31677-93-7

Basic information

• Product Name: Bupropion hydrochloride
• Synonyms: (+-)-alpha-tert-butylamino-3-chloropropiophenonehydrochloride;1-propanone,1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-,hydrochloride,;2-(tert-butylamino)-3’-chloro-,hydrochloride,(+-)-propiophenon;m-chloro-alpha-tert-butylaminoprophenonehydrochloride;wellbatrin;zyban(pharmaceutical);BUPROPION HCL;BUPROPION HYDROCHLORIDE
• CAS NO: 31677-93-7
• Molecular Formula: C13H19Cl2NO
• Molecular Weight: 276.2
• EINECS: 250-759-9
• Product Categories: Aromatics Compounds;Aromatics;Intermediates & Fine Chemicals;Pharmaceuticals;Adrenoceptor;Amines;API;Isotope;Amines, Aromatics, Pharmaceuticals, Intermediates & Fine Chemicals;WELLBUTRIN
• Mol File: 31677-93-7.mol

Chemical Properties

• Melting Point: 233-234 °C
• Boiling Point: 334.8 °C at 760 mmHg
• Flash Point: 9℃
• Appearance: white/solid
• Density: ==
• Vapor Pressure: 0.000125mmHg at 25°C
• Storage Temp.: Desiccate at RT
• Solubility: ethanol: 193 mg/mL solutions may be stored for several days
• Water Solubility: Soluble in water (>25 mg/ml), ethanol 193mg/ml, 0.1 N HCl 333 mg/ml
• CAS DataBase Reference: Bupropion hydrochloride(CAS DataBase Reference)
• NIST Chemistry Reference: Bupropion hydrochloride(31677-93-7)
• EPA Substance Registry System: Bupropion hydrochloride(31677-93-7)

Safety Data

• Hazard Codes: Xn,Xi,T,F
• Statements: 22-39/23/24/25-23/24/25-11
• Safety Statements: 36-45-36/37-16-7
• RIDADR: UN1230 - class 3 - PG 2 - Methanol, solution
• WGK Germany: 3
• RTECS: UG8858000
• Hazardous Substances Data: 31677-93-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Bupropion hydrochloride is used as an antidepressant for the treatment of major depressive disorder (MDD). It works by inhibiting the reuptake of dopamine and norepinephrine, leading to an increase in their levels in the brain, which helps alleviate symptoms of depression.
Additionally, Bupropion hydrochloride SR (Zyban) is used as an aid to smoking cessation treatment. It helps reduce the cravings for nicotine and withdrawal symptoms associated with quitting smoking, making it easier for individuals to quit and maintain abstinence from tobacco use.

Originator

Bupropion hydrochloride,AroKor Holdings Inc.

Drug interactions

Relatively few data are available on interactions of bupropion hydrochloride with other drugs. Increased adverse experiences were reported when the drug was administered concomitantly with l-dopa. MAOIs may increase the acute toxicity of bupropion. Although bupropion is not metabolized by the CYP2D6 enzyme, the drug and its metabolite, morpholinol, inhibit this enzyme in vitro. Therefore, extreme caution should be exercised when coadministering any drug metabolized by that enzyme, and initial dosage of the drug should be as low as possible.

Therapeutic Function

Antidepressant; Smoking cessation aid

Biological Activity

Non-selective inhibitor of dopamine and noradrenalin transporters (K i values are 1.4, 2.8 and 45 μ M for NET, DAT and SERT transporters respectively). Also inhibits neuronal nicotinic acetylcholine receptors. Displays antidepressant activity and augments nicotine self-administration at low doses in vivo .

Side effects

Bupropion hydrochloride can cause serious side effects. The most common side effects of Bupropion hydrochloride include:headachedizzinessdry mouthsore throatnauseaconstipationtrouble sleeping

Mode of action

The exact mechanism of the antidepressant action of bupropion is not known, but is presumed to be related to noradrenergic and/or dopaminergic mechanisms. Bupropion is a relatively weak inhibitor of the neuronal reuptake of norepinephrine and dopamine, and does not inhibit the reuptake of serotonin. Bupropion does not inhibit monoamine oxidase.

InChI:InChI=1/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/t9-;/m0./s1

Upstream product

• 34841-39-9 bupropion 
• 34911-51-8 2-bromo-3'-chloropropiophenone 
• 75-64-9 tert-butylamine 
• 34841-35-5 3'-chloro-propiophenone 
• 92264-82-9 (R,R)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 

Downstream Products

• 92264-82-9 (S,S)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 
• 92264-82-9 (R,R)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol 
• 905818-69-1 bupropion hydrobromide 

Relevant articles and documents

Convenient and scalable process for the preparation of bupropion hydrochloride via efficient bromination of m-chloropropiophenone with n-bromosuccinimide

A convenient, scalable, and commercially viable process for the production of the antidepressant drug bupropion hydrochloride (1) is reported. The process relies upon an improved, large-scale synthesis of the key intermediate, m-chloro-bromopropiophenone (4). During process development, bromine was replaced with N-bromosuccinimide (NBS) in the presence of para-toluene sulfonic acid (p-TSA), for the bromination of m-chloropropiophenone (3), in either a very low volume of acetonitrile or under solvent-free conditions, to furnish 4. Intermediate 4 was further reacted with t-butylamine in N-methyl-2-pyrrolidinone (NMP) to afford bupropion free base (5), followed by treatment with a saturated solution of hydrochloric acid in isopropyl alcohol (IPA-HCl) to afford bupropion hydrochloride (1). This improved process provides pure bupropion hydrochloride (1) in good yields and at considerably lower cost than existing processes, and it does not involve the use of hazardous reagents. Copyright

