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Record Information
Version4.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2018-05-20 20:14:12 UTC
HMDB IDHMDB0015072
Secondary Accession Numbers
  • HMDB15072
Metabolite Identification
Common NameDiethylpropion
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.
Structure
Thumb
Synonyms
ValueSource
(+-)-DiethylpropionChEBI
1-Phenyl-2-diethylamino-1-propanoneChEBI
2-(diethylamino)-1-Phenyl-1-propanoneChEBI
2-(diethylamino)PropiophenoneChEBI
alpha-BenzoyltriethylamineChEBI
alpha-DiethylaminopropiophenoneChEBI
AmfepramoneChEBI
AmfepramonumChEBI
AnfepramonaChEBI
a-BenzoyltriethylamineGenerator
α-benzoyltriethylamineGenerator
a-DiethylaminopropiophenoneGenerator
α-diethylaminopropiophenoneGenerator
DEA no. 1610HMDB
DiethylcathinoneHMDB
DiethylpropioneHMDB
3m Brand OF amfepramone hydrochlorideMeSH
AnorexMeSH
Crinex brand OF amfepramone hydrochlorideMeSH
DelgamerMeSH
LipominMeSH
Marion merrell dow brand OF amfepramone hydrochlorideMeSH
NobesineMeSH
PréfamoneMeSH
Théranol brand OF amfepramone hydrochlorideMeSH
Uriach brand OF amfepramone hydrochlorideMeSH
2-DiethylaminopropiophenoneMeSH
dexo Brand OF amfepramone hydrochlorideMeSH
Ifa norexMeSH
Medic brand OF amfepramone hydrochlorideMeSH
NeobesMeSH
RegibonMeSH
Dietil retardMeSH
DietilretardMeSH
Hydrochloride, diethylpropionMeSH
MaruateMeSH
Medix brand OF amfepramone hydrochlorideMeSH
Norex, ifaMeSH
PropionMeSH
Vortech brand OF amfepramone hydrochlorideMeSH
AmfepramonMeSH
Artegodan brand OF amfepramone hydrochlorideMeSH
Diethylpropion hydrochlorideMeSH
Dietil-retardMeSH
Hoechst brand OF amfepramone hydrochlorideMeSH
Investigacion farmaceutica brand OF amfepramone hydrochlorideMeSH
Marion merrell brand OF amfepramone hydrochlorideMeSH
ModératanMeSH
Nadeau brand OF amfepramone hydrochlorideMeSH
PhepranonMeSH
pro DOC Brand OF amfepramone hydrochlorideMeSH
RegenonMeSH
Temmler brand OF amfepramone hydrochlorideMeSH
TenuateMeSH
TepanilMeSH
Chemical FormulaC13H19NO
Average Molecular Weight205.2961
Monoisotopic Molecular Weight205.146664235
IUPAC Name2-(diethylamino)-1-phenylpropan-1-one
Traditional Namediethylpropion
CAS Registry Number134-80-5
SMILES
CCN(CC)C(C)C(=O)C1=CC=CC=C1
InChI Identifier
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
InChI KeyXXEPPPIWZFICOJ-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound 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
Ontology
Physiological effect

Health effect:

Disposition

Route of exposure:

Biological location:

Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.22 g/LNot Available
LogP2.8Not Available
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 Key
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e385View in MoNA
GC-MSGC-MS Spectrum - EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e385View in MoNA
Predicted GC-MSPredicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4900000000-dfe406cfb26414d42c91View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0a4i-0390000000-ce898493104c3b4c2c47View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0pb9-1920000000-96569e0397bae3f7dad7View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0kor-9400000000-099deea1407beaa58a50View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-0190000000-95dcba361e53234bdef9View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-5590000000-1b565cac019e1aaf4095View in MoNA
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0kl0-8900000000-7a17ddfd7a2fe78351c6View in MoNA
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-43214c102b76f59ba4d1View in MoNA
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00937 details
UrineExpected but not Quantified Not AvailableNot AvailableTaking drug identified by DrugBank entry DB00937 details
Abnormal Concentrations
Not Available
Predicted Concentrations
BiospecimenValueOriginal ageOriginal sexOriginal conditionComments
Blood0.000 uMAdult (>18 years old)BothNormalPredicted based on drug qualities
Blood0.000 umol/mmol creatinineAdult (>18 years old)BothNormalPredicted based on drug qualities
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00937
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID6762
KEGG Compound IDC06954
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkDiethylpropion
METLIN IDNot Available
PubChem Compound7029
PDB IDNot Available
ChEBI ID4530
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. 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. [PubMed:19897080 ]
  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. [PubMed:18353447 ]

Enzymes

General function:
Involved in neurotransmitter:sodium symporter 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
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:11131159 ]
  2. 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. [PubMed:19897080 ]

Transporters

General function:
Involved in neurotransmitter: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
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:17139284 ]
  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:17016423 ]
  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. [PubMed:19897080 ]