Pipradrol hydrochlorideProduct ingredient for Pipradrol

Name
Pipradrol hydrochloride
Drug Entry
Pipradrol

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.

Accession Number
DBSALT001777
Structure
Synonyms
Pipradrol HCl
UNII
F6E46VR9Y2
CAS Number
71-78-3
Weight
Average: 303.83
Monoisotopic: 303.138992
Chemical Formula
C18H22ClNO
InChI Key
KIFIYUHFHGSNHL-UHFFFAOYSA-N
InChI
InChI=1S/C18H21NO.ClH/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;1H
IUPAC Name
diphenyl(piperidin-2-yl)methanol hydrochloride
SMILES
Cl.OC(C1CCCCN1)(C1=CC=CC=C1)C1=CC=CC=C1
KEGG Drug
D01876
ChemSpider
59400
ChEBI
32009
ChEMBL
CHEMBL2106720
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
Polarizability30.64 Å3Chemaxon
Number of Rings3Chemaxon
Bioavailability1Chemaxon
Rule of FiveYesChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleNoChemaxon