Identification

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Name
Pipradrol
Accession Number
DB11584
Type
Small Molecule
Groups
Approved
Description

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.

Structure
Thumb
Synonyms
  • Pipradrol
External IDs
207-394-5
Product Ingredients
IngredientUNIICASInChI Key
Pipradrol hydrochlorideF6E46VR9Y271-78-3KIFIYUHFHGSNHL-UHFFFAOYSA-N
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
AlertonicPipradrol hydrochloride (0.044 mg) + Choline (2.222 mg) + Inositol (2.222 mg) + Nicotinamide (1.111 mg) + Pyridoxine hydrochloride (0.042 mg) + Riboflavin (0.111 mg) + Thiamine hydrochloride (0.222 mg)ElixirOralOdan Laboratories Ltd1995-12-31Not applicableCanada
AlertonicPipradrol hydrochloride (.044 mg) + Choline (2.222 mg) + Inositol (2.222 mg) + Nicotinamide (1.111 mg) + Pyridoxine hydrochloride (.042 mg) + Riboflavin (.111 mg) + Thiamine hydrochloride (.222 mg)LiquidOralMerrell Pharms Inc., Division Of Merrell Dow (Can)1967-12-311996-09-09Canada
Categories
UNII
S6I030E0DA
CAS number
467-60-7
Weight
Average: 267.372
Monoisotopic: 267.1623143
Chemical Formula
C18H21NO
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

Pharmacology

Indication

Used to manage fatigue 10 and depression 5, 1, 8, 11. Used as an adjunct therapy in the management of obesity 10.

Associated Conditions
Pharmacodynamics

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.

TargetActionsOrganism
UD(1) dopamine receptor
agonist
Humans
Additional Data Available
Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available
Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available
Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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.

Toxicity

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.

Affected organisms
  • Humans and other mammals
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
Not Available

References

General References
  1. 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. [PubMed:24486525]
  2. BEERSTECHER E Jr, EDMONDS EJ: Inhibition of bacterial growth by pipradrol. J Bacteriol. 1957 Oct;74(4):539-40. [PubMed:13475278]
  3. 10. (2013). In Novel Psychoactive Substances. Academic Press.
  4. Walter S. Root, Frederick G. Hofmann (2015). The Nervous System: Central Nervous System Drugs. Academic Press.
  5. Pripradrol PubChem [Link]
  6. Use of Pripradrol in Obstetrics and Gynecology [Link]
  7. ToxNet, Pripradrol [Link]
  8. Norepinephrine-dopamine reuptake inhibitor [Link]
  9. Use and acute toxicity associated with the novel psychoactive substances diphenylprolinol (D2PM) and desoxypipradrol (2-DPMP) [Link]
  10. NIH Inxight Drugs: Pipradrol [Link]
  11. Psychiatric uses of Meratran [Link]
  12. Pipradrol and derivatives [Link]
  13. Conditioned Place Preference [Link]
External Links
ChemSpider
9681
ChEBI
135101
ChEMBL
CHEMBL2110938
Wikipedia
Pipradrol
ATC Codes
N06BX15 — Pipradrol
MSDS
Download (28.8 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
ElixirOral
LiquidOral
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0306 mg/mLALOGPS
logP3.36ALOGPS
logP3.32ChemAxon
logS-3.9ALOGPS
pKa (Strongest Acidic)12.88ChemAxon
pKa (Strongest Basic)9.53ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count2ChemAxon
Polar Surface Area32.26 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity81.78 m3·mol-1ChemAxon
Polarizability30.59 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

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
Diphenylmethane / Aralkylamine / Piperidine / Tertiary alcohol / 1,2-aminoalcohol / Secondary aliphatic amine / Secondary amine / Organoheterocyclic compound / Azacycle / Alcohol
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
Not Available

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
  1. Pripradrol PubChem [Link]

Drug created on April 27, 2016 14:17 / Updated on February 06, 2020 13:10