Benzphetamine

Benzphetamine

Systematic (IUPAC) name
(2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine
Clinical data
Trade names	Didrex, Recede
AHFS/Drugs.com	Consumer Drug Information
Pregnancy category	US: X (Contraindicated)
Legal status	DE: Anlage I (Controlled) US: Schedule III
Dependence liability	High
Routes of administration	oral
Pharmacokinetic data
Protein binding	75–99%
Biological half-life	4-6 Hours
Identifiers
CAS Number	156-08-1 Y
ATC code	none
PubChem	CID: 5311017
DrugBank	DB00865 Y
ChemSpider	4470556 Y
UNII	0M3S43XK27 Y
ChEBI	CHEBI:3044 Y
ChEMBL	CHEMBL1201358 N
Synonyms	N-benzyl-N-methylamphetamine
Chemical data
Formula	C17H21N
Molecular mass	239.355 g/mol
SMILES N(C)(Cc1ccccc1)[C@@H](C)Cc2ccccc2
InChI InChI=1S/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 Y Key:YXKTVDFXDRQTKV-HNNXBMFYSA-N Y
NY (what is this?)  (verify)

Benzphetamine (brand name Didrex) is a substituted amphetamine used short-term along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program for weight loss. It is prescribed for obesity in individuals who have been unable to lose weight through exercise and dieting alone. It is a prodrug to amphetamine.

Benzphetamine is an anorectic, primarily promoting weight loss through reduced appetite. Benzphetamine also slightly increases metabolism.

Pharmacology

Benzphetamine is a sympathomimetic amine and is classified as an anorectic. The drug's main function is to reduce appetite, which in turn reduces caloric intake.

Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals of the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated through the binding of benzphetamine to VMAT₂ and inhibiting its function, causing a release of these neurotransmitters into the synaptic cleft through their reuptake transporters. Tachyphylaxis and tolerance have been demonstrated with all drugs of this class.

Benzphetamine has a half-life of 4-6 hours.

Contraindications

Benzphetamine is contraindicated in patients with advanced arteriosclerosis, symptomatic cardiovascular disease, moderate to severe hypertension, hyper-thyroidism, known hypersensitivity or idiosyncrasy to sympathomimetic amines, and glaucoma, or who have recently used a MAOI. Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug abuse.

Controlled substance classification

Benzphetamine is unique in its classification as a Schedule III drug in the United States. (Most members of the amphetamine family are classified in the more highly regulated Schedule II.) Benzphetamine is metabolized by the human body into amphetamine and methamphetamine, making it one of a number of drugs to undergo in vivo conversion to a substance of higher addiction and abuse potential.