methylhexaneamine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Cross-References

ID Source	ID
PubMed CID	7753
CHEBI ID	134754
SCHEMBL ID	243596
MeSH ID	M0573315

Synonyms (47)

Synonym
AC-369
ai3-16556
brn 1731697
nsc 1106
einecs 203-296-1
pentylamine, 1,3-dimethyl-
105-41-9
nsc1106
wln: zy & 1y2
methylhexaneamine
pentylamine,3-dimethyl-
4-methyl-2-hexylamine
2-hexanamine, 4-methyl-
2-amino-4-methylhexane
forthan
1,3-dimethylpentylamine
nsc-1106
1,3-dimethylamylamine
forthane
CHEBI:134754
4-methylhexan-2-amine
geranamine
methylhexanamine
hsdb 8164
4-04-00-00747 (beilstein handbook reference)
4-methyl-2-hexanamine
x49c572yqo ,
dmaa [dietary supplement]
dimethylamylamine
1,3-dmaa
unii-x49c572yqo
AKOS011598451
floradrene
methylhexaneamine [mi]
methylhexaneamine [who-dd]
SCHEMBL243596
W-108787
mfcd00025613
1,3-dimethylamylamine, analytical standard
methylhexanamine hydrochloride, >=98% (hplc)
BCP18792
DTXSID60861715
1,3-dimethyl-pentylamine
Q2594649
D88161
1,3-dimethylamylamine 100 microg/ml in acetonitrile
EN300-92161

Research Excerpts

Effects

Excerpt	Reference	Relevance
"Methylhexaneamine (MHA) has been marketed in dietary supplements based on arguments that it is a constituent of geranium (Pelargonium graveolens) leaves, stems, roots or oil, and therefore qualifies as a dietary ingredient. "	( Pelargonium oil and methyl hexaneamine (MHA): analytical approaches supporting the absence of MHA in authenticated Pelargonium graveolens plant material and oil. Avula, B; Bowers, LD; Chittiboyina, AG; Eichner, A; Elsohly, KM; Elsohly, MA; Gul, W; Khan, I; Murphy, TP; Weerasooriya, A, 2012)	1.82

Toxicity

Excerpt	Reference	Relevance
" Adverse effects reported in association with preworkout supplements include gastrointestinal symptoms, cardiac arrhythmia, blood pressure increases, and potential effects on lipids and blood glucose."	( Efficacy and safety of ingredients found in preworkout supplements. Ambrose, PJ; Eudy, AE; Gordon, LL; Hockaday, BC; Lee, DA; Lee, V; Luu, D; Martinez, CA, 2013)	0.39
"From February 2012 to February 2014, FDA received 114 reports of adverse events of all kinds involving consumers who ingested OxyELITE Pro."	( The Role of Adverse Event Reporting in the FDA Response to a Multistate Outbreak of Liver Disease Associated with a Dietary Supplement. DeBeck, HJ; Gensheimer, K; Klontz, KC; Lance, SE; LeBlanc, P; Mogen, KM; Monahan, C; Sabo, JL; Salter, M; Seelman, SL; Steigman, DS; Wolpert, BJ, )	0.13
"Vigilant surveillance is required for adverse events linked to the use of dietary supplements."	( The Role of Adverse Event Reporting in the FDA Response to a Multistate Outbreak of Liver Disease Associated with a Dietary Supplement. DeBeck, HJ; Gensheimer, K; Klontz, KC; Lance, SE; LeBlanc, P; Mogen, KM; Monahan, C; Sabo, JL; Salter, M; Seelman, SL; Steigman, DS; Wolpert, BJ, )	0.13
"Military services could readily monitor adverse events associated with dietary supplements using electronic surveys and medical records."	( Surveillance of the armed forces as a sentinel system for detecting adverse effects of dietary supplements in the general population. Austin, KG; Farina, EK; Lieberman, HR, 2018)	0.48

Pharmacokinetics

Excerpt	Reference	Relevance
" To our knowledge, no studies have been conducted to determine both the pharmacokinetic profile and physiologic responses of DMAA."	( Physiological and pharmacokinetic effects of oral 1,3-dimethylamylamine administration in men. Bloomer, RJ; Hammond, KG; Presley, CS; Schilling, BK; Yates, CR, 2013)	0.39
"These are the first data to characterize the oral pharmacokinetic profile of DMAA."	( Physiological and pharmacokinetic effects of oral 1,3-dimethylamylamine administration in men. Bloomer, RJ; Hammond, KG; Presley, CS; Schilling, BK; Yates, CR, 2013)	0.39

[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

Class	Description
alkylamine	Any primary amine in which the substituent attached to nitrogen is an alkyl group.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Research

Studies (35)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	1 (2.86)	18.7374
1990's	0 (0.00)	18.2507
2000's	0 (0.00)	29.6817
2010's	31 (88.57)	24.3611
2020's	3 (8.57)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 37.26

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be strong demand-to-supply ratio for research on this compound.

