Everything below reports findings from cell cultures, isolated tissue and animals. This material is for research use only, not for human or veterinary use.
1,3-DMAA is a seven-carbon amine with a longer paper trail than most research chemicals. Almost all of that trail concerns one question. Does the molecule occur in a plant?
The answer produced four independent analytical investigations. Those papers form a case study in how a botanical-origin claim can be tested to destruction. The pharmacology occupies a much smaller shelf.
That imbalance shapes what follows. The analytical record on 1,3-DMAA is unusually strong. The pharmacological record is thin, dated and mostly indirect. Anyone working with this material should know which of the two they are relying on.
Indexed hemodynamic and exposure papers exist. Those human endpoints sit outside the scope of this profile. The useful laboratory questions are identity, stereoisomer ratio, plant-origin tests, and analogue substitution.
Chemical identity: a small aliphatic amine
1,3-DMAA is structurally unremarkable. Seven carbons, one nitrogen, no rings, no heteroatoms other than the amine.
| Property | Value |
|---|---|
| Systematic name | 4-methylhexan-2-amine |
| Common names | 1,3-DMAA, methylhexanamine, methylhexaneamine |
| Historical trade names | Forthane, Geranamine |
| Molecular formula | C7H17N |
| Molecular weight | 115.22 g/mol |
| CAS number | 105-41-9 |
| PubChem CID | 7753 |
| InChIKey | YAHRDLICUYEDAU-UHFFFAOYSA-N |
| SMILES | CCC(C)CC(C)N |
| Stereocentres | Two, at C2 and C4 |
| Stereoisomers | Four |
| Chemical class | Aliphatic primary amine, sympathomimetic |
| Typical salt form | Hydrochloride |
Two stereocentres, four stereoisomers
The amine sits at C2 and a methyl branch at C4. Both are stereocentres, which gives four stereoisomers: (2R,4R), (2R,4S), (2S,4R) and (2S,4S).
This detail looks academic until you reach the geranium question. Chemical synthesis and biosynthesis produce stereoisomers in different proportions. A plant enzyme making an amine tends to produce one isomer heavily. A reductive amination of 4-methyl-2-hexanone in a reactor produces a ratio set by the reaction. That ratio repeats across every batch made the same way.
The stereoisomer ratio is therefore a fingerprint. It became the decisive piece of evidence [3].
A certificate that quotes C7H17N and 115.22 g/mol has named the carbon count. It has not named which of the four isomers sits in the vial. Mass spectrometry at unit resolution cannot do that job. Chiral gas chromatography can.
The InChIKey ends in -UHFFFAOYSA-N. That block marks a record with no defined configuration. PubChem CID 7753 is the flat amine, not a single enantiomer. A lot sold as “the natural isomer” needs a rotation or a chiral trace. The CID alone cannot carry that claim.
The naming carries history
The compound answers to at least six names, and each belongs to a different era.
Methylhexaneamine is the older pharmaceutical name. Forthane was the trade name on that register. 1,3-dimethylamylamine and its abbreviation DMAA came later, from a market that wanted a technical-sounding label. Geranamine is a coined trademark, and the coining is the whole story of this article. Methylhexanamine is the spelling that anti-doping literature settled on [13].
Searching one name returns one slice of the record. Searching all of them returns a coherent picture.
Names, codes and the Forthane label
The compound was not invented for a modern research catalogue. Eli Lilly registered methylhexaneamine under the name Forthane in the 1940s. That register is a naming fact. It is not a use document.
The product later left the market. When the same chain returned in the late 2000s it arrived without that older framing, as a botanical extract.
The distinction matters for the literature. A compound that once sat on a mid-century register carries dated pharmacology behind it. Almost none of that work reached PubMed’s indexed era. Anyone expecting a modern mechanistic package will not find one. What exists instead is a set of studies driven by regulators and anti-doping laboratories, asking narrow identity questions.
DMAA as a catalogue name therefore hides two older labels. Forthane points at the register. Geranamine points at the plant claim. A methods section that uses only one of those strings will miss half the analytical record.
Where the geranium claim came from
The claim was specific: 1,3-DMAA is a natural constituent of geranium oil, obtained from Pelargonium graveolens. Some versions cited a 1996 Chinese paper reporting the compound in geranium oil.
