1,3-Dimethylamylamine Chemical Properties

Melting point:

-19°C (estimate)

Boiling point:

bp760 130-135°

Density 

0.7620-0.7655

refractive index 

n20/D1.417-1.419

Flash point:

43℃

pka

pKa 10.54(H2O,t =24±1,I=0.002) (Uncertain)

InChI

InChI=1S/C7H17N/c1-4-6(2)5-7(3)8/h6-7H,4-5,8H2,1-3H3

InChIKey

YAHRDLICUYEDAU-UHFFFAOYSA-N

SMILES

CC(N)CC(C)CC

CAS DataBase Reference

105-41-9(CAS DataBase Reference)

NIST Chemistry Reference

2-Hexanamine, 4-methyl-(105-41-9)

Safety Information

Hazard Codes 

C

Risk Statements 

10-22-34

Safety Statements 

26-36/37/39-45

RIDADR 

UN 2734PSN1 3(8) / PGII

WGK Germany 

3

RTECS 

SC0800000

Hazardous Substances Data

105-41-9(Hazardous Substances Data)

1,3-Dimethylamylamine Usage And Synthesis

Description

1,3-dimethylamylamine or methylexaneamine (DMAA) is a synthetic pharmaceutical patented in the 1940s as a nasal decongestant which can be used as a recreational stimulant. Alleged to occur in nature，DMAA has become a widely used ingredient in sports food supplements, despite its status as a doping agent and concerns over its safety. The most popular brands containing DMAA include Jack3d? and OxyElite Pro?, both marketed by USP Labs and both detained by the FDA in July 2013 (however, some can still be found on Amazon and other online retail stores).

Chemical Properties

White or almost white powder

Originator

Forthane,Lilly,US,1948

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.

Application

1,3-Dimethylamylamine (1,3-DMAA) is a neural stimulant with a structure similar to ephedrine and adrenaline that has been used as a pre-workout stimulant. It is useful in compositions, for example as dietary supplements, and for appetite suppression. Methylhexaneamine is a botanical ingredient in dietary supplements. Methylhexaneamine and caffeine has been combined in attempts to improve exercise performance and related variables.

Definition

ChEBI: Methylhexaneamine is an alkylamine.

Definition

Compared to the commonly available stimulant caffeine, DMAA has a longer t1/2, in this case 8.4 h vs. 5.4 hr for caffeine, as well as a shorter lag time of 0.14 h vs. 0.37 h for caffeine. Previous reports have indicated that DMAA is absorbed over 4–12 hours.

Manufacturing Process

One molecular equivalent of 4-methylhexanone-2 is reacted with slightly more than one molecular equivalent of hydroxylamine. Desirably, the hydroxylamine is prepared in the presence of the 4-methylhexanone-2 by reacting the hydrochloride or sulfate or other salt of the hydroxylamine with a suitable base, such as sodium carbonate or sodium hydroxide. Desirably, the reaction mixture is agitated for a few hours to insure the conversion of the 4- methylhexanone-2 to 4-methylhexanone-2 oxime.
The resulting 4-methylhexanone-2 oxime separates and is dried by any suitable means, such as with a dehydrating agent, for example, sodium sulfate or magnesium sulfate. After drying, 4-methylhexanone-2 oxime is reduced with hydrogen by means of a catalyst, such as Raney nickel, or by reaction of sodium and a primary alcohol, such as ethanol. The resulting 2- amino-4-methylhexane may be purified by distillation, as described in US Patent 2,350,318.
115 g (1 mol) of 2-amino-4-methylhexane and 9 g (0.5 mol) of water are placed in a tared 500 cc 3-necked flask which is equipped with a mechanical stirrer, a thermometer, and a gas delivery tube. The flask is surrounded by a cooling bath of ice and water. Dry carbon dioxide gas is introduced into the solution through the gas delivery tube, with constant stirring, until the increase in weight is approximately 22 g (0.5 mol). The temperature during this addition is maintained between 20° and 30°C. A viscous liquid results, and consists essentially of 2-amino-4-methylhexane carbonate. This also dissociates very slowly at room temperature to the free amine, carbon dioxide, and water; and is effective as an inhalant, according to US Patent 2,386,273.

Therapeutic Function

Nasal decongestant

Pharmacokinetics

Oral Clearance (CL) values (CL/F; F represents oral bioavailability) were found to be relatively low (20±5.0 L/hr), whereas oral Volume of distribution (V/F) was relatively high (236±38.0 L). A 25 mg single oral dose resulted in a maximum plasma concentration (Cmax) of 76.5 ng/mL, which occurred approximately 4 hours post-ingestion. Cmaxvalues were approximately 15-30 times lower than those reported in case studies linking 1,3-Dimethylamylamine (DMAA) intake with severe adverse events, suggesting that the reported adverse events were associated with a DMAA intake much higher than the 25 mg dose in our study [9,10]. Additionally, the potential impact of drug-drug interactions should be considered when interpreting DMAA adverse event reports. Because DMAA PK data suggest that a significant fraction of an orally administered DMAA dose is metabolized, concomitant administration of common ingredients that are also metabolized (e.g., caffeine), may lead to exaggerated DMAA concentrations by inhibiting DMAA clearance.

Side effects

Taking 1,3-Dimethylamylamine (DMAA) can raise blood pressure and lead to cardiovascular problems ranging from shortness of breath and tightening in the chest to heart attack. It  may also cause stroke, a condition called lactic acidosis, heart attack, liver injury, and death.

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