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Bupropion

Bupropion Struktur
34911-55-2
CAS-Nr.
34911-55-2
Englisch Name:
Bupropion
Synonyma:
BUPROPION HCL;AMFEBUTAMONE;Amfebutamon;ZYNTABAC;Bupropion;AMFEBUTAMONE HCL;Bupropion 34911-55-2;Wellbatrin:Wellbutrin;BUPROPION/AMFEBUTAMONE;Bupropion controlled release
CBNumber:
CB8140067
Summenformel:
C13H18ClNO
Molgewicht:
239.74
MOL-Datei:
34911-55-2.mol

Bupropion Eigenschaften

Schmelzpunkt:
233-234°C
Siedepunkt:
bp.005 52°
Dichte
1.066±0.06 g/cm3(Predicted)
L?slichkeit
ethanol: 193 mg/mL solutions may be stored for several days at 4 °C.
Aggregatzustand
solid
pka
pKa 7.0 (Uncertain)
Farbe
white
BCS Class
1
CAS Datenbank
34911-55-2(CAS DataBase Reference)
EPA chemische Informationen
1-Propanone, 1-(3-chlorophenyl)-2-[(1,1-dimethylethyl)amino]- (34911-55-2)

Sicherheit

Kennzeichnung gef?hrlicher Xn
R-S?tze: 22
S-S?tze: 36
WGK Germany  3
RTECS-Nr. UG8858000
HazardClass  IRRITANT
Giftige Stoffe Daten 34911-55-2(Hazardous Substances Data)

Bupropion Chemische Eigenschaften,Einsatz,Produktion Methoden

R-S?tze Betriebsanweisung:

R22:Gesundheitssch?dlich beim Verschlucken.

S-S?tze Betriebsanweisung:

S36:DE: Bei der Arbeit geeignete Schutzkleidung tragen.

Beschreibung

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.

Verwenden

vasoconstrictor;non-selective agonist of all adrenergic receptors

Biologische Funktion

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.

Allgemeine Beschreibung

The mechanism of action of bupropion (Wellbutrin) is consideredcomplex and reportedly involves a block of DA reuptakevia the dopamine transporter (DAT), but the overallantidepressant action is noradrenergic. A metabolite thatcontributes to the overall action and its formation can beeasily rationalized. Oxidation of one of the methyl groupson the t-butyl substituent yields hydroxybupropion, an activemetabolite. Reduction of the keto group also occurs,yielding threohydrobupropion and erythrohydrobupropion.Both of these metabolites are also active.
Hydroxybupropion is half as potent as the parent bupropion,and the hydrobupropion isomers are five times less potent.The presence of these metabolites, especially hydroxybupropionwhich is formed by cytochrome P450 2D6(CYP2D6), suggests that there will be a myriad of drug interactionswith bupropion.

Pharmakologie

Bupropion is an α-aminoketone that is structurally related to amphetamines, and it exhibits unique activity comparable to that of other antidepressants. It is believed that bupropion restores the total amount of norepinephrine in the body. This compound is a poor reuptake inhibitor of dopamine, and does not exhibit anticholinergic activity or inhibit MAO. Its efficacy as an antidepressant is comparable to that of tricyclic antidepressants, and as a serotonin uptake inhibitor it is comparable to fluoxetine.

Bupropion Upstream-Materialien And Downstream Produkte

Upstream-Materialien

Downstream Produkte

34911-55-2()Verwandte Suche:


  • m-chloro-a-(tert-butylamino)propiophenone
  • Bupropion
  • BUPROPION/AMFEBUTAMONE
  • Wellbatrin:Wellbutrin
  • rac-(R*)-1-(3-Chlorophenyl)-2-(tert-butylamino)-1-propanone
  • Buproprion thioMorpholine carboxylic acid
  • Bupropion controlled release
  • 1-Propanone,1-(3-chlorophenyl)-2-[(1,1-diMethylethyl)aMino]-
  • (+-)-1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-1-propanone
  • 1-dimethylethyl)amino)-1-(3-chlorophenyl)-2-(((+-)-1-propanon
  • alpha-(tert-butylamino)-m-chloropropiophenone
  • Wellbutrin1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino)-1-propamone
  • DL-1-(3-CHLOROPHENYL)-2-[(1,1-DIMETHYLETHYL)AMINO]-1-PROPANONE HYDROCHLORIDE
  • AMFEBUTAMONE HCL
  • (a-2-(tert-butylamino)-3¢
  • 2-tert-butylamino-1-(3-chlorophenyl)-propan-1-one
  • (2R)-2-(tert-butylamino)-1-(3-chlorophenyl)-1-propanone
  • ZYNTABAC
  • Bupropion 34911-55-2
  • Amfebutamon
  • BUPROPION HCL
  • AMFEBUTAMONE
  • 34911-55-2
  • 3167-93-7
  • 31677-93-4
  • C13H19Cl2NO
  • C14H19ClNO
  • C13H18CINO
  • Inhibits the dopamine and norepinephrine transporters with Kis of 2.8 uM and 1.4 uM, respectively. Does not inhibit the serotonin transporter (Ki = 45 uM). Antidepressant.
  • Isotope
  • APIs
  • BDO
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