Pipradrol

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Pipradrol
Pipradrol.svg
Clinical data
ATC code
Legal status
Legal status
Identifiers
  • Diphenyl(piperidin-2-yl)methanol
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard 100.006.723 OOjs UI icon edit-ltr-progressive.svg
Chemical and physical data
Formula C18H21NO
Molar mass 267.372 g·mol−1
3D model (JSmol)
  • OC(c1ccccc1)(c2ccccc2)C3NCCCC3
  • InChI=1S/C18H21NO/c20-18(15-9-3-1-4-10-15,16-11-5-2-6-12-16)17-13-7-8-14-19-17/h1-6,9-12,17,19-20H,7-8,13-14H2 Yes check.svgY
  • Key:XSWHNYGMWWVAIE-UHFFFAOYSA-N Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

Pipradrol, also known by its brand name Meratran, is a mild central nervous system stimulant that acts as a norepinephrine-dopamine reuptake inhibitor. [2] Developed in the United States in the 1940s and patented in 1953, [3] pipradrol was initially marketed as an antidepressant in the mid-1950s. [2] It was subsequently used as an adjunct treatment for various conditions, including obesity, senile dementia, narcolepsy, and schizophrenia. [2] [4]

Contents

Despite its initial promise and relatively mild stimulant effects compared to stronger alternatives, concerns about its abuse potential led to its regulation and withdrawal from widespread use in many countries during the late 1970s. [2] Pipradrol is now classified as a controlled substance in several nations, including the United Kingdom, where it is typically placed in less restrictive drug schedules due to its lower abuse potential compared to other stimulants. [5]

Dosage

Elixir "Alertonic" with Pipradrol hydrochloride content of 0.044 mg/mL was recommended to adults only, 1 tablespoonful (15 ml.), three times daily 30 minutes before meals for limited periods only. [6] [7]

Side effects

Common side effects include insomnia, anorexia, tachycardia, and anxiety. Rarer side effects include dry mouth, tremor, hypertension, euphoria, depression, and very rarely psychosis or convulsions. [2]

Pharmacology

Pharmacodynamics

Pipradrol is a central nervous system stimulant that acts primarily as a norepinephrine and dopamine reuptake inhibitor. [2] Its mechanism of action involves blocking the reuptake of these neurotransmitters, leading to increased levels in the synaptic cleft and prolonged stimulation of postsynaptic neurons. Studies have shown that pipradrol's rewarding effects may be mediated through activation of the dopamine receptor D1. [2] Unlike amphetamines, pipradrol exhibits a more intense action on higher brain centers without significantly affecting blood pressure or respiration. [2] It also does not decrease appetite or cause post-excitement depression typically associated with amphetamines. [2]

Pharmacokinetics

Pipradrol is rapidly absorbed and distributed to the liver, kidney, and brain tissue. [2] The drug is quickly metabolized and eliminated from the body, with approximately 3.5% excreted in urine and 5% in stool. [2]

History

Pipradrol was initially developed in the United States in the 1940s, [8] patented in 1953, [3] and marketed in the mid 1950s as the antidepressant drug Meratran. [9] It was subsequently used as an adjunct for the treatment of obesity [10] and management of senile dementia symptoms. [11] There have also been numerous reports demonstrating favorable effects on a variety of conditions such as ADHD, narcolepsy, schizophrenia, and spasmodic torticollis. [2] Pipradrol proved useful for these applications as its relatively mild stimulant effects gave it a good safety profile compared to stronger stimulants.[ medical citation needed ] It was also studied as an adjutant treatment for depression and schizophrenia although it was never widely used for these purposes.

Pipradrol was made illegal in many countries in the late 1970s, at the same time as many other drugs which had a history of abuse. The relatively mild stimulant effects of pipradrol meant that it was scheduled under the less restrictive classes in most countries (i.e. Class C in United Kingdom and New Zealand) but was still considered of sufficient abuse potential to be made an illegal drug. It is now an obscure compound that is virtually unknown as an illicit drug of abuse, but is still used for some scientific research, often as a comparison drug for testing other stimulants against.

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; it is also used to treat binge eating disorder in the form of its inactive prodrug lisdexamfetamine. 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">Psychopharmacology</span> Study of the effects of psychoactive drugs

Psychopharmacology is the scientific study of the effects drugs have on mood, sensation, thinking, behavior, judgment and evaluation, and memory. It is distinguished from neuropsychopharmacology, which emphasizes the correlation between drug-induced changes in the functioning of cells in the nervous system and changes in consciousness and behavior.

