Mephentermine
|
Systematic (IUPAC) name |
N,2-dimethyl-1-phenylpropan-2-amine
|
Clinical data |
Routes of
administration |
IM/IV |
Pharmacokinetic data |
Metabolism |
Rapidly demethylated in the body followed by hydroxylation. |
Excretion |
Via urine (as unchanged and metabolites); more rapid in acidic urine. |
Identifiers |
CAS Registry Number |
100-92-5 Y |
ATC code |
C01CA11 |
PubChem |
CID: 3677 |
IUPHAR/BPS |
7222 |
DrugBank |
DB01365 Y |
ChemSpider |
3549 Y |
UNII |
TEZ91L71V4 Y |
KEGG |
D08180 Y |
ChEMBL |
CHEMBL1201234 N |
Synonyms |
methyl(2-methyl-1-phenylpropan-2-yl)amine |
Chemical data |
Formula |
C11H17N |
Molecular mass |
163.259 g/mol |
|
InChI
-
InChI=1S/C11H17N/c1-11(2,12-3)9-10-7-5-4-6-8-10/h4-8,12H,9H2,1-3H3 Y
-
Key:RXQCGGRTAILOIN-UHFFFAOYSA-N Y
|
N (what is this?) (verify) |
Mephentermine is a cardiac stimulant. It was formerly used in Wyamine nasal decongestant inhalers and before that as a stimulant in psychiatry.
It has been used as a treatment for low blood pressure.[1]
ATC Classification: C01CA11 - mephentermine ; Belongs to the class of adrenergic and dopaminergic cardiac stimulants excluding glycosides. Used in the treatment of heart failure.
Contents
- 1 Mechanism of Action
- 2 Indication & Dosage
- 3 Caution
- 3.1 Contraindications
- 3.2 Special Precautions
- 3.3 Adverse Drug Reactions
- 3.4 Drug Interactions
- 4 References
Mechanism of Action
Mephentermine appears to act by indirect stimulation of β-adrenergic receptors causing the release of norepinephrine from its storage sites. It has a positive inotropic effect on the myocardium. AV conduction and refractory period of AV node is shortened with an increase in ventricular conduction velocity. It dilates arteries and arterioles in the skeletal muscle and mesenteric vascular beds, leading to an increase in venous return.
Onset: 5–15 minutes (IM), immediate (IV).
Duration: 4 hr (IM), 30 minutes (IV).
Indication & Dosage
Maintenance of blood pressure in hypotensive states Adult: 30–45 mg as a single dose, repeated as necessary or followed by IV infusion of 0.1% mephentermine in 5% dextrose, rate and duration of administration will depend on patient's response.
Hypotension secondary to spinal anaesthesia in obstetric patients Adult: 15 mg as a single dose, repeat if needed.
Caution
Contraindications
Low blood pressure caused by phenothiazines. Hypertension. Pheochromocytoma.
Special Precautions
Patient on MAOIs. For shock due to loss of blood or fluid, give fluid replacement therapy primarily, CVS disease, hypertension, hyperthyroidism, chronic illnesses, lactation, pregnancy.
Adverse Drug Reactions
Drowsiness, incoherence, hallucinations, convulsions, fast heart rate. Fear, anxiety, restlessness, tremor, insomnia, confusion, irritability, and psychosis. Nausea, vomiting, reduced appetite, urinary retention, dyspnea, weakness.
Potentially Fatal: AV block, CNS stimulation. Cerebral hemorrhage and pulmonary edema, ventricular arrhythmias.
Drug Interactions
Antagonizes effect of agents that lower blood pressure. Severe hypertension with MAOIs and possibly tricyclic antidepressants. Additive vasoconstricting effects with ergot alkaloids, oxytocin.
Potentially Fatal: Risk of abnormal heart rhythm in people undergoing anesthesia with cyclopropane and halothane.
References
- ^ WHITTINGTON RM (May 1963). "Mephentemine Sulphate as a Hypertensive Agent in General Practice". J Coll Gen Pract 6 (2): 336–7. PMC 1878111. PMID 14000433.
