Benzphetamine

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Benzphetamine
Benzphetamine.svg
Benzphetamine 3d.gif
Clinical data
Trade names Didrex, Recede
Other namesN-benzyl-N-methylamphetamine
AHFS/Drugs.com Professional Drug Facts
License data
Dependence
liability
High [1]
Routes of
administration
By mouth
ATC code
  • None
Legal status
Legal status
Pharmacokinetic data
Protein binding 75–99%
Elimination half-life 4-6 hours
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
Formula C17H21N
Molar mass 239.362 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 Yes check.svgY
  • Key:YXKTVDFXDRQTKV-HNNXBMFYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (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 to people who have been unable to lose weight through exercise and dieting alone. It is a prodrug to dextroamphetamine and dextromethamphetamine. [3] [4] [5]

Contents

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

Pharmacology

Benzphetamine is a sympathomimetic amine and is classified as an anorectic. [6] The drug's main function is to reduce appetite, which in turn reduces caloric intake.[ medical citation needed ]

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.[ medical citation needed ]

Benzphetamine has a half-life of 4–6 hours. [7]

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. [8]

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. [9]

Related Research Articles

<span class="mw-page-title-main">Amphetamine</span> Central nervous system stimulant

Amphetamine is a central nervous system (CNS) stimulant that is used in the treatment of attention deficit hyperactivity disorder (ADHD), narcolepsy, and obesity. Amphetamine was discovered as a chemical in 1887 by Lazăr Edeleanu, and then as a drug in the late 1920s. It exists as two enantiomers: levoamphetamine and dextroamphetamine. Amphetamine properly refers to a specific chemical, the racemic free base, which is equal parts of the two enantiomers in their pure amine forms. The term is frequently used informally to refer to any combination of the enantiomers, or to either of them alone. Historically, it has been used to treat nasal congestion and depression. Amphetamine is also used as an athletic performance enhancer and cognitive enhancer, and recreationally as an aphrodisiac and euphoriant. It is a prescription drug in many countries, and unauthorized possession and distribution of amphetamine are often tightly controlled due to the significant health risks associated with recreational use.

<span class="mw-page-title-main">Ephedrine</span> Medication and stimulant

Ephedrine is a central nervous system (CNS) stimulant that is often used to prevent low blood pressure during anesthesia. It has also been used for asthma, narcolepsy, and obesity but is not the preferred treatment. It is of unclear benefit in nasal congestion. It can be taken by mouth or by injection into a muscle, vein, or just under the skin. Onset with intravenous use is fast, while injection into a muscle can take 20 minutes, and by mouth can take an hour for effect. When given by injection it lasts about an hour and when taken by mouth it can last up to four hours.

An anorectic or anorexic is a drug which reduces appetite, resulting in lower food consumption, leading to weight loss. By contrast, an appetite stimulant is referred to as orexigenic.

<span class="mw-page-title-main">Phenylpropanolamine</span> Sympathomimetic agent

Phenylpropanolamine (PPA) is a sympathomimetic agent which is used as a decongestant and appetite suppressant. It was commonly used in prescription and over-the-counter cough and cold preparations. In veterinary medicine, it is used to control urinary incontinence in dogs.

<span class="mw-page-title-main">3,4-Methylenedioxyamphetamine</span> Empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family

3,4-Methylenedioxyamphetamine is an empathogen-entactogen, psychostimulant, and psychedelic drug of the amphetamine family that is encountered mainly as a recreational drug. In its pharmacology, MDA is a serotonin–norepinephrine–dopamine releasing agent (SNDRA). In most countries, the drug is a controlled substance and its possession and sale are illegal.

<span class="mw-page-title-main">Propylhexedrine</span> Topical nasal decongestant

Propylhexedrine, commonly sold under the brand name Benzedrex, is an alkylamine primarily utilized as a topical nasal decongestant. Its main indications are relief of congestion due to colds, allergies, and allergic rhinitis.

