458-24-2 Usage
Originator
Obenon,Neofarma
Uses
Anorexic.
Definition
ChEBI: A secondary amino compound that is 1-phenyl-propan-2-amine in which one of the meta-hydrogens is substituted by trifluoromethyl, and one of the hydrogens attached to the nitrogen is substituted by an ethyl group. It binds to the serotonin reu
take pump, causing inhbition of serotonin uptake and release of serotonin. The resulting increased levels of serotonin lead to greater serotonin receptor activation which in turn lead to enhancement of serotoninergic transmission in the centres of feeding
ehavior located in the hypothalamus. This suppresses the appetite for carbohydrates. Fenfluramine was used as the hydrochloride for treatment of diabetes and obesity. It was withdrawn worldwide after reports of heart valve disease and pulmonary hypertensio
.
Manufacturing Process
38.5 parts of (trifluoromethyl-3'-phenyl)-1-oximino-2-propane in 550 parts of
ethanol (with ammonia) was hydrogenated under pressure of hydrogen 90 kg
with a catalyst nickel Reney (20 parts). After a completion of reaction to the
reaction mixture was added 1000 parts of water and 300 parts of hydrochloric
acid. The mixture was concentrated in vacuo and extracted with 450 parts of
ether. To an aqueous phase was added the sodium carbonate and the mixture
was extracted with 500 parts of ether. Organic phase was concentrated in
vacuo to obtain 29 g of 1-(meta-trifluoromethyl-phenyl)-2-ethylaminopropane.
B.P. 96°C at 17 mm.
Therapeutic Function
Anorexic
World Health Organization (WHO)
Fenfluramine, dexfenfluramine and phentermine were approved
individually more than 20 years ago in the USA for single-drug, short-term
treatment of obesity. The manufacturers of fenfluramine and dexfenfluramine have
since voluntarily withdrawn both products from the market worldwide.
Phentermine remains available.
Check Digit Verification of cas no
The CAS Registry Mumber 458-24-2 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 4,5 and 8 respectively; the second part has 2 digits, 2 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 458-24:
(5*4)+(4*5)+(3*8)+(2*2)+(1*4)=72
72 % 10 = 2
So 458-24-2 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
458-24-2Relevant 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.
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
Method of treating nausea and vomiting with certain substituted-phenylalkylamino (and aminoacid) derivatives and other serotonin depleting agents
-
, (2008/06/13)
A method for the treatment of emesis in a mammal, which method comprises administering to said mammal an emesis inhibiting amount of a compound which depletes serotonin in the brain of mammals; among which are compounds having the formula: STR1 wherein, R is selected from hydrogen, loweralkyl, trifluoromethyl, carboxyl, or loweralkoxycarbonyl; R1 and R2 are hydrogen or loweralkyl; Z is trifluoromethyl or halogen; the optical isomers and pharmaceutically acceptable salts thereof; two of the preferred compounds of the invention are fenfluramine and norfenfluramine.
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