The provenance of that citation is worth stating plainly. The report is hard to obtain, was not published in a widely indexed journal, and predates the analytical methods that later groups applied. It was never replicated by a laboratory working with botanically authenticated material. A single unreplicated detection carried the regulatory weight for an ingredient sold in millions of units.
The trademark Geranamine encoded the claim in the product name. Labels listed “geranium oil extract” or “geranium stem and leaves”, and the listed ingredient did the regulatory work.
Why the claim was load-bearing
Under the US Dietary Supplement Health and Education Act, a pre-1994 food-supply ingredient faces a lower barrier than a new chemical entity. A synthetic amine is a new dietary ingredient requiring notification. A constituent of a plant already in commerce is not.
So the geranium claim was not decoration. It determined whether the ingredient could be sold at all. That is why it drew analytical attention no ordinary marketing claim would attract.
Online discussion of the compound tracked the same fault line. A qualitative study of user forums found the community split. Some posters treated the compound as a plant product, others as a synthetic stimulant, and the botanical framing sat at the centre of that split [10].
Four analytical tests of the geranium claim
Between 2012 and 2015, four independent groups tested the claim. The methods differ, the laboratories differ, and the conclusions converge.
| Study | Material tested | Method | Detection limit | Finding |
|---|---|---|---|---|
| Zhang 2012 [3] | 8 geranium extracts, 13 supplements | Chiral GC-MS | 10 ppb | Not detected in plants |
| Gauthier 2013 [6] | Published reports | Literature synthesis | n/a | Conflicting, source-dependent |
| ElSohly 2014 [8] | 18 plant samples, 6 species, 9 oils | LC-MS/MS and GC-MS, four laboratories | ~10 ppb | Not detected |
| Avula 2015 [9] | Authentic P. graveolens, pelargonium oil | DART-QToF-MS | n/a | Not detected |
The stereoisomer fingerprint
Zhang and colleagues did two things at once. They looked for the compound in eight geranium extracts and found nothing at a 10 ppb limit. Then they measured stereoisomer ratios in thirteen commercial supplements and compared them against synthetic reference standards [3].
The supplement ratios were indistinguishable from the synthetic standards.
That is a stronger result than absence alone. Absence can be argued away with claims about cultivar, harvest or extraction. A synthetic stereoisomer signature in the finished product says the material in the bottle came out of a reactor, whatever the label says.
Chiral GC-MS is the method that made that comparison possible. The column resolves the four isomers. The peak-area pattern then matches a synthetic standard or it does not. A plant enzyme would have to copy a reactor ratio by chance for the botanical story to survive that test. No authenticated Pelargonium lot has done so.
The multi-centre replication
ElSohly and colleagues addressed the obvious objection. One laboratory examining a few samples could miss the compound in the right plant material [8].
They tested eighteen plant samples spanning six Pelargonium species plus nine commercial oils. The work was split across four laboratories, using both LC-MS/MS and GC-MS. Nothing was found at roughly 10 ppb in any sample, at any laboratory, by either technique.
A negative result replicated across four laboratories and two orthogonal methods is about as firm as analytical chemistry gets.
Ambient ionisation as an independent check
Avula and colleagues used direct analysis in real time coupled to quadrupole time-of-flight mass spectrometry [9]. DART-QToF-MS skips chromatographic separation and sample preparation. That removes one escape route for a positive claim, since no extraction step could have destroyed the analyte first.
Authentic P. graveolens material and pelargonium oil again gave nothing.
The dissenting reports
A handful of papers did report detecting the compound in geranium material. Naming them is more useful than ignoring them. Gauthier reviewed the conflicting evidence and examined why results diverged (PMID 23843687) [6].
The pattern that emerges concerns provenance. Positive reports tended to involve material of uncertain origin or extraction conditions that could generate artefacts. Negative results dominated where the plant material was botanically authenticated and the method validated against reference standards.
Weight of evidence sits with absence. The Zhang stereoisomer work is the piece that no dissenting report has addressed [3].
Class inference for DMAA, not a binding panel
Mechanistic work on 1,3-DMAA is sparse. The compound is a branched aliphatic primary amine, structurally analogous to other indirect sympathomimetics. Class behaviour explains the usual account: displacement of noradrenaline from peripheral stores.
The class inference is not the same as a measured mechanism for this molecule. No modern receptor-binding panel or transporter assay has been published for 1,3-DMAA at the level available for better-studied stimulants.
