CAS 31677-93-7|CAS 34911-55-2|2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride|bupropion hydrochloride|Bupropion hydrochloride| Bupropion|Amfebutamone hydrochloride|Wellbutrin|Voxra|...

General Information

Structure

Molecular Formula

C₁₃H₁₉Cl₂NO

Molecular Mass

276.20206

Exact Mass

275.08436959

Charge

InChI

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

Canonic Smiles

Clc1cccc(c1)C(=O)C(NC(C)(C)C)C.Cl

Isomeric Smiles

C(=O)(c1cc(Cl)ccc1)C(NC(C)(C)C)C.Cl

Calculated Properties

JChem

Acid pKa

18.286419

H Acceptors

H Donor

LogD (pH = 5.5)

0.6626676

LogD (pH = 7.4)

2.3901906

Log P

3.2661126

Molar Refractivity

67.6994

Polarizability

26.657854

Polar Surface Area

29.1

Rotatable Bonds

Lipinski's Rule of Five

true

Data Source

Names and Identifiers

IUPAC Traditional name

bupropion hydrochloride 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

IUPAC name

2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

Synonyms

Bupropion hydrochloride BupropionVoxraWellbutrinZybanAmfebutamone hydrochloride(±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochlorideBUPROPION1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone HydrochlorideBupropion hydrochlorideAmfebutamone HydrochlorideBupropion HydrochlorideBupropion SR HydrochlorideAmfebutamon Hydrochloride(±)-Bupropion Hydrochlorideα-(tert-Butylamino)-m-chloropropiophenone HydrochlorideElontril HydrochlorideAplenzin Hydrochloride(±)-1-(3-Chlorophenyl)-2-[(1,1-dimethylethyl)amino]-1-propanone hydrochloride2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

Names and Identifiers

Registration numbers

MDL Number

PubChem SID

CAS Number

EC Number

PubChem CID

Registration numbers

Properties

Pharmacology Properties

Gene Information

human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

Mechanism of Action

Dopamine reuptake inhibitor

Properties

Related Proteins

No Data Available

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Molecular Spectra

No Data Available

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Molecule Details

Selleck Chemicals

S2452

Research Area: Neurological Disease
Biological Activity:
Amfebutamone (Bupropion) is a selective norepinephrine-dopamine reuptake inhibitor with IC50 of 6.5 and 3.4µM for the reuptake of dopamine and norepinephrine, respectively. Its primary pharmacological action is Norepinephrine-dopamine reuptake inhibition. It binds selectively to the dopamine transporter, but its behavioural effects have often been attributed to its inhibition of norepinephrine reuptake. It also acts as a nicotinic acetylcholine receptor antagonist. [1][2][3]

MP Biomedicals

02153760

Hydrochloride
Dopamine uptake inhibitor

Sigma Aldrich

B102

Biochem/physiol Actions
Inhibits the dopamine and norepinephrine transporters with Kis of 2.8 μM and 1.4 μM, respectively. Does not inhibit the serotonin transporter (Ki = 45 μM). Antidepressant.

TRC

B689625

A selective inhibitor of dopamine uptake. An antidepressant of the aminoketone class; aid in smoking cessation.

Molecule Details

References

PubChem Literature

From Data Sources

• Slemmer JE et al. J Pharmacol Exp Ther. 2000 Oct

• Tucker, W.E., J. Clin. Psychiatry, 44, 60 (1977)

• Soroko, F., et al.: J. Pharm. Pharmacol., 29, 769 (1977)

• Hsyu, P-H., et al.: J. Clin. Pharmacol., 37, 737 (1977)

• West, R., et al.: Expert Opin. Pharmacother., 4, 533 (1977)

• Ger. Pat., 1971, Wellcome, 2 059 618; CA, 76, 3551k, (synth, pharmacol)

• Dufresne, R.L. et al., Drug Intell. Clin. Pharm., 1984, 18, 957, (rev)

• Peck, A.W. et al., Br. J. Clin. Pharmacol., 1979, 7, 469, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, WBJ500

• Bryant, S.G. et al., Clin. Pharm., 1983, 2, 525, (rev)

• Holm, K.J. et al., Drugs, 2000, 59, 1007-1024

• Maxwell, R.A. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 1, (rev)

• Suckow, R.F. et al., Drug Metab. Dispos., 1986, 14, 692, (metab)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 280

References

Bioactivity

PubChem BioAssay

Bioactivity

Names and Identifiers

IUPAC Traditional name

bupropion hydrochloride 2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

IUPAC name

2-(tert-butylamino)-1-(3-chlorophenyl)propan-1-one hydrochloride

Synonyms

Registration numbers

MDL Number

PubChem SID

CAS Number

EC Number

PubChem CID

Molecule Details

S2452

Hydrochloride
Dopamine uptake inhibitor

Sigma Aldrich

B102

Biochem/physiol Actions
Inhibits the dopamine and norepinephrine transporters with Kis of 2.8 μM and 1.4 μM, respectively. Does not inhibit the serotonin transporter (Ki = 45 μM). Antidepressant.

TRC

B689625

A selective inhibitor of dopamine uptake. An antidepressant of the aminoketone class; aid in smoking cessation.

References

PubChem Literature

From Data Sources

• Slemmer JE et al. J Pharmacol Exp Ther. 2000 Oct

• Tucker, W.E., J. Clin. Psychiatry, 44, 60 (1977)

• Soroko, F., et al.: J. Pharm. Pharmacol., 29, 769 (1977)

• Hsyu, P-H., et al.: J. Clin. Pharmacol., 37, 737 (1977)

• West, R., et al.: Expert Opin. Pharmacother., 4, 533 (1977)

• Ger. Pat., 1971, Wellcome, 2 059 618; CA, 76, 3551k, (synth, pharmacol)

• Dufresne, R.L. et al., Drug Intell. Clin. Pharm., 1984, 18, 957, (rev)

• Peck, A.W. et al., Br. J. Clin. Pharmacol., 1979, 7, 469, (pharmacol)

• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, WBJ500

• Bryant, S.G. et al., Clin. Pharm., 1983, 2, 525, (rev)

• Holm, K.J. et al., Drugs, 2000, 59, 1007-1024

• Maxwell, R.A. et al., Pharmacol. Biochem. Prop. Drug Subst., 1981, 3, 1, (rev)

• Suckow, R.F. et al., Drug Metab. Dispos., 1986, 14, 692, (metab)

• Martindale, The Extra Pharmacopoeia, 32nd edn., Pharmaceutical Press, 1999, 280

Bioactivity

PubChem BioAssay

Properties

Pharmacology Properties

Gene Information

human ... DRD1(1812), DRD2(1813), DRD3(1814), DRD4(1815), DRD5(1816)

Mechanism of Action

Dopamine reuptake inhibitor

Molecule

ID:44448