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| Trade names | Metron, Susat |
| Other names | N-Isopropyl-1,5-dimethylhexylamine;N-Isopropyloctodrine |
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| CompTox Dashboard(EPA) | |
| ECHA InfoCard | 100.034.283 |
| Chemical and physical data | |
| Formula | C11H25N |
| Molar mass | 171.328 g·mol−1 |
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Iproheptine, also known asN-isopropyl-1,5-dimethylhexylamine orN-isopropyloctodrine and sold under the brand namesMetron andSusat, is anasal decongestant which has been marketed inJapan.[1][2][3] It is described as avasoconstrictor andantihistamine.[1][2][3] The drug is availableover-the-counter in Japan.[4]
Iproheptine is described as adecongestant,vasoconstrictor, andantihistamine.[1][2][3] Itspharmacology was characterized in a series of severalpreclinical studies published in the 1960s.[5][6][7][8][9][10]
The drug was found to haveanticholinergic- and antihistamine-like effects that were described as morepotent than those ofephedrine.[6][8][10] It was said to havehypotensive andcardiac inhibitive actions that made it differ from other knownalkylamine andarylalkylaminesympathomimetics.[6][8] The effects of iproheptine onblood vessels,pupils, andsaliva secretion were all said to be very weak.[6] It producedbronchodilation,vasoconstriction, andhemostasis similarly to ephedrine ormethoxyphenamine.[7][10] Iproheptine showed no effect againsthexobarbital-inducedsleep.[7] Conversely, it showed anantidepressant- orstimulant-like effect in theforced swim test (FST).[9]
Closeanalogues of iproheptine, such asmethylhexanamine andtuaminoheptane, are known to act asnorepinephrine and/ordopamine releasing agents by interacting with themonoamine transporters, and this is thought to underlie their sympathomimetic and stimulant effects.[11][12][13][14][15][16]
In contrast toarylalkylamines likephenethylamines andtryptamines, iproheptine is notmetabolized bymonoamine oxidase (MAO).[9]
Iproheptine, also known asN-isopropyl-1,5-dimethylhexylamine or asN-isopropyloctodrine, is analkylamine and theN-isopropylderivative ofoctodrine (2-amino-6-methylheptane or 1,5-dimethylhexylamine (1,5-DMHA)).[1][2][3]
Aside from octodrine, it is also closelystructurally related to other alkylamines, including1,3-dimethylbutylamine (1,3-DMBA),1,4-dimethylamylamine (1,4-DMAA),heptaminol (2-methyl-6-amino-2-heptanol),isometheptene (2-methyl-6-methylamino-2-heptene),methylhexanamine (1,3-dimethylamylamine (1,3-DMAA)), andtuaminoheptane (tuamine; 2-aminoheptane or 1-methylhexylamine).[1][2][3]
Iproheptine shows structural similarity to what would be 3- or 4-methyl-N-isopropylamphetamine, but with the equivalent of thephenyl ring open and incomplete (i.e., missing twocarbonatoms,saturated, and the carbons not connected to form a ring).[17][1]
The predictedlog P (XLogP3) of iproheptine is 3.6.[17]
Iproheptine was first described in thescientific literature by 1960[5][6] and was firstpatented by 1962.[1] It remained marketed inJapan in 2004.[2]
Iproheptine is thegeneric name of the drug and itsINNTooltip International Nonproprietary Name.[1][2] In the case of thehydrochloridesalt, its generic name isiproheptine hydrochloride and this is itsJANTooltip Japanese Accepted Name.[2] The drug is marketed under the brand namesMetron andSusat (both as the hydrochloride salt).[1][2]
Iproheptine appears to have been marketed only inJapan.[2] It is availableover-the-counter in this country.[4]
Iproheptine 13946-02-6 6243 CHAN N-Isopropyl-1,5-dimethylhexylamine. Metron; Metron S. Antihistaminic.