Cardiac stimulants excluding cardiac glycosides (C01C)
|
|
Adrenergic and
dopaminergic agents |
Adrenergic agonists |
α |
- Metaraminol
- Phenylephrine
- Methoxamine
- Norfenefrine
- Oxedrine
- Midodrine
- Mephentermine
|
|
β |
- Dobutamine
- Arbutamine
- Isoprenaline
- Prenalterol
|
|
mixed |
- Amezinium metilsulfate
- Epinephrine #
- Norepinephrine
- Etilefrine
|
|
|
Dopamine agonists |
|
|
Both |
- Dopamine #
- Dopexamine
- Ibopamine
- Octopamine
|
|
Unknown/ungrouped |
- Dimetofrine
- Gepefrine
- Cafedrine
- Theodrenaline
|
|
|
Phosphodiesterase inhibitors (PDE3I) |
- Amrinone
- Milrinone
- Enoximone
- Bucladesine
|
|
Other cardiac stimulants |
- Angiotensinamide
- Xamoterol
- Levosimendan
- Pimobendan
|
|
- #WHO-EM
- ‡Withdrawn from market
- Clinical trials:
- †Phase III
- §Never to phase III
Index of the heart
|
|
Description |
- Anatomy
- Physiology
- Development
|
|
Disease |
- Injury
- Congenital
- Neoplasms and cancer
- Other
- Symptoms and signs
- Blood tests
|
|
Treatment |
- Procedures
- Drugs
- glycosides
- other stimulants
- antiarrhythmics
- vasodilators
|
|
|
Adrenergics
|
|
Receptor ligands
|
|
α1 |
- Agonists
- 6-FNE
- Amidephrine
- Anisodamine
- Anisodine
- Buspirone
- Cirazoline
- Corbadrine
- Dipivefrine
- Dopamine
- Ephedrine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Indanidine
- Metaraminol
- Methoxamine
- Methyldopa
- Midodrine
- Naphazoline
- Norepinephrine
- Octopamine
- Oxymetazoline
- Phenylephrine
- Phenylpropanolamine
- Pseudoephedrine
- Synephrine
- Tetrahydrozoline
|
|
- Antagonists
- Abanoquil
- Adimolol
- Ajmalicine
- Alfuzosin
- Amosulalol
- Arotinolol
- Atiprosin
- Atypical antipsychotics (e.g., clozapine, olanzapine, quetiapine, risperidone)
- Benoxathian
- Buflomedil
- Bunazosin
- Carvedilol
- Corynanthine
- Dapiprazole
- Domesticine
- Doxazosin
- Ergolines (e.g., ergotamine, dihydroergotamine, lisuride, terguride)
- Etoperidone
- Eugenodilol
- Fenspiride
- Hydroxyzine
- Indoramin
- Ketanserin
- L-765,314
- Labetalol
- mCPP
- Mepiprazole
- Metazosin
- Monatepil
- Moxisylyte
- Naftopidil
- Nantenine
- Nefazodone
- Neldazosin
- Niaprazine
- Nicergoline
- Niguldipine
- Pardoprunox
- Pelanserin
- Phendioxan
- Phenoxybenzamine
- Phentolamine
- Piperoxan
- Prazosin
- Quinazosin
- Ritanserin
- Silodosin
- Spiperone
- Talipexole
- Tamsulosin
- Terazosin
- Tiodazosin
- Tolazoline
- Trazodone
- Tetracyclic antidepressants (e.g., amoxapine, maprotiline, mianserin)
- Tricyclic antidepressants (e.g., amitriptyline, clomipramine, doxepin, imipramine, trimipramine)
- Trimazosin
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Urapidil
- WB-4101
- Zolertine
|
|
|
α2 |
- Agonists
- (R)-3-Nitrobiphenyline
- 4-NEMD
- 6-FNE
- Amitraz
- Apraclonidine
- Brimonidine
- Cannabivarin
- Clonidine
- Corbadrine
- Detomidine
- Dexmedetomidine
- Dihydroergotamine
- Dipivefrine
- Dopamine
- Ephedrine
- Ergotamine
- Epinephrine
- Etilefrine
- Ethylnorepinephrine
- Guanabenz
- Guanfacine
- Guanoxabenz
