{"Abbreviation":["1,3-DMAA"],"Absorption, Distribution and Excretion":"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.","Aliases":["1,3-Dimethylamylamine","1,3-Dimethylpentylamine","Methylhexaneamine","Forthane","2-Amino-4-methylhexane","4-Methyl-2-hexanamine","Forthan","4-Methyl-2-hexylamine","Dimethylamylamine","Geranamine","floradrene","1,3-DMAA","NSC-1106","Dtxsid60861715","Dtxcid00810601","203-296-1","Methylhexanamine","2-Hexanamine, 4-methyl-","NSC 1106","Pentylamine, 1,3-dimethyl-","Mfcd00025613","AI3-16556","Einecs 203-296-1","DMAA","Brn 1731697","Unii-x49c572yqo","1,3-Dimethylpentanamine","HSDB 8164","Pentylamine,3-dimethyl-","1,3-dimethyl-pentylamine","hexane, 2-amino-4-methyl-","4-04-00-00747","Schembl243596","Schembl7093108","Schembl9215337","Wln: zy \u0026 1y2","NSC1106","Chebi:134754","AC-369","Akos011598451","FD22389","1,3-Dimethylamylamine, analytical standard","DB-040620","NS00015404","En300-92161","D88161","Methylhexanamine hydrochloride, \u003e=98%","1,3-Dimethylamylamine 100 microg/mL in Acetonitrile"],"Biological Half-Life":"Analysis...showed DMAA had ... terminal half-life of 8.45+/- 1.9 hr.","Boiling Point":"132.5 °C","CAS":"105-41-9","ChemicalClasses":[],"Chirality":"racemic","Classes":["Stimulant"],"Color/Form":"Liquid","Density":"0.7655 g/cu cm at 20 °C g/cm\u003csup\u003e3\u003c/sup\u003e","Drug Warnings":"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.","EliminationHalfLife":"~8.5 hours","Erowid Experience Reports":[{"Author":"Lapiseyed","Id":71178,"Title":"Just Need to Tweak the Dosages"},{"Author":"7zyzz7","Id":93001,"Title":"Better Than Any Amphetamine I've Tried"},{"Author":"Not.A.Jackass","Id":91865,"Title":"Extremely Fun But Short-Lived"}],"Esters":[],"European Community (EC) Number":"203-296-1","Formating":[],"HMDB ID":"HMDB0244169","HeavyAtomCount":8,"Human Drugs":"Pharmaceuticals","IUPACName":"4-methylhexan-2-amine","InChI":"InChI=1S/C7H17N/c1-4-6(2)5-7(3)8/h6-7H,4-5,8H2,1-3H3","InChIKey":"YAHRDLICUYEDAU-UHFFFAOYSA-N","MeSH Headers":[{"Id":"M0573315","Link":"https://id.nlm.nih.gov/mesh/M0573315.html","Name":"methylhexaneamine","Ref":36},{"Id":"M0573464","Link":"https://id.nlm.nih.gov/mesh/M0573464.html","Name":"1,3-dimethylamylamine","Ref":37},{"Id":"DescTree","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":"MeSH Tree","Ref":38},{"Id":"PubMed from MeSH","Link":"https://www.nlm.nih.gov/mesh/meshhome.html","Name":null,"Ref":49}],"Mechanism of Action":"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.","MolecularFormula":"C\u003csub\u003e7\u003c/sub\u003eH\u003csub\u003e17\u003c/sub\u003eN","MolecularWeight":"115.22 g/mol","Non-Human Toxicity Values":"LD50 Mice i.p. 185 mg/kg","Odor":"Amine odor","Opticalactivity":"UNSPECIFIED","PubChemId":7753,"Record Description":["Wikipedia|List of designer drugs|Stimulants|Misc"],"Records":{"UNII":{"Impurities":[]}},"RefChem":"818621","RefCount":8,"RefCur":"","References":[{"Name":"Wikipedia","Urls":[{"Link":"https://en.wikipedia.org/wiki/Methylhexanamine","Name":"Methylhexanamine","Sub":false}]},{"Name":"Wikidata","Urls":[{"Link":"https://www.wikidata.org/wiki/Q2594649","Name":"Methylhexanamine","Sub":false}]},{"Name":"DrugBank","Urls":[{"Link":"https://go.drugbank.com/DB19370","Name":"Methylhexanamine","Sub":false}]},{"Name":"PubChem","Urls":[{"Link":"https://pubchem.ncbi.nlm.nih.gov/compound/7753","Name":"Methylhexanamine","Sub":false}]},{"Name":"Common