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Identification
NameMephentermine
Accession NumberDB01365
TypeSmall Molecule
GroupsApproved
Description

A sympathomimetic agent with mainly indirect effects on adrenergic receptors. It is used to maintain blood pressure in hypotensive states, for example, following spinal anesthesia. Although the central stimulant effects of mephentermine are much less than those of amphetamine, its use may lead to amphetamine-type dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1248)

Structure
Thumb
Synonyms
SynonymLanguageCode
MephentermineNot AvailableNot Available
SID11112475Not AvailableNot Available
Salts
Name/CAS Structure Properties
Mephentermine sulfate
Thumb Not applicable DBSALT001074
Brand names
NameCompany
WyamineNot Available
WyfenterminaNot Available
Brand mixturesNot Available
Categories
CAS number100-92-5
WeightAverage: 163.2594
Monoisotopic: 163.136099549
Chemical FormulaC11H17N
InChI KeyRXQCGGRTAILOIN-UHFFFAOYSA-N
InChI
InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3
IUPAC Name
methyl(2-methyl-1-phenylpropan-2-yl)amine
SMILES
CNC(C)(C)CC1=CC=CC=C1
Mass Specshow(7.87 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassPhenethylamines
Direct parentAmphetamines and Derivatives
Alternative parentsPolyamines; Dialkylamines
Substituentspolyamine; secondary aliphatic amine; secondary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the amphetamines and derivatives. These are organic compounds containing or derived from 1-phenylpropan-2-amine.
Pharmacology
IndicationUsed to maintain blood pressure in hypotensive states.
PharmacodynamicsMephentermine is a sympathomimetic agent with mainly indirect effects on adrenergic receptors. It is used to maintain blood pressure in hypotensive states, for example, following spinal anesthesia. Although the central stimulant effects of mephentermine are much less than those of amphetamine, its use may lead to amphetamine-type dependence. (From Martindale, The Extra Pharmacopoeia, 30th ed, p1248)
Mechanism of actionMephentermine is an alpha adrenergic receptor agonist, but also acts indirectly by releasing endogenous norepinephrine. Cardiac output and systolic and diastolic pressures are usually increased. A change in heart rate is variable, depending on the degree of vagal tone. Sometimes the net vascular effect may be vasodilation. Large doses may depress the myocardium or produce central nervous system (CNS) effects.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Hepatic, by N-demethylation and then p-hydroxylation.

Route of eliminationNot Available
Half life17 to 18 hours.
ClearanceNot Available
ToxicityNot Available
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9925
Blood Brain Barrier + 0.9664
Caco-2 permeable + 0.7962
P-glycoprotein substrate Non-substrate 0.5711
P-glycoprotein inhibitor I Non-inhibitor 0.8782
P-glycoprotein inhibitor II Non-inhibitor 0.9574
Renal organic cation transporter Non-inhibitor 0.775
CYP450 2C9 substrate Non-substrate 0.7797
CYP450 2D6 substrate Substrate 0.7109
CYP450 3A4 substrate Non-substrate 0.5507
CYP450 1A2 substrate Non-inhibitor 0.9046
CYP450 2C9 substrate Non-inhibitor 0.923
CYP450 2D6 substrate Inhibitor 0.8932
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.8388
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.8682
Ames test Non AMES toxic 0.979
Carcinogenicity Non-carcinogens 0.8079
Biodegradation Not ready biodegradable 0.9633
Rat acute toxicity 2.8952 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9804
hERG inhibition (predictor II) Non-inhibitor 0.872
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage formsNot Available
PricesNot Available
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
melting point< 25 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.457ALOGPS
logP2.54ALOGPS
logP2.52ChemAxon
logS-2.5ALOGPS
pKa (Strongest Basic)10.3ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area12.03 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity53.12 m3·mol-1ChemAxon
Polarizability19.79 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG CompoundC07889
PubChem Compound3677
PubChem Substance46505918
ChemSpider3549
Therapeutic Targets DatabaseDAP000898
PharmGKBPA164745533
ATC CodesC01CA11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AmitriptylineThe tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of mephentermine.
AmoxapineThe tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of mephentermine.
ClomipramineThe tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of mephentermine.
DesipramineThe tricyclic antidepressant, desipramine, increases the sympathomimetic effect of mephentermine.
DoxepinThe tricyclic antidepressant, doxepin, increases the sympathomimetic effect of mephentermine.
ImipramineThe tricyclic antidepressant, imipramine, increases the sympathomimetic effect of mephentermine.
IsocarboxazidIncreased arterial pressure
LinezolidPossible increase of arterial pressure
MethyldopaIncreased arterial pressure
MidodrineIncreased arterial pressure
MoclobemideMoclobemide increases the sympathomimetic effect of mephentermine.
NortriptylineThe tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of mephentermine.
PhenelzineIncreased arterial pressure
RasagilineIncreased arterial pressure
ReserpineIncreased arterial pressure
TranylcypromineThe MAO inhibitor, Tranylcypromine, may increase the vasopressor effect of the alpha1-agonist, Mephentermine. Concomitant therapy should be avoided.
TrimipramineTrimipramine may increase the vasopressor effect of the alpha1-agonist, Mephentermine. Avoid combination if possible. Monitor sympathetic response to therapy if used concomitantly.
Food InteractionsNot Available

Targets

1. Alpha adrenergic receptor

Kind: protein group

Organism: Human

Pharmacological action: yes

Actions: agonist

Components

Name UniProt ID Details
Alpha-1A adrenergic receptor P35348 Details
Alpha-1B adrenergic receptor P35368 Details
Alpha-1D adrenergic receptor P25100 Details
Alpha-2A adrenergic receptor P08913 Details
Alpha-2B adrenergic receptor P18089 Details
Alpha-2C adrenergic receptor P18825 Details

References:

  1. Ahlquist RP: Present state of alpha- and beta-adrenergic drugs I. The adrenergic receptor. Am Heart J. 1976 Nov;92(5):661-4. Pubmed
  2. Mohta M, Janani SS, Sethi AK, Agarwal D, Tyagi A: Comparison of phenylephrine hydrochloride and mephentermine sulphate for prevention of post spinal hypotension. Anaesthesia. 2010 Dec;65(12):1200-5. doi: 10.1111/j.1365-2044.2010.06559.×. Pubmed

2. Beta adrenergic receptor

Kind: protein group

Organism: Human

Pharmacological action: unknown

Actions: agonist

Components

Name UniProt ID Details
Beta-1 adrenergic receptor P08588 Details
Beta-2 adrenergic receptor P07550 Details
Beta-3 adrenergic receptor P13945 Details

References:

  1. Mohta M, Janani SS, Sethi AK, Agarwal D, Tyagi A: Comparison of phenylephrine hydrochloride and mephentermine sulphate for prevention of post spinal hypotension. Anaesthesia. 2010 Dec;65(12):1200-5. doi: 10.1111/j.1365-2044.2010.06559.×. Pubmed

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Drug created on July 06, 2007 13:56 / Updated on April 11, 2014 14:37