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Details

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

SHOW SMILES / InChI
Structure of Amfepramone, (R)-

SMILES

CCN(CC)[C@H](C)C(=O)C1=CC=CC=C1

InChI

InChIKey=XXEPPPIWZFICOJ-LLVKDONJSA-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/t11-/m1/s1

HIDE SMILES / InChI

Molecular Formula C13H19NO
Molecular Weight 205.2961
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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
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
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
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
The safety and efficacy of pharmaceutical and herbal caffeine and ephedrine use as a weight loss agent.
2001 Aug
[Uneasiness about the safety of bupropion as an aid to smoking cessation unjustified].
2001 Oct 20
Neurotoxicity of diethylpropion: neurochemical and behavioral findings in rats.
2002 Jun
WHO Expert Committee on Drug Dependence.
2003
Treatment of obesity: an update on anti-obesity medications.
2003 Feb
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
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
Safety of drug therapies used for weight loss and treatment of obesity.
2006
Weight loss medications--where do they fit in?
2006 Aug
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
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
A randomized double-blind placebo-controlled study of the long-term efficacy and safety of diethylpropion in the treatment of obese subjects.
2009 Aug
Abuse liability and safety of oral lisdexamfetamine dimesylate in individuals with a history of stimulant abuse.
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
Substance Class Chemical
Created
by admin
on Sat Dec 16 09:46:55 GMT 2023
Edited
by admin
on Sat Dec 16 09:46:55 GMT 2023
Record UNII
P1A5AE6Q2R
Record Status Validated (UNII)
Record Version
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Name Type Language
Amfepramone, (R)-
Common Name English
(-)-2-DIETHYLAMINOPROPIOPHENONE
Systematic Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-, (2R)-
Systematic Name English
(-)-Amfepramone
Common Name English
Amfepramone, (-)-
Common Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-, (-)-
Systematic Name English
DIETHYLPROPION, (R)-
Common Name English
DIETHYLPROPION, (-)-
Common Name English
Code System Code Type Description
PUBCHEM
2201750
Created by admin on Sat Dec 16 09:46:55 GMT 2023 , Edited by admin on Sat Dec 16 09:46:55 GMT 2023
PRIMARY
CAS
39648-50-5
Created by admin on Sat Dec 16 09:46:55 GMT 2023 , Edited by admin on Sat Dec 16 09:46:55 GMT 2023
PRIMARY
FDA UNII
P1A5AE6Q2R
Created by admin on Sat Dec 16 09:46:55 GMT 2023 , Edited by admin on Sat Dec 16 09:46:55 GMT 2023
PRIMARY
Related Record Type Details
RACEMATE -> ENANTIOMER