1,4-Dimethylamylamine (1,4-DMAA ), also known as 1,4-dimethylpentylamine or as 5-methylhexan-2-amine , is a stimulant drug of the alkylamine family related to methylhexanamine (1,3-DMAA; geranamine).[ 1] [ 2] naturally present in geranium plants and has also been found in certain other plants.[ 3] [ 4] [ 1]
1,4-DMAA has been identified in dietary supplements.[ 1] [ 2] [ 1] [ 5] [ 6] [ 7] [ 8] octodrine and methylhexanamine, 1,4-DMAA has never been used as a pharmaceutical drug.[ 1]
References
↑ 1.0 1.1 1.2 1.3 1.4 "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)" . Clinical Toxicology 56 (6): 421–426. June 2018. doi :10.1080/15563650.2017.1398328 . PMID 29115866 . http://nrs.harvard.edu/urn-3:HUL.InstRepos:40997745 . ↑ 2.0 2.1 "Nine prohibited stimulants found in sports and weight loss supplements: deterenol, phenpromethamine (Vonedrine), oxilofrine, octodrine, beta-methylphenylethylamine (BMPEA), 1,3-dimethylamylamine (1,3-DMAA), 1,4-dimethylamylamine (1,4-DMAA), 1,3-dimethylbutylamine (1,3-DMBA) and higenamine". Clinical Toxicology 59 (11): 975–981. November 2021. doi :10.1080/15563650.2021.1894333 . PMID 33755516 . ↑ "Identification and quantification of dimethylamylamine in geranium by liquid chromatography tandem mass spectrometry" . Analytical Chemistry Insights 7 : 47–58. 2012. doi :10.4137/ACI.S9969 . PMID 22915838 . ↑ "Analysis and Confirmation of 1,3-DMAA and 1,4-DMAA in Geranium Plants Using High Performance Liquid Chromatography with Tandem Mass Spectrometry at ng/g Concentrations" . Analytical Chemistry Insights 7 : 59–78. 2012. doi :10.4137/ACI.S10445 . PMID 23225994 . ↑ "The comparative pharmacology of the isomeric hyptylamines". The Journal of Pharmacology and Experimental Therapeutics 94 (3): 225–231. November 1948. doi :10.1016/S0022-3565(25)03552-9 . PMID 18894881 . ↑ "The Alkylamine Stimulant 1,3-Dimethylamylamine Exhibits Substrate-Like Regulation of Dopamine Transporter Function and Localization" . The Journal of Pharmacology and Experimental Therapeutics 386 (2): 266–273. August 2023. doi :10.1124/jpet.122.001573 . PMID 37348963 . ↑ "Pharmacology of Drugs Used as Stimulants". Journal of Clinical Pharmacology 61 (Suppl 2): S53–S69. August 2021. doi :10.1002/jcph.1918 . PMID 34396557 . ↑ "Methylhexaneamine causes tachycardia and pressor responses indirectly by releasing noradrenaline in the rat". European Journal of Pharmacology 843 : 121–125. January 2019. doi :10.1016/j.ejphar.2018.10.047 . PMID 30395850 .
Adamantanes Adenosine antagonists Alkylamines Ampakines Arylcyclohexylamines Benzazepines Cholinergics Convulsants Eugeroics Oxazolines Phenethylamines
1-(4-Methylphenyl)-2-aminobutane 1-Methylamino-1-(3,4-methylenedioxyphenyl)propane 2-Fuoroamphetamine 2-Fuoromethamphetamine 2-OH-PEA 2-Phenyl-3-aminobutane 2,3-MDA 3-Fuoroamphetamine 3-Fluoroethamphetamine 3-Fluoromethcathinone 3-Methoxyamphetamine 3-Methylamphetamine 3,4-DMMC 4-BMC 4-CMC 4-Fluoroamphetamine 4-Fluoromethamphetamine 4-MA 4-Methylbuphedrone 4-Methylcathinone 4-MEAP 4-MMA 4-Methylpentedrone 4-MTA 6-FNE AL-1095 Alfetamine a-Ethylphenethylamine Amfecloral Amfepentorex Amfepramone Amidephrine 2-Amino-1,2-dihydronaphthalene 2-Aminoindane 5-(2-Aminopropyl)indole 2-Aminotetralin Acridorex Amphetamine (Dextroamphetamine , Levoamphetamine )Amphetaminil Arbutamine β-Methylphenethylamine β-Phenylmethamphetamine Benfluorex Benzedrone Benzphetamine BDB BOH 3-Benzhydrylmorpholine BPAP Buphedrone Bupropion Butylone Camfetamine Cathine Cathinone Chlorphentermine Cilobamine Cinnamedrine Clenbuterol Clobenzorex Cloforex Clortermine Cypenamine D -DeprenylDenopamine Dimethoxyamphetamine Dimethylamphetamine Dimethylcathinone Dobutamine DOPA (Dextrodopa , Levodopa )Dopamine Dopexamine Droxidopa EBDB Ephedrine Epinephrine Epinine Etafedrine Ethcathinone Ethylnorepinephrine Ethylone Etilamfetamine Etilefrine Famprofazone Fencamfamin Fencamine Fenethylline Fenfluramine (Dexfenfluramine , Levofenfluramine )Fenproporex Feprosidnine Flephedrone Fludorex Formetorex Furfenorex Gepefrine Hexapradol Hexedrone HMMA Hordenine 4-Hydroxyamphetamine 5-Iodo-2-aminoindane Ibopamine Indanylamphetamine Iofetamine Isoetarine Isoethcathinone Isoprenaline L -DeprenylLefetamine Lisdexamfetamine Lophophine MBDB MDA (tenamfetamine) MDBU MDEA MDMA (midomafetamine) MDMPEA MDOH MDPR MDPEA Mefenorex Mephedrone Mephentermine Metanephrine Metaraminol Mesocarb Methamphetamine (Dextromethamphetamine , Levomethamphetamine )Methoxamine Methoxyphenamine MMA Methcathinone Methedrone Methoxyphenamine Methylenedioxycathinone Methylone Mexedrone MMDA MMDMA MMMA Morforex N,alpha-Diethylphenylethylamine N-Ethylbuphedrone N-Ethylhexedrone N,N-Dimethylphenethylamine Naphthylamphetamine Nisoxetine Norepinephrine Norfenefrine Norfenfluramine Normetanephrine L -NorpseudoephedrineOctopamine (drug) Orciprenaline Ortetamine Oxifentorex Oxilofrine PBA PCA PCMA PHA Pentorex Pentedrone Pentylone Phenatine Phenpromethamine Phentermine Phenylalanine Phenylephrine Phenylpropanolamine Pholedrine PIA PMA PMEA PMMA PPAP Phthalimidopropiophenone Prenylamine Propylamphetamine Pseudoephedrine Ropinirole Salbutamol (Levosalbutamol )Sibutramine Solriamfetol Synephrine Theodrenaline Tiflorex Tranylcypromine Tyramine Tyrosine Xylopropamine Zylofuramine Phenylmorpholines Piperazines Piperidines Pyrrolidines Racetams Tropanes Tryptamines Others
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