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

• ChemBase ID: 813
• Molecular Formular: C13H19NO
• Molecular Mass: 205.29606
• Monoisotopic Mass: 205.14666423
• SMILES: O=C(C(N(CC)CC)C)c1ccccc1
• Canonical SMILES: CCN(C(C(=O)c1ccccc1)C)CC
• 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
• InChIKey: XXEPPPIWZFICOJ-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(diethylamino)-1-phenylpropan-1-one
• IUPAC Traditional name: diethylpropion
• Brand Name: 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
• Synonyms: Amfepramonum [INN-Latin]; Amfepramone Hydrochloride; Amfepramone HCL; alpha-Diethylaminopropiophenone; alpha-Benzoyltriethylamine; Amphepramonum hydrochloride; Anfepramona [INN-Spanish]; DEA No. 1610; Diethylcathinone; Diethylpropion HCL; Diethylpropione hydrochloride; Diethylpropione; Diethylpropion Hydrochloride; Amfepramone; Diethylpropion

Database IDs

• CAS Number: 134-80-5
• PubChem SID: 160964276; 46506622
• PubChem CID: 7029

CALCULATED PROPERTIES

JChem

• Acid pKa: 17.427208
• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.7699641
• LogD (pH = 7.4): 2.3825548
• Log P: 2.704772
• Molar Refractivity: 63.8809 cm^3
• Polarizability: 24.823383 Å^3
• Polar Surface Area: 20.31 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

ALOGPS 2.1

• Log P: 2.8
• LOG S: -2.23
• Solubility (Water): 1.22e+00 g/l

PROPERTIES

Physical Property

• Hydrophobicity(logP): 2.8

DETAILS

DrugBank - DB00937

• Drug 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)
• 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.
• Pharmacology: 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.
• 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
• Biotransformation: 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.
• Absorption: Diethylpropion is rapidly absorbed from the GI tract after oral administration.
• 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.
• 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.
• References: 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] ; 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: Wikipedia; RxList; PDRhealth; Drugs.com

REFERENCES

• 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
• Arias HR, Santamaria A, Ali SF: Pharmacological and neurotoxicological actions mediated by bupropion and diethylpropion. Int Rev Neurobiol. 2009;88:223-55. Pubmed