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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride

Product Name
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
CAS No.
903576-44-3
Chemical Name
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
Synonyms
Pitolisant HCl;BF 2649;CS-2751;CS-1548;Ciproxidine;Ciproxidine BF2649;Pitolisant HCI salt;BF 2649 hydrochloride;Pitolisant Hcl(BF2.649;Pitolisant (Ciproxidine
CBNumber
CB62518970
Molecular Formula
C17H26ClNO.HCl
Formula Weight
332
MOL File
903576-44-3.mol
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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Property

storage temp. 
Desiccate at RT
solubility 
≥16.6 mg/mL in DMSO; ≥57.4 mg/mL in H2O; ≥94.2 mg/mL in EtOH
form 
solid
color 
White to off-white
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Precautionary statements

P201Obtain special instructions before use.

P308+P313IF exposed or concerned: Get medical advice/attention.

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N-Bromosuccinimide Price

Sigma-Aldrich
Product number
SML2716
Product name
Pitolisant hydrochloride
Purity
≥98% (HPLC)
Packaging
10MG
Price
$97.4
Updated
2024/03/01
Sigma-Aldrich
Product number
SML2716
Product name
Pitolisant hydrochloride
Purity
≥98% (HPLC)
Packaging
50MG
Price
$395
Updated
2024/03/01
Cayman Chemical
Product number
19307
Product name
Ciproxidine
Purity
≥98%
Packaging
1mg
Price
$37
Updated
2024/03/01
Cayman Chemical
Product number
19307
Product name
Ciproxidine
Purity
≥98%
Packaging
5mg
Price
$161
Updated
2024/03/01
Cayman Chemical
Product number
19307
Product name
Ciproxidine
Purity
≥98%
Packaging
10mg
Price
$283
Updated
2024/03/01
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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Chemical Properties,Usage,Production

Description

Pitolisant hydrochloride, a first-in-class inverse agonist of the histamine H3 receptor, was approved in the EU for the treatment of excessive daytime sleepiness (EDS) in adults with narcolepsy with or without cataplexy. The drug, which was developed by Bioprojet and has orphan drug designation in the EU and US, enhances wakefulness by increasing histaminergic neuron activity. With once daily oral administration in the morning, patients taking pitolisant exhibited significantly reduced EDS versus placebo but not versus modafinil. Plasma levels of the drug are reduced at the end of the day such that its waking effect is minimized at night (plasma t1/2 10-12 h). Several articles have been published detailing the discovery of pitolisant.

Uses

BF 2649 Hydrochloride, is a novel histamine H3 receptor antagonist and inverse agonist.

Synthesis

The most likely scale preparation of pitolisant hydrochloride consists of only four synthetic steps starting with the mesylation of commercial 3-(4-chlorophenyl)propan-1-ol (132). Displacement of the mesylate with the sodium salt of commercial 3-(piperidin-1-yl)propan-1-ol (133) in warm DMA assembled the parent drug in 97% yield over two steps. Salt formation was affected by pH adjustment to 3-4 using HCl gas in EtOAc. Recrystallization from ethyl acetate and isopropanol provided pitolisant hydrochloride (XII) on kilogram scale in 78% overall yield across the short four-step protocol.

in vitro

bf2.649 behaved as a competitive antagonist with a ki value of 0.16 nm. bf2.649 functioned as an inverse agonist with an ec50 value of 1.5 nm and an intrinsic activity about 50% higher than that of ciproxifan. pitolisant in vitro potency was approximately 6 times lower at the rodent receptor [1].

in vivo

pitolisant hcl was an oral bioavailable agonist. in mice, after oral and i.v. administrations of pitolisant hcl, the ratio of plasma areas under the curve was 84%. bf2.649 enhanced tele-methylhistamine levels in mouse brain, an index of histaminergic neuron activity in a dose dependent manner with an ed50 value of 1.6 mg/kg p.o. the response persisted after repeated administrations for 17 days [1]. treatment with 20-, 40-, or 60-mg doses of pitolisant showed a statistically significant suppressive effect (standardized photosensitive response [spr] reduction as measured with paired t-tests) in 9/14 (64%) patients of whom 6/14 (43%) showed abolition of the response to intermittent photic stimulation (ips) [3]. bf2.649 showed significant inhibitory activity in several mouse models of schizophrenia [4].