A laboratory that wants a mechanism for this lot runs a transporter assay. Structural analogy is a hypothesis, not a certificate line.
Indexed cardiovascular papers remain in the reference list so a reader can find them. This profile does not quote those endpoints. A pressor reading in people is a use document, not an identity result.
Label content and lot variability
Monakhova and colleagues quantified the compound in commercial products by quantitative proton NMR [7]. Nine of sixteen products tested positive. Content ranged from 3.1 to 415 g/kg.
That is a spread of more than two orders of magnitude across products sold under related labels.
Two consequences follow. Any study that treated a commercial bottle as a defined reagent carried an unknown actual load. That weakens any paper that skipped its own assay. And any analytical work on this compound needs its own quantification rather than a label figure.
Proton NMR is a good fit for a molecule this small. The spectrum is short. Integration against an internal standard gives content without a separate calibration curve for every analogue. That is what Monakhova exploited [7].
A certificate that reports “present” without a number has not finished the job. Presence at 3 g/kg and presence at 400 g/kg are different lots.
Anti-doping status and detection
The World Anti-Doping Agency prohibits methylhexanamine as a specified stimulant in competition. The compound has generated a disproportionate share of positive tests.
Rule violations as a labelling problem
Lauritzen examined anti-doping rule violations attributed to supplement use and found methylhexanamine implicated in 16 of 27 cases [13].
The dominance is a labelling problem as much as a chemical one. Athletes reported products whose labels named a botanical rather than the compound. The ingredient reaching the analytical laboratory was not the ingredient on the panel.
That is the same fault line as the geranium claim. A botanical string on a label does not identify the amine in the vial. WADA methods identify the amine.
Wastewater surveillance
Causanilles and colleagues applied wastewater analysis to doping surveillance, measuring stimulant residues at the population level [12]. The approach sidesteps individual testing and gives a community-scale estimate of residue.
Methylhexanamine appears in this work as a detectable and quantifiable residue. Population residue continued after the regulatory action.
Wastewater methods treat DMAA as an analytical target, not as a use protocol. The useful fact for a laboratory is that the amine survives in that matrix long enough to quantify.
The analogue succession
Cohen and colleagues analysed six supplement brands whose labels named ingredients that might be analogues of the banned compound [11].
They identified four stimulants: octodrine (2-amino-6-methylheptane), 1,4-DMAA, 1,3-DMAA itself and 1,3-DMBA. In one product, 1,3-DMAA and 1,4-DMAA appeared together.
The finding matters for anyone sourcing reference material. Compounds in this family are close structural neighbours and share fragmentation behaviour. A certificate identifying one of them by mass alone does not exclude the others.
Carbon skeletons that unit mass cannot split
1,3-DMAA is 4-methylhexan-2-amine. 1,4-DMAA moves the branch. 1,3-DMBA shortens the chain by one methylene. Octodrine lengthens it. All four are small aliphatic primary amines. All four produce similar iminium fragments under electron ionisation.
Unit-resolution GC-MS can report “a C7 amine” and still miss which isomer it saw. Cohen’s group used reference standards in two independent laboratories for exactly this reason [11].
A methods section that names DMAA and then quotes a retention time that belongs to 1,4-DMAA has described a different reagent. Run the authentic standard on the same column before treating the peak as 1,3-DMAA.
| Analogue | Skeleton note | Why mass alone fails |
|---|---|---|
| 1,3-DMAA | 4-methylhexan-2-amine | Index compound |
| 1,4-DMAA | Branch moved along the chain | Same C7H17N count |
| 1,3-DMBA | One methylene shorter | Close fragment ions |
| Octodrine | 2-amino-6-methylheptane | Neighbouring C8 amine |
Verifying research material
Given the substitution record, identity confirmation is not optional for this compound.
Identity
Chiral GC-MS has the most published precedent. It resolves the stereoisomers and supports the ratio comparison Zhang used (PMID 22786761) [3]. A synthetic ratio is the expected pattern for any modern material.
Proton NMR gives independent structural confirmation. It also quantifies without a reference standard for every analyte, which is what Monakhova exploited [7]. For a molecule this small, the spectrum is straightforward to interpret.
LC-MS/MS with a validated method distinguishes 1,3-DMAA from 1,4-DMAA and 1,3-DMBA. Unit-resolution mass spectrometry alone does not. Cohen’s work used reference standards in two independent laboratories for exactly this reason [11].
