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

Details

Stereochemistry RACEMIC
Molecular Formula C13H19NO.ClH
Molecular Weight 241.757
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of Diethylpropion Hydrochloride

SMILES

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

InChI

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

HIDE SMILES / InChI

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C13H19NO
Molecular Weight 205.2961
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

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
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
Effects of amphetamine, dexfenfluramine, diazepam, and other pharmacological and dietary manipulations on food "seeking" and "taking" behavior in non-human primates.
2001 Oct
[Uneasiness about the safety of bupropion as an aid to smoking cessation unjustified].
2001 Oct 20
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
Obesity.
2003 Dec
Effects of diethylpropion treatment and withdrawal on aorta reactivity, endothelial factors and rat behavior.
2003 Jul 15
High prevalence of fenfluramine-related aortic regurgitation in women with end-stage renal disease secondary to Chinese herb nephropathy.
2003 May
Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation.
2003 Sep
Obesity: an overview on its current perspectives and treatment options.
2004 Apr 14
Homeopathic products, not as innocent and safe as they seem? A case report.
2004 Aug
Pharmacological and surgical treatment of obesity.
2004 Jul
Obesity.
2004 Jun
[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
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
Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata).
2005 Mar 21
Safety of obesity drugs.
2005 Nov
Anti-obesity drugs and neural circuits of feeding.
2008 Apr
Update on the management of attention-deficit/hyperactivity disorder in children and adults: patient considerations and the role of lisdexamfetamine.
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
Patents

Sample Use Guides

In Vivo Use Guide
Unknown
Route of Administration: Unknown
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Fri Dec 15 17:02:57 GMT 2023
Edited
by admin
on Fri Dec 15 17:02:57 GMT 2023
Record UNII
19V2PL39NG
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
Diethylpropion Hydrochloride
MART.   MI   ORANGE BOOK   USP   VANDF  
USP  
Official Name English
TENUATE
Brand Name English
PREFAMONE
Brand Name English
DIETHYLPROPION HYDROCHLORIDE [MI]
Common Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-, HYDROCHLORIDE
Systematic Name English
Amfepramone hydrochloride
WHO-DD  
Common Name English
Amfepramone hydrochloride [WHO-DD]
Common Name English
DOBESIN
Brand Name English
DIETHYLPROPION HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
DIETHYLPROPION HYDROCHLORIDE CIV
USP-RS  
Common Name English
DIETHYLPROPION HYDROCHLORIDE [VANDF]
Common Name English
DIETHYLPROPION HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DIETHYLPROPION HCL
Common Name English
D03801
Code English
TEPANIL
Brand Name English
DIETHYLPROPION HYDROCHLORIDE [USP-RS]
Common Name English
REGENON
Brand Name English
MODERATAN
Brand Name English
2-(Diethylamino)propiophenone hydrochloride
Systematic Name English
.ALPHA.-BENZOYLTRIETHYLAMINE HYDROCHLORIDE
Common Name English
2-DIETHYLAMINOPROPIOPHENONE HYDROCHLORIDE
Systematic Name English
2-(DIETHYLAMINO)-1-PHENYL-1-PROPANONE HYDROCHLORIDE
Systematic Name English
ANOREX
Brand Name English
DIETHYLPROPION HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29728
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
NCI_THESAURUS C47795
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
Code System Code Type Description
CAS
134-80-5
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
RS_ITEM_NUM
1194009
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
NCI_THESAURUS
C47486
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
ECHA (EC/EINECS)
205-156-5
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
EVMPD
SUB00434MIG
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
ChEMBL
CHEMBL1194666
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
EPA CompTox
DTXSID4047838
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
CHEBI
643703
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
MERCK INDEX
m4415
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY Merck Index
SMS_ID
100000085421
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
PUBCHEM
91442
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
FDA UNII
19V2PL39NG
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
DAILYMED
19V2PL39NG
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
DRUG BANK
DBSALT000484
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY
RXCUI
81998
Created by admin on Fri Dec 15 17:02:57 GMT 2023 , Edited by admin on Fri Dec 15 17:02:57 GMT 2023
PRIMARY RxNorm
Related Record Type Details
PARENT -> SALT/SOLVATE