Metric	This Compound (vs All)
Research Demand Index	37.26 (24.57)
Research Supply Index	3.83 (2.92)
Research Growth Index	4.35 (4.65)
Search Engine Demand Index	53.49 (26.88)
Search Engine Supply Index	2.00 (0.95)

This Compound (37.26)

All Compounds (24.57)

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	2 (4.65%)	5.53%
Reviews	4 (9.30%)	6.00%
Case Studies	9 (20.93%)	4.05%
Observational	0 (0.00%)	0.25%
Other	28 (65.12%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Trials	Classes	Roles
beta-alanine [no description available]	3.18	1	0	amino acid zwitterion; beta-amino acid	agonist; fundamental metabolite; human metabolite; inhibitor; neurotransmitter
creatine [no description available]	4.12	2	0	glycine derivative; guanidines; zwitterion	geroprotector; human metabolite; mouse metabolite; neuroprotective agent; nutraceutical
glycine [no description available]	3.23	1	0	alpha-amino acid; amino acid zwitterion; proteinogenic amino acid; serine family amino acid	EC 2.1.2.1 (glycine hydroxymethyltransferase) inhibitor; fundamental metabolite; hepatoprotective agent; micronutrient; neurotransmitter; NMDA receptor agonist; nutraceutical
glycocyamine glycocyamine: RN given refers to parent cpd; structure. guanidinoacetate : A monocarboxylic acid anion that is the conjugate base of guanidinoacetic acid, obtained by deprotonation of the carboxy group.. guanidinoacetic acid : The N-amidino derivative of glycine.	3.23	1	0	guanidinoacetic acids; zwitterion	bacterial metabolite; human metabolite; mouse metabolite; nutraceutical; rat metabolite
nitrates Nitrates: Inorganic or organic salts and esters of nitric acid. These compounds contain the NO3- radical.	3.23	1	0	monovalent inorganic anion; nitrogen oxoanion; reactive nitrogen species
caffeine [no description available]	5.52	4	1	purine alkaloid; trimethylxanthine	adenosine A2A receptor antagonist; adenosine receptor antagonist; adjuvant; central nervous system stimulant; diuretic; EC 2.7.11.1 (non-specific serine/threonine protein kinase) inhibitor; EC 3.1.4.* (phosphoric diester hydrolase) inhibitor; environmental contaminant; food additive; fungal metabolite; geroprotector; human blood serum metabolite; mouse metabolite; mutagen; plant metabolite; psychotropic drug; ryanodine receptor agonist; xenobiotic
clenbuterol Clenbuterol: A substituted phenylaminoethanol that has beta-2 adrenomimetic properties at very low doses. It is used as a bronchodilator in asthma.. clenbuterol : A substituted aniline that is 2,6-dichloroaniline in which the hydrogen at position 4 has been replaced by a 2-(tert-butylamino)-1-hydroxyethyl group.	2.25	1	0	amino alcohol; dichlorobenzene; ethanolamines; primary arylamine; secondary amino compound; substituted aniline	beta-adrenergic agonist; bronchodilator agent; sympathomimetic agent
amphetamine Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.	2.6	1	0	primary amine
octopamine Octopamine: An alpha-adrenergic sympathomimetic amine, biosynthesized from tyramine in the CNS and platelets and also in invertebrate nervous systems. It is used to treat hypotension and as a cardiotonic. The natural D(-) form is more potent than the L(+) form in producing cardiovascular adrenergic responses. It is also a neurotransmitter in some invertebrates.. octopamine : A member of the class of phenylethanolamines that is phenol which is substituted at the para- position by a 2-amino-1-hydroxyethyl group. A biogenic phenylethanolamine which has been found to act as a neurotransmitter, neurohormone or neuromodulator in invertebrates.	2.31	1	0	phenylethanolamines; tyramines	neurotransmitter
