1,3-Dimethylbutylamine

Last updated
1,3-Dimethylbutylamine
Dimethylbutylamine.svg
(2S)-4-Methyl-2-aminopentan.svg
(2S)-DMBA
(2R)-4-Methyl-2-aminopentan.svg
(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 OOjs UI icon edit-ltr-progressive.svg
PubChem CID
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.svgHealth 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]

DMBA is not an agonist of the rodent or human trace amine-associated receptor 1 (TAAR1). [10]

See also

References

  1. 1 2 "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. 1 2 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. 1 2 "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. Archived from the original on April 13, 2013. Retrieved March 10, 2015.
  7. ↑ "DMBA in Dietary Supplements". Food and Drug Administration. Archived from the original on May 1, 2015.
  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.
  10. ↑ Rickli A, Hoener MC, Liechti ME (September 2019). "Pharmacological profiles of compounds in preworkout supplements ("boosters")". Eur J Pharmacol. 859: 172515. doi:10.1016/j.ejphar.2019.172515. PMID   31265842. TAAR1 activation may reduce the rewarding properties of stimulant-type drugs of abuse (AsifMalik et al., 2017; Cotter et al., 2015; Di Cara et al., 2011; Pei et al., 2015; Simmler et al., 2016) and may theoretically counteract addictive properties of other stimulants that are contained in preworkout boosters or used concomitantly. In contrast to phenethylamines, TAAR1 was not activated by the alkylamines 1,3-dimethylamylamine and 1,3-dimethylbutylamine.


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