ChemicalBook CAS DataBase List 3200-06-4

3200-06-4

Name	alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate
CAS	3200-06-4
EINECS(EC#)	221-703-0
Molecular Formula	C26H35NO7
MDL Number	MFCD00079473
Molecular Weight	473.56
MOL File	3200-06-4.mol

Synonyms

ls121 Iridus eu-1806 CLARANTIN Acid oxalate NAFRONYL OXALATE naftidrofuryloxalate hylester,oxalate(1:1) Nafronyl acid oxalate NAFRONYL OXALATE SALT Nafronyl oxalate salt ,96% Nafronyl oxalate salt ,99% Nafronyl oxalate salt ,98% Nafronyl oxalate salt USP/EP/BP 2-(diethylamino)ethyltetrahydro-alpha-(1-naphthylmethyl)-2-furanpropionateo α-(1-naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate α-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate 2-(Diethylamino)ethyl tetrahydro-.alpha.-(1-naphthylmethyl)-2-furanpropionate oxalate (1:1) 2-(DiethylaMino)ethyl 3-(naphthalen-1-yl)-2-((tetrahydrofuran-2-yl)Methyl)propanoate oxalate ALPHA-[1-NAPHTHYLMETHYL]-2-TETRAHYDROFURANPROPIONIC ACID DIETHYLAMINOETHYL ESTER OXALATE SALT diethyl[2-[2-(1-naphthylmethyl)-3-(tetrahydro-2-furyl)propionyloxy]ethyl]ammonium hydrogen oxalate alpha-(1-Naphthylmethyl)-2-tetrahydrofuranpropionic acid diethylaminoethyl ester oxalate USP/EP/BP 2-Furanpropionic acid, tetrahydro-.alpha.-(1-naphthylmethyl)-, 2-(diethylamino)ethyl esteroxalate (1:1) 2-Furanpropionic acid, tetrahydro-.alpha.-(1-naphthylmethyl)-, 2-(diethylamino)ethyl ester oxalate (1:1) 2-Furanpropanoic acid, tetrahydro-.alpha.-(1-naphthalenylmethyl)-, 2-(diethylamino)ethyl ester, ethanedioate (1:1)

Chemical Properties

Melting point	110-111°
Boiling point	574°C (rough estimate)
density	1.2205 (rough estimate)
refractive index	1.6000 (estimate)
storage temp.	Store at -20°C
solubility	Freely soluble in water, freely soluble or soluble in ethanol (96 per cent), slightly or sparingly soluble in acetone.
form	Solid
color	White to off-white
Major Application	forensics and toxicology pharmaceutical (small molecule)
InChIKey	SSAJNPNVUYMUCI-UHFFFAOYSA-N
SMILES	OC(=O)C(O)=O.CCN(CC)CCOC(=O)C(CC1CCCO1)Cc2cccc3ccccc23

Safety Data

Hazard Codes	Xn,Xi
Risk Statements	22 less more
Safety Statements	36 less more
WGK Germany	3
RTECS	LU5805000
HS Code	29321900
Storage Class	11 - Combustible Solids
Hazard Classifications	Acute Tox. 4 Dermal Acute Tox. 4 Oral
Toxicity	LD50 oral in rat: 711mg/kg less more

Raw materials And Preparation Products

Hazard Information

Chemical Properties

White solid

Originator

Dusodril,Roland,W. Germany,1968

Uses

antineoplastic

Manufacturing Process

30 grams (0.106 mol) of β-(1-naphthyl)-β'-tetrahydrofuryl isobutyric acid are heated under reflux for 8 1/2 hours in 230 cc of isopropanol with 14 grams (0.103 mol) of β-chloroethyl-N-diethylamine. After evaporation of the isopropanol in vacuo, the syrupy residue is treated with a solution of K2CO3. Extraction with ether is carried out after drying over Na2SO4.
Distillation of the extract yields 28.5 grams of a very viscous yellow liquid with a BP0.95-1.09millibar = 198° to 202°C. The yield is 70.5% (theoretical quantity = 40.5 grams).1.3 grams (0.0103 mol) of dihydrated oxalic acid are dissolved while being made tepid in 8 cc of acetone. The cooled solution has added thereto 4 grams (0.0104 mol) of N-diethylaminoethyl-β-(1-naphthyl)-β'- tetrahydrofuryl isobutyrate, obtained according to the process described above and dissolved in 10 cc of acetone. The solution is brought to boiling point for 15 minutes. After cooling to ambient temperature, it is placed in a refrigerator. Crystallization occurs after 2 hours, the crystals which have formed are separated by centrifuging, and after washing in hexane and drying in vacuo 3.5 grams of white crystals are obtained. After being recrystallized three times, in alcohol and then in a mixture of alcohol and ethyl acetate, the product is analytically pure and has a MP = 110° to 111°C (heating stage).

Brand name

Praxilene (Lipha, S.A., France).

Therapeutic Function

Vasodilator

Biological Activity

Vasodilator

Clinical Use

Vasodilator:
Peripheral and cerebral vascular disease

Drug interactions

Potentially hazardous interactions with other drugs
None known

Metabolism

Metabolised by plasma pseudo-cholinesterases to 3 active metabolites.

Spectrum Detail

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J & K SCIENTIFIC LTD.

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