156-08-1

Basic information

• Product Name: Benzphetamine
• Synonyms: Benzphetamine;N-benzyl-N-methyl-1-phenyl-propan-2-amine;Benzfetamine;(αS)-N,α-Dimethyl-N-(phenylmethyl)benzeneethaneamine;[αS,(+)]-N,α-Dimethyl-N-benzylbenzeneethanamine;C07538;N-Benzylmethamphetamine;YXKTVDFXDRQTKV-HNNXBMFYSA-N
• CAS NO: 156-08-1
• Molecular Formula: C₁₇H₂₁N
• Molecular Weight: 239.35534
• Mol File: 156-08-1.mol

Chemical Properties

• Boiling Point: bp0.02 127°
• Flash Point: 141.5°C
• Appearance: /
• Density: 1.0137 (rough estimate)
• Vapor Pressure: 0.000129mmHg at 25°C
• Refractive Index: nD19 1.5515
• PKA: pKa 6.55 (Uncertain)
• CAS DataBase Reference: Benzphetamine(CAS DataBase Reference)
• NIST Chemistry Reference: Benzphetamine(156-08-1)
• EPA Substance Registry System: Benzphetamine(156-08-1)

Safety Data

• RIDADR: 3249
• HazardClass: 6.1(b)
• PackingGroup: III
• Hazardous Substances Data: 156-08-1(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Benzphetamine is used as an appetite suppressant for the treatment of obesity. It helps in controlling the appetite and reducing the overall food intake, which aids in weight management.
Used in Research and Development:
Benzphetamine is also used to assay certain isozymes of cytochrome P-450. This application is crucial in understanding the metabolic pathways and enzyme interactions related to various drugs and substances, contributing to the advancement of medical research and drug development.

Originator

Didrex,Upjohn,US,1960

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.

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

Upstream product

• 5411-22-3 benzfetamine hydrochloride 
• 537-46-2 Methamphetamin 
• 100-44-7 benzyl chloride 
• 100-39-0 benzyl bromide 
• 51-57-0 S-methamphetamine hydrochloride 
• 345-78-8 Novafed 
• 152614-95-4 BOC-pseudoephedrine 
• 1334921-74-2 C₁₅H₂₃NO₂ 
• 100-52-7 benzaldehyde 
• 673-06-3 D-(R)-phenylalanine 
• 5267-64-1 (R)-2-amino-3-phenylpropanol 
• 13906-90-6 2-benzylaziridine 
• 77184-95-3 (R)-2-benzylaziridine 
• 501-52-0 3-Phenylpropionic acid 

Downstream Products

• 5411-22-3 benzfetamine hydrochloride 
• 15062-72-3 N-Demethylbenzphetamine 

Related news

Analysis of Benzphetamine (cas 156-08-1) and its metabolites in rat urine by liquid chromatography–electrospray ionization mass spectrometry09/30/2019

An analytical method to identify and determine benzphetamine (BMA) and its five metabolites in urine was developed by liquid chromatography–electrospray ionization mass spectrometry (LC–ESI–MS) using the solid-phase extraction column Bond Elut SCX. Deuterium-labeled compounds, used as interna...detailed

Relevant articles and documents

Preparation method of benzphetamine hydrochloride

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.

Benzphetamine hydrochloride preparation method

The invention relates to the field of chemical pharmacy, particularly to a benzphetamine hydrochloride preparation method. According to the invention, the method avoids the use of ephedrine, pseudoephedrine, deoxyephedrine and other management and control products, has characteristics of inexpensive and easily-available raw materials and synthesis cost reducing, can obtain the high-purity target compound at high yield, and is suitable for industrial large-scale production.

A concise enantioselective synthesis of (R)-selegiline, (S)-benzphetamine and formal synthesis of (R)-sitagliptin via electrophilic azidation of chiral imide enolates

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%).

A short enantioselective synthesis of ephedrine, amphetamine and their analogues via two stereocentered Co(III)-catalyzed hydrolytic kinetic resolution of racemic syn-benzyloxy epoxide

An efficient route for the synthesis of 6 drugs belonging to phenethylamine and amphetamine classes in excellent overall yields and high optical purity has been described. The strategy involves introduction of stereogenic centers by means of two-stereocentered Co(III)-catalyzed hydrolytic kinetic resolution (HKR) of racemic syn-benzyloxy epoxide followed by Pd-catalyzed regioselective cationic hydrogenation of amino alcohols as the key reactions.

An efficient, scalable process for benzphetamine hydrochloride

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.

PROCESS FOR PREPARATION OF BENZPHETAMINE AND ITS PHARMACEUTICALLY ACCEPTABLE SALTS

The present invention provides a simple method for preparation of benzphetamine and its acid addition salt comprising reaction of methamphetamine hydrochloride of formula (III) with benzyl chloride and treating the isolated benzphetamine of formula (II) with an acid dissolved in an organic solvent to provide benzphetamine acid addition salt, more specifically, benzphetamine hydrochloride of formula (I).

Enantiospecific Stereodivergent Synthesis of trans- and cis-N(2), 3-Dimethyl- 4-phenyl-1, 2, 3, 4-tetrahydroisoquinolines

The acid-promoted cyclizations of a range of N-benzylethanolamines (derived from pseudoephedrine or ephedrine) give the corresponding trans-N(2), 3-dimethyl-4-phenyl-1, 2, 3, 4- tetrahydroisoquinolines with high levels of diastereoselectivity and in good yields of isolated product. The cyclizations of the corresponding chromium tricarbonyl complexes are rendered completely stereoselective. Acidpromoted cyclization of N-(3′, 4′- dimethoxybenzyl) ephedrine and its chromium tricarbonyl complex occur with complementary diastereoselectivities to give trans- and cis-N(2), 3-dimethyl-4- phenyl-6, 7-dimethoxy-1, 2, 3, 4-tetrahydro- isoquinoline, respectively, in >99:1 d.r. The latter is consistent with a "double inversion" mechanism, which involves neighboring group participation by the chromium tricarbonyl moiety followed by rearomatization to give the corresponding cis-tetrahydroisoquinoline with overall retention of configuration.

PROCESS FOR PREPARING BENZYLATED AMINES

This present invention relates to a process for preparing benzylated amines by the reaction of an amine selected from methamphetamine and propylhexedrine with benzyl halide. Numerous improvements are obtained by employing the amine in molar excess with respect to benzyl halide, preferably in a molar ratio of 2 to 1. The excess amine is employed to selectively neutralize by-product acid as the amine salt. The amine salt is then separated from the reaction mixture and basified to reclaim starting amine for recycle to the process.

PROCESS FOR THE PURIFICATION OF BENZPHETAMINE HYDROCHLORIDE

The present invention relates to the economical and separation of benzphetamine hydrochloride and methamphetamine by liquid extraction. An extraction process employing a suitable organic solvent and water at a pH in the range of from about 6 to about 8 provides excellent removal of the methamphetamine by dissolution in the water phase while the benzphetamine dissolves in the organic phase. Simple separation of the two phases results in separation of the two amines.