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Record Information
Version2.0
Creation Date2009-07-21 20:27:59 UTC
Update Date2014-12-24 20:25:53 UTC
Accession NumberT3D2935
Identification
Common NameDiethylpropion
ClassSmall Molecule
DescriptionDiethylpropion is only found in individuals that have used or taken this drug. It is 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)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.
Compound Type
  • Amine
  • Anorexigenic Agent
  • Appetite Depressant
  • Drug
  • Ester
  • Metabolite
  • Organic Compound
  • Stimulant
  • Synthetic Compound
Chemical Structure
Thumb
Synonyms
Synonym
(+-)-Diethylpropion
(±)-diethylpropion
1-phenyl-2-diethylamino-1-propanone
2-(Diethylamino)-1-phenyl-1-propanone
2-(Diethylamino)propiophenone
alpha-Benzoyltriethylamine
alpha-Diethylaminopropiophenone
Amfepramone
Amfepramonum
Anfepramona
Anorex
DEA No. 1610
Diethylcathinone
Diethylpropione
Dobesin
Frekentine
Linea
Moderatan
Neobes
Nobesine
Prefamone
Regenon
Tenuate
Tepanil
Tylinal
Chemical FormulaC13H19NO
Average Molecular Mass205.296 g/mol
Monoisotopic Mass205.147 g/mol
CAS Registry Number90-84-6
IUPAC Name2-(diethylamino)-1-phenylpropan-1-one
Traditional Namediethylpropion
SMILESCCN(CC)C(C)C(=O)C1=CC=CC=C1
InChI IdentifierInChI=1/C13H19NO/c1-4-14(5-2)11(3)13(15)12-9-7-6-8-10-12/h6-11H,4-5H2,1-3H3
InChI KeyInChIKey=XXEPPPIWZFICOJ-UHFFFAOYNA-N
Chemical Taxonomy
Description belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
KingdomOrganic compounds
Super ClassOrganic oxygen compounds
ClassOrganooxygen compounds
Sub ClassCarbonyl compounds
Direct ParentAlkyl-phenylketones
Alternative Parents
Substituents
  • Alkyl-phenylketone
  • Phenylpropane
  • Benzoyl
  • Aryl alkyl ketone
  • Benzenoid
  • Monocyclic benzene moiety
  • Alpha-aminoketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Hydrocarbon derivative
  • Amine
  • Organic nitrogen compound
  • Organonitrogen compound
  • Organopnictogen compound
  • Organic oxide
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Biological Properties
StatusDetected and Not Quantified
OriginExogenous
Cellular Locations
  • Membrane
Biofluid LocationsNot Available
Tissue LocationsNot Available
PathwaysNot Available
Applications
Biological RolesNot Available
Chemical RolesNot Available
Physical Properties
StateSolid
AppearanceWhite powder.
Experimental Properties
PropertyValue
Melting Point168°C
Boiling PointNot Available
Solubility1.22e+00 g/L
LogP2.8
Predicted Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP2.8ALOGPS
logP2.7ChemAxon
logS-2.2ALOGPS
pKa (Strongest Acidic)17.43ChemAxon
pKa (Strongest Basic)7.44ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area20.31 ŲChemAxon
Rotatable Bond Count5ChemAxon
Refractivity63.88 m³·mol⁻¹ChemAxon
Polarizability24.12 ųChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Spectra
Spectrum TypeDescriptionSplash KeyView
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e385JSpectraViewer | MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e385JSpectraViewer | MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4900000000-dfe406cfb26414d42c91JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-ce898493104c3b4c2c47JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-1920000000-96569e0397bae3f7dad7JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kor-9400000000-099deea1407beaa58a50JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-95dcba361e53234bdef9JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5590000000-1b565cac019e1aaf4095JSpectraViewer
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kl0-8900000000-7a17ddfd7a2fe78351c6JSpectraViewer
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-43214c102b76f59ba4d1JSpectraViewer | MoNA
Toxicity Profile
Route of ExposureDiethylpropion is rapidly absorbed from the GI tract after oral administration.
Mechanism of ToxicityDiethylpropion 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.
MetabolismExtensively 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.
Toxicity ValuesLD50: 600 mg/kg (Oral, Mouse) (1) LD50: 50 mg/kg (Oral, Rat) (1) LD50: 225 mg/kg (Oral, Dog) (1)
Lethal DoseNot Available
Carcinogenicity (IARC Classification)No indication of carcinogenicity to humans (not listed by IARC).
Uses/SourcesUsed as an antidepressant. [Wikipedia]. 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.
Minimum Risk LevelNot Available
Health EffectsUsing large amounts of these drugs can result in a condition known as amphetamine psychosis -- which can result in auditory, visual and tactile hallucinations, intense paranoia, irrational thoughts and beliefs, delusions, and mental confusion.
SymptomsManifestation of acute overdosage include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, and panic states.
TreatmentManagement of acute diethylpropion hydrochloride intoxication is largely symptomatic and includes lavage and sedation with a barbiturate. Experience with hemodialysis or peritoneal dialysis is inadequate to permit recommendation in this regard. Intravenous phentolamine (Regitine
Normal Concentrations
Not Available
Abnormal Concentrations
Not Available
DrugBank IDDB00937
HMDB IDHMDB15072
PubChem Compound ID7029
ChEMBL IDCHEMBL1194666
ChemSpider ID6762
KEGG IDC06954
UniProt IDNot Available
OMIM ID
ChEBI ID4530
BioCyc IDNot Available
CTD IDNot Available
Stitch IDDiethylpropion
PDB IDNot Available
ACToR IDNot Available
Wikipedia LinkDiethylpropion
References
Synthesis Reference

Schutte, J.; U.S. Patent 3,001,910; September 26, 1961; assigned to Firma Ternmler-Werke
(W. Germany).

MSDSLink
General References
  1. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M: DrugBank: a knowledgebase for drugs, drug actions and drug targets. Nucleic Acids Res. 2008 Jan;36(Database issue):D901-6. Epub 2007 Nov 29. [18048412 ]
  2. Adan RA, Vanderschuren LJ, la Fleur SE: Anti-obesity drugs and neural circuits of feeding. Trends Pharmacol Sci. 2008 Apr;29(4):208-17. doi: 10.1016/j.tips.2008.01.008. Epub 2008 Mar 18. [18353447 ]
  3. Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. doi: 10.1016/S0074-7742(09)88009-4. [19897080 ]
Gene Regulation
Up-Regulated GenesNot Available
Down-Regulated GenesNot Available

Targets

General Function:
Monoamine transmembrane transporter activity
Specific Function:
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A3
Uniprot ID:
Q01959
Molecular Weight:
68494.255 Da
General Function:
Norepinephrine:sodium symporter activity
Specific Function:
Amine transporter. Terminates the action of noradrenaline by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name:
SLC6A2
Uniprot ID:
P23975
Molecular Weight:
69331.42 Da