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Record Information
Version5.0
StatusExpected but not Quantified
Creation Date2012-09-06 15:16:51 UTC
Update Date2021-09-14 15:46:59 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
Data?1582753255
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 hydrochlorideHMDB
AnorexHMDB
Crinex brand OF amfepramone hydrochlorideHMDB
DelgamerHMDB
LipominHMDB
Marion merrell dow brand OF amfepramone hydrochlorideHMDB
NobesineHMDB
PréfamoneHMDB
Théranol brand OF amfepramone hydrochlorideHMDB
Uriach brand OF amfepramone hydrochlorideHMDB
2-DiethylaminopropiophenoneHMDB
Dexo brand OF amfepramone hydrochlorideHMDB
Ifa norexHMDB
Medic brand OF amfepramone hydrochlorideHMDB
NeobesHMDB
RegibonHMDB
Dietil retardHMDB
DietilretardHMDB
Hydrochloride, diethylpropionHMDB
MaruateHMDB
Medix brand OF amfepramone hydrochlorideHMDB
Norex, ifaHMDB
PropionHMDB
Vortech brand OF amfepramone hydrochlorideHMDB
AmfepramonHMDB
Artegodan brand OF amfepramone hydrochlorideHMDB
Diethylpropion hydrochlorideHMDB
Dietil-retardHMDB
Hoechst brand OF amfepramone hydrochlorideHMDB
Investigacion farmaceutica brand OF amfepramone hydrochlorideHMDB
Marion merrell brand OF amfepramone hydrochlorideHMDB
ModératanHMDB
Nadeau brand OF amfepramone hydrochlorideHMDB
PhepranonHMDB
Pro DOC brand OF amfepramone hydrochlorideHMDB
RegenonHMDB
Temmler brand OF amfepramone hydrochlorideHMDB
TenuateHMDB
TepanilHMDB
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
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
Ontology
Disposition

Biological location

Source

Route of exposure

Physical Properties
StateSolid
Experimental Molecular Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.22 g/LNot Available
LogP2.8Not Available
Experimental Spectral Properties

Experimental Collision Cross Sections

PredictorAdduct TypeData SourceCCS Value (Å2)Reference
DeepCCS[M+H]+CBM148.030932474
Predicted Molecular Properties
PropertyValueSource
Water Solubility1.22 g/LALOGPS
logP10(2.8) g/LALOGPS
logP10(2.7) g/LChemAxon
logS10(-2.2) g/LALOGPS
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
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted Spectral Properties

Predicted Collision Cross Sections

PredictorAdduct TypeCCS Value (Å2)Reference
DarkChem[M+H]+148.20931661259
DarkChem[M-H]-145.78131661259

Predicted Kovats Retention Indices

Not Available
Spectra

GC-MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Experimental GC-MSGC-MS Spectrum - Diethylpropion EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e3852017-09-12HMDB team, MONA, MassBankView Spectrum
Experimental GC-MSGC-MS Spectrum - Diethylpropion EI-B (Non-derivatized)splash10-0udi-9600000000-6ee5a640521355e9e3852018-05-18HMDB team, MONA, MassBankView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diethylpropion GC-MS (Non-derivatized) - 70eV, Positivesplash10-0pb9-4900000000-dfe406cfb26414d42c912017-09-01Wishart LabView Spectrum
Predicted GC-MSPredicted GC-MS Spectrum - Diethylpropion GC-MS (Non-derivatized) - 70eV, PositiveNot Available2021-10-12Wishart LabView Spectrum
MSMass Spectrum (Electron Ionization)splash10-0udi-2900000000-43214c102b76f59ba4d12014-09-20Not AvailableView Spectrum

MS/MS Spectra

Spectrum TypeDescriptionSplash KeyDeposition DateSourceView
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 10V, Positive-QTOFsplash10-0a4i-0390000000-ce898493104c3b4c2c472016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 20V, Positive-QTOFsplash10-0pb9-1920000000-96569e0397bae3f7dad72016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 40V, Positive-QTOFsplash10-0kor-9400000000-099deea1407beaa58a502016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 10V, Negative-QTOFsplash10-0udi-0190000000-95dcba361e53234bdef92016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 20V, Negative-QTOFsplash10-0udi-5590000000-1b565cac019e1aaf40952016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 40V, Negative-QTOFsplash10-0kl0-8900000000-7a17ddfd7a2fe78351c62016-08-03Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 10V, Positive-QTOFsplash10-0a4i-0290000000-e6b4a514d0501abfde522021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 20V, Positive-QTOFsplash10-0zfr-1920000000-454738ae8af99f1764282021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 40V, Positive-QTOFsplash10-0fb9-9500000000-1d8dda4d3070e4f07ca52021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 10V, Negative-QTOFsplash10-0udi-0090000000-cd886772587c719fa7c62021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 20V, Negative-QTOFsplash10-0ufr-6690000000-31723177ed3fe72472542021-10-11Wishart LabView Spectrum
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - Diethylpropion 40V, Negative-QTOFsplash10-004i-9100000000-96fa4edb3fe7918f89092021-10-11Wishart LabView Spectrum
Biological Properties
Cellular Locations
  • Membrane
Biospecimen Locations
  • Blood
  • Urine
Tissue LocationsNot Available
Pathways
Normal Concentrations
BiospecimenStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot QuantifiedNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00937 details
UrineExpected but not QuantifiedNot QuantifiedNot 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
FooDB 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
Food Biomarker OntologyNot Available
VMH IDNot Available
MarkerDB IDNot Available
Good Scents IDNot Available
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 ]