Mephentermine
Identification
- Name
- Mephentermine
- Accession Number
- DB01365
- 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)
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Mephentermine (DB01365)
- Weight
- Average: 163.2594
Monoisotopic: 163.136099549 - Chemical Formula
- C11H17N
- Synonyms
- Mefentermina
- Mephentermine
- Mephenterminum
- External IDs
- WY-585
Pharmacology
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Used to maintain blood pressure in hypotensive states.
- Contraindications & Blackbox Warnings
Contraindications & Blackbox WarningsWith our commercial data, access important information on dangerous risks, contraindications, and adverse effects.Our Blackbox Warnings cover Risks, Contraindications, and Adverse Effects- 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.
Target Actions Organism AAlpha adrenergic receptor agonistHumans UBeta adrenergic receptor agonistHumans - 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
- Adverse Effects
Reduce medical errorsand improve treatment outcomes with our comprehensive & structured data on drug adverse effects.Reduce medical errors & improve treatment outcomes with our adverse effects data- Toxicity
- Not Available
- 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.
Drug Interaction Integrate drug-drug
interactions in your softwareAbaloparatide The risk or severity of adverse effects can be increased when Mephentermine is combined with Abaloparatide. Acebutolol The therapeutic efficacy of Acebutolol can be decreased when used in combination with Mephentermine. Aceclofenac The risk or severity of hypertension can be increased when Mephentermine is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Mephentermine is combined with Acemetacin. Acetazolamide Acetazolamide may decrease the excretion rate of Mephentermine which could result in a higher serum level. Acetophenazine Acetophenazine may decrease the stimulatory activities of Mephentermine. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Mephentermine. Aclidinium The risk or severity of Tachycardia can be increased when Mephentermine is combined with Aclidinium. Acrivastine Mephentermine may decrease the sedative and stimulatory activities of Acrivastine. Adenosine The risk or severity of Tachycardia can be increased when Adenosine is combined with Mephentermine. 
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- Not Available
Products
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Ingredient UNII CAS InChI Key Mephentermine sulfate 580655Z8RR 1212-72-2 DNKCFBJMFIUNRS-UHFFFAOYSA-N - International/Other Brands
- Wyamine / Wyfentermina
- Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Wyamine Sulfate Injection Liq 30mg/ml Liquid Intramuscular; Intravenous Wyeth Ayerst Canada Inc. 1994-12-31 1998-12-15 Canada 
Categories
- ATC Codes
- C01CA11 — Mephentermine
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic alpha-1 Receptor Agonists
- Adrenergic alpha-Agonists
- Adrenergic and Dopaminergic Agents
- Agents producing tachycardia
- Agents that produce hypertension
- Amines
- Amphetamines
- Autonomic Agents
- Cardiac Stimulants Excl. Cardiac Glycosides
- Cardiac Therapy
- Cardiovascular Agents
- Ethylamines
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Phenethylamines
- Serotonergic Drugs Shown to Increase Risk of Serotonin Syndrome
- Sympathomimetics
- Vasoconstrictor Agents
- 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 / Aralkylamines / Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Amine / Amphetamine or derivatives / Aralkylamine / Aromatic homomonocyclic compound / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Phenylpropane / Secondary aliphatic amine
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- amphetamines (CHEBI:6755)
Chemical Identifiers
- UNII
- TEZ91L71V4
- CAS number
- 100-92-5
- 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
References
- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0015452
- KEGG Drug
- D08180
- KEGG Compound
- C07889
- PubChem Compound
- 3677
- PubChem Substance
- 46505918
- ChemSpider
- 3549
- BindingDB
- 81455
- 6756
- ChEBI
- 6755
- ChEMBL
- CHEMBL1201234
- ZINC
- ZINC000008132748
- Therapeutic Targets Database
- DAP000898
- PharmGKB
- PA164745533
- Wikipedia
- Mephentermine
Clinical Trials
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Liquid Intramuscular; Intravenous - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) < 25 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.457 mg/mL ALOGPS logP 2.54 ALOGPS logP 2.52 ChemAxon logS -2.6 ALOGPS pKa (Strongest Basic) 10.3 ChemAxon Physiological Charge 1 ChemAxon Hydrogen Acceptor Count 1 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 12.03 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 53.12 m3·mol-1 ChemAxon Polarizability 19.79 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 1 ChemAxon Rule of Five Yes ChemAxon Ghose Filter Yes ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - 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 inhibitor Non-inhibitor 0.923 CYP450 2D6 inhibitor Inhibitor 0.8932 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor 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
Spectra
- Mass Spec (NIST)
- Download (7.87 KB)
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available
Targets
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- Kind
- Protein group
- 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...
Components:
References
- 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]
- 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
- Humans
- 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:
| Name | UniProt ID |
|---|---|
| Beta-1 adrenergic receptor | P08588 |
| Beta-2 adrenergic receptor | P07550 |
| Beta-3 adrenergic receptor | P13945 |
References
- 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 19:56 / Updated on June 12, 2020 16:51