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| Trade names | Wyamine, Fentermin, Mephentine[1][2][3] |
| Other names | Mephenterdrine; Mephetedrine;N-Methylphentermine;N,α,α-Trimethylphenethylamine;N,α,Dimethylampetamine; α-Methylmethamphetamine; Mephenteramine |
| Routes of administration | Intravenous,intramuscular,oral,inhalation[4][5] |
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| ECHA InfoCard | 100.002.638 |
| Chemical and physical data | |
| Formula | C11H17N |
| Molar mass | 163.264 g·mol−1 |
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Mephentermine, sold under the brand nameWyamine among others, is asympathomimeticmedication which was previously used in the treatment oflow blood pressure but is mostly no longer marketed.[6][5][4][7][8] It is used byinjection into a vein ormuscle,by inhalation, andby mouth.[4][5]
Side effects of mephentermine includedry mouth,sedation,reflex bradycardia,arrhythmias, andhypertension.[4] Mephentermineinduces the release of norepinephrine and dopamine and is described as an indirectly acting sympathomimetic andpsychostimulant.[4] Its sympathomimetic effects are mediated by indirect activation ofα- andβ-adrenergic receptors.[5] Chemically, it is asubstituted phenethylamine andamphetamine and is closely related tophentermine andmethamphetamine.[4][9][1]
Mephentermine was first described and introduced for medical use by 1952.[10] It was discontinued in theUnited States between 2000 and 2004.[2][7] The medication appears to remain available only inIndia.[4][7][8]Misuse of mephentermine forrecreational andperformance-enhancing purposes has been increasingly encountered in modern times, especially in India.[11][4]
For maintenance of blood pressure in hypotensive states, the dose for adults is 30 to 45 mg as a single dose, repeated as necessary or followed by intravenous infusion of 0.1% mephentermine in 5% dextrose, with the rate and duration of administration depending on the patient's response.[citation needed]
For hypotension secondary to spinal anesthesia in obstetric patients, the dose for adults is 15 mg as a single dose, repeated if needed. The maximum dose 30 mg.[citation needed]
Mephentermine has also been used as adecongestant.[6][5]
Mephentermine is available in the form of 15 and 30 mg/mLsolutions forintravenous infusion orintramuscular injection and in the form of 10 mgoraltablets.[4] It has also been available in the form ofinhalers.[5]
Low blood pressure caused byphenothiazines,hypertension, andpheochromocytoma.[citation needed]
Patients receivingmonoamine oxidase inhibitors.[citation needed]
For shock due to loss of blood or fluid, give fluid replacement therapy primarily, cardiovascular disease, hypertension,hyperthyroidism, chronic illnesses, lactation, pregnancy, skin dryness. headache.[citation needed]
The most commonside effects of mephentermine are drowsiness, incoherence, hallucinations, convulsions, slow heart rate (reflex bradycardia). Fear, anxiety, restlessness, tremor, insomnia, confusion, irritability, and psychosis. Nausea, vomiting, reduced appetite, urinary retention, dyspnea, weakness, and neck pain.[citation needed]
Potentially fatal reactions are due to atrioventricular block, central nervous system stimulation, cerebral hemorrhage, pulmonary edema, and ventricular arrhythmias.[citation needed]
Mephentermine antagonizes effect of agents that lower blood pressure. Severe hypertension may occur with monoamine oxidase inhibitors and possiblytricyclic antidepressants. Additive vasoconstricting effects occur withergot alkaloids, andoxytocin.[citation needed]
Potentially fatal drug interactions are the risk of abnormal heart rhythm in people undergoing anesthesia withcyclopropane andhalothane.[citation needed]
Mephentermine is thought to act as areleasing agent of norepinephrine and dopamine.[4] It is described as an indirectly actingsympathomimetic,cardiac stimulant,adrenergic,vasoconstrictor,antihypotensive agent, andpsychostimulant.[1][2][8][4] Its sympathomimetic effects are mediated by indirect activation ofα- andβ-adrenergic receptors.[5][6]
Mephentermine appears to act by indirect stimulation of β-adrenergic receptors through causing the release of norepinephrine from its storage sites. It has apositive inotropic effect on themyocardium. AV conduction and refractory period ofAV 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.[citation needed]
Itsonset of action is 5 to 15 minutes withintramuscular injection and is immediate withintravenous administration.[citation needed] Itsduration of action is 4 hours with intramuscular injection and 30 minutes with intravenous administration.[citation needed]
Mephentermine, along withphentermine, is known to be produced as ametabolite of theorally administeredlocal anestheticoxetacaine (oxethazaine).[12][13]
Mephentermine, also known asN,α,α-trimethylphenethylamine orN,α-dimethylampetamine, is aphenethylamine andamphetaminederivative.[9][1][4] It is theN-methylatedanalogue ofphentermine (α-methylamphetamine) and is also known asN-methylphentermine.[9][1] In addition, mephentermine is the α-methylated analogue ofmethamphetamine or the α,α-dimethylated derivative ofamphetamine.[9][4] Thecathinone (β-keto) derivative of mephentermine isα-methylmethcathinone (βk-mephentermine; RAD-081).[14][15][16]
Mephentermine can by synthesized beginning with aHenry reaction betweenbenzaldehyde (1) and2-nitropropane (2) to give 2-methyl-2-nitro-1-phenylpropan-1-ol (3).[17] The nitro group is reduced with zinc in sulfuric acid giving 2-phenyl-1,1-dimethylethanolamine (4). Imine formation by dehydration with benzaldehyde gives (5). Alkylation withiodomethane leads to (6). Halogenation withthionyl chloride gives (7). Lastly, aRosenmund reduction completes the synthesis of mephentermine (8).
Mephentermine can also be synthesized bycondensation of phentermine with benzaldehyde to get aSchiff base which can be alkylated with methyl iodide to give mephentermine.[18]
Mephentermine was first described in the literature and was introduced for medical use under the brand name Wyamine by 1952.[10] It was discontinued in theUnited States between 2000 and 2004.[2][7]
Mephentermine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name,BANTooltip British Approved Name, andDCFTooltip Dénomination Commune Française.[1][2][3] In the case of thesulfatesalt, itsUSANTooltip United States Adopted Name ismephentermine sulfate and itsBANMTooltip British Approved Name ismephentermine sulphate.[3][2][7] Synonyms of mephentermine includemephetedrine andmephenterdrine.[2][7][9] Brand names of mephentermine includeWyamine (USTooltip United States),Fentermin (PTTooltip Portugal), andMephentine (INTooltip India).[1][2][7]
Mephentermine is no longer available in theUnited States and remains available in few or no other countries.[7][8] However, it appears to remain available inIndia.[8][7] It has also remained available inBrazil for use inveterinary medicine.[5]
Misuse of mephentermine forrecreational and/orperformance-enhancing purposes has been reported along withaddiction anddependence and serious health complications.[19][20][21][22][5][23][24][25][11][26][27][28][29][4] It has been especially encountered inIndia, the only country in which mephentermine appears to remain available for medical use.[4][7][8]
Mephentermine has been used as aperformance-enhancing drug inexercise andsports.[6][11][4] It is on theWorld Anti-Doping Agency (WADA)list of prohibited substances.[30][29]
Mephentermine was evaluated in the treatment ofcongestive heart failure in one small clinical study but was found to be ineffective.[31][32]
Mephentermine has been used inveterinary medicine inBrazil under the brand names Potenay and Potemax.[5]