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1. 1,3-dimethylamylamine
1. 105-41-9
2. 4-methylhexan-2-amine
3. Methylhexaneamine
4. Forthane
5. 2-amino-4-methylhexane
6. 1,3-dimethylamylamine
7. Forthan
8. 2-hexanamine, 4-methyl-
9. 4-methyl-2-hexylamine
10. Methylhexanamine
11. Dimethylamylamine
12. 4-methyl-2-hexanamine
13. Geranamine
14. Nsc 1106
15. Pentylamine, 1,3-dimethyl-
16. Ai3-16556
17. X49c572yqo
18. Nsc-1106
19. Einecs 203-296-1
20. Dmaa [dietary Supplement]
21. Brn 1731697
22. Floradrene
23. Unii-x49c572yqo
24. 1,3-dmaa
25. Hsdb 8164
26. Pentylamine,3-dimethyl-
27. 1,3-dimethyl-pentylamine
28. 4-04-00-00747 (beilstein Handbook Reference)
29. Methylhexaneamine [mi]
30. Schembl243596
31. Wln: Zy & 1y2
32. Dtxsid60861715
33. Nsc1106
34. Chebi:134754
35. Methylhexaneamine [who-dd]
36. Bcp18792
37. 1,3 Dimethylamylamine Hcl (dmaa)
38. Ac-369
39. Mfcd00025613
40. Akos011598451
41. 1,3-dimethylamylamine, Analytical Standard
42. Db-040620
43. D88161
44. Methylhexanamine Hydrochloride, >=98% (hplc)
45. 105d419
46. Q2594649
47. W-108787
48. 1,3-dimethylamylamine 100 Microg/ml In Acetonitrile
| Molecular Weight | 115.22 g/mol |
|---|---|
| Molecular Formula | C7H17N |
| XLogP3 | 1.9 |
| Hydrogen Bond Donor Count | 1 |
| Hydrogen Bond Acceptor Count | 1 |
| Rotatable Bond Count | 3 |
| Exact Mass | 115.136099547 g/mol |
| Monoisotopic Mass | 115.136099547 g/mol |
| Topological Polar Surface Area | 26 Ų |
| Heavy Atom Count | 8 |
| Formal Charge | 0 |
| Complexity | 52.3 |
| Isotope Atom Count | 0 |
| Defined Atom Stereocenter Count | 0 |
| Undefined Atom Stereocenter Count | 2 |
| Defined Bond Stereocenter Count | 0 |
| Undefined Bond Stereocenter Count | 0 |
| Covalently Bonded Unit Count | 1 |
DMAA (1,3-dimethylamylamine) is an amphetamine derivative that has been widely used in sports supplements sold in the United States. Also known as methylhexanamine or geranium extract, DMAA is often touted as a "natural" stimulant, with many claimed functional uses including a body-building aid, an athletic performance enhancer, and a weight-loss aid. Although DMAA at one time was approved as a drug for nasal decongestion, no medical use of DMAA is recognized today. FDA is not aware of any reliable science indicating that DMAA exists naturally in plants.
USFA; Dietary Supplements: DMAA in Dietary Supplements; Available from, as of March 4, 2014: https://www.fda.gov/Food/DietarySupplements/QADietarySupplements/ucm346576.htm
DMAA, also known as 1,3-dimethylamylamine, methylhexanamine or geranium extract, is an ingredient found illegally in some dietary supplements and often touted as a "natural" stimulant. DMAA, especially in combination with other ingredients such as caffeine, can be a health risk to consumers. Ingestion of DMAA can elevate blood pressure and lead to cardiovascular problems ranging from shortness of breath and tightening in the chest to heart attack. Dietary supplements containing DMAA are illegal and FDA is doing everything within its authority to remove these products from the market. In 2012, FDA issued warning letters to companies notifying them products with DMAA need to be taken off the market or reformulated to remove this substance. Most companies warned are no longer distributing products with DMAA. While FDA is working to get these products off the market, consumers should not buy or use any dietary supplement product containing DMAA.
USFA; Dietary Supplements: DMAA in Dietary Supplements; Available from, as of March 4, 2014: https://www.fda.gov/Food/DietarySupplements/QADietarySupplements/ucm346576.htm
1,3-dimethylamylamine (DMAA) has been a component of dietary supplements and is also used within "party pills," often in conjunction with alcohol and other drugs. Ingestion of higher than recommended doses results in untoward effects including cerebral hemorrhage. To our knowledge, no studies have been conducted to determine both the pharmacokinetic profile and physiologic responses of DMAA. Eight men reported to the lab in the morning following an overnight fast and received a single 25 mg oral dose of DMAA. Blood samples were collected before and through 24 hours post-DMAA ingestion and analyzed for plasma DMAA concentration using high-performance liquid chromatography-mass spectrometry. Resting heart rate, blood pressure, and body temperature was also measured. One subject was excluded from the data analysis due to abnormal DMAA levels. Analysis of the remaining seven participants showed DMAA had an oral clearance of 20.02+/- 5 L/hr, an oral volume of distribution of 236+/- 38 L, and terminal half-life of 8.45+/- 1.9 hr. Lag time, the delay in appearance of DMAA in the circulation following extravascular administration, varied among participants but averaged approximately 8 minutes (0.14+/- 0.13 hr). The peak DMAA concentration for all subjects was observed within 3-5 hours following ingestion and was very similar across subjects, with a mean of ~70 ng/mL. Heart rate, blood pressure, and body temperature were largely unaffected by DMAA treatment. These are the first data to characterize the oral pharmacokinetic profile of DMAA. These findings indicate a consistent pattern of increase across subjects with regards to peak DMAA concentration, with peak values approximately 15-30 times lower than those reported in case studies linking DMAA intake with adverse events. Finally, a single 25 mg dose of DMAA does not meaningfully impact resting heart rate, blood pressure, or body temperature.
PMID:24090077 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3852303 Schilling BK et al; BMC Pharmacol Toxicol. 14:52 (2013)
Analysis...showed DMAA had ... terminal half-life of 8.45+/- 1.9 hr.
PMID:24090077 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3852303 Schilling BK et al; BMC Pharmacol Toxicol. 14:52 (2013)
Physiology studies of the compound in the 1940s and 1950s demonstrated its sympathomimetic physiological effects that mimic the action of epinephrine with both peripheral sympathetic neuron and central nervous system effects. These include increases in blood pressure due to the constriction of peripheral blood vessels, increased heart rate due to cardiac stimulation and increased blood sugar levels.
US Department of Defense; Report of the Department of Defense. 1,3-Dimethylamylamine (DMAA) Safety Review Panel (June 3, 2013). Available from, as of March 4, 2014: https://home.fhpr.osd.mil/Libraries/pdf/Report_of_the_DoD_DMAA_Safety_Review_Panel_2013.sflb.ashx
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