methylhexanamine

Also known as 4-methylhexan-2-amine, methylhexamine, 1,3-dimethylamylamine, dimethylamylamine

Methylhexanamine (also known as methylhexamine, 1,3-dimethylamylamine, 1,3-DMAA, dimethylamylamine, and DMAA; trade names Forthane and Geranamine) is an indirect sympathomimetic drug invented and developed by Eli Lilly and Company and marketed as an inhaled nasal decongestant from 1948 until it was voluntarily withdrawn from the market in the 1980s.

Key facts

Drug.Verifiedfields: changed
Drug.Watchedfields: changed
Drug.IUPAC_name: 4-Methylhexan-2-amine
Drug.image: Geranamine.svg
Drug.image_class: skin-invert-image
Drug.image2: Geranamine-3D-balls.png
Drug.image_class2: bg-transparent
Drug.legal_AU: S10
Drug.legal_BR: F2
Drug.legal_US: Unapproved drug; use in dietary supplements, food, or medicine is unlawful.
Drug.routes_of_administration: Nasal spray, oral
Drug.elimination_half life: ~8.5 hours
Drug.CAS_number: 105-41-9
Drug.UNII: X49C572YQO
Drug.ATC_prefix: None
Drug.PubChem: 7753
Drug.ChemSpiderID: 7467
Drug.C: 7

via Wikipedia infobox

Chemical data

Formula: C7H17N
Molecular weight: 115.22 g/mol
IUPAC name: 4-methylhexan-2-amine
SMILES: CCC(C)CC(C)N
InChIKey: YAHRDLICUYEDAU-UHFFFAOYSA-N
XLogP: 1.9
Polar surface area: 26 Å²
H-bond donors: 1
H-bond acceptors: 1
Formal charge: 0

via PubChem

Wikidata facts

Mass: 115.136099544

Show 3 more facts

chemical formula: C₇H₁₇N
canonical SMILES: CCC(C)CC(C)N
Commons category: Methylhexanamine

Sources (2)

via Wikidata · CC0

~16 min read

Article

14 sections

Contents

History
Marketing as dietary supplement
Pharmacology
Detection in body fluids
Safety
Deaths and injuries
Chemistry
Regulation
Sports authorities
Governmental agencies
See also
Notes
References
External links

Since 2006 methylhexanamine has been sold extensively under many names as a stimulant or energy-boosting dietary supplement under the claim that it is similar to certain compounds found in geraniums, but its safety has been questioned as a number of adverse events and at least five deaths have been associated with methylhexanamine-containing supplements. It is banned by many sports authorities and governmental agencies. Despite multiple warning letters from the FDA, as of 2019, the stimulant remains available in sports and weight loss supplements in the US.