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34911-55-2 molecular structure
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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 and InChIs

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

Cite this record

CBID:44448 http://www.chembase.cn/molecule-44448.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
CAS Number
34911-55-2
31677-93-7
EC Number
250-759-9
MDL Number
MFCD00055209
PubChem SID
162049211
24277884
PubChem CID
62884

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem
Acid pKa 18.286419  H Acceptors
H Donor LogD (pH = 5.5) 0.6626676 
LogD (pH = 7.4) 2.3901906  Log P 3.2661126 
Molar Refractivity 67.6994 cm3 Polarizability 26.657854 Å3
Polar Surface Area 29.1 Å2 Rotatable Bonds
Lipinski's Rule of Five true 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
1 M HCl: soluble333 mg/mL (solutions may be stored for several days at 4 °C.) expand Show data source
Ethanol expand Show data source
ethanol: soluble193 mg/mL (solutions may be stored for several days at 4 °C.) expand Show data source
H2O: soluble312 mg/mL (solutions may be stored for several days at 4 °C.) expand Show data source
Methanol expand Show data source
Water expand Show data source
Apperance
white solid expand Show data source
White Solid expand Show data source
Melting Point
211-214°C expand Show data source
233-234°C expand Show data source
Storage Condition
-20°C expand Show data source
Hygroscopic, -20°C Freezer, Under inert atmosphere expand Show data source
Room Temperature (15-30°C) expand Show data source
Storage Warning
IRRITANT expand Show data source
RTECS
UG8858000 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
Download expand Show data source
German water hazard class
3 expand Show data source
Risk Statements
22 expand Show data source
R:22 expand Show data source
Safety Statements
36 expand Show data source
S:36/37/39 expand Show data source
TSCA Listed
false expand Show data source
GHS Pictograms
GHS07 expand Show data source
GHS Signal Word
Warning expand Show data source
GHS Hazard statements
H302 expand Show data source
Personal Protective Equipment
dust mask type N95 (US), Eyeshields, Faceshields, Gloves expand Show data source
Gene Information
human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816) expand Show data source
Mechanism of Action
Dopamine reuptake inhibitor expand Show data source
Purity
≥98% (HPLC) expand Show data source
95+% expand Show data source
98% expand Show data source
Salt Data
HCl expand Show data source
hydrochloride expand Show data source
Certificate of Analysis
Download expand Show data source
Download expand Show data source
Application(s)
Antidepressant expand Show data source
Used as a smoking cessation aid expand Show data source

DETAILS

DETAILS

MP Biomedicals MP Biomedicals Selleck Chemicals Selleck Chemicals Sigma Aldrich Sigma Aldrich TRC TRC
MP Biomedicals - 02153760 external link
Hydrochloride
Dopamine uptake inhibitor
Selleck Chemicals - S2452 external link
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 external link
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 external link
A selective inhibitor of dopamine uptake. An antidepressant of the aminoketone class; aid in smoking cessation.

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • •  Slemmer JE et al. J Pharmacol Exp Ther. 2000 Oct
  • • Soroko, F., et al.: J. Pharm. Pharmacol., 29, 769 (1977)
  • • Tucker, W.E., J. Clin. Psychiatry, 44, 60 (1977)
  • • Hsyu, P-H., et al.: J. Clin. Pharmacol., 37, 737 (1977)
  • • West, R., et al.: Expert Opin. Pharmacother., 4, 533 (1977)
  • • Ger. Pat., 1971, Wellcome, 2 059 618; CA, 76, 3551k, (synth, pharmacol)
  • • Peck, A.W. et al., Br. J. Clin. Pharmacol., 1979, 7, 469, (pharmacol)
  • • Maxwell, R.A. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 1, (rev)
  • • Bryant, S.G. et al., Clin. Pharm., 1983, 2, 525, (rev)
  • • Dufresne, R.L. et al., Drug Intell. Clin. Pharm., 1984, 18, 957, (rev)
  • • Suckow, R.F. et al., Drug Metab. Dispos., 1986, 14, 692, (metab)
  • • Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 280
  • • Holm, K.J. et al., Drugs, 2000, 59, 1007-1024
  • • Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, WBJ500
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PATENTS

PATENTS

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INTERNET

INTERNET

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