Home > Compound List > Compound details
31677-93-7 molecular structure
click picture or here to close

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

ChemBase ID: 1027
Molecular Formular: C13H18ClNO
Molecular Mass: 239.74112
Monoisotopic Mass: 239.10769188
SMILES and InChIs

SMILES:
Clc1cc(C(=O)C(NC(C)(C)C)C)ccc1
Canonical SMILES:
Clc1cccc(c1)C(=O)C(NC(C)(C)C)C
InChI:
InChI=1S/C13H18ClNO/c1-9(15-13(2,3)4)12(16)10-6-5-7-11(14)8-10/h5-9,15H,1-4H3
InChIKey:
SNPPWIUOZRMYNY-UHFFFAOYSA-N

Cite this record

CBID:1027 http://www.chembase.cn/molecule-1027.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one
IUPAC Traditional name
bupropion
Brand Name
Wellbatrin
Wellbutrin
Wellbutrin SR
Wellbutrin XL
Zyban
Wellbutrin, Zyban
Synonyms
Bupropion Hcl
Amfebutamone
Bupropion
BUPROPION HYDROCHLORIDE
CAS Number
31677-93-7
34841-39-9
PubChem SID
160964490
46506896
PubChem CID
444
CHEBI ID
3219
ATC CODE
N06AX12
CHEMBL
894
Chemspider ID
431
DrugBank ID
DB01156
KEGG ID
D07591
Unique Ingredient Identifier
01ZG3TPX31
Wikipedia Title
Bupropion
Medline Plus
a695033

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID Price
A&J Pharmtech
AJA-O38773 external link Add to cart Please log in.

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
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 
Log P 3.28  LOG S -3.54 
Solubility (Water) 6.93e-02 g/l 

PROPERTIES

PROPERTIES

Physical Property Pharmacology Properties Product Information Bioassay(PubChem)
Solubility
312 mg/ml expand Show data source
Hydrophobicity(logP)
3.6 expand Show data source
Admin Routes
Oral expand Show data source
Bioavailability
5 to 20% in animals; no studies in humans expand Show data source
Excretion
Renal (87%), fecal (10%) expand Show data source
Half Life
20 hours expand Show data source
Metabolism
Hepatic—important CYP2B6 and 2D6 involvement expand Show data source
Protein Bound
84% expand Show data source
Legal Status
POM (UK) expand Show data source
Rx-only (US) expand Show data source
Pregnancy Category
B2 (Australia) expand Show data source
C (US) expand Show data source
US Licence
Bupropion expand Show data source
Purity
98% expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Wikipedia Wikipedia
DrugBank - DB01156 external link
Item Information
Drug Groups approved
Description A unicyclic, aminoketone antidepressant. The mechanism of its therapeutic actions is not well understood, but it does appear to block dopamine uptake. The hydrochloride is available as an aid to smoking cessation treatment. [PubChem]
Indication For the treatment of depression and as aid to smoking cessation.
Pharmacology Bupropion, an antidepressant of the aminoketone class and a non-nicotine aid to smoking cessation, is chemically unrelated to tricyclic, tetracyclic, selective serotonin re-uptake inhibitor, or other known antidepressant agents. Compared to classical tricyclic antidepressants, Bupropion is a relatively weak inhibitor of the neuronal uptake of norepinephrine, serotonin, and dopamine. In addition, Bupropion does not inhibit monoamine oxidase. Bupropion produces dose-related central nervous system (CNS) stimulant effects in animals, as evidenced by increased locomotor activity, increased rates of responding in various schedule-controlled operant behavior tasks, and, at high doses, induction of mild stereotyped behavior.
Toxicity Symptoms of overdose include seizures, hallucinations, loss of consciousness, tachycardia, and cardiac arrest.
Affected Organisms
Humans and other mammals
Biotransformation Reduction of the carbonyl groupand/or hydroxylation of the tert-butyl group of bupropion.
Absorption For sustained release, peak plasma concentrations are achieved within 3 hours.
Half Life 24 hours
Protein Binding 84 %
Elimination Bupropion is extensively metabolized in humans. Oxidation of the bupropion side chain results in the formation of a glycine conjugate of metachlorobenzoic acid, which is then excreted as the major urinary metabolite. Following oral administration of 200 mg of 14C-bupropion in humans, 87% and 10% of the radioactive dose were recovered in the urine and feces, respectively. However, the fraction of the oral dose of bupropion excreted unchanged was only 0.5%, a finding consistent with the extensive metabolism of bupropion.
References
Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. [Pubmed]
Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. [Pubmed]
Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. [Pubmed]
: Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. [Pubmed]
Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. [Pubmed]
External Links
Wikipedia
RxList
PDRhealth
Drugs.com

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • Fryer JD, Lukas RJ: Noncompetitive functional inhibition at diverse, human nicotinic acetylcholine receptor subtypes by bupropion, phencyclidine, and ibogaine. J Pharmacol Exp Ther. 1999 Jan;288(1):88-92. Pubmed
  • • Fava M, Rush AJ, Thase ME, Clayton A, Stahl SM, Pradko JF, Johnston JA: 15 years of clinical experience with bupropion HCl: from bupropion to bupropion SR to bupropion XL. Prim Care Companion J Clin Psychiatry. 2005;7(3):106-13. Pubmed
  • • Thase ME, Haight BR, Richard N, Rockett CB, Mitton M, Modell JG, VanMeter S, Harriett AE, Wang Y: Remission rates following antidepressant therapy with bupropion or selective serotonin reuptake inhibitors: a meta-analysis of original data from 7 randomized controlled trials. J Clin Psychiatry. 2005 Aug;66(8):974-81. Pubmed
  • • : Annual report on the results of treatment in gynecological cancer. Twenty-first volume. Statements of results obtained in patients treated in 1982 to 1986, inclusive 3 and 5-year survival up to 1990. Int J Gynaecol Obstet. 1991 Sep;36 Suppl:1-315. Pubmed
  • • Thase ME, Clayton AH, Haight BR, Thompson AH, Modell JG, Johnston JA: A double-blind comparison between bupropion XL and venlafaxine XR: sexual functioning, antidepressant efficacy, and tolerability. J Clin Psychopharmacol. 2006 Oct;26(5):482-8. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle