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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, (S)-

SMILES

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

InChI

InChIKey=XXEPPPIWZFICOJ-NSHDSACASA-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-/m0/s1

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
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
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
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
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
Obesity.
2003 Dec
Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation.
2003 Sep
Pharmacological and surgical treatment of obesity.
2004 Jul
Obesity.
2004 Jun
[Pharmacotherapy of obesity].
2004 Oct 7
Pharmacotherapy for obesity.
2005
Serotonin1A-receptor antagonism blocks psychostimulant properties of diethylpropion in marmosets (Callithrix penicillata).
2005 Mar 21
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
Obesity: pathophysiology and clinical management.
2009
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
Amfepramone, (S)-
Common Name English
DIETHYLPROPION, (S)-
Common Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-, (+)-
Systematic Name English
1-PROPANONE, 2-(DIETHYLAMINO)-1-PHENYL-, (2S)-
Systematic Name English
Amfepramone, (+)-
Common Name English
(+)-2-DIETHYLAMINOPROPIOPHENONE
Systematic Name English
DIETHYLPROPION, (+)-
Common Name English
(+)-Amfepramone
Common Name English
Code System Code Type Description
CAS
39648-49-2
Created by admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
PRIMARY
PUBCHEM
667427
Created by admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
PRIMARY
FDA UNII
I535TOV6LY
Created by admin on Sat Dec 16 09:46:54 GMT 2023 , Edited by admin on Sat Dec 16 09:46:54 GMT 2023
PRIMARY