ContaminantDB: Diethylpropion

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (3)XML

Record Information

Version

1.0

Creation Date

2009-07-21 20:27:59 UTC

Update Date

2026-05-14 16:53:22 UTC

Accession Number

CHEM002306

Identification

Common Name

Diethylpropion

Class

Small Molecule

Description

Diethylpropion 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.

Contaminant Sources

HMDB Contaminants - Urine
T3DB toxins

Contaminant Type

Amine
Anorexigenic Agent
Appetite Depressant
Drug
Ester
Human Neurotoxin
Metabolite
Organic Compound
Stimulant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
(+-)-Diethylpropion	ChEBI
1-Phenyl-2-diethylamino-1-propanone	ChEBI
2-(Diethylamino)-1-phenyl-1-propanone	ChEBI
2-(Diethylamino)propiophenone	ChEBI
alpha-Benzoyltriethylamine	ChEBI
alpha-Diethylaminopropiophenone	ChEBI
Amfepramone	ChEBI
Amfepramonum	ChEBI
Anfepramona	ChEBI
a-Benzoyltriethylamine	Generator
Α-benzoyltriethylamine	Generator
a-Diethylaminopropiophenone	Generator
Α-diethylaminopropiophenone	Generator
DEA no. 1610	HMDB
Diethylcathinone	HMDB
Diethylpropione	HMDB
3m Brand OF amfepramone hydrochloride	HMDB
Anorex	HMDB
Crinex brand OF amfepramone hydrochloride	HMDB
Delgamer	HMDB
Lipomin	HMDB
Marion merrell dow brand OF amfepramone hydrochloride	HMDB
Nobesine	HMDB
Préfamone	HMDB
Théranol brand OF amfepramone hydrochloride	HMDB
Uriach brand OF amfepramone hydrochloride	HMDB
2-Diethylaminopropiophenone	HMDB
Dexo brand OF amfepramone hydrochloride	HMDB
Ifa norex	HMDB
Medic brand OF amfepramone hydrochloride	HMDB
Neobes	HMDB
Regibon	HMDB
Dietil retard	HMDB
Dietilretard	HMDB
Hydrochloride, diethylpropion	HMDB
Maruate	HMDB
Medix brand OF amfepramone hydrochloride	HMDB
Norex, ifa	HMDB
Propion	HMDB
Vortech brand OF amfepramone hydrochloride	HMDB
Amfepramon	HMDB
Artegodan brand OF amfepramone hydrochloride	HMDB
Diethylpropion hydrochloride	HMDB
Dietil-retard	HMDB
Hoechst brand OF amfepramone hydrochloride	HMDB
Investigacion farmaceutica brand OF amfepramone hydrochloride	HMDB
Marion merrell brand OF amfepramone hydrochloride	HMDB
Modératan	HMDB
Nadeau brand OF amfepramone hydrochloride	HMDB
Phepranon	HMDB
Pro DOC brand OF amfepramone hydrochloride	HMDB
Regenon	HMDB
Temmler brand OF amfepramone hydrochloride	HMDB
Tenuate	HMDB
Tepanil	HMDB

Chemical Formula

C₁₃H₁₉NO

Average Molecular Mass

205.296 g/mol

Monoisotopic Mass

205.147 g/mol

CAS Registry Number

90-84-6

IUPAC Name

2-(diethylamino)-1-phenylpropan-1-one

Traditional Name

diethylpropion

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 Key

XXEPPPIWZFICOJ-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.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Alkyl-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 Framework

Aromatic homomonocyclic compounds

External Descriptors

tertiary amine (CHEBI:4530 )
aromatic ketone (CHEBI:4530 )

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Membrane

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

appetite depressant

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	168°C
Boiling Point	Not Available
Solubility	1.22e+00 g/L

Predicted Properties

Property	Value	Source
Water Solubility	1.22 g/L	ALOGPS
logP	2.8	ALOGPS
logP	2.7	ChemAxon
logS	-2.2	ALOGPS
pKa (Strongest Acidic)	17.43	ChemAxon
pKa (Strongest Basic)	7.44	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	20.31 Å²	ChemAxon
Rotatable Bond Count	5	ChemAxon
Refractivity	63.88 m³·mol⁻¹	ChemAxon
Polarizability	24.12 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-9600000000-6ee5a640521355e9e385	Spectrum
GC-MS	GC-MS Spectrum - EI-B (Non-derivatized)	splash10-0udi-9600000000-6ee5a640521355e9e385	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	splash10-0pb9-4900000000-dfe406cfb26414d42c91	Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - GC-MS (Non-derivatized) - 70eV, Positive	Not Available	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0390000000-ce898493104c3b4c2c47	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0pb9-1920000000-96569e0397bae3f7dad7	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0kor-9400000000-099deea1407beaa58a50	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0190000000-95dcba361e53234bdef9	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0udi-5590000000-1b565cac019e1aaf4095	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0kl0-8900000000-7a17ddfd7a2fe78351c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0290000000-e6b4a514d0501abfde52	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0zfr-1920000000-454738ae8af99f176428	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0fb9-9500000000-1d8dda4d3070e4f07ca5	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0udi-0090000000-cd886772587c719fa7c6	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0ufr-6690000000-31723177ed3fe7247254	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-004i-9100000000-96fa4edb3fe7918f8909	Spectrum
MS	Mass Spectrum (Electron Ionization)	splash10-0udi-2900000000-43214c102b76f59ba4d1	Spectrum

Toxicity Profile

Route of Exposure

Diethylpropion is rapidly absorbed from the GI tract after oral administration.

Mechanism of Toxicity

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.

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.

Toxicity Values

LD50: 600 mg/kg (Oral, Mouse) (1) LD50: 50 mg/kg (Oral, Rat) (1) LD50: 225 mg/kg (Oral, Dog) (1)

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

No indication of carcinogenicity to humans (not listed by IARC).

Uses/Sources

Used 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 Level

Not Available

Health Effects

Using 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.

Symptoms

Manifestation of acute overdosage include restlessness, tremor, hyperreflexia, rapid respiration, confusion, assaultiveness, hallucinations, and panic states.

Treatment

Management 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

Concentrations

Not Available

External Links

DrugBank ID

DB00937

HMDB ID

HMDB0015072

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID