Identification

Name
Benzphetamine
Accession Number
DB00865
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)

Type
Small Molecule
Groups
Approved, Illicit
Structure
Thumb
Weight
Average: 239.3553
Monoisotopic: 239.167399677
Chemical Formula
C17H21N
Synonyms
  • (+)-benzphetamine
  • (+)-N-benzyl-N,α-dimethylphenethylamine
  • (+)-N,α-dimethyl-N-(phenylmethyl)-benzeneethanamine
  • (S)-(+)-benzphetamine
  • (S)-(+)-N-benzyl-N,α-dimethylphenethylamine
  • (S)-benzphetamine
  • (αS)-N,α-dimethylphenethylamine
  • Benzaphetamine
  • Benzfetamina
  • Benzfetamine
  • Benzfetaminum
  • Benzphetamine
  • Benzylamphetamine
  • d-N-methyl-N-benzyl-β-phenylisopropylamine
  • N-methyl-1-phenyl-N-(phenylmethyl)propan-2-amine

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

Associated Conditions
Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
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Pharmacodynamics

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.

Mechanism of action

The mechanism of action of these drugs is not fully understood, however it may be similar to that of amphetamines. Amphetamines stimulate noepinephrine and dopamine release in nerve endings in the lateral hypothalamic feeding centre, decreasing appetite. This release is mediated by the binding of benzphetamine to centrally located adrenergic receptors.

TargetActionsOrganism
ASynaptic vesicular amine transporter
inducer
Humans
AAlpha-2A adrenergic receptor
agonist
Humans
AAlpha-1A adrenergic receptor
agonist
Humans
USodium-dependent dopamine transporter
inhibitor
Humans
Absorption

Readily absorbed from the gastro-intestinal tract and buccal mucosa. It Is resistant to metabolism by monoamine oxidase.

Volume of distribution
Not Available
Protein binding

75-99%

Metabolism

Hepatic. Benzphetamine's metabolites include amphetamine and methamphetamine.

Hover over products below to view reaction partners

Route of elimination
Not Available
Half-life

16 to 31 hours

Clearance
Not Available
Adverse Effects
Learn about our commercial Adverse Effects data.
Learn More
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
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
AbaloparatideThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Abaloparatide.
AbametapirThe serum concentration of Benzphetamine can be increased when it is combined with Abametapir.
AbataceptThe metabolism of Benzphetamine can be increased when combined with Abatacept.
AcebutololThe therapeutic efficacy of Acebutolol can be decreased when used in combination with Benzphetamine.
AceclofenacThe risk or severity of hypertension can be increased when Benzphetamine is combined with Aceclofenac.
AcemetacinThe risk or severity of hypertension can be increased when Benzphetamine is combined with Acemetacin.
AcenocoumarolThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Acenocoumarol.
AcetazolamideAcetazolamide may decrease the excretion rate of Benzphetamine which could result in a higher serum level.
AcetophenazineAcetophenazine may decrease the stimulatory activities of Benzphetamine.
Acetylsalicylic acidThe risk or severity of hypertension can be increased when Benzphetamine is combined with Acetylsalicylic acid.
Additional Data Available
  • Extended Description
    Extended Description

    Extended description of the mechanism of action and particular properties of each drug interaction.

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  • Severity
    Severity

    A severity rating for each drug interaction, from minor to major.

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  • Evidence Level
    Evidence Level

    A rating for the strength of the evidence supporting each drug interaction.

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  • Action
    Action

    An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions
  • Limit caffeine intake. Excess caffeine intake may increase the CNS stimulation caused by benzphetamine hydrochloride.

