1,3-Dimethylbutylamine

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.

1,3-Dimethylbutylamine

(2S)-DMBA (2R)-DMBA
Names
Preferred IUPAC name 4-Methylpentan-2-amine
Other names (4-Methylpentan-2-yl)amine
Identifiers
CAS Number	108-09-8 Y
3D model (JSmol)	Interactive image
ChemSpider	7620
ECHA InfoCard	100.003.227
PubChem CID	7908 CID 7908
UNII	KXP599H5R6 Y
CompTox Dashboard (EPA)	DTXSID4025113
InChI 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
SMILES CC(C)CC(C)N
Properties
Chemical formula	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	BR: Class F2 (Prohibited psychotropics)[2]
Hazards
NFPA 704 (fire diamond)	2 3 0
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

The hydrochloride and citrate salts of DMBA has been identified as unapproved ingredients in some over-the-counter dietary supplements,^[3][4][5][6] in which it is used in an apparent attempt to circumvent bans on methylhexanamine.^[7] The U.S. Food and Drug Administration (FDA) considers any dietary supplement containing DMBA to be "adulterated".^[8] Despite the FDA's opposition, DMBA continues to be sold in the US.^[9]

There are no known human safety studies on DMBA and its health effects are entirely unknown.^[3][4][10]

References

1. "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. 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. "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. "Reliable Home Testing Kits". Retrieved 2024-08-20.
7. "Stimulant Potentially Dangerous to Health, FDA Warns". U.S. Food and Drug Administration. April 11, 2013. Retrieved March 10, 2015.
8. "DMBA in Dietary Supplements". Food and Drug Administration.
9. 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.
10. "Revealing the hidden dangers of dietary supplements". Science. 20 August 2015. doi:10.1126/science.aad1651.