1,4-Dimethylamylamine

1,3-Dimethylamylamine vanc 6 5-Methyl-2-hexylamine.svg skin-invert-image 200px Stimulant; Sympathomimetic; Monoamine releasing agent 28292-43-5 34204 31520 RJ36ZF28PW 2-Amino-5-methylhexane; 1,4-Dimethylpentylamine 5-methylhexan-2-amine 7 17 1 CC(C)CCC(C)N 1S/C7H17N/c1-6(2)4-5-7(3)8/h6-7H,4-5,8H2,1-3H3 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). Cohen PA, Travis JC, Keizers PH, Deuster P, Venhuis BJ 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 June 2018 29115866 10.1080/15563650.2017.1398328 http://nrs.harvard.edu/urn-3:HUL.InstRepos:40997745 10029/621559 free Cohen PA, Travis JC, Vanhee C, Ohana D, Venhuis BJ 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 November 2021 33755516 10.1080/15563650.2021.1894333 10029/624873 free It is naturally present in geranium plants and has also been found in certain other plants. Li JS, Chen M, Li ZC Identification and quantification of dimethylamylamine in geranium by liquid chromatography tandem mass spectrometry Analytical Chemistry Insights 7 47–58 2012 22915838 3422085 10.4137/ACI.S9969 free Fleming HL, Ranaivo PL, Simone PS 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 2012 23225994 10.4137/ACI.S10445 free 3512447 1,4-DMAA has been identified in dietary supplements. It produces sympathomimetic effects in animals and humans. Marsh DF The comparative pharmacology of the isomeric hyptylamines The Journal of Pharmacology and Experimental Therapeutics 94 3 225–231 November 1948 18894881 10.1016/S0022-3565(25)03552-9 1,4-DMAA and other alkylamine stimulants may act as catecholamine releasing agents. Small C, Cheng MH, Belay SS, Bulloch SL, Zimmerman B, Sorkin A, Block ER 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 August 2023 37348963 10353075 10.1124/jpet.122.001573 Docherty JR, Alsufyani HA Pharmacology of Drugs Used as Stimulants Journal of Clinical Pharmacology 61 Suppl 2 S53–S69 August 2021 34396557 10.1002/jcph.1918 free Alsufyani HA, Docherty JR Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat European Journal of Pharmacology 843 121–125 January 2019 30395850 10.1016/j.ejphar.2018.10.047 Unlike octodrine and methylhexanamine, 1,4-DMAA has never been used as a pharmaceutical drug. References Category:Abandoned drugs Category:Alkylamines Category:Bodybuilding supplements Category:Monoamine releasing agents Category:Sympathomimetics Category:Stimulants