Benzphetamine

Chemical compound From Wikipedia, the free encyclopedia

Benzphetamine

Benzphetamine, sold under the brand name Didrex among others, is an amphetamine-type stimulant and appetite suppressant used short-term for weight loss along with a doctor-approved, reduced-calorie diet, exercise, and behavioral program. It is prescribed for obesity to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug of dextromethamphetamine and dextroamphetamine.[4][5][6]

Quick Facts Clinical data, Trade names ...
Benzphetamine
INN: Benzfetamine
Clinical data
Trade namesDidrex, Recede
Other namesBenzfetamine; d-Benzphetamine; (+)-Benzphetamine; (S)-(+)-Benzphetamine; (S)-Benzphetamine; (2S)-N-Benzyl-N-methylamphetamine; dextro-N-Benzyl-N-methylamphetamine; N-Benzyldextromethamphetamine; (+)-N-Benzyl-N,α-dimethylphenethylamine
AHFS/Drugs.comProfessional Drug Facts
License data
Dependence
liability
High[1]
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Protein binding75–99%
MetabolitesDextromethamphetamine
Dextroamphetamine
Elimination half-life4–6 hours[3]
Identifiers
  • (2S)-N-Benzyl-N-methyl-1-phenylpropan-2-amine
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC17H21N
Molar mass239.362 g·mol−1
3D model (JSmol)
  • N(C)(Cc1ccccc1)[C@@H](C)Cc2ccccc2
  • 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
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Mechanism of Action

Benzphetamine promotes weight loss by reducing appetite and slightly increasing metabolism.[citation needed] It is the parent compound of clobenzorex, the latter of which is not subject to the Federal Analogue Act, nor scheduled per the Controlled Substances Act of 1970.

Contraindications

Benzphetamine is contraindicated in patients with advanced arteriosclerosis, symptomatic cardiovascular disease, moderate to severe hypertension, hyperthyroidism, known hypersensitivity or idiosyncrasy to sympathomimetic amines, and glaucoma, or who have recently used a monoamine oxidase inhibitor (MAOI).[7] Benzphetamine should not be given to patients who are in an agitated state or who have a history of drug misuse.[8]

Pharmacology

Benzphetamine is a sympathomimetic amine and is classified as an anorectic.[9] The drug's main function is to reduce appetite, which in turn reduces caloric intake.[10][11]

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.[12][13]

Benzphetamine has a half-life of 4 to 6 hours.[3]

Society and culture

Names

Benzfetamine is the international nonproprietary name.[14]

United States

Benzphetamine is unique in its classification as a Schedule III substance in the United States, given that most members of the amphetamine family are classified in the more highly regulated Schedule II tier. Benzphetamine is metabolized by the human body into amphetamine and methamphetamine, making it a prodrugs the aforementioned molcecules, as well as one of a number of substances that convert in vivo conversion into a substance of higher addiction and abuse potential.[15] Clobenzorex, as previously stated, is completely uncontrolled by the Controlled Substances or Federal Analogue Acts, yet is an analog and derivative of benzphetamine.

References

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