Iproheptine

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Chemical compound

title: "Iproheptine" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["decongestants", "drugs-with-unknown-mechanisms-of-action", "isopropylamino-compounds", "secondary-amines", "sympathomimetics", "vasoconstrictors"] description: "Chemical compound" topic_path: "general/decongestants" source: "https://en.wikipedia.org/wiki/Iproheptine" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Chemical compound ::

::data[format=table title="Infobox drug"]

FieldValue
imageIproheptine.png
image_classskin-invert-image
width200px
tradenameMetron, Susat
CAS_number_Ref
CAS_number13946-02-6
PubChem19917
ChemSpiderID_Ref
ChemSpiderID18760
UNII_Ref
UNIIP021X7VTG0
KEGGD01515
ChEBI134804
ChEMBL2103925
synonymsN-Isopropyl-1,5-dimethylhexylamine; N-Isopropyloctodrine
IUPAC_name6-methyl-N-propan-2-ylheptan-2-amine
C11
SMILESCC(C)CCCC(C)NC(C)C
StdInChI1S/C11H25N/c1-9(2)7-6-8-11(5)12-10(3)4/h9-12H,6-8H2,1-5H3
StdInChI_Ref
StdInChIKeyNKGYBXHAQAKSSG-UHFFFAOYSA-N
StdInChIKey_Ref
::

| drug_name = | image = Iproheptine.png | image_class = skin-invert-image | width = 200px | caption =

| pronounce = | tradename = Metron, Susat | Drugs.com = | MedlinePlus = | licence_CA = | licence_EU = | DailyMedID = | licence_US = | pregnancy_AU = | pregnancy_category = | dependency_liability = | addiction_liability = | routes_of_administration = | class = | ATC_prefix = | ATC_suffix =

| legal_status =

| bioavailability = | protein_bound = | metabolism = | metabolites = | onset = | elimination_half-life = | duration_of_action = | excretion =

| CAS_number_Ref = | CAS_number = 13946-02-6 | CAS_supplemental = | PubChem = 19917 | IUPHAR_ligand = | DrugBank = | ChemSpiderID_Ref = | ChemSpiderID = 18760 | UNII_Ref = | UNII = P021X7VTG0 | KEGG = D01515 | ChEBI = 134804 | ChEMBL = 2103925 | NIAID_ChemDB = | PDB_ligand = | synonyms = N-Isopropyl-1,5-dimethylhexylamine; N-Isopropyloctodrine

| IUPAC_name = 6-methyl-N-propan-2-ylheptan-2-amine | C=11 | H=25 | N=1 | SMILES = CC(C)CCCC(C)NC(C)C | StdInChI = 1S/C11H25N/c1-9(2)7-6-8-11(5)12-10(3)4/h9-12H,6-8H2,1-5H3 | StdInChI_Ref = | StdInChIKey = NKGYBXHAQAKSSG-UHFFFAOYSA-N | StdInChIKey_Ref =

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. It is described as a vasoconstrictor and antihistamine. The drug is available over-the-counter in Japan.

Pharmacology

Pharmacodynamics

Iproheptine is described as a decongestant, vasoconstrictor, and antihistamine. Its pharmacology was characterized in a series of several preclinical studies published in the 1960s.

The drug was found to have anticholinergic- and antihistamine-like effects that were described as more potent than those of ephedrine. It was said to have hypotensive and cardiac inhibitive actions that made it differ from other known alkylamine and arylalkylamine sympathomimetics. The effects of iproheptine on blood vessels, pupils, and saliva secretion were all said to be very weak. It produced bronchodilation, vasoconstriction, and hemostasis similarly to ephedrine or methoxyphenamine. Iproheptine showed no effect against hexobarbital-induced sleep. Conversely, it showed an antidepressant- or stimulant-like effect in the forced swim test (FST).

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.

Pharmacokinetics

In contrast to arylalkylamines like phenethylamines and tryptamines, iproheptine is not metabolized by monoamine oxidase (MAO).

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)).

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).

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).

The predicted log P (XLogP3) of iproheptine is 3.6.

History

Iproheptine was first described in the scientific literature by 1960 and was first patented by 1962. It remained marketed in Japan in 2004.

Society and culture

Names

Iproheptine is the generic name of the drug and its . In the case of the hydrochloride salt, its generic name is iproheptine hydrochloride and this is its . The drug is marketed under the brand names Metron and Susat (both as the hydrochloride salt).

Availability

Iproheptine appears to have been marketed only in Japan. It is available over-the-counter in this country.

References

References

  1. (2014). "The Dictionary of Drugs: Chemical Data: Chemical Data, Structures and Bibliographies". Springer US.
  2. Schweizerischer Apotheker-Verein. (2004). "Index Nominum: International Drug Directory". Medpharm Scientific Publishers.
  3. (2018). "Drugs: Synonyms and Properties". Taylor & Francis.
  4. "KEGG DRUG: Iproheptine Hydrochloride".
  5. (1960). "Pharmacological Studies on Alkylaminoheptane Derivatives. I: Tracheal Muscle Spasmolytic Action of N-Alkyl-1, 5-dimethylhexylamine Derivatives". Yakugaku Zasshi.
  6. (1960). "Pharmacological Studies on Alkylaminoheptane Derivatives. II: Pharmacological Action of N-Isopropyl-1, 5-dimethylhexylamine Hydrochloride. (1)". Yakugaku Zasshi.
  7. (1961). "Pharmacological Studies on Alkylaminoheptane Derivatives. III: Pharmacological Action of N-Isopropyl-1, 5-dimethylhexylamine Hydrochloride. (2)". Yakugaku Zasshi.
  8. (1961). "Pharmacological Studies on Alkylaminoheptane Derivatives. IV: Blood Pressor, Antispasmodic and Capillary Permeability Inhibiting Action of N-Alkyl-1, 5-dimethylhexylamine Derivatives". Yakugaku Zasshi.
  9. (1961). "Pharmacological Studies on Alkylaminoheptane Derivatives. V: Pharmacological Action of N-isopropyl-1, 5-dimethylhexylamine Hydrochloride. (3)". Yakugaku Zasshi.
  10. (1961). "Pharmacological Studies on Alkylaminoheptane Derivatives. VI: Pharmacological Action of N-Isopropyl-1, 5-dimethyl-hexylamine Hydrochloride. (4)". Yakugaku Zasshi.
  11. (August 2023). "The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization". J Pharmacol Exp Ther.
  12. (June 2008). "Pharmacology of stimulants prohibited by the World Anti-Doping Agency (WADA)". Br J Pharmacol.
  13. (August 1990). "Effect of tuamine, heptaminol and two analogues on uptake and release of catecholamines in cultured chromaffin cells". Biochem Pharmacol.
  14. (January 2019). "Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat". Eur J Pharmacol.
  15. (September 2011). "Structure-based discovery of prescription drugs that interact with the norepinephrine transporter, NET". Proc Natl Acad Sci U S A.
  16. (September 2019). "Pharmacological profiles of compounds in preworkout supplements ("boosters")". Eur J Pharmacol.
  17. "Iproheptine".

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decongestantsdrugs-with-unknown-mechanisms-of-actionisopropylamino-compoundssecondary-aminessympathomimeticsvasoconstrictors