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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

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
Diethylpropion and psychosis.
1988 Apr
Transient ischemic attacks associated with amfepramone therapy: a case report.
1993 Sep-Oct
Clinical and oculographic response to Tenuate Dospan (diethylpropionate) in a patient with congenital nystagmus.
2002 Jan
Progression rate of Chinese herb nephropathy: impact of Aristolochia fangchi ingested dose.
2002 Mar
Primary pulmonary hypertension after amfepramone (diethylpropion) with BMPR2 mutation.
2003 Sep
Pharmacological and surgical treatment of obesity.
2004 Jul
Obesity.
2004 Jun
Amfepramone does not cause primary pulmonary hypertension.
2004 May
Pharmacotherapy for obesity.
2005
Phentermine and anaesthesia.
2005 Aug
Non-paracetamol drug-induced fulminant hepatic failure among adults in Scotland.
2005 Feb
Obesity.
2005 Jun
Anti-obesity drugs and neural circuits of feeding.
2008 Apr
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
Neurochemical and behavioral effects elicited by bupropion and diethylpropion in rats.
2010 Jul 29
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 09:46:54 GMT 2023
Edited
by admin
on Sat Dec 16 09:46:54 GMT 2023
Record UNII
I535TOV6LY
Record Status Validated (UNII)
Record Version
  • Download
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
Related Record Type Details
RACEMATE -> ENANTIOMER