Iproheptine, also known as N-isopropyl-1,5-dimethylhexylamine or N-isopropyloctodrine and sold under the brand names Metron and Susat, is a nasal decongestant which has been marketed in Japan.[1][2][3] It is described as a vasoconstrictor and antihistamine.[1][2][3] The drug is available over-the-counter in Japan.[4]
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| Clinical data | |
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| Trade names | Metron, Susat |
| Other names | N-Isopropyl-1,5-dimethylhexylamine; N-Isopropyloctodrine |
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| ECHA InfoCard | 100.034.283 |
| Chemical and physical data | |
| Formula | C11H25N |
| Molar mass | 171.328 g·mol−1 |
| 3D model (JSmol) | |
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Pharmacology
Pharmacodynamics
Iproheptine is described as a decongestant, vasoconstrictor, and antihistamine.[1][2][3] Its pharmacology was characterized in a series of several preclinical studies published in the 1960s.[5][6][7][8][9][10]
The drug was found to have anticholinergic- and antihistamine-like effects that were described as more potent than those of ephedrine.[6][8][10] It was said to have hypotensive and cardiac inhibitive actions that made it differ from other known alkylamine and arylalkylamine sympathomimetics.[6][8] The effects of iproheptine on blood vessels, pupils, and saliva secretion were all said to be very weak.[6] It produced bronchodilation, vasoconstriction, and hemostasis similarly to ephedrine or methoxyphenamine.[7][10] Iproheptine showed no effect against hexobarbital-induced sleep.[7] Conversely, it showed an antidepressant- or stimulant-like effect in the forced swim test (FST).[9]
Close analogues of iproheptine, such as methylhexanamine and tuaminoheptane, are known to act as norepinephrine and/or dopamine releasing agents by interacting with the monoamine transporters, and this is thought to underlie their sympathomimetic and stimulant effects.[11][12][13][14][15][16]
Pharmacokinetics
In contrast to arylalkylamines like phenethylamines and tryptamines, iproheptine is not metabolized by monoamine oxidase (MAO).[9]
Chemistry
Iproheptine, also known as N-isopropyl-1,5-dimethylhexylamine or as N-isopropyloctodrine, is an alkylamine and the N-isopropyl derivative of octodrine (2-amino-6-methylheptane or 1,5-dimethylhexylamine (1,5-DMHA)).[1][2][3]
Aside from octodrine, it is also closely structurally related to other alkylamines, including 1,3-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)), and tuaminoheptane (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 the phenyl ring open and incomplete (i.e., missing two carbon atoms, saturated, and the carbons not connected to form a ring).[17][1]
History
Iproheptine was first described in the scientific literature by 1960[5][6] and was first patented by 1962.[1] It remained marketed in Japan in 2004.[2]
Society and culture
Names
Iproheptine is the generic name of the drug and its INN.[1][2] In the case of the hydrochloride salt, its generic name is iproheptine hydrochloride and this is its JAN.[2] The drug is marketed under the brand names Metron and Susat (both as the hydrochloride salt).[1][2]
Availability
Iproheptine appears to have been marketed only in Japan.[2] It is available over-the-counter in this country.[4]
See also
References
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