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1,4-Dimethylamylamine

From Wikipedia, the free encyclopedia
(Redirected from1,4-dimethylamylamine)
Not to be confused with1,3-Dimethylamylamine.

Pharmaceutical compound
1,4-Dimethylamylamine
Clinical data
Other names2-Amino-5-methylhexane; 1,4-Dimethylpentylamine
Drug classStimulant;Sympathomimetic;Monoamine releasing agent
Identifiers
  • 5-methylhexan-2-amine
CAS Number
PubChemCID
ChemSpider
UNII
CompTox Dashboard(EPA)
ECHA InfoCard100.044.477Edit this at Wikidata
Chemical and physical data
FormulaC7H17N
Molar mass115.220 g·mol−1
3D model (JSmol)
  • CC(C)CCC(C)N
  • 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 as1,4-dimethylpentylamine or as5-methylhexan-2-amine, is astimulantdrug of thealkylamine family related tomethylhexanamine (1,3-DMAA; geranamine).[1][2] It isnaturally present ingeraniumplants and has also been found in certain other plants.[3][4][1]

1,4-DMAA has been identified indietary supplements.[1][2] It producessympathomimetic effects in animals and humans.[1][5] 1,4-DMAA and other alkylamine stimulants may act ascatecholamine releasing agents.[6][7][8] Unlikeoctodrine and methylhexanamine, 1,4-DMAA has never been used as apharmaceutical drug.[1]

References

[edit]
  1. ^abcdeCohen 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. ^abCohen 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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