3239-44-9 Usage
Description
(+)-Fenfluramine hydrochloride, also known as the S-enantiomer of fenfluramine, is a pharmaceutical compound that was used to stimulate the release of serotonin and selectively inhibit its reuptake. Unlike fenfluramine, it does not possess catecholamine agonist activity. It was formerly administered orally as a treatment for obesity, but was withdrawn worldwide due to reports of valvular heart defects.
Brand names for (+)-Fenfluramine hydrochloride include Redux (Interneuron) and Diomeride.
Uses
Used in Pharmaceutical Industry:
(+)-Fenfluramine hydrochloride was used as an appetite suppressant for the treatment of obesity. It worked by stimulating the release of serotonin and inhibiting its reuptake, which helped to reduce appetite and promote weight loss.
However, it is important to note that (+)-Fenfluramine hydrochloride has been withdrawn from the market due to its association with valvular heart defects. As a result, it is no longer used for this application in the pharmaceutical industry.
Originator
Dexfenfluramine,Interneuron
Pharmaceuticals
(Lexington, Mass),
for Wyeth
Laboratories Inc
Manufacturing Process
To 10.65 parts acetic anhydride there were added, with cooling, 8 parts 1-(3-
trifluoromethylphenyl)-2-aminopropane and 100 parts water. The mixture was
neutralized with 30 parts sodium carbonate. The organic layer was extracted
twice with 50 parts ether. The ether solutions were washed with 25 parts
water and dried over potassium carbonate. On distillation there were obtained
9 parts 1-(3-trifluoromethylphenyl)-2-acetyl-aminopropane. 9 parts of it were
reduced in solution in 100 parts ether with 1.7 parts lithium and aluminium
hydride with 20 parts ether. The suspension was refluxed for 4 hours,
hydrolysed with 2 parts water, 2 parts 4 N sodium hydroxide and then 6 parts
water. The precipitate was drained washed with 50 parts ether, the filtrate was
extracted twice with 50 parts 0.5 N sulfuric acid. The acidic layers were
separated by sedimentation and neutralized with 100 parts 4 N sodium
hydroxide, the separated amine was extracted with 200 parts ether. There
were obtained 6 parts 1-(3-trifluoromethylphenyl)-2-ethylaminopropane
(boiling point 108°-112°C at 12 mm). The hydrochloride thereof was
recrystallized from mixture of ethyl alcohol and ether (melting point 166°C).S-Isomer was prepared the next way. To a solution of 160 parts of dibenzoyl
d-tartaric acid in 1600 parts of anhydrous ethanol were added for 15 minutes
80 parts of dl-1-(3-trifluoromethylphenyl)-2-ethylaminopropane. After 15
additional minutes, 90.5 parts of crystalline solid were isolated. When this
product was recrystallized from 1300 parts of anhydrous ethanol, there was
obtained 70 parts of dibenzoyl d-tartarate acid salt of L-1-(3-
trifluoromethylphenyl)-2-ethylaminopropane. This salt was treated with 500
parts of 4 N NaOH. The mixture was extracted with 2x200-part portions of
diethyl ether and the ether extract was re-extracted with 100 parts of 4 N
hydrodiboric acid. After treatment with 120 parts of 4 N NaOH, the free amine
amounting to 25 parts distills at 105°-107°C (17.5 mm.). [α]D25: - 9.6°
(c=8% in ethanol).
Therapeutic Function
Antiobesity
Check Digit Verification of cas no
The CAS Registry Mumber 3239-44-9 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 3,2,3 and 9 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 3239-44:
(6*3)+(5*2)+(4*3)+(3*9)+(2*4)+(1*4)=79
79 % 10 = 9
So 3239-44-9 is a valid CAS Registry Number.
InChI:InChI=1/C12H16F3N/c1-3-16-9(2)7-10-5-4-6-11(8-10)12(13,14)15/h4-6,8-9,16H,3,7H2,1-2H3/t9-/m0/s1
3239-44-9Relevant articles and documents
NEW METHOD FOR SYNTHESIS OF FENFLURAMINE, AND NEW COMPOSITIONS COMPRISING IT
-
Paragraph 0071; 0080; 0103, (2018/08/09)
A new process for preparing the fenfluramine molecule and new compositions containing fenfluramine obtainable with the claimed process.
Asymmetric syntheses of (S)-Fenfluramine using Sharpless Epoxidation Methods
Goument, Bertrand,Duhamel, Lucette,Mauge, Robert
, p. 171 - 188 (2007/10/02)
We describe one synthesis of (S)-fenfluramine and several syntheses of its precursors (R)- and (S)-1-(meta-trifluoromethylphenyl)propan-2-ols.They were obtained from the asymmetric epoxidation of the primary allylic alcohol 5 and from the kinetic resolution with asymmetric epoxidation of teh secondary allylic alcohol 6.
Epoxides, amino alcohols, and aziridines as key intermediates in the asymmetric synthesis of (S)-fenfluramine
Goument, B.,Duhamel, L.,Mauge, R.
, p. 459 - 466 (2007/10/02)
The epoxides 3E, 3Z and 8 were obtained from the isomeric alkenes 2E, 2Z and 7.The epoxides were ring-opened by ethylamine in ethanol yielding mixtures of the amino alcohols 4E and 11E, 4T and 11T, and 9, respectively, which were transformed into the aziridines 5trans, 5cis and 12.The regiospecific Pd/C-catalyzed reduction of these aziridines gave fenfluramine 1.The three epoxides 3trans, 3cis and 8 were reduced regiospecifically into 1-propan-2-ol 6, a potent precursor to fenfluramine 1.The validity of our method for asymmettric synthesis has been demonstrated by a synthesis of (S)-fenfluramine 1 starting from the amino alcohol (S)-9.Keyword - fenfluramine / asymmetric synthesis / epoxide / amino alcohol / aziridine / regiospecific catalytic hydrogenation / 1-propan-2-ols
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