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
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
Pupillary changes associated with the development of stimulant-induced mania: a case report.
1997 Jun
WHO Expert Committee on Drug Dependence. Thirty-second report.
2001
The safety and efficacy of pharmaceutical and herbal caffeine and ephedrine use as a weight loss agent.
2001 Aug
Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus.
2002 Jan
Neurotoxicity of diethylpropion: neurochemical and behavioral findings in rats.
2002 Jun
Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose.
2002 Mar
WHO Expert Committee on Drug Dependence.
2003
Treatment of obesity: an update on anti-obesity medications.
2003 Feb
High prevalence of fenfluramine-related aortic regurgitation in women with end-stage renal disease secondary to Chinese herb nephropathy.
2003 May
[Determination of fenfluramine, diethylpropion and mazindol in slimming foods by gas chromatography-mass spectrometry].
2004 May
Amfepramone does not cause primary pulmonary hypertension.
2004 May
[Pharmacotherapy of obesity].
2004 Oct 7
Diabesity: are weight loss medications effective?
2005
Meta-analysis: pharmacologic treatment of obesity.
2005 Apr 5
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
Obesity.
2005 Jun
Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata).
2005 Mar 21
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
Maternal fluoxetine treatment decreases behavioral response to dopaminergic drugs in female pups.
2008 Nov-Dec
Obesity: pathophysiology and clinical management.
2009
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
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
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WHO-VATC QA08AA03
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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