Products

Product Ingredients
IngredientUNIICASInChI Key
Benzphetamine hydrochloride43DWT87QT75411-22-3ANFSNXAXVLRZCG-UHFFFAOYSA-N
Brand Name Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DidrexTablet50 mg/1OralPharmacia and Upjohn Company LLC1960-10-262015-09-30US flag
DidrexTablet50 mg/1OralA S Medication Solutions1960-10-26Not applicableUS flag
DidrexTablet50 mg/1OralA-S Medication Solutions1960-10-262015-05-31US flag
DidrexTablet50 mg/1OralPd Rx Pharmaceuticals, Inc.1960-10-262016-12-15US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
BenzphetamineTablet25 mg/1OralTedor Pharma Inc.2016-02-012016-02-01US flag
Benzphetamine HydrochlorideTablet50 mg/1OralSolco Healthcare US LLC2011-08-012018-05-01US flag
Benzphetamine HydrochlorideTablet50 mg/1OralAidarex Pharmaceuticals LLC2010-07-21Not applicableUS flag
Benzphetamine HydrochlorideTablet50 mg/1OralImpax Generics2008-12-012010-04-30US flag
Benzphetamine HydrochlorideTablet50 mg/1OralPd Rx Pharmaceuticals, Inc.2011-11-012018-04-12US flag
Benzphetamine HydrochlorideTablet, film coated50 mg/1OralEpic Pharma, LLC2015-12-16Not applicableUS flag
Benzphetamine HydrochlorideTablet50 mg/1OralKVK-TECH, INC2010-07-21Not applicableUS flag
Benzphetamine HydrochlorideTablet50 mg/1OralNivagen Pharmaceuticals, Inc.2016-01-15Not applicableUS flag
Benzphetamine HydrochlorideTablet50 mg/1Oralbryant ranch prepack2010-02-01Not applicableUS flag
Benzphetamine HydrochlorideTablet50 mg/1OralC.O. Truxton, Inc.2011-11-012013-10-17US flag
Additional Data Available
  • Application Number
    Application Number

    A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

    Learn more
  • Product Code
    Product Code

    A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

Drug Categories
Chemical TaxonomyProvided by Classyfire
Description
This compound belongs to the class of organic compounds known as amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Kingdom
Organic compounds
Super Class
Benzenoids
Class
Benzene and substituted derivatives
Sub Class
Phenethylamines
Direct Parent
Amphetamines and derivatives
Alternative Parents
Phenylpropanes / Phenylmethylamines / Benzylamines / Aralkylamines / Trialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Benzylamine / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylmethylamine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
tertiary amine, amphetamines (CHEBI:3044)

Chemical Identifiers

UNII
0M3S43XK27
CAS number
156-08-1
InChI Key
YXKTVDFXDRQTKV-HNNXBMFYSA-N
InChI
InChI=1S/C17H21N/c1-15(13-16-9-5-3-6-10-16)18(2)14-17-11-7-4-8-12-17/h3-12,15H,13-14H2,1-2H3/t15-/m0/s1
IUPAC Name
benzyl(methyl)[(2S)-1-phenylpropan-2-yl]amine
SMILES
C[[email protected]@H](CC1=CC=CC=C1)N(C)CC1=CC=CC=C1

References

Synthesis Reference

Dennis J. Kalota, Keith G. Tomazi, "Crystallization Method for Benzphetamine." U.S. Patent US20080262268, issued October 23, 2008.

