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Details

Stereochemistry ACHIRAL
Molecular Formula C11H17N
Molecular Weight 163.2598
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPHENTERMINE

SMILES

CC(C)(Cc1ccccc1)NC

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

HIDE SMILES / InChI

Molecular Formula C11H17N
Molecular Weight 163.2598
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Secondary
WYAMINE SULFATE

Approved Use

Unknown

Launch Date

-5.683392E11
Doses

Doses

DosePopulationAdverse 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
Aggressive behavior
Abusive behavior
Sources:
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

AEs

AESignificanceDosePopulation
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

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as victim

Drug as victim

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
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
Total spinal anaesthesia following epidural test dose in an ankylosing spondylitic patient with anticipated difficult airway undergoing total hip replacement.
2006 Oct
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
Potency of mephentermine for prevention of post-spinal hypotension.
2009 Jul
Mephentermine dependence without psychosis.
2009 Mar
Oxethazaine as the source of mephentermine and phentermine in athlete's urine.
2009 Mar 10
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
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
Up-down study--is the analysis adequate?
2010 Jan
Comparison of bolus phenylephrine, ephedrine and mephentermine for maintenance of arterial pressure during spinal anesthesia in cesarean section.
2010 Jan-Mar
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
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

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
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:44:22 UTC 2021
Edited
by admin
on Sat Jun 26 03:44:22 UTC 2021
Record UNII
TEZ91L71V4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
MEPHENTERMINE
HSDB   INN   MI   VANDF   WHO-DD  
INN  
Official Name English
MEPHENTERMINE [INN]
Common Name English
MEPHENTERMINE [HSDB]
Common Name English
MEPHENTERMINE [WHO-DD]
Common Name English
MEPHENTERMINE [MI]
Common Name English
MEPHENTERMINE [VANDF]
Common Name English
BENZENEETHANAMINE, N,.ALPHA.,.ALPHA.-TRIMETHYL-
Systematic Name English
N,.ALPHA.,.ALPHA.-TRIMETHYLPHENETHYLAMINE
Systematic Name English
Classification Tree Code System Code
NCI_THESAURUS C47795
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
WHO-VATC QC01CA11
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
WHO-ATC C01CA11
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C66089
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
CAS
100-92-5
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
ECHA (EC/EINECS)
202-901-6
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
EVMPD
SUB08748MIG
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
RXCUI
6756
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY RxNorm
FDA UNII
TEZ91L71V4
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
MESH
D008616
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
DRUG BANK
DB01365
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
WIKIPEDIA
MEPHENTERMINE
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
ChEMBL
CHEMBL1201234
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
INN
495
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
EPA CompTox
100-92-5
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
PUBCHEM
3677
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
DRUG CENTRAL
1694
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
HSDB
2172
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
MERCK INDEX
M7189
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY Merck Index
IUPHAR
7222
Created by admin on Sat Jun 26 03:44:22 UTC 2021 , Edited by admin on Sat Jun 26 03:44:22 UTC 2021
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
SALT/SOLVATE -> PARENT
Related Record Type Details
ACTIVE MOIETY