Chemistry","Urls":[{"Link":"https://commonchemistry.cas.org/detail?cas_rn=105-41-9","Name":"Methylhexanamine","Sub":false}]},{"Name":"HMDB","Urls":[{"Link":"https://hmdb.ca/metabolites/HMDB0244169","Name":"Methylhexanamine","Sub":false}]},{"Name":"UNII","Urls":[{"Link":"https://gsrs.ncats.nih.gov/ginas/app/ui/substances/X49C572YQO","Name":"Methylhexanamine","Sub":false}]},{"Name":"EPA DSSTox","Urls":[{"Link":"https://comptox.epa.gov/dashboard/chemical/details/DTXSID60861715","Name":"Methylhexanamine","Sub":false}]}],"Refs":["National Center for Biotechnology Information. PubChem Compound Summary for CID 7753, 1,3-Dimethylamylamine. Accessed May 5, 2026. \u003ca href=https://pubchem.ncbi.nlm.nih.gov/compound/7753\u003ehttps://pubchem.ncbi.nlm.nih.gov/compound/7753\u003c/a\u003e","U.S. Food and Drug Administration; National Center for Advancing Translational Sciences. Methylhexanamine. UNII: X49C572YQO. Global Substance Registration System. Accessed May 5, 2026. \u003ca href=https://gsrs.ncats.nih.gov/ginas/app/beta/substances/X49C572YQO\u003ehttps://gsrs.ncats.nih.gov/ginas/app/beta/substances/X49C572YQO\u003c/a\u003e","Anvisa. RDC Nº 804 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial. Diário Oficial da União. July 24, 2023. Accessed May 5, 2026. \u003ca href=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003ehttps://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-804-de-24-de-julho-de-2023-498447451\u003c/a\u003e","DMAA: A prohibited stimulant. DoD. October 12, 2022. Accessed May 5, 2026. \u003ca href=https://www.opss.org/article/dmaa-prohibited-stimulant\u003ehttps://www.opss.org/article/dmaa-prohibited-stimulant\u003c/a\u003e","DMAA in Products Marketed as Dietary Supplements. February 22, 2023. Accessed May 5, 2026. \u003ca href=https://www.fda.gov/food/information-select-dietary-supplement-ingredients-and-other-substances/dmaa-products-marketed-dietary-supplements?ref=smartchoicelist.com\u003ehttps://www.fda.gov/food/information-select-dietary-supplement-ingredients-and-other-substances/dmaa-products-marketed-dietary-supplements?ref=smartchoicelist.com\u003c/a\u003e","United States v. Hi-Tech Pharmaceuticals, Inc., No. 17-13376 (11th Cir. 2019). August 30, 2019. Accessed May 5, 2026. \u003ca href=https://law.justia.com/cases/federal/appellate-courts/ca11/17-13376/17-13376-2019-08-30.html\u003ehttps://law.justia.com/cases/federal/appellate-courts/ca11/17-13376/17-13376-2019-08-30.html\u003c/a\u003e","Meyer H. E. R. Squibb \u0026 Sons, inc. et al.; Withdrawal of Approval of New Drug Applications. Food and Drug Administration. November 9, 1983. Accessed May 5, 2026. \u003ca href=https://www.govinfo.gov/content/pkg/FR-1983-11-09/pdf/FR-1983-11-09.pdf\u003ehttps://www.govinfo.gov/content/pkg/FR-1983-11-09/pdf/FR-1983-11-09.pdf\u003c/a\u003e"],"SMILES":"CCC(C)CC(C)N","SaltData":[],"Salts":[],"Scheduling":[{"gov":"Australia","ref":[],"schedule":"S10 substance"},{"gov":"Brazil","ref":["3"],"schedule":"F2 substance"},{"gov":"United States","ref":["4","5","6","7"],"schedule":"Unapproved drug; use in dietary supplements, food, or medicine is unlawful.{-{Efn|The N.D.A (New Drug Application) for methylhexanamine was withdrawn in 1983. Consequently, any product containing methylhexanamine cannot be marketed in the United States until a new application is approved.