Bupropion
bupropion
CAS: 34911-55-2;34841-39-9
Molecular Formula: C13H18ClNO
Bupropion - Names and Identifiers
Bupropion - Physico-chemical Properties
| Molecular Formula | C13H18ClNO |
| Molar Mass | 239.74 |
| Density | 1.066±0.06 g/cm3(Predicted) |
| Melting Point | 233-234°C |
| Boling Point | bp.005 52° |
| Solubility | ethanol: 193mg/mL solutions may be stored for several days at 4 °C. |
| Appearance | solid |
| Color | white |
| pKa | pKa 7.0 (Uncertain) |
| Physical and Chemical Properties | Light yellow oil, boiling point 52 °c/0.667. Easy to absorb moisture, easy to decompose. Soluble in methanol, ethanol, acetone, ether or benzene. Acute toxicity LD50 male and female mice, male and female rats (mg/kg):544±29,636±23,607±51,482±91 oral. Acute toxicity LD50 male mice, male rats (mg/kg):273±4,263±18 intraperitoneal injection. Bupropion Hydrochloride: C13H18C1NO? HCl. [31677-93-7]. Crystallization from isopropanol and absolute ethanol, melting point 233-234 °c. Solubility (mg/m1): Water 312, ethanol 193,0.1mol/L hydrochloric acid 333. Acute toxicity LD50 mice, rats (mg/kg):230,210 intraperitoneal injection; 575,600 oral. |
| Use | Central nervous system drugs |
Bupropion - Risk and Safety
| Hazard Symbols | Xn - Harmful |
| Risk Codes | 22 - Harmful if swallowed |
| Safety Description | 36 - Wear suitable protective clothing. |
| WGK Germany | 3 |
| RTECS | UG8858000 |
| Hazard Class | IRRITANT |
Bupropion - Nature
Open Data Verified Data
light yellow oil. 52 degrees Celsius. Easy to absorb moisture, easy to decompose. Soluble in methanol, ethanol, acetone, ether or benzene.
Last Update：2024-01-02 23:10:35
Bupropion - Preparation Method
Open Data Verified Data
to the ethyl magnesium bromide solution, a solution of O-chlorophenylacetonitrile in diethyl ether was added, and the reaction solution was hydrolyzed with cold dilute hydrochloric acid. After the diethyl ether was distilled off, the remaining aqueous solution was heated for a certain period of time. After cooling, seed crystals were placed. The solid was collected by filtration, washed with cold water, and recrystallized from methanol to give O-chlorophenylacetone. The O-chlorophenylacetone was dissolved in dichloromethane, stirred with activated carbon and magnesium sulfate, and filtered. A solution of bromine in dichloromethane was added with stirring. When the bromine color completely disappeared, the solvent was removed by vacuum concentration, and the remaining oil was O-chloro-cr bromophenylacetone. The O-chloro-cr bromophenylacetone was dissolved in acetonitrile and a solution of tert-butylamine in acetonitrile was added. Water and diethyl ether were added for partitioning. After treatment, it is finally washed with acetone and recrystallized from a mixture of isopropanol and absolute ethanol. Bupropion hydrochloride.
Last Update：2022-01-01 09:09:36
Bupropion - Use
Open Data Verified Data
developed by Wellcome, Inc., launched in 1989. A new type of antidepressant is indicated for the treatment of patients with depression who have no obvious effect or cannot tolerate other antidepressants.
Last Update：2022-01-01 09:09:36
Bupropion - Safety
Open Data Verified Data
mouse, rat LD50( mg/kg):230,210 intraperitoneal injection; 575, 600 orally.
Last Update：2022-01-01 09:09:37
Bupropion - Reference Information
| EPA chemical information | Information provided by: ofmpub.epa.gov (external link) |
| use | bupropion is a safe and effective antidepressant drug widely used in clinical practice. in recent years, studies have found that it has a very good effect on smoking cessation and can greatly improve the success rate of active smoking cessation. therefore, it is approved as the only prescription smoking cessation drug in the United States. A new type of antidepressant, with an amino ketone structure, chemically has nothing to do with tricyclic, teacyclic and monoamine oxidase inhibitors or other standard drugs. Used against depression. This product is an antidepressant. The oral LD50 was 575mg/kg for mice and 600mg/kg for rats. is a central nervous system drug |
| toxicological study | genotoxicity: 2 of the 5 strains in the bupropion Ames test showed positive results (the mutation rate was 2-3 times that of the control group). The chromosome aberration rate was increased in one of the three rat bone marrow cytogenetic tests. Reproductive toxicity: The rats were given bupropion by mouth up to 300mg/Kg without damage to fertility. Pregnant rats and rabbits were given bupropion doses as high as 450mg/Kg and 150mg/Kg respectively (calculated by body surface area, equivalent to 7~11 times and 7 times of the maximum recommended human dose respectively), and no drug-related fetal toxicity was found. Carcinogenic effect: In the long-term administration study, rats and mice were given bupropion doses as high as 300mg/Kg and 150mg/Kg (calculated by body surface area, which are equivalent to 7 times and 2 times of the maximum recommended human dose respectively) for 104 weeks and 96 weeks. The dose of 100~300mg/Kg can cause nodular hyperplasia of rat liver. Whether the hyperplasia is precursors of neoplasm is not clear, but similar lesions were not seen in mice. No increased incidence of liver and other organ malignancies was observed in both trials. |
