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Details

Stereochemistry RACEMIC
Molecular Formula C18H21NO.ClH
Molecular Weight 303.826
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPRADROL HYDROCHLORIDE

SMILES

Cl.OC(C1CCCCN1)(C2=CC=CC=C2)C3=CC=CC=C3

InChI

InChIKey=KIFIYUHFHGSNHL-UHFFFAOYSA-N
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

HIDE SMILES / InChI
Pipradrol (Meratran) is a psychoactive agent and a central nervous system stimulant useful in the field of psychiatry. In vitro study has shown that pipradrol inhibits the reuptake of and stimulates the release of dopamine and norepinephrine. In these pharmacodynamic actions it is less potent than d-amphetamine. It was shown that pipradrol conditioned place preference (CPP) was blocked by selective D1 dopamine antagonist SCH23390 suggesting that a rewarding effect of pipradrol establishment of a CPP may involve activation of D1 dopamine receptors. Pipradrol was initially used as an adjunct in the dietary management of obesity as well as for the treatment of dementia. There have been a number of reports on the properties of pipradrol showing its favorable effects in the treatment of depression and fatigue status as well as a variety of other conditions including narcolepsy, spasmodic torticollis, schizophrenia and in geriatric practice. Pipradrol has a definite cerebral stimulating effect without affecting the blood pressure or respiration and has been used to counteract post-anasthetic 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 centres, it lacks pressor activity, there is no post-excitement depression, and it does not depress the desire for food as occurs with amphetamine. The drug however is enhancing the existing pathologic behavior such as exacerbating pre-existing anxiety and is considered the drug of abuse. Meratran has certain indications and contraindications. Indications are schizophrenics without delusions having restriction of interest and activity and with depressant features, psycho-motor retardation and/or blocking of communication, long-term hospitalized schizophrenics with severe deterioration while contraindications are patients with delusions, anxiety, disturbed patients with cerebral arteriosclerosis. Pipradrol was made illegal in many countries in 1970s due to its abuse potential. It is classified under the Misuse of Drugs Act as a Class C substance. The combination of pipradrol with multivitamins and minerals marketed as Alertonic Elixir is used as adjunctive therapy in combating fatigue resulting from emotional or nutritional causes.

Originator

Curator's Comment: Pipradrol was developed in the 1950s

Approval Year

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
ALERTONIC Elixir

Approved Use

Alertonic is recommended for patients with functional or psychogenic fatigue. This frequently occurs in the absence of organic disease, during convalesence, the post-partum period and following infections, especially those of viral origin. Fatigue may also be present due to a nutritional deficiency which may occur in patients with an inadequate food intake or incorrect eating habits, in geriatric patients who have lost interest in food or in patients with, or recovering from, a debilitating illness or other stressful situations. Alertonic is indicated as a dietary supplement in nutritional fatigue when such fatigue is caused by a deficiency of those vitamins, minerals and trace elements supplied by Alertonic. While Alertonic cannot be expected to influence the basic course of a disease state, it can be useful as adjunctive therapy in combating fatigue resulting from emotional or nutritional causes.

Launch Date

1975
Doses

Doses

DosePopulationAdverse events​
7.5 mg 1 times / day multiple, oral
Studied dose
Dose: 7.5 mg, 1 times / day
Route: oral
Route: multiple
Dose: 7.5 mg, 1 times / day
Sources:
unhealthy, 42 years
n = 47
Health Status: unhealthy
Condition: mild depression
Age Group: 42 years
Sex: M+F
Population Size: 47
Sources:
PubMed

PubMed

TitleDatePubMed
Drugs which stimulate affective behaviour. 3. Comparison of the effect of picrotoxin, pentylenetetrazol, bemigride, pipradrol, ectylurea, vanillic acid diethylamide and deanol.
1960 Jul
Recreational drugs, 3,4-Methylenedioxymethamphetamine(MDMA), 3,4-methylenedioxyamphetamine (MDA) and diphenylprolinol, inhibit neurite outgrowth in PC12 cells.
2010 Jun
Patents

Patents

Sample Use Guides

Alertonic Elixir (each 5 ml contains 0.67 mg pipradrol hydrochloride with vitamins and minerals) administred in adults 3 medicine measurefuls (15 ml), children over 15 years : 1 - 2 medicine measurefuls, children 4 - 15 years: 1 medicine measureful. To be taken three times daily 30 minutes before meals.
Route of Administration: Oral
In Vitro Use Guide
The inhibitory potencies of 27 compounds including pipradrol on the accumulation of 3H-dopamine (DA) in synaptosome-rich striatal homogenates of normal and reserpinized rats were determined.
Name Type Language
PIPRADROL HYDROCHLORIDE
JAN   MART.   MI   WHO-DD  
Common Name English
MERATONIC
Common Name English
PIPRADOLE HYDROCHLORIDE
Common Name English
2-PIPERIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, HYDROCHLORIDE
Systematic Name English
PIPRADROL HYDROCHLORIDE [JAN]
Common Name English
MERATRAN HYDROCHLORIDE
Common Name English
PIPRADROL HCL
Common Name English
PIPRADROL HYDROCHLORIDE [MI]
Common Name English
MERATRANS
Common Name English
.ALPHA.,.ALPHA.-DIPHENYL-2-PIPERIDINEMETHANOL HYDROCHLORIDE
Systematic Name English
LEPTIDROL
Brand Name English
PIPRAL
Common Name English
GERODIL
Common Name English
STIMOLAG FORTIS
Common Name English
DETARIL
Brand Name English
Pipradrol hydrochloride [WHO-DD]
Common Name English
MERATRAN
Brand Name English
LUXIDIN
Brand Name English
PIPRADROL HYDROCHLORIDE [MART.]
Common Name English
2-PIPERIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-, HYDROCHLORIDE (1:1)
Systematic Name English
PIPERADROL HYDROCHLORIDE
Common Name English
Code System Code Type Description
MERCK INDEX
m8867
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY Merck Index
FDA UNII
F6E46VR9Y2
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY
EVMPD
SUB03864MIG
Created by admin on Fri Dec 15 16:56:11 GMT 2023 , Edited by admin on Fri Dec 15 16:56:11 GMT 2023
PRIMARY
SMS_ID
100000085310
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY
PUBCHEM
66008
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110938
Created by admin on Fri Dec 15 16:56:11 GMT 2023 , Edited by admin on Fri Dec 15 16:56:11 GMT 2023
PRIMARY
CAS
71-78-3
Created by admin on Fri Dec 15 16:56:11 GMT 2023 , Edited by admin on Fri Dec 15 16:56:11 GMT 2023
PRIMARY
EPA CompTox
DTXSID50991292
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY
ECHA (EC/EINECS)
200-764-7
Created by admin on Fri Dec 15 16:56:12 GMT 2023 , Edited by admin on Fri Dec 15 16:56:12 GMT 2023
PRIMARY
DRUG BANK
DBSALT001777
Created by admin on Fri Dec 15 16:56:11 GMT 2023 , Edited by admin on Fri Dec 15 16:56:11 GMT 2023
PRIMARY