110429-35-1

Basic information

• Product Name: PAROXETINE-D4 HCL
• Synonyms: Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, hydrochloride, hydrate (2:1), (3S,4R)- (9CI);Piperidine, 3-[(1,3-benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)-, hydrochloride, hydrate (2:1), (3S-trans)-;Paroxetine Hydrochloride (350 mg);Paroxetine Hydrochloride (350 mg)G0D0030.972mg/mg(ai);Paroxetine-D4 hydrochloride;(3S,4R)-(-)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine Hydrochloride;Piperidine,3-[(1,3-benzodioxol-5-yloxy)Methyl]-4-(4-fluorophenyl)-, hydrochloride, hydrate(2:2:1), (3S,4R)-;Paroxetine hydrochloride (3S-trans)-3-[(1,3-Benzodioxol-5-yloxy)methyl]-4-(4-fluorophenyl)piperidine hydrochloride
• CAS NO: 110429-35-1
• Molecular Formula: C₁₉H₂₀FNO₃*ClH
• Molecular Weight: 369.85
• Product Categories: Active Pharmaceutical Ingredients;Cnbio;Serotonin
• Mol File: 110429-35-1.mol

Chemical Properties

• Melting Point: 121-131 C
• Boiling Point: 451.7oC at 760mmHg
• Flash Point: 227oC
• Appearance: white/
• Density: 1.213g/cm3
• Storage Temp.: under inert gas (nitrogen or Argon) at 2-8°C
• Solubility: Slightly soluble in water, freely soluble in methanol, sparingly soluble in ethanol (96 per cent) and in methylene chloride.
• Merck: 14,7043
• CAS DataBase Reference: PAROXETINE-D4 HCL(CAS DataBase Reference)
• NIST Chemistry Reference: PAROXETINE-D4 HCL(110429-35-1)
• EPA Substance Registry System: PAROXETINE-D4 HCL(110429-35-1)

Safety Data

• Hazard Codes: F,C,Xn
• Statements: 11-34-36/37/38-22
• Safety Statements: 16-26-36/37/39-45-36
• RIDADR: UN 3077 9 / PGIII
• WGK Germany: 3
• RTECS: TM4569320
• HazardClass: IRRITANT
• Hazardous Substances Data: 110429-35-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Paroxetine-D4 HCl is used as an antidepressant for treating depression, panic attacks, obsessive-compulsive disorder (OCD), anxiety disorders, post-traumatic stress disorder, and a severe form of premenstrual syndrome (premenstrual dysphoric disorder).
Used in Research:
Paroxetine-D4 HCl is used as a research compound to study its effects on neural stem cells (NSCs) from embryonic rat hippocampus in vitro, as a CYP 2D6 inhibitor to study its effects on the in vitro production of phenolic metabolites by human recombinant CYP 2D6, and as an antidepressant to study its effects on the expression of pituitary adenylate cyclase activating polypeptide (PACAP), its receptors, and brain-derived neurotrophic factor (BDNF) in rat primary hippocampal neurons.
Used in Quality Control:
Paroxetine-D4 HCl serves as a pharmaceutical secondary standard, providing a convenient and cost-effective alternative to the preparation of in-house working standards for quality control in pharmaceutical laboratories and manufacturers.

Biochem/physiol Actions

Paroxetine hydrochloride hemihydrate is one of the most potent and selective of the selective serotonin reuptake inhibitors (SSRI); antidepressant

InChI:InChI=1/C19H20FNO3.ClH/c20-15-3-1-13(2-4-15)17-7-8-21-10-14(17)11-22-16-5-6-18-19(9-16)24-12-23-18;/h1-6,9,14,17,21H,7-8,10-12H2;1H/t14?,17-;/m0./s1

