156-08-1 Usage
Originator
Didrex,Upjohn,US,1960
Uses
Benzphetamine is an appetite suppressant; used to assay certain isozymes of cytochrome P-450.
Definition
ChEBI: Dextroamphetamine in which the the hydrogens attached to the amino group are substituted by a methyl and a benzyl group. A sympathomimetic agent with properties similar to dextroamphetamine, it is used as its hydrochloride salt in the treatment of obesity.
Manufacturing Process
Fifty grams of d-desoxyephedrine hydrochloride was dissolved in a small
amount of water and a molar excess of sodium hydroxide was .added thereto.
The resulting forty grams of precipitated oily d-desoxyephedrine was collected
in ether and the whole was thereafter dried with anhydrous potassium
carbonate. The ether was then removed, the resulting oily residue having an
nD22 of 1.5045 was stirred in a flask with 40 grams of anhydrous sodium
carbonate at 120°C, and 34.6 grams of benzyl chloride was added dropwise
thereto over a period of thirty minutes. Stirring was continued for 2 hours,
whereafter the reaction mixture was extracted with benzene.
The benzene was distilled from the extract and the residue of d-N-methyl-Nbenzyl-β-phenylisopropylamine was distilled at reduced pressure. The thus
obtained free base, distilling at 127°C at a pressure of 0.2 mm of mercury
and having an nD19 of 1.5515, was dissolved in ethyl acetate and a molar
equivalent of ethanolic hydrogen chloride was added thereto. Anhydrous ether
was added to the mixture and d-N-methyl-N-benzyl-β-phenylisopropylamine
hydrochloride precipitated from the reaction mixture as an oil which was
crystallized from ethyl acetate to give crystals melting at 129° to 130°C.
Therapeutic Function
Antiobesity
Hazard
Elevate blood pressure, disturb heart
rhythm, cause restlessness, insomnia, hyperactivity,
headache, euphoria, depression, psychosis, tremor,
dryness of mouth, unpleasant tastes, diarrhea, stom-
ach upset, altered sex drive, impotence, aggressive-
ness, hallucinations, panic.
Check Digit Verification of cas no
The CAS Registry Mumber 156-08-1 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 1,5 and 6 respectively; the second part has 2 digits, 0 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 156-08:
(5*1)+(4*5)+(3*6)+(2*0)+(1*8)=51
51 % 10 = 1
So 156-08-1 is a valid CAS Registry Number.
InChI:InChI=1/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
156-08-1Relevant articles and documents
Preparation method of benzphetamine hydrochloride
-
, (2020/01/25)
The invention relates to the field of chemical pharmacy, and in particular relates to a preparation method of benzphetamine hydrochloride. According to the method, the use of controlled products suchas ephedrine, pseudoephedrine, deoxyephedrine and the like is avoided; the raw materials are cheap and easy to obtain, so that the synthesis cost is reduced; by using the preparation method disclosedby the invention, the high-purity target compound can be obtained at high yield, and industrial large-scale production is easy.
A concise enantioselective synthesis of (R)-selegiline, (S)-benzphetamine and formal synthesis of (R)-sitagliptin via electrophilic azidation of chiral imide enolates
Dey, Soumen,Sudalai, Arumugam
, p. 67 - 72 (2015/02/02)
A concise and high yielding enantioselective synthesis of (R)-selegiline, an anti-Parkinson's drug, (S)-benzphetamine, an anti-obesity agent, and (S)-sitagliptin, an anti-diabetic drug has been described starting from commercially available starting materials employing Evans' electrophilic azidation of chiral imide enolates as a key chiral inducing step, which proceeds in a highly diastereoselective manner (>99%).
An efficient, scalable process for benzphetamine hydrochloride
Pramanik, Chinmoy,Bapat, Kiran,Chaudhari, Ashok,Kulkarni, Mukund G.,Kolla, Rangarao,Sompalli, Srinivasarao,Tripathy, Narendra K.,Gurjar, Mukund K.
, p. 495 - 500 (2014/05/06)
Commercial manufacturing of benzphetamine hydrochloride along with its impurity profiling is disclosed. Deoxygenation of pseudoephedrine is reported with ～100% retention by shielding the amine group as its tert-butyl carbamate, which is very straightforward to eliminate at the end. Four unknown process-related impurities are isolated from the samples of final API and characterized on the basis of their NMR and mass spectral analysis. Structures of the isolated impurities are confirmed by independent syntheses and coinjecting with the isolated one.
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