Identification
- Summary
Pipradrol is a central nervous stimulant ingredient in a product used to treat functional fatigue.
- Brand Names
- Alertonic
- Generic Name
- Pipradrol
- DrugBank Accession Number
- DB11584
- Background
Pipradrol (Meratran) 11 was initially developed in the 1950s as an antidepressant, however, the adverse effects associated with its use and its abuse potential led to its withdrawal and international regulation 12. Pipradrol was made illegal in many countries in 1970s because of its potential for abuse. It is currently classified under the Misuse of Drugs Act as a Class C substance 10.
Experimentation with the drug and its derivatives for recreational purposes has led to many cases of acute toxicity and has been linked to three fatalities. The social and in particular acute clinical harms of pipradrol derivatives have led to their control under the Misuse of Drugs Act 1971 in the UK in 2012 3.
Interestingly, this drug has been studied for bactericidal properties, however, is not currently, used for this purpose 2. In addition to this, it has shown favorable effects in postpartum depressive symptoms 6.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pipradrol (DB11584)
- Weight
- Average: 267.372
Monoisotopic: 267.1623143 - Chemical Formula
- C18H21NO
- Synonyms
- Pipradrol
- External IDs
- 207-394-5
Pharmacology
- Indication
Used to manage fatigue 10 and depression 5, 1, 8, 11. Used as an adjunct therapy in the management of obesity 10.
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Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Used in combination to manage Depression ••• ••• Used in combination to manage Fatigue ••• ••• Used as adjunct in combination to manage Obesity ••• ••• - Contraindications & Blackbox Warnings
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Pipradrol (Meratran) is a psychoactive agent and a central nervous system stimulant that has proven useful in the field of psychiatry 10.
Pipradrol was initially used as an adjunct in the dietary management of obesity as well as for the management of dementia symptoms. Numerous reports have been made on the properties of pipradrol, demonstrating its favorable effects in the treatment of depression and fatigue in addition to a variety of other conditions including narcolepsy, spasmodic torticollis, schizophrenia and in geriatric practice 10.
- Mechanism of action
Pipradrol and pipradrol derivatives are norepinephrine and dopamine reuptake inhibitors 3.
In a pharmacokinetic study, it was shown that pipradrol conditioned place preference (CPP) 13 was blocked by selective D1 dopamine antagonist, implicating that a rewarding effect of pipradrol may involve the activation of D1 dopamine receptors.
Pipradrol has a definite cerebral stimulating effect without affecting the blood pressure or respiration and has been used to counteract post-anaesthetic and chlorpromazine depression in man. Structurally related to phenylmethylamphetamine, a potent stimulant with a long half-life, pipradrol differs from amphetamine in that its action is more intense at higher centers, it does not exhibit pressor activity, there is no post-excitement depression, and this drug does not decrease appetite, as occurs with amphetamine 10.
Target Actions Organism UD(1) dopamine receptor agonistHumans - Absorption
Rapidly absorbed 4.
- Volume of distribution
Distributed in the liver, kidney and brain tissue 4.
- Protein binding
Not Available
- Metabolism
Rapidly metabolized, and not found in plasma approximately 4 hours post administration 4.
- Route of elimination
Quickly excreted in the urine (3.5%) and stool (5%) 3.
- Half-life
Not Available
- Clearance
Rapidly cleared 4.
- Adverse Effects
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Toxicity Data: Oral LD50 (rat): 180 mg/kg; Oral LD50 (mouse): 120 mg/kg; Oral LD50 (rabbit): 180 mg/kg MSDS.
The toxicity of this drug is dependent on the dose ingested, and is owed to its central nervous stimulant activity 3, 4.
Overdoses of pipradrol hydrochloride cause nausea, anxiety, insomnia and abdominal pain, however, these symptoms often disappear when the drug is withdrawn. In severe cases, convulsions may occur 5, 4. This drug is contraindicated in anxiety, psychosis states, and schizophrenia, as it can worsen these symptoms. Hallucinations have been reported after taking this drug 3.
Over the last decade there has been greater use of novel psychoactive substances (‘legal highs’) across Europe and the United States, including increasing frequency of reports of diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP) use 9.
