1,4-Dimethylamylamine

1,4-Dimethylamylamine
Clinical data
Other names2-Amino-5-methylhexane; 1,4-Dimethylpentylamine
Drug classStimulant; Sympathomimetic; Monoamine releasing agent
Identifiers
IUPAC name
  • 5-methylhexan-2-amine
CAS Number
PubChem CID
ChemSpider
UNII
CompTox Dashboard (EPA)
ECHA InfoCard100.044.477
Chemical and physical data
FormulaC7H17N
Molar mass115.220 g·mol−1
3D model (JSmol)
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. ^ a b c d e 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. ^ a b 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.
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