1,4-Dimethylamylamine

Not to be confused with 1,3-Dimethylamylamine.

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-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-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]

References

1. Cohen PA, Travis JC, Keizers PH, Deuster P, Venhuis BJ (June 2018). "Four experimental stimulants found in sports and weight loss supplements: 2-amino-6-methylheptane (octodrine), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylamylamine (1,3-DMAA) and 1,3-dimethylbutylamine (1,3-DMBA)". Clinical Toxicology. 56 (6): 421–426. doi:10.1080/15563650.2017.1398328. PMID   29115866.
2. Cohen PA, Travis JC, Vanhee C, Ohana D, Venhuis BJ (November 2021). "Nine prohibited stimulants found in sports and weight loss supplements: deterenol, phenpromethamine (Vonedrine), oxilofrine, octodrine, beta-methylphenylethylamine (BMPEA), 1,3-dimethylamylamine (1,3-DMAA), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylbutylamine (1,3-DMBA) and higenamine". Clinical Toxicology. 59 (11): 975–981. doi:10.1080/15563650.2021.1894333. PMID   33755516.
3. Li JS, Chen M, Li ZC (2012). "Identification and quantification of dimethylamylamine in geranium by liquid chromatography tandem mass spectrometry". Analytical Chemistry Insights. 7: 47–58. doi:10.4137/ACI.S9969. PMC   3422085 . PMID   22915838.
4. Fleming HL, Ranaivo PL, Simone PS (2012). "Analysis and Confirmation of 1,3-DMAA and 1,4-DMAA in Geranium Plants Using High Performance Liquid Chromatography with Tandem Mass Spectrometry at ng/g Concentrations". Analytical Chemistry Insights. 7: 59–78. doi:10.4137/ACI.S10445. PMC   3512447 . PMID   23225994.
5. Marsh DF (November 1948). "The comparative pharmacology of the isomeric hyptylamines". The Journal of Pharmacology and Experimental Therapeutics. 94 (3): 225–231. doi:10.1016/S0022-3565(25)03552-9. PMID   18894881.
6. Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, et al. (August 2023). "The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization". The Journal of Pharmacology and Experimental Therapeutics. 386 (2): 266–273. doi:10.1124/jpet.122.001573. PMC   10353075 . PMID   37348963.
7. Docherty JR, Alsufyani HA (August 2021). "Pharmacology of Drugs Used as Stimulants". Journal of Clinical Pharmacology. 61 (Suppl 2): S53 –S69. doi: 10.1002/jcph.1918 . PMID   34396557.
8. Alsufyani HA, Docherty JR (January 2019). "Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat". European Journal of Pharmacology. 843: 121–125. doi:10.1016/j.ejphar.2018.10.047. PMID   30395850.