|group=note}-} substance"}],"Solubility":"Slightly soluble in water; very soluble in ethanol, ether, chloroform and dilute acid","StereoisomerData":[{"SMILES":"CC[C@H](C)C[C@H](C)N","Structure":"\u003csvg xmlns=\"http://www.w3.org/2000/svg\" preserveAspectRatio=\"none\" style=\"display:block\" viewBox=\"0 0 76.341 26.78\"\u003e\u003crect width=\"100%\" height=\"100%\" fill=\"#fff\"/\u003e\u003cdesc\u003eGenerated by the Chemistry Development Kit (http://github.com/cdk)\u003c/desc\u003e\u003cg fill=\"#3050f8\" stroke=\"#000\" stroke-linecap=\"round\" stroke-linejoin=\"round\" stroke-width=\".7\"\u003e\u003cpath fill=\"#fff\" stroke=\"none\" d=\"M0 0h77v27H0z\"/\u003e\u003cg class=\"mol\"\u003e\u003cpath d=\"m1.038 10.63 13.198-7.62M14.236 3.01l13.199 7.62\" class=\"bond\"/\u003e\u003cpath fill=\"#000\" stroke=\"none\" d=\"M27.785 10.63h-.7l-1.751 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23.693h-3.701M29.535 25.87h-4.201\"/\u003e\u003c/g\u003e\u003cpath d=\"m27.435 10.63 13.198-7.62M40.633 3.01l13.198 7.62M53.831 10.63v15.24\" class=\"bond\"/\u003e\u003cg class=\"bond\"\u003e\u003cpath d=\"m53.656 10.327.35.606\"/\u003e\u003cpath stroke=\"#3050f8\" d=\"m55.417 9.021.6 1.04M57.177 7.716l.85 1.473M58.937 6.411l1.101 1.906M60.698 5.106l1.35 2.339M62.458 3.801l1.6 2.772\"/\u003e\u003c/g\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M68.97 5.459h-.72l-2.62-4.066h-.029l.029.596q.024.357.024.732v2.738h-.565V.56h.714l2.607 4.054h.03l-.018-.327q-.012-.221-.023-.477-.006-.262-.006-.482V.56h.577zM73.276 5.459h-.619V3.173h-2.512v2.286h-.613V.56h.613v2.072h2.512V.56h.619zM75.781 6.949h-1.943v-.3l.771-.779q.222-.221.372-.393.153-.175.232-.339.079-.168.079-.364 0-.243-.147-.368-.143-.129-.371-.129-.215 0-.379.075-.161.075-.329.207l-.192-.243q.171-.146.393-.246.225-.1.507-.1.41 0 .65.207.239.207.239.575 0 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10.63v15.24M53.831 10.63l10.045-5.8\" class=\"bond\"/\u003e\u003cg stroke=\"none\" class=\"atom\"\u003e\u003cpath d=\"M68.97 5.459h-.72l-2.62-4.066h-.029l.029.596q.024.357.024.732v2.738h-.565V.56h.714l2.607 4.054h.03l-.018-.327q-.012-.221-.023-.477-.006-.262-.006-.482V.56h.577zM73.276 5.459h-.619V3.173h-2.512v2.286h-.613V.56h.613v2.072h2.512V.56h.619zM75.781 6.949h-1.943v-.3l.771-.779q.222-.221.372-.393.153-.175.232-.339.079-.168.079-.364 0-.243-.147-.368-.143-.129-.371-.129-.215 0-.379.075-.161.075-.329.207l-.192-.243q.171-.146.393-.246.225-.1.507-.1.41 0 .65.207.239.207.239.575 0 .229-.096.432-.093.2-.265.397-.168.196-.393.418l-.614.603v.018h1.486z\"/\u003e\u003c/g\u003e\u003cpath stroke=\"#3050f8\" d=\"m63.876 4.83-5.023 2.9\" class=\"hi\"/\u003e\u003c/g\u003e\u003c/g\u003e\u003c/svg\u003e","Subjective Effects":{"Cognitive Effects":["Analysis enhancement","Ego inflation","Focus enhancement","Increased music appreciation","Motivation enhancement","Thought acceleration","Wakefulness","Disinhibition","Suggestibility suppression","Cognitive euphoria","Compulsive redosing","Mania"],"Physical Effects":["Increased libido","Stamina enhancement","Stimulation","Appetite suppression","Dehydration","Dry mouth","Restless legs","Shakiness","Teeth grinding","Abnormal heartbeat","Increased blood pressure","Increased heart rate","Vasoconstriction"],"Visual Effects":[]},"Therapeutic Uses":"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.","Title":"Methylhexanamine","UNII":"X49C572YQO","Wikidata":"Q2594649","Wikipedia":"Methylhexanamine","XLogP":1.9}