105-41-9

Basic information

• Product Name: 1,3-Dimethylpentylamine
• Synonyms: Fouramin;Metexaminum;Methexaminum;Methylhexamine;GERANAMINE;2-AMINO-4-METHYLHEXANE HYDROCHLORIDE 98%;2-Hexanamine, 4-methyl-;4-Methylhexan-2-amine
• CAS NO: 105-41-9
• Molecular Formula: C₇H₁₇N
• Molecular Weight: 115.22
• EINECS: 203-296-1
• Product Categories: Small molecule;Aliphatics;Amines;Intermediates & Fine Chemicals;Pharmaceuticals;intermediates
• Mol File: 105-41-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: -19°C (estimate)
• Boiling Point: bp760 130-135°
• Flash Point: 43℃
• Appearance: white or category of white crystal powder
• Density: 0.7620-0.7655
• Vapor Pressure: 0.651mmHg at 25°C
• Refractive Index: n20/D1.417-1.419
• PKA: pKa 10.54(H2O,t =24±1,I=0.002) (Uncertain)
• CAS DataBase Reference: 1,3-Dimethylpentylamine(CAS DataBase Reference)
• NIST Chemistry Reference: 1,3-Dimethylpentylamine(105-41-9)
• EPA Substance Registry System: 1,3-Dimethylpentylamine(105-41-9)

Safety Data

• Hazard Codes: C
• 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)

Usage

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.

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

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

Synthetic route

4-methylhexan-2-one (105-42-0) → 1,3-dimethylamylamine (105-41-9)

4-methyl-hexan-2-one oxime → 1,3-dimethylamylamine (105-41-9)

Conditions	Yield
With ethanol; sodium; toluene

1,3-dimethylamylamine (105-41-9) + chloroacetic acid (79-11-8) → 1,3-dimethylpentylglycine hydrochloride

Conditions	Yield
Stage #1: 1,3-dimethylamylamine; chloroacetic acid With sodium hydrogencarbonate In water at 70℃; Stage #2: With hydrogenchloride In water for 168h; pH=2;	96%

2-Picolinic acid (98-98-6) + 1,3-dimethylamylamine (105-41-9) → N-(4-methylhexan-2-yl)picolinamide

Conditions	Yield
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃;	62%

octanol (111-87-5) + 1,3-dimethylamylamine (105-41-9) + cuminol (536-60-7) → C25H45N

Conditions	Yield
With Cu2Al3Ox-HT In toluene at 160℃; for 24h; Sealed tube; Inert atmosphere;	21%

1,3-dimethylamylamine (105-41-9) + propionaldehyde (123-38-6) → (1,3-dimethyl-pentyl)-propyliden-amine

Conditions	Yield
at 0℃;

1,3-dimethylamylamine (105-41-9) + chloroacetaldehyde diethyl acetal (621-62-5) → (2,2-diethoxy-ethyl)-(1,3-dimethyl-pentyl)-amine (100799-37-9)

Conditions	Yield
at 120℃;

(1,1-dimethyl-propylperoxy)-methanol (17742-79-9) + 1,3-dimethylamylamine (105-41-9) → 2--4-methylhexan (33028-49-8)

hydroxymethyl tert-butyl peroxide (17742-78-8) + 1,3-dimethylamylamine (105-41-9) → 2--4-methylhexan (32950-93-9)

1,3-dimethylamylamine (105-41-9) + (1,1-dimethyl-butylperoxy)-methanol (26330-26-7) → 2--4-methylhexan (32930-88-4)

1,3-dimethylamylamine (105-41-9) + propionyl chloride (79-03-8) → N-(1,3-Dimethyl-pentyl)-propionamide

1,3-dimethylamylamine (105-41-9) + chloroformic acid ethyl ester (541-41-3) → 5-N-Carbaethoxyamino-3-methyl-hexan

Conditions	Yield
With triethylamine In diethyl ether

1,3-dimethylamylamine (105-41-9) + 5-(4-chlorophenyl)-1-(2,4-dichlorophenyl)-4-methyl-1H-pyrazole-3-carbonyl chloride (168273-05-0) → 5-(4-chloro-phenyl)-1-(2,4-dichloro-phenyl)-4-methyl-1H-pyrazole-3-carboxylic acid (1,3-dimethyl-pentyl)-amide

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;

1,3-dimethylamylamine (105-41-9) + 3,7-dichloro-4H-1,2,4-benzothiadiazine 1,1-dioxide (59943-32-7) → 7-Chloro-3-(1,3-dimethylpentyl)amino-4H-1,2,4-benzothiadiazine 1,1-dioxide

1,3-dimethylamylamine (105-41-9) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-(4-methylhexan-2-yl)-4-nitrobenzenesulfonamide

Conditions	Yield
With triethylamine In dichloromethane at 0 - 20℃;

1,3-dimethylamylamine (105-41-9) + 4-Nitrobenzenesulfonyl chloride (98-74-8) → N-chloro-N-(4-methylhexan-2-yl)-4-nitrobenzenesulfonamide

Conditions	Yield
Multi-step reaction with 2 steps 1: triethylamine / dichloromethane / 0 - 20 °C 2: phthaloyl peroxide; tetrabutyl-ammonium chloride / 1,2-dichloro-ethane / 12 h / 20 °C / Irradiation; Inert atmosphere; Schlenk technique View Scheme

1,3-dimethylamylamine (105-41-9) + methyl 4-iodobenzoate (619-44-3) → C15H23NO2

Conditions	Yield
With 5-nitro-2-hydroxypyridine; 1,1,1,3',3',3'-hexafluoro-propanol; 2-(2-methoxyphenyl)-2-oxoacetic acid; water; palladium diacetate; silver trifluoroacetate at 120℃; for 48h; Sealed tube;	n/a

2-Picolinic acid (98-98-6) + 1,3-dimethylamylamine (105-41-9) → N-(4-(4-nitrobenzyl)hexan-2-yl)picolinamide

Conditions	Yield
Multi-step reaction with 2 steps 1: dicyclohexyl-carbodiimide; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / dichloromethane / 20 °C 2: palladium(II) trimethylacetate; 4‐benzyloxy‐2‐hydroxy‐pyridine; silver carbonate; sodium 2,2,2-trifluoroacetate / tert-butyl methyl ether / 36 h / 130 °C View Scheme

Upstream product

• 105-42-0 4-methylhexan-2-one