A third-party certificate of analysis should identify the specific isomer, state the method, and report content rather than presence.
Intact mass 115.22 g/mol and formula C7H17N close the carbon count. They do not close the isomer. Add a chiral trace or an optical rotation before treating the lot as a single stereoisomer.
Purity and related amines
The expected impurities are neighbouring amines from the same reductive-amination feed. 4-methyl-2-hexanone that still holds a carbonyl, or a C8 carry-over, will sit near the main peak on a non-polar column.
A broad HPLC area percent can hide those neighbours. A GC-MS extracted-ion chromatogram against authentic standards finds them. Ask the certificate for the analogue panel, not only a single area percent.
The hydrochloride salt is the usual research form. Free-base mass and salt mass differ by HCl. A certificate that quotes 115.22 against a hydrochloride weigh-out has mixed two figures. Establish which form each number describes before calling a mismatch.
Handling
Keep the hydrochloride cold, dry and dark. The free base is volatile enough that an open vial loses mass to air. The salt holds still.
Storage guidance is a house recommendation. Analytical documentation is per-lot release testing.
Aliquot on receipt rather than sampling one jar through a humid day. A small aliphatic amine hydrochloride pulls water. Successive weighings then overstate water and understate amine.
Kimera publishes third-party certificates of analysis for every lot in its COA database. Laboratories source 1,3-DMAA as a sympathomimetic reference standard. Work on stimulant pharmacology often holds it alongside bromantane and chlodantane, which are adamantane actoprotectors with a different mechanism, or the wakefulness agents adrafinil and modafiendz. Related chemistry appears in the nootropics category.
What the literature does not establish
Several things are absent from the record. Naming them is part of describing it.
There is no modern receptor pharmacology for this molecule. The sympathomimetic attribution rests on structural class, not on binding data.
There is no published human pharmacokinetic study with adequate characterisation of absorption, distribution and elimination.
Indexed hemodynamic papers used small samples and multi-ingredient products of unverified content [1][2] and [5]. Those designs cannot carry a laboratory identity claim. This profile leaves their endpoints unread.
Caffeine is a confound in most of that indexed set. Bloomer’s first paper included separate arms [1]. Later papers used mixed products [2][5]. None of that is a binding constant.
Forum ethnography records how people talked about plant versus synthetic origin [10]. It does not identify a vial.
Common questions about DMAA
Is DMAA a natural product? No published analysis of authenticated plant material supports that description. Four groups tested Pelargonium material and oils by three different techniques and found nothing at roughly 10 ppb [3][8] and [9].
Could the compound occur below 10 ppb? Possibly. A detection limit is a floor, not proof of zero. The point is quantitative. Supplements contained the compound at gram-per-kilogram levels [7], so a trace below 10 ppb in a plant could not be the source of that material.
Why does the stereoisomer argument matter more than absence? Absence invites explanations about cultivar, season and extraction. A stereoisomer ratio matching a synthetic standard is positive evidence about the origin of the material in hand, not an argument about what a plant might contain [3].
Is 1,3-DMAA the same as 1,4-DMAA or DMBA? No. They are separate compounds with separate carbon skeletons, and all three have turned up in products labelled otherwise [11]. Mass alone does not tell them apart.
Why does anti-doping literature keep naming it? WADA lists methylhexanamine as a specified stimulant in competition. It accounted for 16 of 27 supplement-linked violations in one analysis [13]. Labels that named a botanical still produced an amine peak in the laboratory.
What is the biggest gap in the record? Receptor pharmacology and published pharmacokinetics. Absorption, distribution and elimination have not been characterised in a published study. Every concentration comparison in the older file sits loosely anchored.
Does this page report human outcomes? No. Indexed papers remain in the list so they can be found. This profile stops at chemistry, plant-origin tests and analogue identity.
Summary of the evidence
Identity: 4-methylhexan-2-amine, C7H17N, 115.22 g/mol, CAS 105-41-9. Two stereocentres, four stereoisomers. PubChem CID 7753 and InChIKey YAHRDLICUYEDAU-UHFFFAOYSA-N close the flat record.
Origin of the name: a mid-century register under Forthane, later a supplement label under a botanical claim. Geranamine encoded that claim in a trademark.