- Lofexidine
- Medetomidine
- Methamphetamine
- Methyldopa
- Mivazerol
- Naphazoline
- Norepinephrine
- Oxymetazoline
- Phenylpropanolamine
- Piperoxan
- Pseudoephedrine
- Rilmenidine
- Romifidine
- Talipexole
- Tetrahydrozoline
- Tizanidine
- Tolonidine
- Urapidil
- Xylazine
- Xylometazoline
|
|
- Antagonists
- 1-PP
- Adimolol
- Aptazapine
- Atipamezole
- Atypical antipsychotics (e.g., asenapine, clozapine, lurasidone, paliperidone, quetiapine, risperidone, zotepine)
- Azapirones (e.g., buspirone, tandospirone)
- BRL-44408
- Buflomedil
- Cirazoline
- Efaroxan
- Esmirtazapine
- Fenmetozole
- Fluparoxan
- Idazoxan
- mCPP
- Mianserin
- Mirtazapine
- NAN-190
- Olanzapine
- Pardoprunox
- Phentolamine
- Phenoxybenzamine
- Piperoxan
- Piribedil
- Rauwolscine
- Rotigotine
- SB-269970
- Setiptiline
- Spiroxatrine
- Sunepitron
- Tolazoline
- Typical antipsychotics (e.g., chlorpromazine, fluphenazine, loxapine, thioridazine)
- Yohimbine
|
|
|
β |
- Agonists
- Amibegron
- Arbutamine
- Arformoterol
- Arotinolol
- BAAM
- Bambuterol
- Befunolol
- Bitolterol
- Broxaterol
- Buphenine
- Carbuterol
- Cimaterol
- Clenbuterol
- Corbadrine
- Denopamine
- Dipivefrine
- Dobutamine
- Dopamine
- Dopexamine
- Ephedrine
- Epinephrine
- Etafedrine
- Etilefrine
- Ethylnorepinephrine
- Fenoterol
- Formoterol
- Hexoprenaline
- Higenamine
- Indacaterol
- Isoetarine
- Isoprenaline
- Isoxsuprine
- Levosalbutamol
- Mabuterol
- Methoxyphenamine
- Methyldopa
- Mirabegron
- Norepinephrine
- Orciprenaline
- Oxyfedrine
- Phenylpropanolamine
- Pirbuterol
- Prenalterol
- Ractopamine
- Procaterol
- Pseudoephedrine
- Reproterol
- Rimiterol
- Ritodrine
- Salbutamol
- Salmeterol
- Solabegron
- Terbutaline
- Tretoquinol
- Tulobuterol
- Vilanterol
- Xamoterol
- Zilpaterol
- Zinterol
|
|
- Antagonists
- Acebutolol
- Adaprolol
- Adimolol
- Afurolol
- Alprenolol
- Alprenoxime
- Amosulalol
- Ancarolol
- Arnolol
- Arotinolol
- Atenolol
- Befunolol
- Betaxolol
- Bevantolol
- Bisoprolol
- Bopindolol
- Bornaprolol
- Brefonalol
- Bucindolol
- Bucumolol
- Bufetolol
- Bufuralol
- Bunitrolol
- Bunolol
- Bupranolol
- Butaxamine
- Butidrine
- Butofilolol
- Capsinolol
- Carazolol
- Carpindolol
- Carteolol
- Carvedilol
- Celiprolol
- Cetamolol
- Cicloprolol
- Cinamolol
- Cloranolol
- Cyanopindolol
- Dalbraminol
- Dexpropranolol
- Diacetolol
- Dichloroisoprenaline
- Dihydroalprenolol
- Dilevalol
- Diprafenone
- Draquinolol
- Ecastolol
- Epanolol
- Ericolol
- Ersentilide
- Esatenolol
- Esprolol
- Eugenodilol
- Exaprolol
- Falintolol
- Flestolol
- Flusoxolol
- Hydroxycarteolol
- Hydroxytertatolol
- ICI-118,551
- Idropranolol
- Indenolol
- Indopanolol
- Iodocyanopindolol
- Iprocrolol
- Isoxaprolol
- Isamoltane
- Labetalol
- Landiolol
- Levobetaxolol
- Levobunolol
- Levomoprolol
- Medroxalol
- Mepindolol
- Metipranolol
- Metoprolol
- Moprolol
- Nadolol
- Nadoxolol
- Nebivolol
- Nifenalol
- Nipradilol
- Oxprenolol
- Pacrinolol
- Pafenolol
- Pamatolol
- Pargolol
- Penbutolol
- Pindolol
- Practolol
