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Substance Name: Bupropion hydrochloride [USAN:USP:JAN]
RN: 31677-93-7
UNII: ZG7E5POY8O
InChIKey: HEYVINCGKDONRU-UHFFFAOYSA-N

Note

  • 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.

Molecular Formula

  • C13-H18-Cl-N-O.Cl-H

Molecular Weight

  • 276.2051
 

Classification Codes

  • Antidepressant
  • Drug / Therapeutic Agent
  • Human Data

Names and Synonyms

Name of Substance

  • Bupropion hydrochloride [USAN:USP:JAN]

Synonyms

  • (+-)-2-(tert-Butylamino)-3'-chloropropiophenone hydrochloride
  • (+-)-alpha-tert-Butylamino-3-chloropropiophenone hydrochloride
  • 1-Propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, hydrochloride, (+-)-
  • alpha-(tert-Butylamino)-m-chloropropiophenone hydrochloride
  • Amfebutamon hydrochloride
  • Budeprion
  • Budeprion XL
  • Budeprion XL 300
  • Bupropion HCl
  • Bupropion hydrochloride
  • Bupropion SR
  • BW 323
  • EINECS 250-759-9
  • EINECS 252-243-9
  • Forfivo XL
  • m-Chloro-alpha-tert-butylaminopropionphenone hydrochloride
  • m-Chloro-alpha-tert-butylaminopropiophenone hydrochloride
  • NSC 315851
  • UNII-ZG7E5POY8O
  • Wellbutrin
  • Wellbutrin SR
  • Wellbutrin XL
  • Zyban
  • Zyban (pharmaceutical)

Systematic Names

  • 1-Propanone, 1-(3-chlorophenyl)-2-((1,1-dimethylethyl)amino)-, hydrochloride, (+-)-
  • 2-(tert-Butylamino)-3'-chloropropiophenone hydrochloride
  • Propiophenone, 2-(tert-butylamino)-3'-chloro-, hydrochloride, (+-)-

Registry Numbers

CAS Registry Number

  • 31677-93-7

FDA UNII

  • ZG7E5POY8O

Other Registry Number

  • 34841-36-6

System Generated Number

  • 0031677937

Molecular Formulas

Molecular Formula

  • C13-H18-Cl-N-O.Cl-H

Molecular Formula Fragments

  • C13-H18-Cl-N-O
  • Cl-H
  • COMPONENT

Structure Descriptors

InChI

1S/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

InChIKey

HEYVINCGKDONRU-UHFFFAOYSA-N

Smiles

CC(C(=O)c1cccc(c1)Cl)NC(C)(C)C.Cl

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
man LDLo oral 329mg/kg (329mg/kg) CARDIAC: PULSE RATE

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: OTHER CHANGES
Journal of Toxicology, Clinical Toxicology. Vol. 35, Pg. 321, 1997.
man TDLo oral 2143ug/kg/2D- (2.143mg/kg) SKIN AND APPENDAGES (SKIN): "DERMATITIS, OTHER: AFTER SYSTEMIC EXPOSURE"

BEHAVIORAL: MUSCLE WEAKNESS

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"
Annals of Pharmacotherpy. Vol. 33, Pg. 931, 1999.
man TDLo oral 64mg/kg (64mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE
Journal of Toxicology, Clinical Toxicology. Vol. 37, Pg. 634, 1999.
mouse LD50 intraperitoneal 230mg/kg (230mg/kg) BEHAVIORAL: CHANGES IN MOTOR ACTIVITY (SPECIFIC ASSAY)

BEHAVIORAL: ANALGESIA

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)
Journal of Pharmacy and Pharmacology. Vol. 29, Pg. 767, 1977.
mouse LD50 oral 544mg/kg (544mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: ATAXIA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 1, 1981.
rat LD50 intraperitoneal 210mg/kg (210mg/kg) BEHAVIORAL: TREMOR

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Pharmacy and Pharmacology. Vol. 29, Pg. 767, 1977.
rat LD50 oral 482mg/kg (482mg/kg) LUNGS, THORAX, OR RESPIRATION: DYSPNEA

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: ATAXIA
Pharmacological and Biochemical Properties of Drug Substances. Vol. 3, Pg. 1, 1981.
women TDLo oral 2mg/kg (2mg/kg) GASTROINTESTINAL: NAUSEA OR VOMITING

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: FOOD INTAKE (ANIMAL)
American Journal of Psychiatry. Vol. 142, Pg. 1459, 1985.
women TDLo oral 20mg/kg (20mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Clinical Psychiatry. Vol. 54, Pg. 162, 1993.
women TDLo oral 90mg/kg (90mg/kg) CARDIAC: EKG CHANGES NOT DIAGNOSTIC OF ABOVE

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
Journal of Toxicology, Clinical Toxicology. Vol. 37, Pg. 634, 1999.
women TDLo oral 180mg/kg (180mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Journal of Toxicology, Clinical Toxicology. Vol. 37, Pg. 634, 1999.
women TDLo oral 180mg/kg (180mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP
American Journal of Emergency Medicine. Vol. 12, Pg. 183, 1994.