arginine Arginine: An essential amino acid that is physiologically active in the L-form.. arginine : An alpha-amino acid that is glycine in which the alpha-is substituted by a 3-guanidinopropyl group.	3.18	1	0	arginine; glutamine family amino acid; L-alpha-amino acid; proteinogenic amino acid	biomarker; Escherichia coli metabolite; micronutrient; mouse metabolite; nutraceutical
synephrine [no description available]	2.25	1	0	ethanolamines; phenethylamine alkaloid; phenols	alpha-adrenergic agonist; plant metabolite
1,3-dimethylbutylamine 1,3-dimethylbutylamine: a stimulant; structure in first source	2.63	2	0
melamine melamine: RN given refers to parent cpd; structure. melamine : A trimer of cyanamide, with a 1,3,5-triazine skeleton.	3.23	1	0	triamino-1,3,5-triazine	xenobiotic metabolite
n-heptane Heptanes: Seven-carbon alkanes with the formula C7H16.. heptane : A straight-chain alkane with seven carbon atoms. It has been found in Jeffrey pine (Pinus jeffreyi).	2.63	2	0	alkane; volatile organic compound	non-polar solvent; plant metabolite
ephedrine Ephedrine: A phenethylamine found in EPHEDRA SINICA. PSEUDOEPHEDRINE is an isomer. It is an alpha- and beta-adrenergic agonist that may also enhance release of norepinephrine. It has been used for asthma, heart failure, rhinitis, and urinary incontinence, and for its central nervous system stimulatory effects in the treatment of narcolepsy and depression. It has become less extensively used with the advent of more selective agonists.. (-)-ephedrine : A phenethylamine alkaloid that is 2-phenylethanamine substituted by a methyl group at the amino nitrogen and a methyl and a hydroxy group at position 2 and 1 respectively.	2.31	1	0	phenethylamine alkaloid; phenylethanolamines	bacterial metabolite; environmental contaminant; nasal decongestant; plant metabolite; sympathomimetic agent; vasoconstrictor agent; xenobiotic
nandrolone Nandrolone: C18 steroid with androgenic and anabolic properties. It is generally prepared from alkyl ethers of ESTRADIOL to resemble TESTOSTERONE but less one carbon at the 19 position.. nandrolone : A 3-oxo Delta(4)-steroid that is estr-4-en-3-one substituted by a beta-hydroxy group at position 17.	2.25	1	0	17beta-hydroxy steroid; 3-oxo-Delta(4) steroid; anabolic androgenic steroid	human metabolite
octodrine 2-amino-6-methylheptane: 1,3-dimethylamylamine (1,3-DMAA) analog	2.63	2	0	alkylamine
deterenol [no description available]	2.31	1	0
higenamine higenamine: structure; RN given refers to (+-)-isomer	3.69	2	0	norcoclaurine
betadex beta-Cyclodextrins: Cyclic GLUCANS consisting of seven (7) glucopyranose units linked by 1,4-glycosidic bonds.	2.11	1	0	cyclodextrin
cocaine Cocaine: An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.. cocaine : A tropane alkaloid obtained from leaves of the South American shrub Erythroxylon coca.	2.6	1	0	benzoate ester; methyl ester; tertiary amino compound; tropane alkaloid	adrenergic uptake inhibitor; central nervous system stimulant; dopamine uptake inhibitor; environmental contaminant; local anaesthetic; mouse metabolite; plant metabolite; serotonin uptake inhibitor; sodium channel blocker; sympathomimetic agent; vasoconstrictor agent; xenobiotic
eptifibatide [no description available]	2.1	1	0	homodetic cyclic peptide; macrocycle; organic disulfide	anticoagulant; platelet aggregation inhibitor
oxilofrine oxilofrine: RN given refers to cpd without isomeric designation; structure	2.31	1	0	alkylbenzene
phosphorus Phosphorus: A non-metal element that has the atomic symbol P, atomic number 15, and atomic weight 31. It is an essential element that takes part in a broad variety of biochemical reactions.	3.18	1	0	monoatomic phosphorus; nonmetal atom; pnictogen	macronutrient

