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Identification
Name Diethylpropion
Accession Number DB00937 (APRD00919)
Type small molecule
Groups illicit, approved
Description

A appetite depressant considered to produce less central nervous system disturbance than most drugs in this therapeutic category. It is also considered to be among the safest for patients with hypertension. (From AMA Drug Evaluations Annual, 1994, p2290)
Structure Thumb
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
  • alpha-Benzoyltriethylamine
  • alpha-Diethylaminopropiophenone
  • Amfepramone
  • Amfepramone HCL
  • Amfepramone Hydrochloride
  • Amfepramonum [INN-Latin]
  • Amphepramonum hydrochloride
  • Anfepramona [INN-Spanish]
  • DEA No. 1610
  • Diethylcathinone
  • Diethylpropion HCL
  • Diethylpropion Hydrochloride
  • Diethylpropione
  • Diethylpropione hydrochloride
Brand names
  • Adiposon
  • Amfepramon
  • Amfepramone
  • Amphepramon
  • Amphepramone
  • Anfamon
  • Anorex
  • Cegramine
  • Danylen
  • Derfon
  • Dobesin
  • Frekentine
  • Keramik
  • Keramin
  • Magrene
  • Moderatan
  • Modulor
  • Neobes
  • Nopropiophenone
  • Obesitex
  • Parabolin
  • Prefamone
  • Regenon
  • Regenon hydrochloride
  • Reginon
  • Silutin
  • Tenuate
  • Tenuate Dospan
  • Tenuate hydrochloride
  • Tepanil
  • Tepanil Ten-tab
  • Tylinal
Brand name mixtures Not Available
Categories
  • Appetite Depressants
  • Anorexigenic Agents
  • Stimulants
CAS number 134-80-5
Weight Average: 205.2961
Monoisotopic: 205.146664235
Chemical Formula C13H19NO
InChI Key InChIKey=XXEPPPIWZFICOJ-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
2-(diethylamino)-1-phenylpropan-1-one
SMILES
CCN(CC)C(C)C(=O)C1=CC=CC=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenethylamines
  • Acetophenones and Derivatives
  • Amphetamines
Substructures
  • Amino Ketones
  • Benzene and Derivatives
  • Aliphatic and Aryl Amines
  • Phenethylamines
  • Aromatic compounds
  • Benzoyl Derivatives
  • Acetophenones and Derivatives
  • Amphetamines
  • Ketones
Pharmacology
Indication 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.
Pharmacodynamics 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.
Mechanism of action 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.
Absorption Diethylpropion is rapidly absorbed from the GI tract after oral administration.
Volume of distribution Not Available
Protein binding Not Available
Metabolism

Extensively metabolized through a complex pathway of biotransformation involving N-dealkylation and reduction. Many of these metabolites are biologically active and may participate in the therapeutic action of diethylpropion.
Route of elimination Diethylpropion is rapidly absorbed from the GI tract after oral administration and is extensively metabolized through a complex pathway of biotransformation involving N-dealkylation and reduction. Diethylpropion and/or its active metabolites are believed to cross the blood-brain barrier and the placenta. Diethylpropion and its metabolites are excreted mainly by the kidney.
Half life Using a phosphorescence assay that is specific for basic compounds containing benzoyl group, the plasma half-life of the aminoketone metabolites is estimated to be between 4 to 6 hours.
Clearance Not Available
Toxicity The reported oral LD50 for mice is 600 mg/kg, for rats is 250 mg/kg and for dogs is 225 mg/kg. Manifestation of acute overdosage include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, and panic states.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Sanofi aventis us llc
  • Watson pharmaceuticals
  • 3m pharmaceuticals inc
  • Corepharma llc
  • Sandoz inc
  • Teva pharmaceuticals usa inc
  • Tg united labs llc
  • Ucb inc
  • Watson laboratories inc
Packagers
Dosage forms
Form Route Strength
Tablet Oral
Tablet, extended release Oral
Prices
Unit description Cost Unit
Diethylpropion HCl CR 75 mg 24 Hour tablet 1.0 USD tablet
Tenuate 25 mg tablet 0.67 USD tablet
Diethylpropion 25 mg tablet 0.52 USD tablet
Diethylpropion HCl 25 mg tablet 0.29 USD tablet
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties
Property Value Source
logP 2.8 PhysProp
Predicted Properties
Property Value Source
water solubility 1.22e+00 g/l ALOGPS
logP 2.80 ALOGPS
logP 2.70 ChemAxon Molconvert
logS -2.23 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 0 ChemAxon Molconvert
polar surface area 20.31 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 63.88 ChemAxon Molconvert
polarizability 24.12 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference
  1. Adan RA, Vanderschuren LJ, la Fleur SE: Anti-obesity drugs and neural circuits of feeding. Trends Pharmacol Sci. 2008 Apr;29(4):208-17. Epub 2008 Mar 18. Pubmed
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed
External Links
Resource Link
KEGG Compound C06954 Link_out
PubChem Compound 7029 Link_out
PubChem Substance 46506622 Link_out
ChemSpider 6762 Link_out
ChEBI 4530 Link_out
ChEMBL 4530 Link_out
Therapeutic Targets Database DAP001452 Link_out
PharmGKB PA449305 Link_out
Drug Product Database 2047675 Link_out
RxList http://www.rxlist.com/cgi/generic3/diethprop.htm Link_out
Drugs.com http://www.drugs.com/cdi/diethylpropion.html Link_out
PDRhealth http://www.pdrhealth.com/drug_info/rxdrugprofiles/drugs/ten1435.shtml Link_out
Wikipedia http://en.wikipedia.org/wiki/Diethylpropion Link_out
ATC Codes
  • A08AA03
AHFS Codes
  • 28:20.92
PDB Entries Not Available
FDA label show (114.2 KB)
MSDS show (103.3 KB)
Interactions
Drug Interactions Not Available
Food Interactions
  • Take without regard to meals.
Targets

1. Sodium-dependent noradrenaline transporter

Pharmacological action: yes
Actions: inhibitor

Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: P23975 Link_out
Gene: SLC6A2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
  3. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed

2. Sodium-dependent dopamine transporter

Pharmacological action: yes
Actions: inhibitor

Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals

Organism class: human
UniProt ID: Q01959 Link_out
Gene: SLC6A3 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Yu H, Rothman RB, Dersch CM, Partilla JS, Rice KC: Uptake and release effects of diethylpropion and its metabolites with biogenic amine transporters. Bioorg Med Chem. 2000 Dec;8(12):2689-92. Pubmed
  2. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed
Comments
Drug created on June 13, 2005 07:24 / Updated on April 19, 2011 15:07

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.