US20080262268
General References
Not Available
Human Metabolome Database
HMDB0015003
KEGG Compound
C07538
PubChem Compound
5311017
PubChem Substance
46506102
ChemSpider
4470556
RxNav
1422
ChEBI
3044
ChEMBL
CHEMBL3545985
ZINC
ZINC000000968305
Therapeutic Targets Database
DAP001147
PharmGKB
PA448586
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Benzphetamine
MSDS
Download (16.6 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
  • Corepharma llc
  • Impax laboratories inc
  • Kvk tech inc
  • Paddock laboratories inc
  • Tedor pharma inc
  • Tyco healthcare mallinckrodt
  • Pharmacia and upjohn co
Packagers
  • Aidarex Pharmacuticals LLC
  • Apotheca Inc.
  • A-S Medication Solutions LLC
  • Boca Pharmacal
  • Chattem Chemicals Inc.
  • Corepharma LLC
  • Dispensing Solutions
  • Global Pharmaceuticals
  • Impax Laboratories Inc.
  • KVK-Tech Inc.
  • Metrics Inc.
  • Nucare Pharmaceuticals Inc.
  • Paddock Labs
  • Patheon Inc.
  • PD-Rx Pharmaceuticals Inc.
  • Pharmacia Inc.
  • Prepak Systems Inc.
  • Rising Pharmaceuticals
  • Tedor Pharma Inc.
Dosage Forms
FormRouteStrength
TabletOral50 mg/1
Tablet, coatedOral50 mg/1
Tablet, film coatedOral50 mg/1
TabletOral25 mg/1
Prices
Unit descriptionCostUnit
Didrex 50 mg tablet1.71USD tablet
Benzphetamine hcl 50 mg tablet1.43USD tablet
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)129-130Heinzelman, R.V. and Aspergren, B.D.; US. Patent 2,789,138; April 16,1957; assigned to The Upjohn Company.
water solubilityReadily solubleNot Available
logP4.1Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0233 mg/mLALOGPS
logP3.72ALOGPS
logP4.34ChemAxon
logS-4ALOGPS
pKa (Strongest Basic)9.8ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area3.24 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity78.39 m3·mol-1ChemAxon
Polarizability29.03 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET Features
PropertyValueProbability
Human Intestinal Absorption+0.9933
Blood Brain Barrier+0.9864
Caco-2 permeable+0.8815
P-glycoprotein substrateSubstrate0.541
P-glycoprotein inhibitor INon-inhibitor0.8803
P-glycoprotein inhibitor IINon-inhibitor0.9437
Renal organic cation transporterInhibitor0.7013
CYP450 2C9 substrateNon-substrate0.769
CYP450 2D6 substrateNon-substrate0.588
CYP450 3A4 substrateNon-substrate0.5135
CYP450 1A2 substrateInhibitor0.8684
CYP450 2C9 inhibitorNon-inhibitor0.9146
CYP450 2D6 inhibitorInhibitor0.539
CYP450 2C19 inhibitorNon-inhibitor0.5997
CYP450 3A4 inhibitorNon-inhibitor0.8789
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8047
Ames testNon AMES toxic0.888
CarcinogenicityNon-carcinogens0.6584
BiodegradationNot ready biodegradable0.9825
Rat acute toxicity3.1442 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.8779
hERG inhibition (predictor II)Non-inhibitor0.5331
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Download (8.86 KB)
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Targets

Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inducer
General Function
Monoamine transmembrane transporter activity
Specific Function
Involved in the ATP-dependent vesicular transport of biogenic amine neurotransmitters. Pumps cytosolic monoamines including dopamine, norepinephrine, serotonin, and histamine into synaptic vesicles...
Gene Name
SLC18A2
Uniprot ID
Q05940
Uniprot Name
Synaptic vesicular amine transporter
Molecular Weight
55712.075 Da
References
  1. Sulzer D, Chen TK, Lau YY, Kristensen H, Rayport S, Ewing A: Amphetamine redistributes dopamine from synaptic vesicles to the cytosol and promotes reverse transport. J Neurosci. 1995 May;15(5 Pt 2):4102-8. [PubMed:7751968]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Thioesterase binding
Specific Function
Alpha-2 adrenergic receptors mediate the catecholamine-induced inhibition of adenylate cyclase through the action of G proteins. The rank order of potency for agonists of this receptor is oxymetazo...
Gene Name
ADRA2A
Uniprot ID
P08913
Uniprot Name
Alpha-2A adrenergic receptor
Molecular Weight
48956.275 Da
References
  1. Spencer RC, Devilbiss DM, Berridge CW: The cognition-enhancing effects of psychostimulants involve direct action in the prefrontal cortex. Biol Psychiatry. 2015 Jun 1;77(11):940-50. doi: 10.1016/j.biopsych.2014.09.013. Epub 2014 Sep 28. [PubMed:25499957]
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Agonist
General Function
Protein heterodimerization activity
Specific Function
This alpha-adrenergic receptor mediates its action by association with G proteins that activate a phosphatidylinositol-calcium second messenger system. Its effect is mediated by G(q) and G(11) prot...
Gene Name
ADRA1A
Uniprot ID
P35348
Uniprot Name
Alpha-1A adrenergic receptor
Molecular Weight
51486.005 Da
References
  1. Spencer RC, Devilbiss DM, Berridge CW: The cognition-enhancing effects of psychostimulants involve direct action in the prefrontal cortex. Biol Psychiatry. 2015 Jun 1;77(11):940-50. doi: 10.1016/j.biopsych.2014.09.013. Epub 2014 Sep 28. [PubMed:25499957]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Monoamine transmembrane transporter activity
Specific Function
Amine transporter. Terminates the action of dopamine by its high affinity sodium-dependent reuptake into presynaptic terminals.
Gene Name
SLC6A3
Uniprot ID
Q01959
Uniprot Name
Sodium-dependent dopamine transporter
Molecular Weight
68494.255 Da
References
  1. Sulzer D, Sonders MS, Poulsen NW, Galli A: Mechanisms of neurotransmitter release by amphetamines: a review. Prog Neurobiol. 2005 Apr;75(6):406-33. [PubMed:15955613]
  2. Kahlig KM, Binda F, Khoshbouei H, Blakely RD, McMahon DG, Javitch JA, Galli A: Amphetamine induces dopamine efflux through a dopamine transporter channel. Proc Natl Acad Sci U S A. 2005 Mar 1;102(9):3495-500. Epub 2005 Feb 22. [PubMed:15728379]

