Geranamine

Drugbox
IUPAC_name = 4-methylhexan-2-amine


CAS_number = 105-41-9
ATC_prefix =
ATC_suffix =
PubChem = 7753
DrugBank =
C=7 | H=17 | N=1
molecular_weight = 115.22 g/mol
bioavailability =
protein_bound =
metabolism =
elimination_half-life =
excretion =
pregnancy_AU =
pregnancy_US =
pregnancy_category=
legal_status =
routes_of_administration = Oral, Nasal inhaler, Possibly others

Geranamine (IUPAC: 4-methylhexan-2-amine) is a simple aliphatic amine. It is also known as "Forthane" or 1,3-dimethylamylamine. This amine is an adrenergic compound used to provide temporary relief of nasal congestionCitation
inventor-last = Rohrmann
inventor-first =Ewald
issue-date =May 30, 1944
title =AMINOALKANES
country-code =US
patent-number =2350318] , as well as treatment for hypertrophied or hyperplasic oral tissues [Citation
inventor-last = Kosti
issue-date =Apr 1971
title =PROCESS FOR THE TREATMENT OF HYPERTROPHIED GUMS
country-code =US
patent-number =3574859] . Once trademarked under "Forthane" by Eli Lilly in 1971 [US Trademark Serial Number: 72382454] , the trademark has since expired, and so Geranamine should not be confused with Isoflurane, whose proprietary name is also Forthane. It is a vasoconstrictor, and can be administered by inhalation to the nasal mucosa to exert its effect. The trademark Geranamine® is currently owned by Proviant Technologies. Geranamine is also a constituent of flower oil, sold as an integral component of nutritional supplements. [US Trademark Serial Number: 78542697]

Preparation

Geranamine may be prepared by reacting 4-methylhexan-2-one with hydroxylammonium chloride to give the oxime, followed by reduction by sodium in ethanol.

Uses

Although intended by Eli Lilly to be used as a nasal decongestant, Geranamine has been marketed by certain companies as a dietary supplement in combination with caffeine and other ingredients, under trade names such as Geranamine and Floradrene, to be used as an OTC thermogenic or general purpose stimulant. Geranamine itself has not been researched intensively, with its pharmacological profile not looked at since Eli Lilly filed its patent in 1944, stating that the stimulant effects on the CNS are less than that of amphetamine or ephedrine.

Geranamine is not FDA approved in its own right, although it is a component of geranium oil which is approved for use in foods, and so this has been used to justify claims that it should be classified as a dietary supplement rather than a pharmaceutical product. However while it may be technically correct to say that geranamine is a dietary supplement as it is a component of the oil from "Pelargonium graveolens" which is approved for use in foods, geranamine comprises only 0.66% of geranium oil, [Ping Z, Jun Q, Qing L. A Study on the Chemical Constituents of Geranium Oil. "Journal of Guizhou Institute of Technology" 1996 Feb;25(1):82-85.] and pure synthetic geranamine is thus quite different from geranium oil.

Notes