The geranium claim: tested by four independent groups and not supported. Not detected in authenticated Pelargonium material at roughly 10 ppb by any of chiral GC-MS, LC-MS/MS or DART-QToF-MS [3][8] and [9]. Stereoisomer ratios in commercial products match synthetic standards [3]. Conflicting earlier reports trace to material of uncertain provenance [6].
Lot variability: 3.1 to 415 g/kg across nine positive products by qNMR [7].
Doping detection: prohibited in competition, implicated in 16 of 27 supplement-linked rule violations [13], detectable in wastewater surveillance [12].
Substitution risk: three structural analogues found in products labelled as something else [11]. Unit mass does not split them.
Indexed hemodynamic and exposure papers exist and stay in the reference list [4]. Their endpoints are outside this profile.
Status: supplied for laboratory research use only.
References
- Bloomer RJ, Harvey IC, Farney TM, Bell ZW, Canale RE. Effects of 1,3-dimethylamylamine and caffeine alone or in combination on heart rate and blood pressure in healthy men and women. Phys Sportsmed. 2011;39(3):111-120. PMID 22030947. DOI
- Farney TM, McCarthy CG, Canale RE, Allman RJ, Bloomer RJ. Hemodynamic and hematologic profile of healthy adults ingesting dietary supplements containing 1,3-dimethylamylamine and caffeine. Nutr Metab Insights. 2012;5:1-12. PMID 23882143. DOI
- Zhang Y, Woods RM, Breitbach ZS, Armstrong DW. 1,3-Dimethylamylamine (DMAA) in supplements and geranium products: natural or synthetic? Drug Test Anal. 2012;4(12):986-990. PMID 22786761. DOI
- Forrester MB. Exposures to 1,3-dimethylamylamine-containing products reported to Texas poison centers. Hum Exp Toxicol. 2013;32(1):18-23. PMID 23060409. DOI
- Bloomer RJ, Farney TM, Harvey IC, Alleman RJ. Safety profile of caffeine and 1,3-dimethylamylamine supplementation in healthy men. Hum Exp Toxicol. 2013;32(11):1126-1136. PMID 23424215. DOI
- Gauthier TD. Evidence for the presence of 1,3-dimethylamylamine (1,3-DMAA) in geranium plant materials. Anal Chem Insights. 2013;8:29-40. PMID 23843687. DOI
- Monakhova YB, Ilse M, Hengen J, et al. Determination of dimethylamylamine (DMAA) in sports nutrition and dietary supplements using qNMR. Drug Test Anal. 2014;6(9):944-948. PMID 24913715. DOI
- ElSohly MA, Gul W, ElSohly KM, et al. Pelargonium oil and methyl hexaneamine (MHA): analytical approaches supporting the absence of MHA in authenticated Pelargonium graveolens plant material and oil. Drug Test Anal. 2015;7(7):645-654. PMID 25346500. DOI
- Avula B, Wang YH, Duzgoren-Aydin NS, Khan IA. Detection and quantification of 1,3-dimethylamylamine in geranium by DART-QToF and LC-QToF mass spectrometry. J AOAC Int. 2015;98(3):580-586. PMID 26086254. DOI
- Van Hout MC, Hearne E. Plant or poison: a netnographic study of recreational use of 1,3-dimethylamylamine (DMAA). Int J Drug Policy. 2015;26(12):1279-1281. PMID 26001628. DOI
- Cohen PA, Travis JC, Keizers PHJ, Deuster P, Venhuis BJ. Four experimental stimulants found in sports and weight loss supplements: 2-amino-6-methylheptane (octodrine), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylamylamine (1,3-DMAA) and 1,3-dimethylbutylamine (1,3-DMBA). Clin Toxicol (Phila). 2018;56(6):421-426. PMID 29115866. DOI
- Causanilles A, Baz-Lomba JA, Burgard DA, et al. Improving wastewater-based epidemiology to estimate doping prevalence. Anal Bioanal Chem. 2018;410(6):1793-1803. PMID 29335765. DOI
- Lauritzen F. Dietary supplements as a major cause of anti-doping rule violations. Front Sports Act Living. 2022;4:868228. PMID 35399596. DOI
1,3-DMAA is sold for laboratory research use only. Not for human consumption, nor medical, veterinary, or household uses.
Literature retrieved from PubMed.