A psychiatric or psychotropic medication is a psychoactive drug taken to exert an effect on the chemical makeup of the brain and nervous system. Thus, these medications are used to treat mental illnesses. These medications are typically made of synthetic chemical compounds and are usually prescribed in psychiatric settings, potentially involuntarily during commitment. Since the mid-20th century, such medications have been leading treatments for a broad range of mental disorders and have decreased the need for long-term hospitalization, thereby lowering the cost of mental health care. The recidivism or rehospitalization of the mentally ill is at a high rate in many countries, and the reasons for the relapses are under research.

<span class="mw-page-title-main">Stimulant</span> Drug that increases activity of central nervous system

Stimulants are a class of drugs that increase the activity of the brain. They are used for various purposes, such as enhancing alertness, attention, motivation, cognition, mood, and physical performance. Some of the most common stimulants are caffeine, nicotine, amphetamines, cocaine, methylphenidate, and modafinil.

<span class="mw-page-title-main">Methcathinone</span> Psychoactive stimulant

Methcathinone is a monoamine alkaloid and psychoactive stimulant, a substituted cathinone. It is used as a recreational drug due to its potent stimulant and euphoric effects and is considered to be addictive, with both physical and psychological withdrawal occurring if its use is discontinued after prolonged or high-dosage administration. It is usually snorted, but can be smoked, injected, or taken orally.

<span class="mw-page-title-main">Bupropion</span> Medication mainly used for depression and smoking cessation

Bupropion, formerly called amfebutamone, and sold under the brand name Wellbutrin among others, is an atypical antidepressant primarily used to treat major depressive disorder and to support smoking cessation. It is also popular as an add-on medication in the cases of "incomplete response" to the first-line selective serotonin reuptake inhibitor (SSRI) antidepressant. Bupropion has several features that distinguish it from other antidepressants: it does not usually cause sexual dysfunction, it is not associated with weight gain and sleepiness, and it is more effective than SSRIs at improving symptoms of hypersomnia and fatigue. Bupropion, particularly the immediate release formulation, carries a higher risk of seizure than many other antidepressants, hence caution is recommended in patients with a history of seizure disorder. The medication is taken by mouth.

<span class="mw-page-title-main">Monoamine transporter</span> Proteins that function as integral plasma-membrane transporters

Monoamine transporters (MATs) are proteins that function as integral plasma-membrane transporters to regulate concentrations of extracellular monoamine neurotransmitters. The three major classes are serotonin transporters (SERTs), dopamine transporters (DATs), and norepinephrine transporters (NETs) and are responsible for the reuptake of their associated amine neurotransmitters. MATs are located just outside the synaptic cleft (peri-synaptically), transporting monoamine transmitter overflow from the synaptic cleft back to the cytoplasm of the pre-synaptic neuron. MAT regulation generally occurs through protein phosphorylation and post-translational modification. Due to their significance in neuronal signaling, MATs are commonly associated with drugs used to treat mental disorders as well as recreational drugs. Compounds targeting MATs range from medications such as the wide variety of tricyclic antidepressants, selective serotonin reuptake inhibitors such as fluoxetine (Prozac) to stimulant medications such as methylphenidate (Ritalin) and amphetamine in its many forms and derivatives methamphetamine (Desoxyn) and lisdexamfetamine (Vyvanse). Furthermore, drugs such as MDMA and natural alkaloids such as cocaine exert their effects in part by their interaction with MATs, by blocking the transporters from mopping up dopamine, serotonin, and other neurotransmitters from the synapse.

A dopamine reuptake inhibitor (DRI) is a class of drug which acts as a reuptake inhibitor of the monoamine neurotransmitter dopamine by blocking the action of the dopamine transporter (DAT). Reuptake inhibition is achieved when extracellular dopamine not absorbed by the postsynaptic neuron is blocked from re-entering the presynaptic neuron. This results in increased extracellular concentrations of dopamine and increase in dopaminergic neurotransmission.

<span class="mw-page-title-main">Norepinephrine reuptake inhibitor</span> Class of drug

A norepinephrine reuptake inhibitor or noradrenaline reuptake inhibitor or adrenergic reuptake inhibitor (ARI), is a type of drug that acts as a reuptake inhibitor for the neurotransmitters norepinephrine (noradrenaline) and epinephrine (adrenaline) by blocking the action of the norepinephrine transporter (NET). This in turn leads to increased extracellular concentrations of norepinephrine and epinephrine and therefore can increase adrenergic neurotransmission.