| pharmacokinetics | bupropion is a racemic mixture. The pharmacological activities and pharmacokinetics of individual enantiomers have not been studied. The pharmacokinetic curve of bupropion is a two-compartment model. The average half-life of the terminal phase is 21 hours (± 20%), and the average half-life of the distribution phase is 3-4 hours. Absorption: Since bupropion cannot be used for intravenous injection in humans, the absolute bioavailability of bupropion hydrochloride sustained-release tablets has not been studied. After oral administration of bupropion hydrochloride sustained-release tablets in healthy volunteers, the peak blood concentration can be reached within 3 hours. Both pharmacokinetic studies were given a single dose of 150mg of the drug, and the results showed that the average plasma peak concentration Cmax was 91ng/ml and 143ng/ml, respectively. After administration of 150mg bupropion every 12 hours, the Cmax at steady-state blood concentration was 136ng/ml. Distribution: In vitro tests showed that the plasma protein binding rate was 84% when the blood concentration was 200 μg/ml. The protein binding rate of the metabolite oxybupropion is similar to that of bupropion, while the protein binding rate of the other metabolite threonine hydrogenated bupropion is only half that of bupropion. A single dose of 150mg in 17 subjects showed that the distribution volume of bupropion was 1950L(20% CV). Excretion: Two pharmacokinetic studies with a single oral dose (150mg) showed mean clearance of 135L/hr(± 20%) and 209L/hr(± 21%), respectively. The long-term medication study included 34 patients with oral drugs, 150mg each time, twice daily for 14 days, and the average clearance rate at steady state was 160L/hr (23%). A series of research results show that the average half-life of bupropion is about 21 hours. Multiple-dose studies showed that the average half-life of the metabolite oxybupropion was 20 hours (± 25%). The average half-life of Su-type bupropion is 37 hours (± 35%), and that of red-type bupropion is 33 hours (± 30%). Steady-state plasma concentrations of bupropion and its metabolites were reached within 5 and 8 days, respectively. |
| adverse reactions | according to the results of foreign clinical studies and domestic clinical studies, the adverse reactions of bupropion hydrochloride sustained-release tablets are: loss of appetite or anorexia, dry mouth, facial flushing, sweating, tinnitus, tremor, abdominal pain, agitation, anxiety, dizziness, insomnia, myalgia, palpitations, pharyngitis or frequent urination, nausea and vomiting, constipation, blurred vision, headache. Common adverse reactions leading to drug withdrawal are: facial flushing, nausea, agitation and migraine. Less frequent adverse reactions are: diarrhea, bitter taste, stomach discomfort, stomach pain, increased saliva, skin symptoms, weight gain. |
| contraindications | The following patients are prohibited 1. Patients with epileptic seizures; 2. Patients using other drugs containing bupropion; 3. Patients with current or previous diagnosis of bulimia or anorexia, because it may induce seizures; 4. It cannot be combined with monoamine oxidase (MAO) inhibitors. When stopping monoamine oxidase inhibitors and taking this product, the interval should be at least 14 days; 5. Those who are allergic to bupropion or the ingredients of this product; 6. Patients who abruptly quit alcohol or stop sedatives. |
| Production method | Preparation of m-chlorobenzonitrile by m-chloroethyl phenyl ketone, m-chloro-α-bromoethyl phenyl ketone Preparation of ketone hydrochloride. under stirring and cooling, within 40min, o-chlorophenyl acetonitrile (688g,5 mo1) is added to the solution of ethyl magnesium bromide (2L,3mol/L) and dissolved in ether (2.5L). Heat for 5h under mild reflux. The reaction solution is hydrolyzed with cold dilute hydrochloric acid. After the ether is evaporated, the remaining aqueous solution is heated at 90°C for 1h. After cooling, put in the seed crystal. Filter to collect the solid, wash with cold water, and then recrystallize with methanol to obtain 750g of o-chlorophenone with a melting point of 39-40 ℃. Pho-chlorophenone (698g,4.15 mmo1) was dissolved into dichloromethane (3L). The solution was stirred with activated carbon and magnesium sulfate for 2 hours and filtered. 662g(4.15 mo1) of bromine dissolved in dichloromethane (1L) was added under stirring. When the bromine color completely disappears, the solvent is removed by vacuum concentration, and the remaining oil is o-chlorine-α-bromobenzene acetone, which does not need purification and is directly used for the next reaction. The obtained oily residue is dissolved in acetonitrile (1300 m1), and tert-butylamine (733g) is added to a solution of acetonitrile (1300 m1) at a temperature below 32°C. Leave overnight, add 4200ml of water and 2700ml of ether for dispensing. The water layer is extracted with 1300ml ether. After the ether layer is combined, 4200ml of water is added, and hydrochloric acid is added to the water layer with a Ph value of 9. The separated water layer is washed with 500ml ether. The ether layers are combined, 560g of ice and 324ml of concentrated hydrochloric acid are added and stirred together. The ether layer is separated and washed with 200ml of water and 50ml of concentrated hydrochloric acid. The last two acid layers are combined, vacuum concentrated until crystallization occurs, and then cooled to 5 ℃. Filter, wash with acetone, and then recrystallize with a mixture of 3L isopropanol and 800ml absolute ethanol. DL-bupropion hydrochloride was analytically pure and spectrally pure, with a melting point of 233~234 ℃. |
| toxic substance data | information provided by: pubchem.ncbi.nlm.nih.gov (external link) |
Last Update：2024-04-09 20:49:11
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