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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
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
WyamineNot Available
WyfenterminaNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mephentermine sulfate
ThumbNot applicableDBSALT001074
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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenethylamines
Direct ParentAmphetamines and derivatives
Alternative Parents
Substituents
  • Amphetamine or derivatives
  • Phenylpropane
  • Aralkylamine
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Organonitrogen compound
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External DescriptorsNot Available
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
PropertyValueProbability
Human Intestinal Absorption+0.9925
Blood Brain Barrier+0.9664
Caco-2 permeable+0.7962
P-glycoprotein substrateNon-substrate0.5711
P-glycoprotein inhibitor INon-inhibitor0.8782
P-glycoprotein inhibitor IINon-inhibitor0.9574
Renal organic cation transporterNon-inhibitor0.775
CYP450 2C9 substrateNon-substrate0.7797
CYP450 2D6 substrateSubstrate0.7109
CYP450 3A4 substrateNon-substrate0.5507
CYP450 1A2 substrateNon-inhibitor0.9046
CYP450 2C9 substrateNon-inhibitor0.923
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9025
CYP450 3A4 substrateNon-inhibitor0.8388
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8682
Ames testNon AMES toxic0.979
CarcinogenicityNon-carcinogens0.8079
BiodegradationNot ready biodegradable0.9633
Rat acute toxicity2.8952 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9804
hERG inhibition (predictor II)Non-inhibitor0.872
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 Solubility0.457 mg/mLALOGPS
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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Download (7.87 KB)
SpectraNot Available
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ATC CodesC01CA11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AminophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
AmphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
ArformoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
armodafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
ArticaineMay enhance the adverse/toxic effect of other Sympathomimetics.
AtomoxetineAtoMOXetine may enhance the hypertensive effect of Sympathomimetics. AtoMOXetine may enhance the tachycardic effect of Sympathomimetics.
BenzphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
CaffeineMay enhance the adverse/toxic effect of other Sympathomimetics.
CocaineMay enhance the adverse/toxic effect of other Sympathomimetics.
DexmethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
DextroamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DiethylpropionMay enhance the adverse/toxic effect of other Sympathomimetics.
DihydrocodeineMay enhance the adverse/toxic effect of other Sympathomimetics.
DipivefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
DobutamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DopamineMay enhance the adverse/toxic effect of other Sympathomimetics.
DoxapramMay enhance the adverse/toxic effect of other Sympathomimetics.
DronabinolCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
FenoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Fluticasone furoateMay enhance the adverse/toxic effect of other Sympathomimetics.
FormoterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IndacaterolMay enhance the adverse/toxic effect of other Sympathomimetics.
IobenguaneMay diminish the therapeutic effect of Iobenguane I 123.
Ipratropium bromideMay enhance the adverse/toxic effect of other Sympathomimetics.
IsomethepteneMay enhance the adverse/toxic effect of other Sympathomimetics.
LevonordefrinMay enhance the adverse/toxic effect of other Sympathomimetics.
LinezolidLinezolid may enhance the hypertensive effect of Sympathomimetics.
LisdexamfetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethamphetamineMay enhance the adverse/toxic effect of other Sympathomimetics.
MethylphenidateMay enhance the adverse/toxic effect of other Sympathomimetics.
MidodrineMay enhance the adverse/toxic effect of other Sympathomimetics.
ModafinilMay enhance the adverse/toxic effect of other Sympathomimetics.
NabiloneCannabinoid-Containing Products may enhance the tachycardic effect of Sympathomimetics.
NaphazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
NorepinephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
OrciprenalineMay enhance the adverse/toxic effect of other Sympathomimetics.
OxymetazolineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhendimetrazineMay enhance the adverse/toxic effect of other Sympathomimetics.
PheniramineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhentermineMay enhance the adverse/toxic effect of other Sympathomimetics.
PhenylephrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PirbuterolMay enhance the adverse/toxic effect of other Sympathomimetics.
PropylhexedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
PseudoephedrineMay enhance the adverse/toxic effect of other Sympathomimetics.
SalbutamolMay enhance the adverse/toxic effect of other Sympathomimetics.
SalmeterolMay enhance the adverse/toxic effect of other Sympathomimetics.
Tedizolid PhosphateTedizolid may enhance the hypertensive effect of Sympathomimetics. Tedizolid may enhance the tachycardic effect of Sympathomimetics.
TerbutalineMay enhance the adverse/toxic effect of other Sympathomimetics.
TheophyllineMay enhance the adverse/toxic effect of other Sympathomimetics.
TriprolidineMay enhance the adverse/toxic effect of other Sympathomimetics.
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