<span class="mw-page-title-main">Sympathomimetic drug</span> Substance that mimics effects of catecholamines

Sympathomimetic drugs are stimulant compounds which mimic the effects of endogenous agonists of the sympathetic nervous system. Examples of sympathomimetic effects include increases in heart rate, force of cardiac contraction, and blood pressure. The primary endogenous agonists of the sympathetic nervous system are the catecholamines, which function as both neurotransmitters and hormones. Sympathomimetic drugs are used to treat cardiac arrest and low blood pressure, or even delay premature labor, among other things.

<span class="mw-page-title-main">Phentermine</span> Weight loss medication

Phentermine (phenyl-tertiary-butylamine), with several brand names including Ionamin and Sentis, is a medication used together with diet and exercise to treat obesity. It is taken by mouth for up to a few weeks at a time, after which the benefits subside. It is also available as the combination phentermine/topiramate.

<span class="mw-page-title-main">Levomethamphetamine</span> Nasal decongestant and optical isomer of methamphetamine

Levomethamphetamine is the levorotatory (L-enantiomer) form of methamphetamine. Levomethamphetamine is a sympathomimetic vasoconstrictor that is the active ingredient in some over-the-counter (OTC) nasal decongestant inhalers in the United States.

<span class="mw-page-title-main">Aminorex</span> Chemical compound

Aminorex is a weight loss (anorectic) stimulant drug. It was withdrawn from the market after it was found to cause pulmonary hypertension. In the U.S., it is an illegal Schedule I drug, meaning it has high abuse potential, no accepted medical use, and a poor safety profile.

<span class="mw-page-title-main">Dexfenfluramine</span> Serotonergic anorectic medication

Dexfenfluramine, marketed as dexfenfluramine hydrochloride under the name Redux, is a serotonergic anorectic drug: it reduces appetite by increasing the amount of extracellular serotonin in the brain. It is the d-enantiomer of fenfluramine and is structurally similar to amphetamine, but lacks any psychologically stimulating effects.

<span class="mw-page-title-main">Ethylone</span> Chemical compound

Ethylone, also known as 3,4-methylenedioxy-N-ethylcathinone, is a recreational designer drug classified as an entactogen, stimulant, and psychedelic of the phenethylamine, amphetamine, and cathinone chemical classes. It is the β-keto analogue of MDEA ("Eve"). Ethylone has only a short history of human use and is reported to be less potent than its relative methylone. In the United States, it began to be found in cathinone products in late 2011.

<span class="mw-page-title-main">Clobenzorex</span> Stimulant drug used as an appetite suppressant

Clobenzorex is a stimulant drug of the amphetamine chemical class used as an appetite suppressant. The drug is legally distributed in Mexico under the trade name Asenlix by Aventis.

<span class="mw-page-title-main">Etilamfetamine</span> Chemical compound

Etilamfetamine is a stimulant drug of the phenethylamine and amphetamine chemical classes. It was invented in the early 20th century and was subsequently used as an anorectic or appetite suppressant in the 1950s, but was not as commonly used as other amphetamines such as amphetamine, methamphetamine, and benzphetamine, and was largely discontinued once newer drugs such as phenmetrazine were introduced. It most likely acts primarily as a dopamine releasing agent. Its activity as a norepinephrine or serotonin releasing agent is not known.

<span class="mw-page-title-main">Propylamphetamine</span> Chemical compound

Propylamphetamine is a psychoactive drug and research chemical of the phenethylamine and amphetamine chemical classes which acts as a stimulant. It was first developed in the 1970s, mainly for research into the metabolism of, and as a comparison tool to, other amphetamines. A study in rats found propylamphetamine to be 1/4 as potent as amphetamine.

<span class="mw-page-title-main">Mazindol</span> Stimulant drug and appetite suppressant

Mazindol is a stimulant drug which is used as an appetite suppressant. It was developed by Sandoz-Wander in the 1960s.

