Benzphetamine

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Benzphetamine
Systematic (IUPAC) name
(2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine
Clinical data
Trade namesDidrex
AHFS/Drugs.comConsumer Drug Information
Legal statusSchedule III (US)
Pharmacokinetic data
Protein binding75–99%
Identifiers
CAS number156-08-1 YesY
ATC codeNone
PubChemCID 5311017
DrugBankDB00865
ChemSpider4470556 YesY
UNII0M3S43XK27 YesY
ChEBICHEBI:3044 YesY
ChEMBLCHEMBL1201358 N
SynonymsN-benzyl-N-methylamphetamine
Chemical data
FormulaC17H21N 
Mol. mass239.355 g/mol
 N (what is this?)  (verify)
 
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Benzphetamine
Systematic (IUPAC) name
(2S)-N-benzyl-N-methyl-1-phenylpropan-2-amine
Clinical data
Trade namesDidrex
AHFS/Drugs.comConsumer Drug Information
Legal statusSchedule III (US)
Pharmacokinetic data
Protein binding75–99%
Identifiers
CAS number156-08-1 YesY
ATC codeNone
PubChemCID 5311017
DrugBankDB00865
ChemSpider4470556 YesY
UNII0M3S43XK27 YesY
ChEBICHEBI:3044 YesY
ChEMBLCHEMBL1201358 N
SynonymsN-benzyl-N-methylamphetamine
Chemical data
FormulaC17H21N 
Mol. mass239.355 g/mol
 N (what is this?)  (verify)

Benzphetamine (Didrex) is an anorectic drug marketed under this brand in the USA by Pharmacia. Benzphetamine is used as a short term adjunct in management of exogenous obesity. It is closely related to amphetamine.

Pharmacology[edit]

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. Benzphetamine can cause vivid hallucinations if taken for the wrong purpose.

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.

Contraindications[edit]

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. Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug abuse.

Controlled substance classification[edit]

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.[1] Benzphetamine itself does not have as high abuse potential as its metabolites (Schedule III) because of the time necessary for the liver to metabolize it into amphetamine and methamphetamine, regardless of route of administration. This gives benzphetamine an inherent 'sustained-release' effect.[citation needed]

References[edit]

  1. ^ Musshoff F (February 2000). "Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine". Drug Metab. Rev. 32 (1): 15–44. doi:10.1081/DMR-100100562. PMID 10711406.