There are increasing reports that D2PM (desoxy analogue of pipradrol) and 2-DPMP (a pyrrolidine analogue of pipradrol) are used in Europe as drugs of abuse. 2-DPMP has sympathomimetic properties similar to cocaine and, in addition, prolonged and clinically significant neuropsychiatric symptoms have been reported 9. The binding and activity of D2PM at the dopamine re-uptake transporter, is also similar to cocaine, though it appears that D2PM has less potent biological activity 9.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.Not Available
- Food Interactions
- No interactions found.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pipradrol hydrochloride F6E46VR9Y2 71-78-3 KIFIYUHFHGSNHL-UHFFFAOYSA-N - Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image Alertonic Pipradrol hydrochloride (0.044 mg / mL) + Choline (2.222 mg / mL) + Inositol (2.222 mg / mL) + Nicotinamide (1.111 mg / mL) + Pyridoxine hydrochloride (0.042 mg / mL) + Riboflavin (0.111 mg / mL) + Thiamine hydrochloride (0.222 mg / mL) Elixir Oral Odan Laboratories Ltd 1995-12-31 Not applicable Canada 
Alertonic Pipradrol hydrochloride (.044 mg / mL) + Choline (2.222 mg / mL) + Inositol (2.222 mg / mL) + Nicotinamide (1.111 mg / mL) + Pyridoxine hydrochloride (.042 mg / mL) + Riboflavin (.111 mg / mL) + Thiamine hydrochloride (.222 mg / mL) Liquid Oral Merrell Pharms Inc., Division Of Merrell Dow (Can) 1967-12-31 1996-09-09 Canada
Categories
- ATC Codes
- N06BX15 — Pipradrol
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as diphenylmethanes. These are compounds containing a diphenylmethane moiety, which consists of a methane wherein two hydrogen atoms are replaced by two phenyl groups.
- Kingdom
- Organic compounds
- Super Class
- Benzenoids
- Class
- Benzene and substituted derivatives
- Sub Class
- Diphenylmethanes
- Direct Parent
- Diphenylmethanes
- Alternative Parents
- Aralkylamines / Piperidines / Tertiary alcohols / 1,2-aminoalcohols / Dialkylamines / Azacyclic compounds / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
- Substituents
- 1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Diphenylmethane / Hydrocarbon derivative / Organic nitrogen compound
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- Not Available
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- S6I030E0DA
- CAS number
- 467-60-7
- InChI Key
- XSWHNYGMWWVAIE-UHFFFAOYSA-N
- InChI
- 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
- IUPAC Name
- diphenyl(piperidin-2-yl)methanol
- SMILES
- [H]N1CCCCC1C(O)(C1=CC=CC=C1)C1=CC=CC=C1
References
- General References
- Simmler LD, Rickli A, Schramm Y, Hoener MC, Liechti ME: Pharmacological profiles of aminoindanes, piperazines, and pipradrol derivatives. Biochem Pharmacol. 2014 Mar 15;88(2):237-44. doi: 10.1016/j.bcp.2014.01.024. Epub 2014 Jan 28. [Article]
- BEERSTECHER E Jr, EDMONDS EJ: Inhibition of bacterial growth by pipradrol. J Bacteriol. 1957 Oct;74(4):539-40. [Article]
- 10. (2013). In Novel Psychoactive Substances. Academic Press.
- Walter S. Root, Frederick G. Hofmann (2015). The Nervous System: Central Nervous System Drugs. Academic Press.
- Pripradrol PubChem [Link]
- Use of Pripradrol in Obstetrics and Gynecology [Link]
- ToxNet, Pripradrol [Link]
- Norepinephrine-dopamine reuptake inhibitor [Link]
- Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP) [Link]
- NIH Inxight Drugs: Pipradrol [Link]
- Psychiatric uses of Meratran [Link]
- Pipradrol and derivatives [Link]
- Conditioned Place Preference [Link]
- External Links
- ChemSpider
- 9681
- ChEBI
- 135101
- ChEMBL
- CHEMBL2110938
- Wikipedia
- Pipradrol
- MSDS
- Download (28.8 KB)
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Elixir Oral Liquid Oral - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0306 mg/mL ALOGPS logP 3.36 ALOGPS logP 3.32 Chemaxon logS -3.9 ALOGPS pKa (Strongest Acidic) 12.88 Chemaxon pKa (Strongest Basic) 9.53 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 2 Chemaxon Hydrogen Donor Count 2 Chemaxon Polar Surface Area 32.26 Å2 Chemaxon Rotatable Bond Count 3 Chemaxon Refractivity 81.78 m3·mol-1 Chemaxon Polarizability 30.59 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-001i-9610000000-93ffbb709d850d4e923e Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-0uxr-0090000000-227eca665e9f1f7098a4 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-014i-0290000000-e74ae4cc7bf7c059a65e Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-0api-3930000000-8598a9298ef0f657f833 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-0gb9-1090000000-bdc4edea9f3c3f92e7a7 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0a4i-0900000000-910bdd25dc937af7b693 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0avi-9620000000-5076b56836c58198bab3 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 165.94675 predictedDeepCCS 1.0 (2019) [M+H]+ 168.30473 predictedDeepCCS 1.0 (2019) [M+Na]+ 174.3979 predictedDeepCCS 1.0 (2019)
Targets
- Kind
- Protein group
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Agonist
- General Function
- G-protein coupled amine receptor activity
- Specific Function
- Dopamine receptor whose activity is mediated by G proteins which activate adenylyl cyclase.
Components:
References
- Pripradrol PubChem [Link]
Drug created at April 27, 2016 20:17 / Updated at February 21, 2021 18:53