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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
Mephentermine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Wyamine Sulfate Injection Liq 30mg/mlliquid30 mgintramuscular; intravenousWyeth Ayerst Canada Inc.1994-12-311998-12-15Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
WyamineNot Available
WyfenterminaNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Mephentermine sulfate
ThumbNot applicableDBSALT001074
Categories
UNIITEZ91L71V4
CAS number100-92-5
WeightAverage: 163.2594
Monoisotopic: 163.136099549
Chemical FormulaC11H17N
InChI KeyInChIKey=RXQCGGRTAILOIN-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.
Related Articles
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 inhibitorNon-inhibitor0.923
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-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
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
ManufacturersNot Available
PackagersNot Available
Dosage forms
FormRouteStrength
Liquidintramuscular; intravenous30 mg
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)
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis ReferenceNot Available
General ReferencesNot Available
External Links
ATC CodesC01CA11
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug Interactions
Drug
AcetaminophenThe risk or severity of adverse effects can be increased when Mephentermine is combined with Acetaminophen.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Mephentermine is combined with Acetylsalicylic acid.
AminophyllineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Aminophylline.
AmphetamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Amphetamine.
ArformoterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Arformoterol.
ArmodafinilThe risk or severity of adverse effects can be increased when Mephentermine is combined with Armodafinil.
ArticaineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Articaine.
AtomoxetineAtomoxetine may increase the hypertensive activities of Mephentermine.
BenzphetamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Benzphetamine.
ButalbitalThe risk or severity of adverse effects can be increased when Mephentermine is combined with Butalbital.
CaffeineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Caffeine.
CocaineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Cocaine.
DexmethylphenidateThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dexmethylphenidate.
DextroamphetamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dextroamphetamine.
DiethylpropionThe risk or severity of adverse effects can be increased when Mephentermine is combined with Diethylpropion.
DihydrocodeineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dihydrocodeine.
DipivefrinThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dipivefrin.
DobutamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dobutamine.
DopamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dopamine.
DoxapramThe risk or severity of adverse effects can be increased when Mephentermine is combined with Doxapram.
DronabinolDronabinol may increase the tachycardic activities of Mephentermine.
DyphyllineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Dyphylline.
EphedrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Ephedrine.
EpinephrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Epinephrine.
FenoterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Fenoterol.
Fluticasone PropionateThe risk or severity of adverse effects can be increased when Mephentermine is combined with Fluticasone Propionate.
FormoterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Formoterol.
IndacaterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Indacaterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Mephentermine.
Ipratropium bromideThe risk or severity of adverse effects can be increased when Mephentermine is combined with Ipratropium bromide.
IsomethepteneThe risk or severity of adverse effects can be increased when Mephentermine is combined with Isometheptene.
LevonordefrinThe risk or severity of adverse effects can be increased when Mephentermine is combined with Levonordefrin.
LinezolidLinezolid may increase the hypertensive activities of Mephentermine.
LisdexamfetamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Lisdexamfetamine.
MepivacaineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Mepivacaine.
MethamphetamineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Methamphetamine.
MethylphenidateThe risk or severity of adverse effects can be increased when Mephentermine is combined with Methylphenidate.
MidodrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Midodrine.
ModafinilThe risk or severity of adverse effects can be increased when Mephentermine is combined with Modafinil.
NabiloneNabilone may increase the tachycardic activities of Mephentermine.
NaphazolineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Naphazoline.
NorepinephrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Norepinephrine.
OlodaterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Olodaterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Oxymetazoline.
PhendimetrazineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Phendimetrazine.
PheniramineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Pheniramine.
PhentermineThe risk or severity of adverse effects can be increased when MePhentermine is combined with Phentermine.
PhenylephrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Phenylephrine.
PirbuterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Pirbuterol.
PropylhexedrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Propylhexedrine.
PseudoephedrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Pseudoephedrine.
RacepinephrineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Racepinephrine.
SalbutamolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Salbutamol.
SalmeterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Salmeterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Mephentermine.
TerbutalineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Terbutaline.
TheophyllineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Theophylline.
TriprolidineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Triprolidine.
VilanterolThe risk or severity of adverse effects can be increased when Mephentermine is combined with Vilanterol.
Food InteractionsNot Available

Targets

Kind
Protein group
Organism
Human
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) proteins. Nuclear ADRA1A-ADRA1B heterooligomers regulate phenylephrine(PE)-stimulated ERK signaling in cardiac myocytes.
Components:
NameUniProt IDDetails
Alpha-1A adrenergic receptorP35348 Details
Alpha-1B adrenergic receptorP35368 Details
Alpha-1D adrenergic receptorP25100 Details
Alpha-2A adrenergic receptorP08913 Details
Alpha-2B adrenergic receptorP18089 Details
Alpha-2C adrenergic receptorP18825 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:10722 ]
  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.x. [PubMed:21182601 ]
Kind
Protein group
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Receptor signaling protein activity
Specific Function:
Beta-adrenergic receptors mediate the catecholamine-induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Components:
NameUniProt IDDetails
Beta-1 adrenergic receptorP08588 Details
Beta-2 adrenergic receptorP07550 Details
Beta-3 adrenergic receptorP13945 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.x. [PubMed:21182601 ]
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Drug created on July 06, 2007 13:56 / Updated on August 17, 2016 12:23