Upstream product

• 200572-35-6 (3S,4R)-1-(tert-butoxycarbonyl)-4-(p-fluorophenyl)-3-[3,4-(methylenedioxy)phenoxymethyl]piperidine 
• 94923-25-8 1-benzyl-1,2,3,6-tetrahydropyridin-4-en-3-one 
• 754206-43-4 (3R,4R)-1-benzyl-4-(4-fluorophenyl)-3-{[(methylsulfonyl)oxy]methyl}piperidine 
• 459-57-4 4-fluorobenzaldehyde 
• 96426-60-7 methyl (2E)-3-(4-fluorophenyl)-2-propenoate 
• 105812-81-5 (3S,4R)-trans-4-(4-fluorophenyl)-3-hydroxymethyl-N-methylpiperidine 
• 61869-08-7 paroxetine 
• 246850-71-5 (3S,4R)-trans-1-benzyloxycarbonyl-4-(4-fluorophenyl)-3-[(3,4-methylenedioxyphenyl)oxymethyl]piperidine 
• 109887-52-7 C₁₅H₁₆FNO₄ 
• 110429-36-2 (3S,4R)-3-((benzo[d][1,3]dioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-1-methylpiperidine 
• 1561215-66-4 (2S,3R)-2-((1,3-dioxoisoindolin-2-yl)methyl)-3-(4-fluorophenyl)pent-4-enal 
• 1561215-68-6 2-((2S,3R)-3-(4-fluorophenyl)-2-(hydroxymethyl)pent-4-en-1-yl)isoindoline-1,3-dione 
• 1561215-69-7 2-((2S,3R)-2-((benzo[d][1,3]dioxol-5-yloxy)methyl)-3-(4-fluorophenyl)pent-4-en-1-yl)isoindoline-1,3-dione 
• 1561215-67-5 2-((2S,3R)-2-((benzo[d][1,3]dioxol-5-yloxy)methyl)-3-(4-fluorophenyl)-5-hydroxypentyl)isoindoline-1,3-dione 

Downstream Products

• 324024-00-2 desfluoro paroxetine 
• 159126-30-4 Desmethylene-Paroxetine 
• 960287-36-9 (3S-trans)-3-((6-bromo-1,3-benzodioxol-5-yloxy)methyl)-4-(4-fluorophenyl)-piperidine 
• 61869-08-7 paroxetine 
• 606968-05-2 C₃₉H₄₀F₂N₂O₆ 
• 64006-44-6 paroxetine maleate 

Relevant articles and documents

Diastereoconvergent Synthesis of (–)-Paroxetine

A diastereoconvergent approach to (–)-paroxetine from diastereomeric 3,4-epoxy-2-piperidones is reported. For this synthesis, a regioselective and stereodivergent CuI-catalyzed epoxide-ring-opening reaction of epoxyamide precursors to give the 4-(4-fluorophenyl)-2-piperidone skeleton with the correct absolute configuration is crucial. Using CuBr·SMe2 as a catalyst, the epoxide-ring-opening reaction takes place with inversion of configuration; the configuration is retained when CuI is used.

Stereodivergent α-allylation of linear aldehydes with dual iridium and amine catalysis

We describe the fully stereodivergent, dual catalytic α-allylation of linear aldehydes. The reaction proceeds via direct iridium-catalyzed substitution of racemic allylic alcohols with enamines generated in situ. The use of an Ir(P,olefin) complex and a diarylsilyl prolinol ether as catalysts in the presence of dimethylhydrogen phosphate as the promoter proved to be crucial for achieving high enantio- and diastereoselectivity (>99% ee, up to >20:1 dr). The utility of the method is demonstrated in a concise enantioselective synthesis of the antidepressant (-)-paroxetine.

Improved process for paroxetine hydrochloride substantially free from potential impurities

An efficient process for production of paroxetine hydrochloride hemihydrate 1, a selective 5-hydroxytryptamine (serotonin) reuptake inhibitor, is described. Identification and control of potential impurities and establishment of efficient downstream workup procedures enabled us to produce paroxetine hydrochloride hemihydrate 1 efficiently.

Controlled Release Compositions of an Antidepressant Agent

The present invention relates to controlled release compositions comprising an anti-depressant compound. More particularly, the present invention relates to controlled release compositions comprising paroxetine hydrochloride.