A Method for the Catalytic Enantioselective Synthesis of Chiral α-Azido and α-Amino Ketones from Racemic α-Bromo Ketones, and Its Generalization to the Formation of Bonds to C, O, and S

A new and practical method has been developed for the transformation of racemic α-bromo ketones to chiral α-azido and α-amino ketones with high enantioselectivity using phase transfer, ion-pair mediated reactions with a recoverable chiral quaternary salt (10 mol %) as catalyst in fluorobenzene-water. The process has been generalized to a variety of other attachments including of C, O, S, and NHR.

Preparation method of bupropion hydrochloride

The invention discloses a preparation method of bupropion hydrochloride. M-chlorophenylacetone is used as a raw material to take bromination reaction with sodium bromide, sulfuric acid and hydrogen peroxide in a water-halohydrocarbon solvent to prepare a brominated intermediate; then the prepared bromide reacts with tert-butylamine to prepare amfebutamone, after the reaction for preparing amfebutamone is completely reacted, the water is directly added, after a reaction solution is layered, the layered organic layer is cleaned and distilled to obtain amfebutamone, and obtained amfebutamone is acidified by virtue of isopropanol hydrochloride to obtain bupropion hydrochloride; and the peparation process of amfebutamone, the alkalinity of a water layer obtained after the layering of the reaction solution is adjusted by using sodium hydroxide, after tert-butylamine is recovered in a distillation manner, the water layer comprising bromine ions is concentrated, the pH value is adjusted to beneutral by using sulfuric acid, the obtained aqueous solution comprising sodium bromide is used for taking the bromination reaction again so as to be circularly utilized. By adopting the preparation method, the environment-friendly circular utilization of bromine is realized, and the production cost is reduced.

Method for preparing bupropion hydrochloride

The invention discloses a novel method for preparing bupropion hydrochloride. According to the invention, m-chlorophenylacetone is taken as an initiator, then is brominated in a hydrobromic acid-hydrogen peroxide system, 3'-chlorine-alpha-bromophenyl ethyl ketone is synthesized; then through replacement by tert-butylamine and acidification by HCl-absolute ethyl alcohol, bupropion hydrochloride is obtained. The preparation method of bupropion hydrochloride replaces traditional bromine bromination, pollution can be effectively reduced, damage due to bromine volatilization on the operators can be greatly mitigated, and the method has the advantages of simple operation, low cost, high yield, and less side reaction, and is very suitable for industrial production.

COMPOSITIONS AND METHODS FOR TREATING DEPRESSION, ADHD AND OTHER CENTRAL NERVOUS SYSTEM DISORDERS EMPLOYING NOVEL BUPROPION COMPOUNDS, AND METHODS FOR PRODUCTION AND USE OF NOVEL BUPROPION COMPOUNDS AND FORMULATIONS

Compositions and methods are disclosed using a purified (R)(-) enantiomer of bupropion to treat central nervous system disorders with fewer side effects compared to those seen in subjects treated with racemic bupropion. Additionally disclosed are methods and intermediates for producing enantiomerically purified (R)(-) bupropion, stable pharmaceutical formulations of (R)(-) bupropion, and pharmaceutical products and kits comprising (R)(-) bupropion for clinical use.

PHENYLPROPANONE MODULATORS OF DOPAMINE RECEPTOR

The present invention relates to new phenylpropanone modulators of dopamine receptors, serotonin receptors, and/or nicotinic acetylcholine receptors, pharmaceutical compositions thereof, and methods of use thereof.

Process for preparing bupropion hydrochloride

This invention described a synthesis method of bupropion hydrochloride. m-chloropropiophenone was brominated directly with bromine, then aminated with t-butylamine and finally reacted with HCl to obtain crude product of bupropion hydrochloride. Pure product was obtained after recrystallization. This method is convenient and suitable for commercial manufacturing because of low cost of production, high yield, less byproducts and being environmental friendly.

Enhancing transdermal delivery of opiod antagonists and agonistis using codrugs links to bupropion or hydroxybupropion

The present invention is directed to novel codrugs comprising bupropion or hydroxybupropion and an opioid antagonist or an opioid agonist joined together by chemical bonding. The codrugs provide a significant increase in the transdermal flux across human skin, as compared to the basic opioid antagonist or opioid agonist.

AN IMPROVED PROCESS FOR PREPARING BUPROPION HYDROCHLORIDE

The present invention relates to an improved process for preparing Bupropion Hydrochloride of formula (I). The present invention also provides a process for purification of Bupropion hydrochloride.

PROCESS FOR CRYSTALLISING BUPROPION HYDROCHLORIDE

Process for crystallising Bupropion hydrochloride comprising the following stages: a) Bupropion hydrochloride is dissolved in a mixture comprising methanol and a precipitating solvent for Bupropion hydrochloride; b) any insoluble residue is removed; c) th