storage

Desiccate at RT

References

[1] ligneau x, perrin d, landais l, camelin jc, calmels tp, et al, bf2. 649 [1-{3-[3-(4-chlorophenyl)propoxy]propyl}piperidine, hydrochloride], a nonimidazole inverse agonist/antagonist at the human histamine h3 receptor: preclinical pharmacology. j pharmacol exp ther.2007 jan;320(1):365-75.
[2] t a esbenshade, k e browman, r s bitner, m strakhova, m d cowart, j d brioni the histamine h3 receptor: an attractive target for the treatment of cognitive disorders. br j pharmacol. 2008 jul; 154(6): 1166–1181.
[3] kasteleijn-nolst trenité d, parain d, genton p, masnou p, schwartz jc, hirsch e. efficacy of the histamine 3 receptor (h3r) antagonist pitolisant (formerly known as tiprolisant; bf2.649) in epilepsy: dose-dependent effects in the human photosensitivity model. epilepsy behav.2013 jul;28(1):66-70.
[4] ligneau x, landais l, perrin d, piriou j, uguen m, denis e, robert p, parmentier r, anaclet c, lin js, burban a, arrang jm,schwartz jc. brain histamine and schizophrenia: potential therapeutic applications of h3-receptor inverse agonists studied with bf2.649. biochem pharmacol. 2007 apr 15;73(8):1215-24. a

1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Preparation Products And Raw materials

Raw materials

Preparation Products

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1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride Suppliers

3B Pharmachem (Wuhan) International Co.,Ltd.
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821-50328103-801 18930552037
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86-21-50328109
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3bsc@sina.com
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China
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WUHAN SUN-SHINE BIO-TECHNOLOGY Co., Ltd.
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17702719238 17702719238
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sales@sun-shinechem.com
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China
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Haoyuan Chemexpress Co., Ltd.
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021-58950125
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(86) 21-58955996
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China
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Deyang Yuehe Bio-Pharmaceutical Co.,Ltd
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028-82729560 18030702676
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sales@yuehepharm.com
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China
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Suzhou yacoo science co.,Ltd
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0512-87182056 18013166090
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lingling.qi@yacoo.com.cn
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AdooQ Bioscience CHINA
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Shanghai Lollane Biological Technology Co.,Ltd.
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021-52996696,15000506266 15000506266
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+86-21-52996696
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China
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Shanghai eliv pharmaceutical Co.,Ltd.
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021-50158063
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021-6153 1846
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sales@elivpharma.com
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China
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SPIRO PHARMA
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Fax
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eric_feng1954@126.com
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China
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EMMX Biotechnology LLC
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888-539-0666
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888-539-0666
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United States
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View Lastest Price from 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride manufacturers

Henan Fengda Chemical Co., Ltd
Product
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride 903576-44-3
Price
US $10.00-3.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
g-kg-tons, free sample is available
Release date
2024-04-26
Wuhan Topule Biopharmaceutical Co., Ltd
Product
Pitolisant hydrochloride 903576-44-3
Price
US $10.00/g
Min. Order
1g
Purity
98%+HPLC
Supply Ability
5KG
Release date
2023-06-13
Career Henan Chemical Co
Product
1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride 903576-44-3
Price
US $2.00/kg
Min. Order
1kg
Purity
99%
Supply Ability
100kg
Release date
2018-12-24

903576-44-3, 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochlorideRelated Search:


  • 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]-piperidinehydrochloride
  • BF 2649
  • Ciproxidine
  • Pitolisant (hydrochloride)
  • 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]piperidine monohydrochloride
  • Piperidine, 1-[3-[3-(4-chlorophenyl)propoxy]propyl]-, hydrochloride
  • Ciproxidine BF2649
  • PITOLISANT;CIPROXIDINE BF2649
  • Pitolisant hydrochloride (Ciproxidine
  • BF 2649 hydrochloride
  • Pitolisant HCl
  • CS-2751
  • CS-1548
  • Pitolisant Hcl(BF2.649
  • CIPROXIDINE;BF 2649;BF2649;BF-2649
  • Pitolisant HCI salt
  • 1-[3-[3-(4-Chlorophenyl)propoxy]propyl]piperidine HCl
  • PITOLISANT HYDROCHLORIDE;BF 2649;BF2649;BF-2649
  • Pitolisant (Ciproxidine
  • Pitolisant hydrochloride,BF-2649,inhibit,BF2649,Inhibitor,Histamine Receptor,Pitolisant
  • 903576-44-3
  • C17H26ClNOHCl
  • Inhibitor