Substituted amphetamines are a class of compounds based upon the amphetamine structure; it includes all derivative compounds which are formed by replacing, or substituting, one or more hydrogen atoms in the amphetamine core structure with substituents. The compounds in this class span a variety of pharmacological subclasses, including stimulants, empathogens, and hallucinogens, among others. Examples of substituted amphetamines are amphetamine (itself), methamphetamine, ephedrine, cathinone, phentermine, mephentermine, tranylcypromine, bupropion, methoxyphenamine, selegiline, amfepramone (diethylpropion), pyrovalerone, MDMA (ecstasy), and DOM (STP).

<i>N</i>-Ethylhexedrone Stimulant of the cathinone class

N-Ethylhexedrone (also known as α-ethylaminocaprophenone, N-ethylnorhexedrone, hexen, and NEH) is a stimulant of the cathinone class that acts as a norepinephrine–dopamine reuptake inhibitor (NDRI) with IC50 values of 0.0978 and 0.0467 μM, respectively. N-Ethylhexedrone was first mentioned in a series of patents by Boehringer Ingelheim in the 1960s which led to the development of the better-known drug methylenedioxypyrovalerone (MDPV). Since the mid-2010s, N-ethylhexedrone has been sold online as a designer drug. In 2018, N-ethylhexedrone was the second most common drug of the cathinone class to be identified in Drug Enforcement Administration seizures.

Amphetamine type stimulants (ATS) are a group of synthetic drugs that are chemical derivatives of the parent compound alpha-methylphenethylamine, also known as amphetamine. Common ATS includes amphetamine, methamphetamine, ephedrine, pseudoephedrine, 3,4-methylenedioxymethamphetamine (MDMA), 3,4-methylenedioxyamphetamine (MDA) and 3,4-methylenedioxyethylamphetamine (MDEA). ATS when used illicitly has street names including ice, meth, crystal, crank, bennies, and speed. Within the group of amphetamine-type stimulants, there are also prescription drugs including mixed amphetamine salts, dextroamphetamine, and lisdexamfetamine.

<span class="mw-page-title-main">Dimethylone</span> Stimulant and empathogenic drug

Dimethylone (βk-MDDMA) is a substituted cathinone derivative with stimulant and empathogenic effects. Unlike the corresponding amphetamine derivative MDDM which is thought to be practically inactive, dimethylone substitutes for methamphetamine and MDMA in animal studies and has been sold as a designer drug.

References

  1. "Benzphetamine". Toxnet. Archived from the original on 2018-11-01.
  2. Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. AHC Media, LLC (17 March 2014). Pediatric Trauma Care II: A clinical reference for physicians and nurses caring for the acutely injured child. AHC Media, LLC. pp. 118–. ISBN   978-1-934863-59-6.
  4. Cody JT, Valtier S (1998). "Detection of amphetamine and methamphetamine following administration of benzphetamine". Journal of Analytical Toxicology. 22 (4): 299–309. doi: 10.1093/jat/22.4.299 . PMID   9681333.
  5. Budd RD, Jain NC (1978). "Short Communication: Metabolism and Excretion of Benzphetamine: Sources of Error in Reporting Results". Journal of Analytical Toxicology. 2 (6): 241. doi:10.1093/jat/2.6.241.
  6. Valentine JL, Middleton R (April 2000). "GC-MS identification of sympathomimetic amine drugs in urine: rapid methodology applicable for emergency clinical toxicology". Journal of Analytical Toxicology. 24 (3): 211–222. doi:10.1093/jat/24.3.211. PMID   10774541.
  7. Woo T (2015-08-03). Pharmacotherapeutics for Advanced Practice Nurse Prescribers, 4th Edition. p. 226. ISBN   978-0-8036-3827-3.
  8. "Benzphetamine". Toxnet. Archived from the original on 2018-11-01.
  9. Musshoff F (February 2000). "Illegal or legitimate use? Precursor compounds to amphetamine and methamphetamine". Drug Metabolism Reviews. 32 (1): 15–44. doi:10.1081/DMR-100100562. PMID   10711406. S2CID   20012024.