Details
Stereochemistry | ACHIRAL |
Molecular Formula | C11H17N |
Molecular Weight | 163.2594 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CNC(C)(C)CC1=CC=CC=C1
InChI
InChIKey=RXQCGGRTAILOIN-UHFFFAOYSA-N
InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3
Mephentermine, an amphetamine-derived phenethylamine, is an alpha 1 adrenergic receptor agonist and a hypertensive drug. Mephentermine is mainly used as a vasopressor agent with a sympathomimetic action, primarily causing release of noradrenaline and increasing cardiac output due to positive inotropic effect on the myocardium. The injectable preparation of mephentermine is commonly used for the short-term treatment of various hypotensive states such as shock or hypotension accompanying myocardial infarction or spinal anesthesia or surgical procedures like cesarean section. There is evidence on the fetal metabolic effect and placental transfer of mephentermine. However, a few studies have shown that mephentermine is as effective as phenylephrine in preventing maternal hypotension after spinal anesthesia and has similar effect on neonatal outcome. It is being widely used in developing countries like India as it is much more economical than phenylephrine and offers ease of use as it does not necessitate multiple dilutions as injectable. It is also available in India as 10 mg oral tablets. Despite it was thought earlier to have a little stimulant effect its abuse potential has increased, especially in sports due to its stimulant properties. Like amphetamines, it has shown to increase athletic performance in strength exercises and endurance in a dose of 14 mg/70 kg body weight. It has been proposed that phentermine, which is the main metabolite of mephentermine, acts by inhibiting monoaminoxidases A and B. Mephentermine adverse effects has been related to CNS simulation, excessive rises in blood pressure, and arrhythmias. Wyamine Sulfate (brand name of mephentermine sulfate) approved by FDA in 1951 was discontinued in USA.
CNS Activity
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2331074 Sources: https://www.drugbank.ca/drugs/DB01365 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Secondary | WYAMINE SULFATE Approved UseUnknown Launch Date1951 |
Doses
Dose | Population | Adverse events |
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1000 mg 1 times / week multiple, intravenous Abused dose Dose: 1000 mg, 1 times / week Route: intravenous Route: multiple Dose: 1000 mg, 1 times / week Sources: |
healthy, 23 years n = 1 Health Status: healthy Age Group: 23 years Sex: M Population Size: 1 Sources: |
Other AEs: Suspiciousness, Aggressive behavior... Other AEs: Suspiciousness Sources: Aggressive behavior Abusive behavior |
30 mg 1 times / day multiple, intravenous Dose: 30 mg, 1 times / day Route: intravenous Route: multiple Dose: 30 mg, 1 times / day Sources: |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: M Population Size: 1 Sources: |
Disc. AE: Cardiomyopathy... AEs leading to discontinuation/dose reduction: Cardiomyopathy Sources: |
AEs
AE | Significance | Dose | Population |
---|---|---|---|
Abusive behavior | 1000 mg 1 times / week multiple, intravenous Abused dose Dose: 1000 mg, 1 times / week Route: intravenous Route: multiple Dose: 1000 mg, 1 times / week Sources: |
healthy, 23 years n = 1 Health Status: healthy Age Group: 23 years Sex: M Population Size: 1 Sources: |
|
Aggressive behavior | 1000 mg 1 times / week multiple, intravenous Abused dose Dose: 1000 mg, 1 times / week Route: intravenous Route: multiple Dose: 1000 mg, 1 times / week Sources: |
healthy, 23 years n = 1 Health Status: healthy Age Group: 23 years Sex: M Population Size: 1 Sources: |
|
Suspiciousness | 1000 mg 1 times / week multiple, intravenous Abused dose Dose: 1000 mg, 1 times / week Route: intravenous Route: multiple Dose: 1000 mg, 1 times / week Sources: |
healthy, 23 years n = 1 Health Status: healthy Age Group: 23 years Sex: M Population Size: 1 Sources: |
|
Cardiomyopathy | Disc. AE | 30 mg 1 times / day multiple, intravenous Dose: 30 mg, 1 times / day Route: intravenous Route: multiple Dose: 30 mg, 1 times / day Sources: |
healthy, 32 years n = 1 Health Status: healthy Age Group: 32 years Sex: M Population Size: 1 Sources: |
Overview
CYP3A4 | CYP2C9 | CYP2D6 | hERG |
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OverviewOther
Other Inhibitor | Other Substrate | Other Inducer |
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Drug as victim
Target | Modality | Activity | Metabolite | Clinical evidence |
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Sources: https://pubmed.ncbi.nlm.nih.gov/8484260/ Page: 6.0 |
yes |
PubMed
Title | Date | PubMed |
---|---|---|
Mephentermine psychosis: misuse of the Wyamine inhaler. | 1970 Mar |
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Survival following 1000 mg of amethocaine. | 1979 May |
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Laparoscopic surgery using spinal anesthesia. | 2008 Apr-Jun |
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Potency of mephentermine for prevention of post-spinal hypotension. | 2009 Jul |
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Mephentermine dependence without psychosis. | 2009 Mar |
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Oxethazaine as the source of mephentermine and phentermine in athlete's urine. | 2009 Mar 10 |
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Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. | 2010 Apr |
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Up-down study--is the analysis adequate? | 2010 Jan |
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Simultaneous determination of eight sympathomimetic amines in urine by gas chromatography/mass spectrometry. | 2010 Jan-Feb |
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Comparison of bolus phenylephrine, ephedrine and mephentermine for maintenance of arterial pressure during spinal anesthesia in cesarean section. | 2010 Jan-Mar |
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Mephentermine dependence without psychosis: a Brazilian case report. | 2010 Jun |
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Respiratory changes during spinal anaesthesia for gynaecological laparoscopic surgery. | 2010 Oct |
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Prophylactic low dose ketamine and ondansetron for prevention of shivering during spinal anaesthesia. | 2010 Oct |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25886435
15 mg/ml or 30 mg/ml mephentermine for the short-term treatment of various hypotensive states, e.g., shock or hypotension accompanying myocardial infarction or spinal anesthesia or surgical procedures like cesarean section
Route of Administration:
Other
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NCI_THESAURUS |
C47795
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WHO-VATC |
QC01CA11
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WHO-ATC |
C01CA11
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C66089
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100-92-5
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202-901-6
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SUB08748MIG
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6756
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100000081476
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TEZ91L71V4
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D008616
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DB01365
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MEPHENTERMINE
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CHEMBL1201234
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495
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DTXSID4023256
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3677
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1694
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2172
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m7189
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7222
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PRIMARY |
ACTIVE MOIETY
SALT/SOLVATE (PARENT)
SALT/SOLVATE (PARENT)