Enzymes

Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Seree EJ, Pisano PJ, Placidi M, Rahmani R, Barra YA: Identification of the human and animal hepatic cytochromes P450 involved in clonazepam metabolism. Fundam Clin Pharmacol. 1993;7(2):69-75. [PubMed:8486332]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Steroid hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally un...
Gene Name
CYP2B6
Uniprot ID
P20813
Uniprot Name
Cytochrome P450 2B6
Molecular Weight
56277.81 Da
References
  1. Bumpus NN, Sridar C, Kent UM, Hollenberg PF: The naturally occurring cytochrome P450 (P450) 2B6 K262R mutant of P450 2B6 exhibits alterations in substrate metabolism and inactivation. Drug Metab Dispos. 2005 Jun;33(6):795-802. Epub 2005 Mar 15. [PubMed:15769884]
  2. Shebley M, Kent UM, Ballou DP, Hollenberg PF: Mechanistic analysis of the inactivation of cytochrome P450 2B6 by phencyclidine: effects on substrate binding, electron transfer, and uncoupling. Drug Metab Dispos. 2009 Apr;37(4):745-52. doi: 10.1124/dmd.108.024661. Epub 2009 Jan 14. [PubMed:19144770]
  3. Rendic S: Summary of information on human CYP enzymes: human P450 metabolism data. Drug Metab Rev. 2002 Feb-May;34(1-2):83-448. [PubMed:11996015]
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Substrate
General Function
Oxidoreductase activity, acting on paired donors, with incorporation or reduction of molecular oxygen, nad(p)h as one donor, and incorporation of one atom of oxygen
Specific Function
This enzyme is required for electron transfer from NADP to cytochrome P450 in microsomes. It can also provide electron transfer to heme oxygenase and cytochrome B5.
Gene Name
POR
Uniprot ID
P16435
Uniprot Name
NADPH--cytochrome P450 reductase
Molecular Weight
76689.12 Da
References
  1. Kanaeva IP, Nikityuk OV, Davydov DR, Dedinskii IR, Koen YM, Kuznetsova GP, Skotselyas ED, Bachmanova GI, Archakov AI: Comparative study of monomeric reconstituted and membrane microsomal monooxygenase systems of the rabbit liver. II. Kinetic parameters of reductase and monooxygenase reactions. Arch Biochem Biophys. 1992 Nov 1;298(2):403-12. [PubMed:1416971]
  2. Matsumoto T, Emi Y, Kawabata S, Omura T: Purification and characterization of three male-specific and one female-specific forms of cytochrome P-450 from rat liver microsomes. J Biochem. 1986 Nov;100(5):1359-71. [PubMed:2434473]
  3. Kojima H, Takahashi K, Sakane F, Koyama J: Purification and characterization of NADPH-cytochrome c reductase from porcine polymorphonuclear leukocytes. J Biochem. 1987 Nov;102(5):1083-8. [PubMed:3125159]
  4. Dutton DR, McMillen SK, Parkinson A: Purification of rat liver microsomal cytochrome P-450b without the use of nonionic detergent. J Biochem Toxicol. 1988 Summer;3:131-45. [PubMed:3148724]
  5. Halpert JR, Miller NE, Gorsky LD: On the mechanism of the inactivation of the major phenobarbital-inducible isozyme of rat liver cytochrome P-450 by chloramphenicol. J Biol Chem. 1985 Jul 15;260(14):8397-403. [PubMed:3924914]

Drug created on June 13, 2005 07:24 / Updated on July 02, 2020 07:26

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