Bupropion Hydrochloride

Base Information

• Chemical Name: Bupropion Hydrochloride
• CAS No.: 34911-55-2
• Deprecated CAS: 34841-36-6
• Molecular Formula: C₁₃H₁₈ClNO
• Molecular Weight: 239.745
• NSC Number: 758686,315851
• UNII: ZG7E5POY8O
• DSSTox Substance ID: DTXSID6044561
• Wikidata: Q27295463
• NCI Thesaurus Code: C1317
• RXCUI: 203204
• ChEMBL ID: CHEMBL1698
• Mol file: 34911-55-2.mol

Synonyms:(+-)-1-(3-Chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone;Amfebutamone;Bupropion;Bupropion Hydrochloride;Bupropion Hydrochloride, (+-)-Isomer;Bupropion, (+-)-Isomer;Quomen;Wellbutrin;Zyban (Anti-Smoking);Zyban (Bupropion);Zyntabac

Chemical Property of Bupropion Hydrochloride

Chemical Property:

• Appearance/Colour: solid light yellow oil
• Melting Point: 233-234 °C
• Boiling Point: 334.8 °C at 760 mmHg
• PKA: pKa 7.0 (Uncertain)
• Flash Point: 156.3 °C
• PSA: 29.10000
• Density: 1.066 g/cm³
• LogP: 3.69020
• Solubility.: ethanol: 193 mg/mL solutions may be stored for several days
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 275.0843696
• Heavy Atom Count: 17
• Complexity: 247

Purity/Quality:

99% ^*data from raw suppliers

Bupropion hydrochloride 95+% ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22
• Safety Statements: 36

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)C1=CC(=CC=C1)Cl)NC(C)(C)C.Cl
• Recent ClinicalTrials: Bupropion Hydrochloride or Patient's Choice for Smoking Cessation in Patients With Squamous Cell Head and Neck Cancer Undergoing Radiation Therapy With or Without Chemotherapy
• Recent EU Clinical Trials: The effect of bupropion in peripheral neuropathic pain. A randomized, double-blind, placebo-controlled study.
• Description: Bupropion hydrochloride, an aminoketone structurally unrelated to tricyclics or tetracyclics, is a dopamine uptake blocker with antidepressant activity. Its clinical efficacy is reportedly comparable to that of amitriptyline, yet unlike most conventional antidepressants, bupropion hydrochloride is not associated with orthostatic hypotension or other cardiovascular side-effects.
• Uses: vasoconstrictor;non-selective agonist of all adrenergic receptors Bupropion Hydrochloride used in methods of treating sleep disorders associated with pain.
• Biological Functions: Bupropion (Wellbutrin) is a pharmacologically unique antidepressant, since it is a weak inhibitor of both dopamine and norepinephrine neuronal reuptake. However, its actual antidepressant activity is not well understood. Bupropion is generally well tolerated and does not block muscarinic, histaminergic, or adrenergic receptors. Unlike the SSRIs and venlafaxine, bupropion does not cause sexual side effects. However, it can cause CNS stimulation, including restlessness and insomnia. High doses of bupropion, given as its original formulation, were associated with a risk of seizures in 0.4% of patients. However, this risk is lower with slow-release bupropion (Wellbutrin SR). This formulation still requires dosing twice a day, and bupropion is contraindicated in patients with a history of seizures. Bupropion inhibits the cytochrome P450 2D6 isoenzyme and may elevate blood levels of drugs metabolized by this route.

Technology Process of Bupropion Hydrochloride

There total 19 articles about Bupropion Hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 100.0%

2-bromo-3'-chloropropiophenone (34911-51-8) + tert-butylamine (75-64-9) → bupropion (34841-39-9,34911-55-2,144445-75-0,144445-76-1)

Guidance literature:

2-bromo-3'-chloropropiophenone; tert-butylamine; In acetonitrile; at 20 ℃; for 5h; Heating / reflux;

With potassium hydroxide; In water; ethyl acetate; acetonitrile;

Reference yield: 90.0%

BUPROPION HYDROCHLORIDE (31677-93-7) → bupropion (34841-39-9,34911-55-2,144445-75-0,144445-76-1)

Guidance literature:

With sodium carbonate; In water;

Reference yield: 75.0%

tert-butylamine (75-64-9) + (+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one (152943-33-4) → bupropion (34841-39-9,34911-55-2,144445-75-0,144445-76-1)

Guidance literature:

(+/-)-1-(3-chlorophenyl)-2-hydroxypropan-1-one; With 2,6-dimethylpyridine; trifluoromethylsulfonic anhydride; In dichloromethane; at -40 ℃; for 0.5h;

tert-butylamine; In dichloromethane; for 12h; Further stages.;

DOI:10.1016/j.tetlet.2008.04.040

upstream raw materials:

3'-chloro-propiophenone

tert-butylamine

2-bromo-3'-chloropropiophenone

BUPROPION HYDROCHLORIDE

Downstream raw materials:

BUPROPION HYDROCHLORIDE

(S,S)-2-(tert-butylamino)-1-(3-chlorophenyl)propanol

erythrohydrobupropion

rac-1-(m-chlorophenyl)-2-(tert-butylamino)-(2-²H)-propan-1-one

Refernces

• 1、 -. "Preparation method of bupropion hydrochloride". Page/Page column 5-7. . Retrieved 2018/10/19.
• 2、 -. "Method for preparing bupropion hydrochloride". Paragraph 0010; 0018; 0019. . Retrieved 2017/05/10.