SULFATED GALACTANS WITH ANTITHROMBOTIC ACTIVITY, PHARMACEUTICAL COMPOSITION, METHOD FOR TREATING OR PROPHYLAXIS OF ARTERIAL OR VENOUS THROMBOSIS, METHOD OF EXTRACTION AND USE THEREOF

The present invention relates to low molecular weight sulfated galactans, obtained from algae, particularly genus Botryocladia, preferably species Botryocladia occidentallis, which have no effect on the factor XII activation of the clotting cascade, having antithrombotic heparinoid activity. The present invention also refers to a pharmaceutical composition comprising said sulfated galactans and the use thejreof, as heparin substitute, in the treatment or prophylaxis of arterial or venous thrombosis in humans and animals. Furthermore, the present invention provides a method of extraction of the said sulfated galactans.

A PROCESS FOR THE PREPARATION OF (-)-TRANS-4-(P-FLUOROPHENYL)-3-[[3,4-(METHYLENEDIOXY)PHENOXY]METHYL)]PIPERIDINE

A process for preparing (-)-trans-4-(4-fluorophenyl)-3-[[3,4-(methylenedioxy)phenoxy]methyl]-piperidine, a compound of formula (I) or pharmaceutically acceptable salts thereof, said process comprising hydrolyzing a compound of formula (II), wherein R may be selected from halo substituted or unsubstituted linear, branched or cyclic alkyl, alkylaryl, arylalkyl, by treatment with a base in a solvent system comprising a polar aprotic water miscible solvent and a hydrocarbon solvent wherein the polar aprotic water miscible solvent is selected from a sulfoxide solvent, an amide solvent or mixture thereof.

Enantioselective total and formal syntheses of paroxetine (PAXIL) via phosphine-catalyzed enone α-arylation using arylbismuth(V) reagents: a regiochemical complement to Heck arylation

Exposure of dihydropyridinone 1 to the arylbismuth(V) reagent (p-F-Ph)3BiCl2 in the presence of substoichiometric quantities of tributylphosphine (10 mol %) results in aryl transfer to the transiently generated (β-phosphonio)enolate to provide the α-arylated enone 2. This transformation, which represents a regiochemical complement to the Mizoroki-Heck arylation, is used strategically in concise formal and enantioselective total syntheses of the blockbuster antidepressant (-)-paroxetine (PAXIL).

PREPARATION OF PAROXETINE HYDROCHLORIDE HEMIHYDRATE

A process for preparing paroxetine hydrochloride hemihydrate.

METHODS OF CRYSTAL PRECIPITATION

Crystals of paroxetine hydrochloride 1/2-hydrate are allowed to separate out by adding water to a solution or suspension comprising paroxetine hydrochloride and a polar organic solvent which contains no water or at most 60% by weight of water to adjust the water content to at least 70% by weight when crystals of paroxetine hydrochloride 1/2-hydrate are allowed to separate out in a water-containing polar organic solvent. Crystals of paroxetine hydrochloride 1/2-hydrate being not colored in pink can be allowed to separate out in the presence of hydrogen chloride when crystals of paroxetine hydrochloride 1/2-hydrate are allowed to separate out in water or a water-containing polar organic solvent.

NOVEL FORM OF ANHYDROUS PAROXETINE HYDROCHLORIDE AND METHOD FOR PREPARATION THEREOF

A novel form of anhydrous Paroxetine hydrochloride is prepared by dissolving Paroxetine base in isopropanol, which is treated with a solution of hydrogen chloride in isopropanol. 50 to 60% of isopropanol used in the reaction is then distilled at atmospheric pressure. The product thus obtained after drying contains isopropanol not more than 3% and water content which is less than 2.0%. The product is found to be stable even after 3 days upon direct exposure to 75% RH at 40°C and the crystallinity of product is unchanged as confirmed by X-ray powder difractogram. The product is also found to be stable for three months as per ICH satiability conditions.