1,4-Dimethylamylamine

Not to be confused with 1,3-Dimethylamylamine.

1,4-Dimethylamylamine (1,4-DMAA), also known as 1,4-dimethylpentylamine or as 5-methylhexan-2-amine, is a stimulant drug of the alkylamine family related to methylhexanamine (1,3-DMAA; geranamine).^[1][2] It is naturally present in geranium plants and has also been found in certain other plants.^[3][4][1]

1,4-Dimethylamylamine

Clinical data
Other names	2-Amino-5-methylhexane; 1,4-Dimethylpentylamine
Drug class	Stimulant; Sympathomimetic; Monoamine releasing agent
Identifiers
IUPAC name 5-methylhexan-2-amine
CAS Number	28292-43-5
PubChem CID	34204
ChemSpider	31520
UNII	RJ36ZF28PW
CompTox Dashboard (EPA)	DTXSID60885416
ECHA InfoCard	100.044.477
Chemical and physical data
Formula	C7H17N
Molar mass	115.220 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC(C)CCC(C)N
InChI InChI=1S/C7H17N/c1-6(2)4-5-7(3)8/h6-7H,4-5,8H2,1-3H3 Key:IZCBXLKODYZSDJ-UHFFFAOYSA-N

1,4-DMAA has been identified in dietary supplements.^[1][2] It produces sympathomimetic effects in animals and humans.^[1][5] 1,4-DMAA and other alkylamine stimulants may act as catecholamine releasing agents.^[6][7][8] Unlike octodrine and methylhexanamine, 1,4-DMAA has never been used as a pharmaceutical drug.^[1]