2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

• ChemBase ID: 44448
• Molecular Formular: C13H19Cl2NO
• Molecular Mass: 276.20206
• Monoisotopic Mass: 275.08436959
• SMILES: C(=O)(c1cc(Cl)ccc1)C(NC(C)(C)C)C.Cl
• Canonical SMILES: Clc1cccc(c1)C(=O)C(NC(C)(C)C)C.Cl
• InChI: InChI=1S/C13H18ClNO.ClH/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10;/h5-9,15H,1-4H3;1H
• InChIKey: HEYVINCGKDONRU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride
• IUPAC Traditional name: bupropion hydrochloride; 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride
• Synonyms: Bupropion hydrochloride; Bupropion; Wellbutrin; Zyban; Voxra; Amfebutamone hydrochloride; 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride; 1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone Hydrochloride; (±)-Bupropion Hydrochloride; Amfebutamon Hydrochloride; Amfebutamone Hydrochloride; Aplenzin Hydrochloride; Bupropion Hydrochloride; Bupropion SR Hydrochloride; Elontril Hydrochloride; α-(tert-Butylamino)-m-chloropropiophenone Hydrochloride; (±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride; Bupropion hydrochloride; (±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride; BUPROPION; More...

Database IDs

• CAS Number: 31677-93-7; 34911-55-2
• EC Number: 250-759-9
• MDL Number: MFCD00055209
• PubChem SID: 162049211; 24277884
• PubChem CID: 62884

CALCULATED PROPERTIES

• Acid pKa: 18.286419
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.6626676
• LogD (pH = 7.4): 2.3901906
• Log P: 3.2661126
• Molar Refractivity: 67.6994 cm^3
• Polarizability: 26.657854 Å^3
• Polar Surface Area: 29.1 Å^2
• Rotatable Bonds: 4
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: 1 M HCl: soluble333 mg/mL (solutions may be stored for several days at 4 °C.); Ethanol; ethanol: soluble193 mg/mL (solutions may be stored for several days at 4 °C.); H2O: soluble312 mg/mL (solutions may be stored for several days at 4 °C.); Methanol; Water
• Apperance: white solid; White Solid
• Melting Point: 211-214°C; 233-234°C

Safety Information

• Storage Condition: -20°C; Hygroscopic, -20°C Freezer, Under inert atmosphere; Room Temperature (15-30°C)
• Storage Warning: IRRITANT
• RTECS: UG8858000
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 22; R:22
• Safety Statements: 36; S:36/37/39
• TSCA Listed: false
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H302
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Faceshields, Gloves

Pharmacology Properties

• Gene Information: human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)
• Mechanism of Action: Dopamine reuptake inhibitor

Product Information

• Purity: ≥98% (HPLC); 95+%; 98%
• Salt Data: HCl; hydrochloride
• Application(s): Antidepressant; Used as a smoking cessation aid

DETAILS

MP Biomedicals - 02153760

Hydrochloride
Dopamine uptake inhibitor

Selleck Chemicals - S2452

Research Area: Neurological Disease
Biological Activity:
Amfebutamone (Bupropion) is a selective norepinephrine-dopamine reuptake inhibitor with IC50 of 6.5 and 3.4µM for the reuptake of dopamine and norepinephrine, respectively. Its primary pharmacological action is Norepinephrine-dopamine reuptake inhibition. It binds selectively to the dopamine transporter, but its behavioural effects have often been attributed to its inhibition of norepinephrine reuptake. It also acts as a nicotinic acetylcholine receptor antagonist. [1][2][3]

Sigma Aldrich - B102

Biochem/physiol Actions
Inhibits the dopamine and norepinephrine transporters with Kis of 2.8 μM and 1.4 μM, respectively. Does not inhibit the serotonin transporter (Ki = 45 μM). Antidepressant.

Toronto Research Chemicals - B689625

A selective inhibitor of dopamine uptake. An antidepressant of the aminoketone class; aid in smoking cessation.

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