- Primidolol
- Procinolol
- Pronethalol
- Propafenone
- Propranolol
- Ridazolol
- Ronactolol
- Soquinolol
- Sotalol
- Spirendolol
- SR 59230A
- Sulfinalol
- Talinolol
- Tazolol
- Tertatolol
- Tienoxolol
- Tilisolol
- Timolol
- Tiprenolol
- Tolamolol
- Toliprolol
- Xibenolol
- Xipranolol
|
|
|
|
|
Reuptake inhibitors
|
|
NET |
- Selective norepinephrine reuptake inhibitors
- Amedalin
- Atomoxetine (tomoxetine)
- Ciclazindol
- Daledalin
- Edivoxetine
- Esreboxetine
- Lortalamine
- Mazindol
- Nisoxetine
- Reboxetine
- Talopram
- Talsupram
- Tandamine
- Viloxazine
|
|
- Norepinephrine-dopamine reuptake inhibitors
- Amineptine
- Bupropion
- Fencamine
- Fencamfamine
- Hydroxybupropion
- Lefetamine
- Levophacetoperane
- LR-5182
- Manifaxine
- Methylphenidate
- Nomifensine
- O-2172
- Radafaxine
|
|
- Serotonin-norepinephrine reuptake inhibitors
- Bicifadine
- Desvenlafaxine
- Duloxetine
- Eclanamine
- Levomilnacipran
- Milnacipran
- N-Methyl-PPPA
- PPPA
- Sibutramine
- Venlafaxine
|
|
- Serotonin-norepinephrine-dopamine reuptake inhibitors
- Brasofensine
- Dasotraline
- Desmethylsertraline
- Diclofensine
- DOV-102,677
- DOV-21,947
- DOV-216,303
- HDMP-28
- JNJ-7925476
- JZ-IV-10
- Liafensine
- Naphyrone
- NS-2359
- Perafensine
- PRC200
- Tesofensine
|
|
- Tricyclic antidepressants
- Amitriptyline
- Butriptyline
- Cianopramine
- Clomipramine
- Desipramine
- Dosulepin
- Doxepin
- Imipramine
- Lofepramine
- Melitracen
- Nortriptyline
- Protriptyline
- Trimipramine
|
|
- Tetracyclic antidepressants
- Amoxapine
- Maprotiline
- Mianserin
- Oxaprotiline
- Setiptiline
|
|
- Others
- Antihistamines (e.g., brompheniramine, chlorphenamine, pheniramine, tripelennamine)
- Arylcyclohexylamines (e.g., ketamine, phencyclidine)
- CP-39,332
- Ethanol
- EXP-561
- Fezolamine
- Ginkgo biloba
- Indeloxazine
- Loxapine
- Nefazodone
- Nefopam
- Opioids (e.g., methadone, pethidine (meperidine), tapentadol, tramadol)
- Pridefine
- Tedatioxetine
- Teniloxazine
- Tofenacin
- Tropanes (e.g., cocaine)
- Ziprasidone
|
|
|
VMATs |
- Amiodarone
- Amphetamines (e.g., amphetamine, methamphetamine, MDMA)
- Bietaserpine
- Deserpidine
- Efavirenz
- GBR-12935
- Ibogaine
- Ketanserin
- Lobeline
- Reserpine
- Rose bengal
- Tetrabenazine
- Vanoxerine (GBR-12909)
|
|
|
|
Releasing agents
|
|
- Morpholines
- Fenbutrazate
- Fenmetramide
- Morazone
- Morforex
- Phendimetrazine
- Phenmetrazine
- Pseudophenmetrazine
|
|
- Oxazolines
- 4-MAR
- Aminorex
- Clominorex
- Cyclazodone
- Fenozolone
- Fluminorex
- Pemoline
- Thozalinone
|
|
- Phenethylamines (also amphetamines, cathinones, etc)
- 2-OH-PEA
- 4-CAB
- 4-FA
- 4-FMA
- 4-MA
- 4-MMA
- Alfetamine
- Amfecloral
- Amfepentorex
- Amfepramone
- Amphetamine
- Dextroamphetamine
- Levoamphetamine
- Amphetaminil
- β-Me-PEA
- BDB
- Benzphetamine
- BOH
- Buphedrone
- Bupropion
- Butylone
- Cathine
- Cathinone
- Clobenzorex
- Clortermine
- Dimethylamphetamine
- DMA
- DMMA
- EBDB
- Ephedrine
- Ethcathinone
- Ethylone
- Etilamfetamine
- Famprofazone
