Benzphetamine Chemical Properties

Boiling point:

bp0.02 127°

Density 

1.0137 (rough estimate)

refractive index 

nD19 1.5515

pka

pKa 6.55 (Uncertain)

Safety Information

RIDADR 

3249

HazardClass 

6.1(b)

PackingGroup 

III

Hazardous Substances Data

156-08-1(Hazardous Substances Data)

Toxicity

man,TDLo,oral,5357ug/kg (5.357mg/kg),AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETICVASCULAR: BP ELEVATION NOT CHARACTERIZED IN AUTONOMIC SECTION,Therapie. Vol. 34, Pg. 205, 1979.

DEA Controlled Substances

CSCN: 1228
CAS SCH: Ⅲ
NARC: N

Benzphetamine Usage And Synthesis

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.