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1,3-Dimethylbutylamine

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(Redirected from1,3-dimethylbutylamine)
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 InfoCard100.003.227Edit 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 mass101.193 g·mol−1
Density0.717 g/mL[1]
Boiling point108–110 °C (226–230 °F; 381–383 K)[1]
Pharmacology
Legal status
Hazards
NFPA 704 (fire diamond)
Except where otherwise noted, data are given for materials in theirstandard state (at 25 °C [77 °F], 100 kPa).
Chemical compound

1,3-Dimethylbutylamine (1,3-DMBA,dimethylbutylamine,DMBA,4-amino-2-methylpentane, orAMP), is astimulantdrugstructurally related tomethylhexanamine where abutyl group replaces thepentyl group. The compound is analiphatic amine.

The hydrochloride and citrate salts of DMBA has been identified as unapproved ingredients in someover-the-counterdietary supplements,[3][4][5] in which it is used in an apparent attempt to circumvent bans on methylhexanamine.[6] TheU.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 anagonist of the rodent or humantrace amine-associated receptor 1 (TAAR1).[10]

See also

[edit]

References

[edit]
  1. ^ab"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. Retrieved2023-08-27.
  3. ^abCohen, 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. ^ab"Unapproved Synthetic Stimulant "DMBA" Found in Multiple Dietary Supplements". NSF International. Archived fromthe original on 2016-11-22. Retrieved2015-03-21.
  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 fromthe original on April 13, 2013. RetrievedMarch 10, 2015.
  7. ^"DMBA in Dietary Supplements".Food and Drug Administration. Archived fromthe 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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