1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride

Iupac Name：4-pyrrolidin-1-yl-1-(2,4,6-trimethoxyphenyl)butan-1-one;hydrochloride

Molecular Weight：307.3847

Modify Date.: 2022-10-31 22:37

Introduction: 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride is used as an vasodilator (peripheral). View more+

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1. Names and Identifiers

1.1 Name: 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride
1.2 Synonyms: (2,4,6-Trimethoxyphenyl) (3-Pyrrolidinopropyl) Ketone Hydrochloride 1-[4-Oxo-4-(2,4,6-trimethoxyphenyl)butyl]pyrrolidinium chloride 1-Butanone, 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-, hydrochloride (1:1) 2',4',6'-Trimethoxy-4-(1-pyrrolidinyl)butyrophenone Hydrochloride 2',4',6-Trimethoxy-4-[1-pyrrolidinyl] butyrophenone hydrochloride 4-(1-Pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone 4-(1-Pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone hydrochloride 4-(1-Pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone,Buflomedil hydrochloride 4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one hydrochloride 4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-one hydrochloride (1:1) 4-(Pyrrolidin-1-yl)-1-(2,4,6-trimethoxyphenyl)butan-1-onhydrochlorid bufedil Buflan Buflocit Buflomedil (hydrochloride) BUFLOMEDIL HCL BUFLOMEDIL HCL EP BUFLOMEDIL HYDROCHLORIDE BuflomedilHclC17H25No4.Hcl Buflomedilhydrochlorid Buflonat Durabuflo EINECS 252-611-9 fenoterol-Cl Irrodan ll1656 Lofton Loftyl MFCD00078965 Provas

1.3 CAS No.: 35543-24-9

1.4 CID: 6420013

1.5 EINECS(EC#): 252-611-9

1.6 Molecular Formula: C17H26ClNO4 (isomer)

1.7 Inchi: InChI=1S/C17H25NO4.ClH/c1-20-13-11-15(21-2)17(16(12-13)22-3)14(19)7-6-10-18-8-4-5-9-18;/h11-12H,4-10H2,1-3H3;1H

1.8 InChkey: ZDPACSAHMZADFZ-UHFFFAOYSA-N

1.9 Canonical Smiles: COC1=CC(=C(C(=C1)OC)C(=O)CCCN2CCCC2)OC.Cl

1.10 Isomers Smiles: COC1=CC(=C(C(=C1)OC)C(=O)CCCN2CCCC2)OC.Cl

2. Properties

2.1 Melting point: 193°C(dec.)(lit.)

2.1 Boiling point: 454.5 °C at 760 mmHg

2.1 Flash Point: 228.7 °C

2.1 Precise Quality: 343.15500

2.1 PSA: 48.00000

2.1 logP: 3.51100

2.1 Appearance: White or off-white crystalline powder

2.2 Chemical Properties: White Solid

2.3 Water Solubility: Freely soluble in water, soluble in ethanol (96 per cent), very slightly soluble in acetone.

2.4 StorageTemp: Inert atmosphere,Room Temperature

3. Use and Manufacturing

3.1 Usage: 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride is used as an vasodilator (peripheral).

4. Safety and Handling

4.1 RIDADR: NONH for all modes of transport

4.1 WGK Germany: 3

4.1 RTECS: EL9885000

4.1 Safety: Safety Information of Buflomedil hydrochloride (CAS NO.35543-24-9):
K Germany: 3
RTECS: EL9885000

4.2 Specification: ?Buflomedil hydrochloride , its CAS NO. is 35543-24-9, the synonyms are 4-(1-Pyrrolidyl)-1-(2,4,6-trimethoxyphenyl)-1-butanone hydrochloride ; Bufedil ; Buflan ; Buflomedil HCl ; Chlorhydrate de (trimethoxy-2-4-6) phenyl-(pyrrolidine-3)
propylacetone ; 1-(3-(2,4,6-Trimethoxybenzoyl)propyl)pyrrolidinium chloride ; 1-Butanone, 4-(1-pyrrolidinyl)-1-(2,4,6-trimethoxyphenyl)-, hydrochloride .