Condition	Relationship Strength	Studies
Tachyarrhythmia [description not available]	3.04	4
Tachycardia Abnormally rapid heartbeat, usually with a HEART RATE above 100 beats per minute for adults. Tachycardia accompanied by disturbance in the cardiac depolarization (cardiac arrhythmia) is called tachyarrhythmia.	8.04	4
Dizzyness [description not available]	2.17	1
Hypesthesia Absent or reduced sensitivity to cutaneous stimulation.	2.17	1
Action Tremor [description not available]	2.17	1
Weight Reduction [description not available]	3.47	2
Dizziness An imprecise term which may refer to a sense of spatial disorientation, motion of the environment, or lightheadedness.	2.17	1
Tremor Cyclical movement of a body part that can represent either a physiologic process or a manifestation of disease. Intention or action tremor, a common manifestation of CEREBELLAR DISEASES, is aggravated by movement. In contrast, resting tremor is maximal when there is no attempt at voluntary movement, and occurs as a relatively frequent manifestation of PARKINSON DISEASE.	2.17	1
Weight Loss Decrease in existing BODY WEIGHT.	3.47	2
Emesis [description not available]	2.49	2
Nausea An unpleasant sensation in the stomach usually accompanied by the urge to vomit. Common causes are early pregnancy, sea and motion sickness, emotional stress, intense pain, food poisoning, and various enteroviruses.	2.49	2
Vomiting The forcible expulsion of the contents of the STOMACH through the MOUTH.	2.49	2
Angor Pectoris [description not available]	2.1	1
Coronary Thrombosis Coagulation of blood in any of the CORONARY VESSELS. The presence of a blood clot (THROMBUS) often leads to MYOCARDIAL INFARCTION.	2.1	1
Cardiovascular Stroke [description not available]	2.1	1
Angina Pectoris The symptom of paroxysmal pain consequent to MYOCARDIAL ISCHEMIA usually of distinctive character, location and radiation. It is thought to be provoked by a transient stressful situation during which the oxygen requirements of the MYOCARDIUM exceed that supplied by the CORONARY CIRCULATION.	2.1	1
Myocardial Infarction NECROSIS of the MYOCARDIUM caused by an obstruction of the blood supply to the heart (CORONARY CIRCULATION).	2.1	1
Out-of-Hospital Cardiac Arrest Occurrence of heart arrest in an individual when there is no immediate access to medical personnel or equipment.	2.11	1
Athletic Injuries Injuries incurred during participation in competitive or non-competitive sports.	2.11	1
Cerebral Concussion [description not available]	2.11	1
Brain Concussion A nonspecific term used to describe transient alterations or loss of consciousness following closed head injuries. The duration of UNCONSCIOUSNESS generally lasts a few seconds, but may persist for several hours. Concussions may be classified as mild, intermediate, and severe. Prolonged periods of unconsciousness (often defined as greater than 6 hours in duration) may be referred to as post-traumatic coma (COMA, POST-HEAD INJURY). (From Rowland, Merritt's Textbook of Neurology, 9th ed, p418)	2.11	1
Drug Overdose Accidental or deliberate use of a medication or street drug in excess of normal dosage.	3.04	1
Body Weight The mass or quantity of heaviness of an individual. It is expressed by units of pounds or kilograms.	3.06	1
Mydriasis Dilation of pupils to greater than 6 mm combined with failure of the pupils to constrict when stimulated with light. This condition may occur due to injury of the pupillary fibers in the oculomotor nerve, in acute angle-closure glaucoma, and in ADIE SYNDROME.	2.07	1
Adverse Drug Event [description not available]	2.07	1
Drug-Related Side Effects and Adverse Reactions Disorders that result from the intended use of PHARMACEUTICAL PREPARATIONS. Included in this heading are a broad variety of chemically-induced adverse conditions due to toxicity, DRUG INTERACTIONS, and metabolic effects of pharmaceuticals.	2.07	1
Brain Hemorrhage [description not available]	2.07	1
Infarct, Lacunar [description not available]	2.07	1
Dejerine-Roussy Syndrome [description not available]	2.07	1
Intracranial Hemorrhages Bleeding within the SKULL, including hemorrhages in the brain and the three membranes of MENINGES. The escape of blood often leads to the formation of HEMATOMA in the cranial epidural, subdural, and subarachnoid spaces.	2.07	1
Blood Poisoning [description not available]	2.07	1
Death, Sudden The abrupt cessation of all vital bodily functions, manifested by the permanent loss of total cerebral, respiratory, and cardiovascular functions.	2.07	1
Coagulation, Disseminated Intravascular [description not available]	2.07	1
Asystole [description not available]	2.07	1
MODS [description not available]	2.07	1
Disseminated Intravascular Coagulation A disorder characterized by procoagulant substances entering the general circulation causing a systemic thrombotic process. The activation of the clotting mechanism may arise from any of a number of disorders. A majority of the patients manifest skin lesions, sometimes leading to PURPURA FULMINANS.	2.07	1
Heart Arrest Cessation of heart beat or MYOCARDIAL CONTRACTION. If it is treated within a few minutes, heart arrest can be reversed in most cases to normal cardiac rhythm and effective circulation.	2.07	1
Multiple Organ Failure A progressive condition usually characterized by combined failure of several organs such as the lungs, liver, kidney, along with some clotting mechanisms, usually postinjury or postoperative.	2.07	1
Sepsis Systemic inflammatory response syndrome with a proven or suspected infectious etiology. When sepsis is associated with organ dysfunction distant from the site of infection, it is called severe sepsis. When sepsis is accompanied by HYPOTENSION despite adequate fluid infusion, it is called SEPTIC SHOCK.	2.07	1

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