QuickView for Benzphetamine (compound)

Summary
General Info

PubChem

PubChem Compound 2341

Name:	Benzphetamine
PubChem Compound ID:	2341
Description:	A sympathomimetic agent with properties similar to DEXTROAMPHETAMINE. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)
Molecular formula:	C₁₇H₂₁N
Molecular weight:	239.355 g/mol
Synonyms:	Benzphetamine; N-Benzyl-N-methyl-1-phenyl-2-propanamine; Benzamphetamine; C07538; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-, (S)-; (R,S)-N-Benzyl-alpha,N-dimethylphenethylamin; U 0441; Benzeneethanamine, N,.alpha.-dimethyl-N- (phenylmethyl)-, hydrochloride, (+)-; N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine; 101-47-3. show more » Benzphetamine; N-Benzyl-N-methyl-1-phenyl-2-propanamine; Benzamphetamine; C07538; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-, (S)-; (R,S)-N-Benzyl-alpha,N-dimethylphenethylamin; U 0441; Benzeneethanamine, N,.alpha.-dimethyl-N- (phenylmethyl)-, hydrochloride, (+)-; N,alpha-Dimethyl-N-(phenylmethyl)-benzeneethanamine; 101-47-3; Benzfetamina [DCIT]; Benzfetamine; HSDB 3294; d-Benzphetamine hydrochloride; D-N-Methyl-N-benzyl-beta-phenylisopropylamine; 5411-22-3; Phenethylamine, N-benzyl-N,.alpha.-dimethyl-, (+)-; BENZPHETAMINE HYDROCHLORIDE; NSC10937; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-; 4-12-00-02594 (Beilstein Handbook Reference); d-Benzphetamine; U-0441; Benzphetaminum [INN-Latin]; N-Benzyl-N,alpha-dimethylphenethylamine; Didrex; Phenethylamine, N-benzyl-N,.alpha.-dimethyl-, hydrochloride, (+)-; Benzfetaminum [Latin]; Benzfetamina [Spanish]; Benzfetaminum [INN-Latin]; N,alpha-Dimethyl-N-(phenylmethyl)benzeneethanamine; Benzofetamina [INN-Spanish]; Benzeneethanamine, N,.alpha.-dimethyl-N-(phenylmethyl)-, (+)-; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-, (+)- (9CI); (+)-Benzphetamine hydrochloride; DEA No. 1228; Phenethylamine, N-benzyl-N,alpha-dimethyl-, (+)-; Inapetyl; 156-08-1; BRN 3203999; Benzfetamina [INN-Spanish]; Benzeneethanamine, N,alpha-dimethyl-N-(phenylmethyl)-, (+)-; N-Benzylmethamphetamin show less «

DrugBank

Identification

Name:	Benzphetamine
Name (isomeric):	DB00865
Drug Type:	small molecule
Description:	A sympathomimetic agent with properties similar to DEXTROAMPHETAMINE. It is used in the treatment of obesity. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1222)
Synonyms:	Benzfetamine; Benzylamphetamine; Benzphetamine Hydrochloride
Brand:	Didrex
Category:	Dopamine Uptake Inhibitors, Adrenergic Agents, Sympathomimetics, Adrenergic Uptake Inhibitors, Central Nervous System Stimulants, Dopamine Agents, Central Nervous System Agents
CAS number:	156-08-1

Pharmacology

Indication:	For the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction
Pharmacology:	Benzphetamine, a phenylalkylamin, is related to amphetamine both chemically and pharmacologically. It is an anorectic agent indicated in the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction. Benzphetamine is a sympathomimetic amine with pharmacologic activity similar... show more » Benzphetamine, a phenylalkylamin, is related to amphetamine both chemically and pharmacologically. It is an anorectic agent indicated in the management of exogenous obesity as a short term adjunct (a few weeks) in a regimen of weight reduction based on caloric restriction. Benzphetamine is a sympathomimetic amine with pharmacologic activity similar to the prototype drugs of this class used in obesity, the amphetamines. Actions include central nervous system stimulation and elevation of blood pressure. Tachyphylaxis and tolerance have been demonstrated with all drugs of this class in which these phenomena have been looked for. show less «
Mechanism of Action:	Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopam... show more » Although the mechanism of action of the sympathomimetic appetite suppressants in the treatment of obesity is not fully known, these medications have pharmacological effects similar to those of amphetamines. Amphetamine and related sympathomimetic medications (such as benzphetamine) are thought to stimulate the release of norepinephrine and/or dopamine from storage sites in nerve terminals in the lateral hypothalamic feeding center, thereby producing a decrease in appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors. show less «
Absorption:	Readily absorbed from the gastro-intestinal tract and buccal mucosa. It Is resistant to metabolism by monoamine oxidase.
Protein binding:	75-99%
Biotransformation:	Hepatic. Benzphetamine's metabolites include amphetamine and methamphetamine.
Half Life:	16 to 31 hours
Toxicity:	LD₅₀=160 mg/kg (orally in rats). Acute overdosage may result in restlessness, tremor, tachypnea, confusion, assaultiveness, and panic states.
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Trifluoperazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Sodium bicarbonate	Alkalinizing agents such as sodium bicarbonate may decrease the excretion of amphetamines like benzphetamine. Increased clinical effects and/or toxicity may occur. Therapy modification should be considered.
Mesoridazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Fluoxetine	Amphetamines may enhance the adverse/toxic effect of Serotonin Modulators. The risk of serotonin syndrome may be increased. Monitor patients closely for signs and symptoms of serotonin syndrome (e.g., agitation, tremor, tachycardia, etc.) when using amphetamines and serotonin modulators in combination.

Trifluoperazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Sodium bicarbonate	Alkalinizing agents such as sodium bicarbonate may decrease the excretion of amphetamines like benzphetamine. Increased clinical effects and/or toxicity may occur. Therapy modification should be considered.
Mesoridazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Tramadol	Increased risk of serotonin syndrome. Monitor for symptoms of serotonin syndrome.
Fluoxetine	Amphetamines may enhance the adverse/toxic effect of Serotonin Modulators. The risk of serotonin syndrome may be increased. Monitor patients closely for signs and symptoms of serotonin syndrome (e.g., agitation, tremor, tachycardia, etc.) when using amphetamines and serotonin modulators in combination.
Telithromycin	Telithromycin may reduce clearance of Benzphetamine. Consider alternate therapy or monitor for changes in the therapeutic/adverse effects of Benzphetamine if Telithromycin is initiated, discontinued or dose changed.
Tranylcypromine	The MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the amphetamine, Benzphetamine. Concomitant therapy should be avoided.
Methotrimeprazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Trandolapril	Benzphetamine may reduce the efficacy of Trandolapril.
Promethazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Voriconazole	Voriconazole, a strong CYP3A4 inhibitor, may increase the serum concentration of benzphetamine by decreasing its metabolism. Monitor for changes in the therapeutic and adverse effects of benzphetamine if voriconazole is initiated, discontinued or dose changed.
Fluvoxamine	Amphetamines may enhance the adverse/toxic effect of Serotonin Modulators. The risk of serotonin syndrome may be increased. Monitor patients closely for signs and symptoms of serotonin syndrome (e.g., agitation, tremor, tachycardia, etc.) when using amphetamines and serotonin modulators in combination.
Prochlorperazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Propericiazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Perphenazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Guanethidine	Benzphetamine may decrease the effect of guanethidine.
Paroxetine	Amphetamines may enhance the adverse/toxic effect of Serotonin Modulators. The risk of serotonin syndrome may be increased. Monitor patients closely for signs and symptoms of serotonin syndrome (e.g., agitation, tremor, tachycardia, etc.) when using amphetamines and serotonin modulators in combination.
Isocarboxazid	MAO Inhibitors may enhance the hypertensive effect of Amphetamines. Concomitant use of amphetamines and monoamine oxidase inhibitors (MAOI) should be avoided. If used concomitantly, careful monitoring of blood pressure must occur. It may take up to 2 weeks after the discontinuation of an MAOI for the effects to dissipate enough to afford safety to the administration of interacting agents.
Thioridazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Chlorpromazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Phenelzine	MAO Inhibitors may enhance the hypertensive effect of Amphetamines. Concomitant use of amphetamines and monoamine oxidase inhibitors (MAOI) should be avoided. If used concomitantly, careful monitoring of blood pressure must occur. It may take up to 2 weeks after the discontinuation of an MAOI for the effects to dissipate enough to afford safety to the administration of interacting agents.
Triprolidine	Triprolidine may reduce the sedative effect of the antihistamine, Benzphetamine.
Fluphenazine	Antipsychotics may diminish the stimulatory effect of Amphetamines. Monitor effectiveness of amphetamine therapy when altering concurrent antipsychotic therapy as antipsychotic agents may impair the stimulatory effect of amphetamines.
Rasagiline	MAO Inhibitors may enhance the hypertensive effect of Amphetamines. Concomitant use of amphetamines and monoamine oxidase inhibitors (MAOI) should be avoided. If used concomitantly, careful monitoring of blood pressure must occur. It may take up to 2 weeks after the discontinuation of an MAOI for the effects to dissipate enough to afford safety to the administration of interacting agents.

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Targets

Synaptic vesicular amine transporter

Alpha-2A adrenergic receptor

Alpha-1A adrenergic receptor

Sodium-dependent dopamine transporter

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2B6

NADPH--cytochrome P450 reductase