4.3 Toxicity

1.	???	orl-wmn TDLo:50?mg/kg:BAH,SYS	???	JTCTDW ?? Journal of Toxicology, Clinical Toxicology. 30 (1992),305.
2.	???	orl-rat LD50:410?mg/kg:BAH,PUL	???	KSRNAM ?? Kiso to Rinsho. Clinical Report. 22 (1988),401.
3.	???	scu-rat LD50:796?mg/kg	???	KSRNAM ?? Kiso to Rinsho. Clinical Report. 22 (1988),401.
4.	???	ivn-rat LD50:58,500?μg/kg	???	KSRNAM ?? Kiso to Rinsho. Clinical Report. 22 (1988),401.
5.	???	orl-mus LD50:275?mg/kg	???	THERAP ?? Therapie. 30 (1975),207.
6.	???	ivn-mus LD50:55?mg/kg	???	THERAP ?? Therapie. 30 (1975),207.
7.	???	ims-mus LD50:250?mg/kg	???	THERAP ?? Therapie. 30 (1975),207.
8.	???	orl-dog LDLo:500?mg/kg	???	THERAP ?? Therapie. 30 (1975),207.
9.	???	ivn-dog LDLo:50?mg/kg	???	THERAP ?? Therapie. 30 (1975),207.

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5. MSDS

2.Hazard identification

2.1 Classification of the substance or mixture

Acute toxicity - Oral, Category 4

2.2 GHS label elements, including precautionary statements

Pictogram(s)
Signal word	Warning
Hazard statement(s)	H302 Harmful if swallowed
Precautionary statement(s)
Prevention	P264 Wash ... thoroughly after handling. P270 Do not eat, drink or smoke when using this product.
Response	P301+P312 IF SWALLOWED: Call a POISON CENTER/doctor/\u2026if you feel unwell. P330 Rinse mouth.
Storage	none
Disposal	P501 Dispose of contents/container to ...

2.3 Other hazards which do not result in classification

none

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6. NMR Spectrum

13C NMR : Predict

1H NMR : Predict

Predict 1H proton NMR

7. Other Information

7.0 Description: Buflomedil hydrochloride is a vasoactive drug with a variety of actions. It is an alpha-adrenoceptor antagonist and a weak calcium channel blocker. It inhibits platelet aggregation and improves erythrocyte deformability. However, its mechanism of action in peripheral vascular disease is not known.
Buflomedil has generally been well tolerated by most patients in clinical trials. The most frequently reported adverse effects include flushing, headache, vertigo, gas-trointestinal discomfort, and dizziness. These rarely require drug withdrawal. In controlled trials, adverse effects have occurred in 20% of patients assigned to buflomedil and 18% of those assigned to placebo; only gastrointestinal discomfort occurred more frequently in buflomedil-treated patients (3.4 versus 2%)

7.1 Uses: Buflomedil hydrochloride is a vasoactive agent. Its mode of action involves increasing the peripheral and cerebral blood flow in ischaemic tissues of patients, who are mostly affected with vascular diseases.
Buflomedil. A review of its pharmacodynamic and pharmacokinetic properties, and therapeutic efficacy in peripheral and cerebral vascular diseases

7.2 Biological Activity: Buflomedil is a non-selective antagonist of α-adrenergic receptors (α-ARs) and vasoactive compound.It binds to rat α1A- and α1B-ARs (Kis = 4.06 and 6.84 μM, respectively) and human platelet α2-ARs (IC50 = 1 μM) in radioligand binding assays.Buflomedil (0.06-60 μM) inhibits contraction of isolated canine saphenous veins induced by phenylephrine, clonidine, sympathetic nerve stimulation, or norepinephrine.It inhibits ADP-, collagen-, or epinephrine-induced aggregation of isolated human platelets when used at a concentration of 100 μM.Buflomedil (10 mg/kg) reduces hippocampal neuronal cell death in a rat model of carotid clamping-induced ischemia-reperfusion injury.
https://www.caymanchem.com

