Showing Compound Bupropion (FDB022664)

Record Information

Version

1.0

Creation date

2011-09-21 00:17:37 UTC

Update date

2019-11-26 03:21:05 UTC

Primary ID

FDB022664

Secondary Accession Numbers

Not Available

Chemical Information

FooDB Name

Bupropion

Description

Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4- nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction.; 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; Bupropion is a selective catecholamine (norepinephrine and dopamine) reuptake inhibitor. It has only a small effect on serotonin reuptake. It does not inhibit MAO. The antidepressant effect of bupropion is considered to be mediated by its dopaminergic and noradrenergic action. Bupropion has also been shown to act as a competitive alpha-3-beta-4-nicotinic antagonist, the alpha-3-beta-4-antagonism has been shown to interrupt addiction in studies of other drugs such as ibogaine. This alpha-3-beta-4-antagonism correlates quite well with the observed effect of interrupting addiction. Bupropion (amfebutamone) (brand names Wellbutrin and Zyban) is an antidepressant of the aminoketone class, chemically unrelated to tricyclics or selective serotonin reuptake inhibitors (SSRIs). It is similar in structure to the stimulant cathinone, and to phenethylamines in general. It is a chemical derivative of diethylpropion, an amphetamine-like substance used as an anorectic. Bupropion is both a dopamine reuptake inhibitor and a norepinephrine reuptake inhibitor. It is often used as a smoking cessation aid. [HMDB]. Bupropion is found in many foods, some of which are cardoon, mung bean, salmonberry, and climbing bean.

CAS Number

34841-39-9

Structure

MOL SDF PDB SMILES InChI

Synonyms

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Search:

Synonym	Source
(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone	MeSH, HMDB
(+-)-Bupropion	HMDB
Amfebutamona	HMDB
Amfebutamone	HMDB, MeSH
Amfebutamonum	HMDB
Bupropion hydrochloride	MeSH, HMDB
Bupropion hydrochloride, (+-)-isomer	MeSH, HMDB
Bupropion, (+-)-isomer	MeSH, HMDB
Esteve brand OF bupropion hydrochloride	MeSH, HMDB
glaxo Wellcome brand 1 OF bupropion hydrochloride	MeSH, HMDB

Showing 1 to 10 of 21 entries

Predicted Properties

Property	Value	Source
Water Solubility	0.069 g/L	ALOGPS
logP	3.28	ALOGPS
logP	3.27	ChemAxon
logS	-3.5	ALOGPS
pKa (Strongest Acidic)	18.29	ChemAxon
pKa (Strongest Basic)	8.22	ChemAxon
Physiological Charge	1	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	29.1 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	67.7 m³·mol⁻¹	ChemAxon
Polarizability	25.93 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Chemical Formula

C13H18ClNO

IUPAC name

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

InChI Identifier

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

InChI Key

SNPPWIUOZRMYNY-UHFFFAOYSA-N

Isomeric SMILES

CC(NC(C)(C)C)C(=O)C1=CC(Cl)=CC=C1

Average Molecular Weight

239.741

Monoisotopic Molecular Weight

239.10769191

Classification

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
Chlorobenzene
Halobenzene
Aryl chloride
Aryl halide
Monocyclic benzene moiety
Benzenoid
Alpha-aminoketone
Secondary aliphatic amine
Secondary amine
Organochloride
Organohalogen compound
Organic oxide
Organopnictogen compound
Organic nitrogen compound
Amine
Organonitrogen compound
Hydrocarbon derivative
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

secondary amino compound (CHEBI:3219 )
monochlorobenzenes (CHEBI:3219 )
propanone (CHEBI:3219 )
aromatic ketone (CHEBI:3219 )

Ontology

Physiological effect

Health effect:

Health condition:

Psychiatric disorders:

Hallucinations

Cardiac disorders:

Cardiac arrest

Nervous system disorders:

Seizure

Observation:

Tachycardia

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Food

Environmental:

Wastewater

Biological:

Animal

Plant:

Biological location:

Subcellular:

Organ and components:

Role

Environmental role:

Environmental contaminant

Industrial application:

Drug

Pharmaceutical industry:

Physico-Chemical Properties

Physico-Chemical Properties - Experimental

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Property	Value	Reference
Boiling Point	Not Available
Charge	Not Available
Density	Not Available
Experimental logP	Not Available
Experimental pKa	Not Available
Experimental Water Solubility	Not Available
Isoelectric point	Not Available
Mass Composition	Not Available
Melting Point	Not Available
Optical Rotation	Not Available

Showing 1 to 10 of 14 entries

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
Predicted GC-MS	Bupropion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-000l-5900000000-1b5fb2e947791614a61d	Spectrum
Predicted GC-MS	Bupropion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum
Predicted GC-MS	Bupropion, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - LC-ESI-qTof , Positive	splash10-001i-0910000000-fa2592b7296c7561333c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-c10af1c8e3619fe0bffc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0490000000-55448af4d9a8ce866a88	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-2883ba18321a8b8228a1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-0900000000-7d6cad849706146ddab3	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-0900000000-0fca8999746b69ee4fc1	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-b64f8d2b50bede574f63	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-2edefa63d5f6f1b08db7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0006-0490000000-b8ea1de058a84547700d	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0910000000-6f471b9150fb1b7f6fcc	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-0159-0900000000-cc966137ee3283828af7	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-00lr-0900000000-7f86f38f740aa41b244b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-e7f2cfdbabbd35a9b643	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-4daf0e10db1e5f2750bf	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-ITFT , positive	splash10-001i-0900000000-f77a450be176593153d2	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-00m0-0910000000-d2eb7265b058766459c9	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - , positive	splash10-001i-0910000000-fa2592b7296c7561333c	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - LC-ESI-QFT , positive	splash10-001i-0900000000-4d831e97d7e7dfff141b	2017-09-14	View Spectrum
MS/MS	LC-MS/MS Spectrum - 60V, Positive	splash10-00lr-0900000000-65c6a707c92719eb037b	2021-09-20	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0006-0290000000-f40e79f27fd0f3448f9a	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-000x-2950000000-e144eddb8d64cdf24711	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0596-9500000000-9c44a89baee334f5ce9c	2016-08-01	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-000i-0090000000-f90eefcb5d4049067bbd	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-000i-2490000000-afd91ae0bad53e4c5c9f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-02mi-6930000000-94751c5f94b6dd91d63e	2016-08-03	View Spectrum