2A receptor while exhibiting 40-fold selectivity over the 5-HT2C receptor and having no significant affinity or activity with the 5-HT2B or dopamine receptors.
• Uses: Pimavanserin tartrate is a 5-HT2A inverse agonist that reverses psychosis-like behaviours and has the potential to treat various other neuropsychiatric disorders such as schizophrenia and Parkinson’s disease.

Technology Process of Pimavanserin

There total 57 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: 100.0%

1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene (639863-75-5) + N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine (359878-47-0) + L-Tartaric acid (87-69-4,138508-61-9) → Pimavanserin tartrate (706782-28-7)

Guidance literature:

1-(isocyanatomethyl)-4-(2-methylpropoxy)benzene; N- [(4-fluorophenyl)methyl]-1-methylpiperidin-4-amine; In tetrahydrofuran; at 40 ℃; for 3h;

L-Tartaric acid; In ethanol; at 20 - 50 ℃; for 1h;

Reference yield: 99.0%

N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1) + L-Tartaric acid (87-69-4,138508-61-9) → 1-(4-fluorobenzyl)-3-(4-isobutoxybenzyl)-1-(1-methylpiperidin-4-yl)urea L-hemitartrate (706782-28-7)

Guidance literature:

In n-heptane; acetone; at 20 - 50 ℃; for 10h; Solvent;

Reference yield: 95.0%

N-(1-methylpiperidin-4-yl)-N-(4-fluorophenylmethyl)-N′-(4-(2-methylpropyloxyl)phenylmethyl)carbamide (706779-91-1) + L-Tartaric acid (87-69-4,138508-61-9) → Pimavanserin tartrate (706782-28-7)

Guidance literature:

In tert-butyl methyl ether; acetone; at 50 - 55 ℃; for 1h;

upstream raw materials:

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

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

L-Tartaric acid

N-hydroxy-2-(4-isobutoxyphenyl)acetamide

Refernces

• 1、 -. "Novel pimavanserin preparation method". Paragraph 0012; 0013. . Retrieved 2020/07/13.
• 2、 -. "PROCESS FOR THE PREPARATION OF A PHARMACEUTICAL AGENT". Page/Page column 17; 16. . Retrieved 2020/10/28.