7.3 Synthesis: The target compound of buflomedil hydrochloride was synthesized from methyl 4-chlorobutyrate by condensation with pyrrolidine,then by hydrolysis,acylation,Fridel-crafts alkylation and salt formation.The structure of the target compound was confirmed by IR,1H-NMR and MS.The synthetic procedure is suitable for industrial production for the advantage of avaible materials,shorter routes,convenient operation and lower cost,the overall yield is improved from the reported 70% to 75.7%.
https://www.semanticscholar.org

7.4 Overdosage: Buflomedil is generally considered to be innocuous at therapeutic dosages. Acute toxicity is due to accidental or intentional overdosage. Overdosage causes generalized seizures and cardiac conduction abnormalities, eventually leading to cardiac arrest (SEDA-21, 215).
Meyler's Side Effects of Cardiovascular Drugs

7.5 Chemical Properties: White Solid

7.6 Originator: Fonzylane,Lafon,France,1976

7.7 Uses: 1-[3-(2,4,6-Trimethoxybenzoyl)propyl]pyrrolidinium chloride is used as an vasodilator (peripheral).

7.8 Manufacturing Process: Introduce 33.6 g (0.2 mol) of 1,3,5-trimethoxybenzene and 100 ml of chlorobenzene into a 500 ml three-neck flask with stirrer, hydrochloric acid bubbler and condenser. Stir to dissolve and add 27.7 g of 4- pyrrolidinobutyronitrile (from 4-chlorobutyronitrile and pyrrolidine). Cool to about 15°-20°C and bubble hydrochloric acid gas in for 4 hours. Cool to about 5°C and add 200 cm3 of water. Stir. Decant the aqueous layer, wash again with 150 cm3 of water. Combine the aqueous layers, drive off the traces of chlorobenzene by distilling 150 cm3 of water, and heat under reflux for one hour. Cool and render alkaline by means of 60 ml of sodium hydroxide solution of 36° Baume. Extract twice with 100 ml of ether. Wash the ether with 100 ml of water. Dry the ether over sodium sulfate and slowly run in 50 ml of 5N hydrogen chloride solution in ether, at the boil. Cool in ice. Filter, wash with ether and dry in a vacuum oven. 33.6 g of crude product are obtained. Recrystallize from 200 ml of isopropanol in the presence of 3 SA carbon black. Filter. Wash and dry in a vacuum oven.
26.9 g of a white, crystalline water-soluble powder are obtained. Yield: 39.2%. Instantaneous melting point: 192°-193°C.

7.9 Therapeutic Function: Vasodilator

8. Computational chemical data

Molecular Weight: 307.3847g/mol
Molecular Formula: C₁₇H₂₆ClNO₄
Compound Is Canonicalized: True
XLogP3-AA: null
Exact Mass: 343.1550360
Monoisotopic Mass: 343.1550360
Complexity: 330
Rotatable Bond Count: 8
Hydrogen Bond Donor Count: 1
Hydrogen Bond Acceptor Count: 5
Topological Polar Surface Area: 48
Heavy Atom Count: 23
Defined Atom Stereocenter Count: 0
Undefined Atom Stereocenter Count: 0
Defined Bond Stereocenter Count: 0
Undefined Bond Stereocenter Count: 0
Isotope Atom Count: 0
Covalently-Bonded Unit Count: 2
CACTVS Substructure Key Fingerprint: AAADceB6OAAEAAAAAAAAAAAAAAAAAWAAAAAwAAAAAAAAAAABAAAAHgAAAAAADATBmAYyBoMABACIAqBSAAACCAAkIAAAiAEOCMgMJzaEtRqEMWAl4BWIqQec7KzOIAAACAAIAABAAAAQABAAAAAAAAAAAA==