Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | 2C11H17N.2H2O.H2O4S |
| Molecular Weight | 460.628 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.OS(O)(=O)=O.CNC(C)(C)CC1=CC=CC=C1.CNC(C)(C)CC2=CC=CC=C2
InChI
InChIKey=JPESSSURNLGQRF-UHFFFAOYSA-N
InChI=1S/2C11H17N.H2O4S.2H2O/c2*1-11(2,12-3)9-10-7-5-4-6-8-10;1-5(2,3)4;;/h2*4-8,12H,9H2,1-3H3;(H2,1,2,3,4);2*1H2
| Molecular Formula | C11H17N |
| Molecular Weight | 163.2594 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O4S |
| Molecular Weight | 98.078 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
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 |
|---|---|---|---|
Target ID: CHEMBL2331074 Sources: https://www.drugbank.ca/drugs/DB01365 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Secondary | WYAMINE SULFATE Approved UseUnknown Launch Date1951 |
Doses
| Dose | Population | Adverse events |
|---|---|---|
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 |
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 |
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 |
|
| 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 |
|
| 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 |
|
| 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 |
Overview
| CYP3A4 | CYP2C9 | CYP2D6 | hERG |
|---|---|---|---|
OverviewOther
| Other Inhibitor | Other Substrate | Other Inducer |
|---|---|---|
Drug as victim
| Target | Modality | Activity | Metabolite | Clinical evidence |
|---|---|---|---|---|
Sources: https://pubmed.ncbi.nlm.nih.gov/8484260/ Page: 6.0 |
yes |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Comparison of bolus phenylephrine, ephedrine and mephentermine for maintenance of arterial pressure during spinal anesthesia in cesarean section. | 2010-12-25 |
|
| Comparison of phenylephrine hydrochloride and mephentermine sulphate for prevention of post spinal hypotension. | 2010-12 |
|
| Respiratory changes during spinal anaesthesia for gynaecological laparoscopic surgery. | 2010-10 |
|
| Prophylactic low dose ketamine and ondansetron for prevention of shivering during spinal anaesthesia. | 2010-10 |
|
| Mephentermine dependence without psychosis: a Brazilian case report. | 2010-06 |
|
| Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine? | 2010-04-30 |
|
| Generic sample preparation combined with high-resolution liquid chromatography-time-of-flight mass spectrometry for unification of urine screening in doping-control laboratories. | 2010-04 |
|
| Simultaneous determination of eight sympathomimetic amines in urine by gas chromatography/mass spectrometry. | 2010-03-26 |
|
| Spinal anesthesia for cesarean section: comparison of 5.0% lignocaine and 0.5% bupivacaine. | 2010-03 |
|
| Acute methaemoglobinaemia due to ingestion of nitrobenzene (paint solvent). | 2010-03 |
|
| Confirming urinary excretion of mephentermine and phentermine following the ingestion of oxethazaine by gas chromatography-mass spectrometry analysis. | 2010-03 |
|
| Up-down study--is the analysis adequate? | 2010-01 |
|
| Potency of mephentermine for prevention of post-spinal hypotension. | 2009-07 |
|
| Bone cement implantation syndrome: a report of four cases. | 2009-04 |
|
| Oxethazaine as the source of mephentermine and phentermine in athlete's urine. | 2009-03-10 |
|
| Mephentermine dependence without psychosis. | 2009-03 |
|
| Comparison of potency of ephedrine and mephentermine for prevention of post-spinal hypotension in caesarean section. | 2008-05 |
|
| Laparoscopic surgery using spinal anesthesia. | 2008-04-26 |
|
| Combination of low doses of intrathecal ketamine and midazolam with bupivacaine improves postoperative analgesia in orthopaedic surgery. | 2008-04 |
|
| Total spinal anaesthesia following epidural test dose in an ankylosing spondylitic patient with anticipated difficult airway undergoing total hip replacement. | 2006-10 |
|
| Randomised trial of intravenous infusion of ephedrine or mephentermine for management of hypotension during spinal anaesthesia for Caesarean section. | 2005-01 |
|
| Analysis of benzene ethylamine derivatives in urine using the programmable dynamic liquid-phase microextraction (LPME) device. | 2003-12 |
|
| Accelerated hypertension after ingestion of mephentermine sulphate. | 1986 |
|
| Survival following 1000 mg of amethocaine. | 1979-05 |
|
| Mephentermine psychosis: misuse of the Wyamine inhaler. | 1970-03 |
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
| Substance Class |
Chemical
Created
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Edited
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| Record UNII |
2SPK6HL7P7
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| Record Status |
Validated (UNII)
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| Record Version |
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ACTIVE MOIETY |