Identification

Name
Mephentermine
Accession Number
DB01365
Type
Small Molecule
Groups
Approved
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
Product Ingredients
IngredientUNIICASInChI Key
Mephentermine sulfate580655Z8RR1212-72-2DNKCFBJMFIUNRS-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Wyamine Sulfate Injection Liq 30mg/mlLiquid30 mgIntramuscular; IntravenousWyeth Ayerst Canada Inc.1994-12-311998-12-15Canada
International/Other Brands
Wyamine / Wyfentermina
Categories
UNII
TEZ91L71V4
CAS number
100-92-5
Weight
Average: 163.2594
Monoisotopic: 163.136099549
Chemical Formula
C11H17N
InChI Key
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

Pharmacology

Indication

Used to maintain blood pressure in hypotensive states.

Pharmacodynamics

Mephentermine 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 action

Mephentermine 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.

TargetActionsOrganism
AAlpha adrenergic receptor
agonist
Human
UBeta adrenergic receptor
agonist
Human
Absorption
Not Available
Volume of distribution
Not Available
Protein binding
Not Available
Metabolism

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

Route of elimination
Not Available
Half life

17 to 18 hours.

Clearance
Not Available
Toxicity
Not Available
Affected organisms
  • Humans and other mammals
Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
2,5-Dimethoxy-4-ethylamphetamineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 2,5-Dimethoxy-4-ethylamphetamine.
2,5-Dimethoxy-4-ethylthioamphetamineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
3-isobutyl-1-methyl-7H-xanthineThe risk or severity of adverse effects can be increased when Mephentermine is combined with 3-isobutyl-1-methyl-7H-xanthine.
3,4-MethylenedioxyamphetamineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 3,4-Methylenedioxyamphetamine.
4-Bromo-2,5-dimethoxyamphetamineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
5-methoxy-N,N-dimethyltryptamineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 5-methoxy-N,N-dimethyltryptamine.
6-O-benzylguanineThe risk or severity of adverse effects can be increased when Mephentermine is combined with 6-O-benzylguanine.
7-DeazaguanineThe risk or severity of adverse effects can be increased when Mephentermine is combined with 7-Deazaguanine.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of serotonin syndrome can be increased when Mephentermine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
7,9-DimethylguanineThe risk or severity of adverse effects can be increased when Mephentermine is combined with 7,9-Dimethylguanine.
Food Interactions
Not Available

References

General References
Not Available
External Links
Human Metabolome Database
HMDB0015452
KEGG Compound
C07889
PubChem Compound
3677
PubChem Substance
46505918
ChemSpider
3549
BindingDB
81455
ChEBI
6755
ChEMBL
CHEMBL1201234
Therapeutic Targets Database
DAP000898
PharmGKB
PA164745533
Wikipedia
Mephentermine
ATC Codes
C01CA11 — Mephentermine

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage forms
FormRouteStrength
LiquidIntramuscular; Intravenous30 mg
Prices
Not Available
Patents
Not Available

Properties

State
Liquid
Experimental Properties
PropertyValueSource
melting point (°C)< 25 °CPhysProp
Predicted Properties
PropertyValueSource
Water Solubility0.457 mg/mLALOGPS
logP2.54ALOGPS
logP2.52ChemAxon
logS-2.6ALOGPS
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
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)

Spectra

Mass Spec (NIST)
Download (7.87 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

Taxonomy

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 / Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
Substituents
Amphetamine or derivatives / Phenylpropane / Aralkylamine / Secondary amine / Secondary aliphatic amine / Organic nitrogen compound / Organopnictogen compound / Hydrocarbon derivative / Organonitrogen compound / Amine
Molecular Framework
Aromatic homomonocyclic compounds
External Descriptors
amphetamines (CHEBI:6755)

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) prot...

Components:
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 e...

Components:
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]

Drug created on July 06, 2007 13:56 / Updated on November 02, 2018 08:46