<span class="mw-page-title-main">Armodafinil</span> Eugeroic medication

Armodafinil, sold under the brand name Nuvigil, is a wakefulness-promoting medication which is used to treat excessive daytime sleepiness associated with obstructive sleep apnea, narcolepsy, and shift work disorder. It is also used off-label for certain other indications. The drug is taken by mouth.

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

Desoxypipradrol, also known as 2-⁠diphenylmethylpiperidine (2-DPMP), is a drug developed by Ciba in the 1950s which acts as a norepinephrine-dopamine reuptake inhibitor (NDRI).

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

Lisdexamfetamine, sold under the brand names Vyvanse and Elvanse among others, is a stimulant medication that is used to treat attention deficit hyperactivity disorder (ADHD) in children and adults and for moderate-to-severe binge eating disorder in adults. Lisdexamfetamine is taken by mouth. Its effects generally begin within two hours and last for up to 14 hours.

<span class="mw-page-title-main">LR-5182</span> Stimulant drug

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A dopamine releasing agent (DRA) is a type of drug which induces the release of dopamine in the body and/or brain.

<span class="mw-page-title-main">Norepinephrine–dopamine reuptake inhibitor</span> Drug that inhibits the reuptake of norepinephrine and dopamine

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<span class="mw-page-title-main">3-Fluoroamphetamine</span> Stimulant drug that acts as an amphetamine

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<span class="mw-page-title-main">Azacyclonol</span> Medication which diminishes hallucinations

Azacyclonol, also known as γ-pipradrol, is a drug which is an ataractive; an agent which diminishes hallucinations in psychotic individuals. It has also been called a tranquilizer and antipsychotic, though these definitions are not accurate as it does not actually possess such properties. Despite being a positional isomer of pipradrol, it is not a psychostimulant, and instead has mild depressant effects.

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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.

References

  1. ↑ Anvisa (2023-03-31). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-04-04). Archived from the original on 2023-08-03. Retrieved 2023-08-16.
  2. 1 2 3 4 5 6 7 8 9 10 11 12 "Pipradrol". go.drugbank.com. Retrieved 2024-10-17.
  3. 1 2 US 2624739,Tilford CH, Werner HW,"Alpha, alpha diaryl piperidino methanols",issued 6 January 1953, assigned to Marion Merrell Dow
  4. ↑ Sargant W, Wayne EJ (May 1958). "Discussion on sedation and stimulation of man". Proceedings of the Royal Society of Medicine. 51 (5): 353–8. doi:10.1177/003591575805100512. PMC   1889636 . PMID   13567677.
  5. ↑ Wood DM, Dargan PI (September 2012). "Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP)". Clinical Toxicology. 50 (8): 727–32. doi:10.3109/15563650.2012.716158. PMID   22882169.
  6. ↑ "Details for: ALERTONIC". Drug and Health Product Portal. Health Canada. Retrieved 2024-10-17.
  7. ↑ Watters WW (1974-11-02). "Alertonic" (PDF). Canadian Medical Association Journal. 111 (9): 900–902. PMC   1955871 . PMID   20312578.
  8. ↑ White M, Archer JR (2013). "Pipradrol and Pipradrol Derivatives". Novel Psychoactive Substances. Elsevier. pp. 233–259. doi:10.1016/b978-0-12-415816-0.00010-9. ISBN   978-0-12-415816-0.
  9. ↑ Fabing HD, Hawkins JR, Moulton JA (May 1955). "Clinical studies on alpha-(2-piperidyl) benzhydrol hydrochloride, a new antidepressant drug". The American Journal of Psychiatry. 111 (11): 832–836. doi:10.1176/ajp.111.11.832. PMID   14361772.
  10. ↑ Gelvin EP, McGAVACK TH, Kenigsberg S (August 1955). "Alpha-(2-piperidyl) benzhydrol hydrochloride (pipradrol) as an adjunct in the dietary management of obesity". New York State Journal of Medicine. 55 (16): 2336–2338. PMID   13244858.
  11. ↑ "Pipradrol Hydrochloride". Inxight Drugs. National Center for Advancing Translational Sciences (NCATS), U.S. National Institutes of Health. Retrieved 2024-10-14.
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