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Details

Stereochemistry ACHIRAL
Molecular Formula C11H17N.ClH
Molecular Weight 199.72
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MEPHENTERMINE HYDROCHLORIDE

SMILES

Cl.CNC(C)(C)CC1=CC=CC=C1

InChI

InChIKey=NRRWAHXGKZKRBW-UHFFFAOYSA-N
InChI=1S/C11H17N.ClH/c1-11(2,12-3)9-10-7-5-4-6-8-10;/h4-8,12H,9H2,1-3H3;1H

HIDE SMILES / InChI
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

1951
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
Total spinal anaesthesia following epidural test dose in an ankylosing spondylitic patient with anticipated difficult airway undergoing total hip replacement.
2006 Oct
Potency of mephentermine for prevention of post-spinal hypotension.
2009 Jul
Oxethazaine as the source of mephentermine and phentermine in athlete's urine.
2009 Mar 10
Vasopressor choice for hypotension in elective Cesarean section: ephedrine or phenylephrine?
2010 Apr 30
Spinal anesthesia for cesarean section: comparison of 5.0% lignocaine and 0.5% bupivacaine.
2010 Mar
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
Name Type Language
MEPHENTERMINE HYDROCHLORIDE
WHO-DD  
Common Name English
N,.ALPHA.,.ALPHA.-TRIMETHYLPHENETHYLAMINE HYDROCHLORIDE
Systematic Name English
MEPHENTERMINE HCL
Common Name English
BENZENEETHANAMINE, N,.ALPHA.,.ALPHA.-TRIMETHYL-, HYDROCHLORIDE (1:1)
Systematic Name English
PHENETHYLAMINE, N,.ALPHA.,.ALPHA.-TRIMETHYL-, HYDROCHLORIDE
Systematic Name English
Mephentermine hydrochloride [WHO-DD]
Common Name English
Code System Code Type Description
SMS_ID
100000086420
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY
RXCUI
236481
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY RxNorm
EVMPD
SUB03155MIG
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY
EPA CompTox
DTXSID60192854
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY
PUBCHEM
199291
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY
CAS
3978-34-5
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY
FDA UNII
V2NCN17P8O
Created by admin on Sat Dec 16 02:17:59 GMT 2023 , Edited by admin on Sat Dec 16 02:17:59 GMT 2023
PRIMARY