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
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 |
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 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 |
---|---|---|---|
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 |
---|---|---|
Mephentermine psychosis: misuse of the Wyamine inhaler. | 1970 Mar |
|
Survival following 1000 mg of amethocaine. | 1979 May |
|
Accelerated hypertension after ingestion of mephentermine sulphate. | 1986 |
|
Analysis of benzene ethylamine derivatives in urine using the programmable dynamic liquid-phase microextraction (LPME) device. | 2003 Dec |
|
Randomised trial of intravenous infusion of ephedrine or mephentermine for management of hypotension during spinal anaesthesia for Caesarean section. | 2005 Jan |
|
Combination of low doses of intrathecal ketamine and midazolam with bupivacaine improves postoperative analgesia in orthopaedic surgery. | 2008 Apr |
|
Laparoscopic surgery using spinal anesthesia. | 2008 Apr-Jun |
|
Comparison of potency of ephedrine and mephentermine for prevention of post-spinal hypotension in caesarean section. | 2008 May |
|
Bone cement implantation syndrome: a report of four cases. | 2009 Apr |
|
Mephentermine dependence without psychosis. | 2009 Mar |
|
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine? | 2010 Apr 30 |
|
Comparison of phenylephrine hydrochloride and mephentermine sulphate for prevention of post spinal hypotension. | 2010 Dec |
|
Simultaneous determination of eight sympathomimetic amines in urine by gas chromatography/mass spectrometry. | 2010 Jan-Feb |
|
Mephentermine dependence without psychosis: a Brazilian case report. | 2010 Jun |
|
Spinal anesthesia for cesarean section: comparison of 5.0% lignocaine and 0.5% bupivacaine. | 2010 Mar |
|
Acute methaemoglobinaemia due to ingestion of nitrobenzene (paint solvent). | 2010 Mar |
|
Confirming urinary excretion of mephentermine and phentermine following the ingestion of oxethazaine by gas chromatography-mass spectrometry analysis. | 2010 Mar |
|
Respiratory changes during spinal anaesthesia for gynaecological laparoscopic surgery. | 2010 Oct |
|
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
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 15:22:13 GMT 2023
by
admin
on
Fri Dec 15 15:22:13 GMT 2023
|
Record UNII |
TEZ91L71V4
|
Record Status |
Validated (UNII)
|
Record Version |
|
-
Download
Name | Type | Language | ||
---|---|---|---|---|
|
Official Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Common Name | English | ||
|
Systematic Name | English | ||
|
Systematic Name | English |
Classification Tree | Code System | Code | ||
---|---|---|---|---|
|
NCI_THESAURUS |
C47795
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
||
|
WHO-VATC |
QC01CA11
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
||
|
WHO-ATC |
C01CA11
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
Code System | Code | Type | Description | ||
---|---|---|---|---|---|
|
C66089
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
100-92-5
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
202-901-6
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
SUB08748MIG
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
6756
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | RxNorm | ||
|
100000081476
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
TEZ91L71V4
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
D008616
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
DB01365
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
MEPHENTERMINE
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
CHEMBL1201234
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
495
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
DTXSID4023256
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
3677
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
1694
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
2172
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | |||
|
m7189
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY | Merck Index | ||
|
7222
Created by
admin on Fri Dec 15 15:22:13 GMT 2023 , Edited by admin on Fri Dec 15 15:22:13 GMT 2023
|
PRIMARY |
Related Record | Type | Details | ||
---|---|---|---|---|
|
SALT/SOLVATE -> PARENT | |||
|
SALT/SOLVATE -> PARENT |
Related Record | Type | Details | ||
---|---|---|---|---|
|
ACTIVE MOIETY |