- Fenethylline
- Fenproporex
- Flephedrone
- Fludorex
- Furfenorex
- Hordenine
- 4-Hydroxyamphetamine
- 5-APDI (IAP)
- 5-MAPDI (IMP)
- Iofetamine (123I)
- Lisdexamfetamine
- Lophophine
- MBDB
- MDA
- MDEA
- MDMA
- Metamfepramone
- MDMPEA
- MDOH
- MDPEA
- Mefenorex
- Mephedrone
- Mephentermine
- Methamphetamine
- Dextromethamphetamine
- Levomethamphetamine
- Methcathinone
- Methedrone
- Methylone
- Morforex
- Naphthylaminopropane
- Ortetamine
- pBA
- pCA
- Pentorex
- Phenethylamine
- Pholedrine
- Phenpromethamine
- Phentermine
- Phenylpropanolamine
- pIA
- Prenylamine
- Propylamphetamine
- Pseudoephedrine
- Selegiline (also D-Deprenyl)
- Tiflorex
- Tyramine
- Xylopropamine
- Zylofuramine
|
|
- Piperazines
- 2C-B-BZP
- BZP
- MBZP
- mCPP
- MDBZP
- MeOPP
- pFPP
|
|
- Others
- 2-ADN
- 2-AI
- 2-AT
- 2-BP
- 4-BP
- 5-IAI
- Clofenciclan
- Cyclopentamine
- Cypenamine
- Cyprodenate
- Feprosidnine
- Gilutensin
- Heptaminol
- Hexacyclonate
- Indanorex
- Isometheptene
- Methylhexanamine
- Octodrine
- Phthalimidopropiophenone
- Propylhexedrine (Levopropylhexedrine)
- Tuaminoheptane
|
|
|
|
Enzyme inhibitors
|
|
PAH |
|
|
TH |
- 3-Iodotyrosine
- Aquayamycin
- Bulbocapnine
- Metirosine
- Oudenone
|
|
AAAD |
- Benserazide
- Carbidopa
- DFMD
- Genistein
- Methyldopa
|
|
DBH |
- Bupicomide
- Disulfiram
- Dopastin
- Fusaric acid
- Nepicastat
- Phenopicolinic acid
- Tropolone
|
|
PNMT |
- CGS-19281A
- SKF-64139
- SKF-7698
|
|
MAO |
- Nonselective
- Benmoxin
- Caroxazone
- Echinopsidine
- Furazolidone
- Hydralazine
- Indantadol
- Iproclozide
- Iproniazid
- Isocarboxazid
- Isoniazid
- Linezolid
- Mebanazine
- Metfendrazine
- Nialamide
- Octamoxin
- Paraxazone
- Phenelzine
- Pheniprazine
- Phenoxypropazine
- Pivhydrazine
- Procarbazine
- Safrazine
- Tranylcypromine
|
|
- MAO-A selective
- Amiflamine
- Bazinaprine
- Befloxatone
- Brofaromine
- Cimoxatone
- Clorgiline
- CX157 (Tyrima)
- Eprobemide
- Esuprone
- Harmala alkaloids
- Harmine
- Harmaline
- Tetrahydroharmine
- Harman
- Methylene blue
- Metralindole
- Minaprine
- Moclobemide
- Pirlindole
- Sercloremine
- Tetrindole
- Toloxatone
|
|
- MAO-B selective
- Ladostigil
- Lazabemide
- Milacemide
- Mofegiline
- Pargyline
- Rasagiline
- Safinamide
- Selegiline (also D-Deprenyl)
|
|
|
COMT |
- Entacapone
- Nitecapone
- Tolcapone
|
|
|
|
Others
|
|
Precursors |
- L-Phenylalanine → L-Tyrosine → L-DOPA (Levodopa) → Dopamine
- L-DOPS (Droxidopa)
|
|
Cofactors |
- Ferrous Iron (Fe2+)
- S-Adenosyl-L-Methionine
- Vitamin B3 (Niacin
- Nicotinamide → NADPH)
- Vitamin B6 (Pyridoxine
- Pyridoxamine
- Pyridoxal → Pyridoxal Phosphate)
- Vitamin B9 (Folic acid → Tetrahydrofolic acid)
- Vitamin C (Ascorbic acid)
- Zinc (Zn2+)
|
|
Neurotoxins |
- DSP-4
- Oxidopamine (6-OHDA)
|
|
Others |
- Activity enhancers
- BPAP
- PPAP
|
|
- Release blockers
- Bethanidine
- Bretylium
- Guanadrel
- Guanazodine
- Guanethidine
- Guanoxan
|
|
|
|
|
- See also:
- Dopaminergics
- Melatonergics
- Serotonergics
- List of adrenergic drugs
|
|