1,3-Dimethylbutylamine
(2S)-DMBA
(2R)-DMBA
Names
Preferred IUPAC name
4-Methylpentan-2-amine
Other names
(4-Methylpentan-2-yl)amine
Identifiers
3D model (JSmol)
ChemSpider
ECHA InfoCard 100.003.227 Edit this at Wikidata
UNII
  • InChI=1S/C6H15N/c1-5(2)4-6(3)7/h5-6H,4,7H2,1-3H3
    Key: UNBMPKNTYKDYCG-UHFFFAOYSA-N
  • InChI=1/C6H15N/c1-5(2)4-6(3)7/h5-6H,4,7H2,1-3H3
    Key: UNBMPKNTYKDYCG-UHFFFAOYAT
  • CC(C)CC(C)N
Properties
C6H15N
Molar mass 101.193 g·mol−1
Density 0.717 g/mL[1]
Boiling point 108–110 °C (226–230 °F; 381–383 K)[1]
Pharmacology
Legal status
Hazards
NFPA 704 (fire diamond)
NFPA 704 four-colored diamondHealth 2: Intense or continued but not chronic exposure could cause temporary incapacitation or possible residual injury. E.g. chloroformFlammability 3: Liquids and solids that can be ignited under almost all ambient temperature conditions. Flash point between 23 and 38 °C (73 and 100 °F). E.g. gasolineInstability 0: Normally stable, even under fire exposure conditions, and is not reactive with water. E.g. liquid nitrogenSpecial hazards (white): no code
2
3
0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

1,3-Dimethylbutylamine (1,3-DMBA, dimethylbutylamine, DMBA, 4-amino-2-methylpentane, or AMP), is a stimulant drug structurally related to methylhexanamine where a butyl group replaces the pentyl group. The compound is an aliphatic amine.

The hydrochloride and citrate salts of DMBA has been identified as unapproved ingredients in some over-the-counter dietary supplements,[3][4][5] in which it is used in an apparent attempt to circumvent bans on methylhexanamine.[6] The U.S. Food and Drug Administration (FDA) considers any dietary supplement containing DMBA to be "adulterated".[7] Despite the FDA's opposition, DMBA continues to be sold in the US.[8]

There are no known human safety studies on DMBA and its health effects are entirely unknown.[3][4][9]

References

  1. ^ a b "1,3-Dimethylbutylamine". Sigma-Aldrich.
  2. ^ Anvisa (2023-07-24). "RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 804 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 2023-07-25). Archived from the original on 2023-08-27. Retrieved 2023-08-27.
  3. ^ a b Cohen, Pieter A.; Travis, John C.; Venhuis, Bastiaan J. (2015). "A synthetic stimulant never tested in humans, 1,3-dimethylbutylamine (DMBA), is identified in multiple dietary supplements". Drug Testing and Analysis. 7 (1): 83–7. doi:10.1002/dta.1735. PMID 25293509.
  4. ^ a b "Unapproved Synthetic Stimulant "DMBA" Found in Multiple Dietary Supplements". NSF International. Archived from the original on 2016-11-22. Retrieved 2015-03-21.
  5. ^ "FDA Warns 14 Sports Supplement Companies Of Illegal DMBA (AMP Citrate)". Forbes. May 6, 2015.
  6. ^ "Stimulant Potentially Dangerous to Health, FDA Warns". U.S. Food and Drug Administration. April 11, 2013. Retrieved March 10, 2015.
  7. ^ "DMBA in Dietary Supplements". Food and Drug Administration.
  8. ^ Cohen, Pieter A.; Wen, Anita; Gerona, Roy (1 December 2018). "Prohibited Stimulants in Dietary Supplements After Enforcement Action by the US Food and Drug Administration". JAMA Internal Medicine. 178 (12): 1721–1723. doi:10.1001/jamainternmed.2018.4846. PMC 6583602. PMID 30422217.
  9. ^ "Revealing the hidden dangers of dietary supplements". Science. 20 August 2015. doi:10.1126/science.aad1651.


Categories