U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry RACEMIC
Molecular Formula C18H21NO
Molecular Weight 267.3654
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIPRADROL

SMILES

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

InChI

InChIKey=XSWHNYGMWWVAIE-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C18H21NO
Molecular Weight 267.3654
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
Picolinoxy group, a new leaving group for anti SN2' selective allylic substitution with aryl anions based on Grignard reagents.
2008 May 1
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.
Substance Class Chemical
Created
by admin
on Fri Dec 15 18:03:46 GMT 2023
Edited
by admin
on Fri Dec 15 18:03:46 GMT 2023
Record UNII
S6I030E0DA
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
PIPRADROL
INN   MI   WHO-DD  
INN  
Official Name English
.ALPHA.,.ALPHA.-DIPHENYL-.ALPHA.-(2-PIPERIDYL)METHANOL
Common Name English
PIPRALON
Common Name English
Pipradrol [WHO-DD]
Common Name English
.ALPHA.-(2-PIPERIDYL)BENZHYDRYL ALCOHOL
Systematic Name English
.ALPHA.-(2-PIPERIDYL)BENZHYDROL
Systematic Name English
GERODYL
Brand Name English
ALPHA-PIPRADOL
Common Name English
PYRIDROL
Common Name English
PIRIDROL
Common Name English
(±)-.ALPHA.,.ALPHA.-DIPHENYL-.ALPHA.-(2-PIPERIDINYL)METHANOL
Common Name English
2-PIPERIDINEMETHANOL, .ALPHA.,.ALPHA.-DIPHENYL-
Systematic Name English
.ALPHA.,.ALPHA.-DIPHENYL-2-PIPERIDINEMETHANOL
Systematic Name English
PIPRADOL
Common Name English
PYRIDROLE
Common Name English
pipradrol [INN]
Common Name English
PIPRADROL [MI]
Common Name English
MRD-108
Code English
Classification Tree Code System Code
WHO-ATC N06BX15
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
DEA NO. 1750
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
WHO-VATC QN06BX15
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
WIKIPEDIA Designer-drugs-Pipradrol
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
Code System Code Type Description
MERCK INDEX
m8867
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY Merck Index
FDA UNII
S6I030E0DA
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
HSDB
8016
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
WIKIPEDIA
PIPRADROL
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
PUBCHEM
10083
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
CAS
467-60-7
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
INN
550
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
ChEMBL
CHEMBL2110938
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
DRUG BANK
DB11584
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
DRUG CENTRAL
2195
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
CAS
18717-93-6
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
SUPERSEDED
MESH
C084823
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
SMS_ID
100000082198
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
EVMPD
SUB09883MIG
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
NCI_THESAURUS
C170324
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
ECHA (EC/EINECS)
207-394-5
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
EPA CompTox
DTXSID2023486
Created by admin on Fri Dec 15 18:03:47 GMT 2023 , Edited by admin on Fri Dec 15 18:03:47 GMT 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY