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

Details

Stereochemistry RACEMIC
Molecular Formula C13H19NO
Molecular Weight 205.2961
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Diethylpropion

SMILES

CCN(CC)C(C)C(=O)C1=CC=CC=C1

InChI

InChIKey=XXEPPPIWZFICOJ-UHFFFAOYSA-N
InChI=1S/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3

HIDE SMILES / InChI

Description

Diethylpropion is a sympathomimetic stimulant drug marketed as an appetite suppressant. Chemically, it is the N,N-diethyl analog of cathinone. Its mechanism of action is similar to other appetite suppressants such as sibutramine, phentermine and dextroamphetamine. Diethylpropion is an amphetamine that stimulates neurons to release or maintain high levels of a particular group of neurotransmitters known as catecholamines; these include dopamine and norepinephrine. High levels of these catecholamines tend to suppress hunger signals and appetite. Diethylpropion (through catecholamine elevation) may also indirectly affect leptin levels in the brain. It is theorized that diethylpropion can raise levels of leptin which signal satiety. It is also theorized that increased levels of the catecholamines are partially responsible for halting another chemical messenger known as neuropeptide Y. This peptide initiates eating, decreases energy expenditure, and increases fat storage. It is used in the management of exogenous obesity as a short-term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction.

CNS Activity

Curator's Comment: exerts its effects in the brain in a similar manner to amphetamine, stimulating the release as well as inhibiting the reuptake of neurotransmitters such as DA, NE, and 5-HT

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
1.014 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TENUATE

Approved Use

TENUATE and TENUATE DOSPAN are indicated in the management of exogenous obesity as a short-term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction in patients with an initial body mass index (BMI) of 30 kg/m2 or higher and who have not responded to appropriate weight reducing regimen (diet and/or exercise) alone.

Launch Date

1959
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
7.04 ng/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIETHYLPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
36.59 ng × h/mL
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIETHYLPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.95 h
75 mg single, oral
dose: 75 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
DIETHYLPROPION plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
120 mg 1 times / day multiple, oral
Studied dose
Dose: 120 mg, 1 times / day
Route: oral
Route: multiple
Dose: 120 mg, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer
Tox targets

Tox targets

TargetModalityActivityMetaboliteClinical evidence
PubMed

PubMed

TitleDatePubMed
Long-term use of diethylpropion in obesity.
1973
Some chemical and stereochemical aspects of diethylpropion metabolism in man.
1973 Dec
Proceedings: Pharmacokinetic and stereo-chemical studies on diethylpropion and related compounds in man.
1974 Dec
The stereochemistry of carbonyl reduction of diethylpropion and related amino-ketones in man.
1974 Dec 1
Schizophrenia-like reaction to diethylpropion.
1976 Nov 27
Cardiovascular effects of amphepramone.
1978 Apr-Jun
A double-blind controlled study of the use of diethylpropion hydrochloride (Tenuate) in obese patients in a rural practice.
1978 Oct 25
Diethylpropion and paranoid psychosis.
1979 Mar
Diethylpropion and psychosis.
1988 Apr
Transient ischemic attacks associated with amfepramone therapy: a case report.
1993 Sep-Oct
High-altitude pulmonary edema with primary pulmonary hypertension.
1996 Jul
Pupillary changes associated with the development of stimulant-induced mania: a case report.
1997 Jun
Kinetics of racemization of (+)- and (-)-diethylpropion: studies in aqueous solution, with and without the addition of cyclodextrins, in organic solvents and in human plasma.
1998
Enantioseparation of amfepramone (rac-diethylpropion): preparative separation of the enantiomers and enantioselective analysis.
1999
Bupropion for smokers. Drug is almost identical in structure to diethylpropion, a controlled drug.
2001 Feb 17
Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus.
2002 Jan
Obesity.
2003 Dec
Obesity.
2004 Jun
[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry].
2004 May
Pharmacotherapy for obesity.
2005
Diabesity: are weight loss medications effective?
2005
Meta-analysis: pharmacologic treatment of obesity.
2005 Apr 5
Phentermine and anaesthesia.
2005 Aug
Drug Insight: appetite suppressants.
2005 Feb
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
Obesity.
2005 Jun
Safety of obesity drugs.
2005 Nov
Safety of drug therapies used for weight loss and treatment of obesity.
2006
Weight loss medications--where do they fit in?
2006 Aug
[Drug treatment of obesity].
2006 Jan 9
Anti-obesity drugs and neural circuits of feeding.
2008 Apr
Rimonabant: the evidence for its use in the treatment of obesity and the metabolic syndrome.
2008 Feb 29
Maternal fluoxetine treatment decreases behavioral response to dopaminergic drugs in female pups.
2008 Nov-Dec
Update on the management of attention-deficit/hyperactivity disorder in children and adults: patient considerations and the role of lisdexamfetamine.
2009
Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion.
2009
Obesity: pathophysiology and clinical management.
2009
A randomized double-blind placebo-controlled study of the long-term efficacy and safety of diethylpropion in the treatment of obese subjects.
2009 Aug
Diethylpropion produces psychostimulant and reward effects.
2009 Feb
Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse.
2009 Jun
Necrotising vasculitis of the skin associated with an herbal medicine containing amfepramone.
2009 Jun
Clinical and economic considerations of antiobesity treatment: a review of orlistat.
2010
The sirenomelia sequence: a case history.
2010
Tackling obesity: new therapeutic agents for assisted weight loss.
2010 Apr 26
The serotonin syndrome-the need for physician's awareness.
2010 Aug 20
Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats.
2010 Jul 29
Long-term pharmacotherapy for obesity in elderly patients: a retrospective evaluation of medical records from a specialized obesity outpatient clinic.
2010 Jun 1
A new method for the simultaneous determination of 1,4-benzodiazepines and amfepramone as adulterants in phytotherapeutic formulations by voltammetry.
2010 Oct 10
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Name Type Language
Diethylpropion
MI   VANDF  
Common Name English
DIETHYLPROPION [MI]
Common Name English
DIETHYLCATHINONE
Common Name English
D07444
Code English
AMFEPRAMONE [HSDB]
Common Name English
Amfepramone
HSDB   INN   WHO-DD  
INN  
Official Name English
DIETHYLPROPION [VANDF]
Common Name English
Amfepramone [WHO-DD]
Common Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-
Systematic Name English
2-(DIETHYLAMINO)-1-PHENYL-1-PROPANONE
Systematic Name English
.ALPHA.-BENZOYLTRIETHYLAMINE
Common Name English
2-(DIETHYLAMINO)PROPIOPHENONE
Systematic Name English
ANFERPRAMON
Common Name English
J4.327C
Code English
2-DIETHYLAMINOPROPIOPHENONE
Systematic Name English
amfepramone [INN]
Common Name English
C06954
Code English
ANFEPRAMONE
Common Name English
Classification Tree Code System Code
DEA NO. 1610
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NDF-RT N0000175423
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NDF-RT N0000175651
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WHO-ATC A08AA03
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NDF-RT N0000175372
Created by admin on Fri Dec 15 17:09:17 GMT 2023 , Edited by admin on Fri Dec 15 17:09:17 GMT 2023
WHO-VATC QA08AA03
Created by admin on Fri Dec 15 17:09:17 GMT 2023 , Edited by admin on Fri Dec 15 17:09:17 GMT 2023
NCI_THESAURUS C29728
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NDF-RT N0000175372
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NCI_THESAURUS C47795
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LIVERTOX NBK548787
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Code System Code Type Description
ChEMBL
CHEMBL1194666
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PRIMARY
ECHA (EC/EINECS)
202-019-1
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PRIMARY
CHEBI
4530
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PRIMARY
FDA UNII
Q94YYU22B8
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PRIMARY
IUPHAR
7161
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PRIMARY
SMS_ID
100000087197
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PRIMARY
MESH
D004053
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PRIMARY
DRUG CENTRAL
874
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PRIMARY
DRUG BANK
DB00937
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PRIMARY
INN
974
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PRIMARY
EVMPD
SUB05417MIG
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PRIMARY
WIKIPEDIA
AMFEPRAMONE
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PRIMARY
DAILYMED
Q94YYU22B8
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PRIMARY
PUBCHEM
7029
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PRIMARY
EPA CompTox
DTXSID6022929
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PRIMARY
NCI_THESAURUS
C61721
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PRIMARY
RXCUI
3389
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PRIMARY RxNorm
CAS
90-84-6
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PRIMARY
MERCK INDEX
m4415
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PRIMARY Merck Index
HSDB
3059
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PRIMARY