An Introduction Of DMAA Biology Essay


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1. Introduction:

Introduction of DMAA

Dimethylamylamine (DMAA) is an organic compound with the formula C7H17N and its molecular weight is 115.22 g mol−1 which is commonly known as 1,3-dimethylamylamine, DMAA or Methylhexanamine. Though it is popular in the consumer market in many names, its use and safety has been always doubted. Also, it is used as a simple aliphatic amine to treat nasal decongestion and to correct hypertrophied or hyperplasic oral tissues. It can be administered nasally by inhalation which exerts influence on the nasal mucosa. It is also used as a popular vasoconstrictor.


Figure . Structure of DMAA

(DMAA) or 1, 3 dimethylamylamine or methylexaneamine is a synthetic pharmaceutical. It was patented in the 1940s as a nasal decongestant. While there is a raging debate whether DMAA exists naturally or can be sourced naturally, it is more famously used as a recreational stimulant. Alleged to occur in nature, DMAA has become more predominantly used in food supplements for sportspersons, though it is often misused as a doping agent and its 0afe use is questioned. (Lorenzo ,CD. et al 2012)

HPLC or high performance liquid chromatography was used to detect the presence of DMMA within extracts from leaves and stems of four types of geranium species and three popular cultivars. At the same time, the quantity of DMAA in commercial geranium or Pelargonium graveolens was also quantified. However, no leaves or stems used in this study could affirm the presence of DMAA. The food supplements have a meager 30 mg per daily dose by which it can be concluded that the amount of DMAA inherent in the food supplement was not sourced by nature. Thus, it can be safely concluded that synthetic DMAA has been added here which is the etiology of several physiological discomforts. (Lorenzo ,CD. et al 2012)

As stated earlier, DMAA hit the headlines with a doping case reported at the recently concluded London Olympics 2012 in which at least one athlete tested positive for DMAA (1,3- Dimethylamylamine or methylhexaneamine) out of 8 athletes who underwent similar test. This makes the case of DMAA being misused as a doping agent or as an ingredient in sports food supplement stronger. Since human health cannot be compromised at any cost. . (Shane Starling, 2012)

The Medicines and Healthcare products Regulatory Agency (MHRA) in the United Kingdom, has banned the sale of all sports supplements containing 1,3-dimethylamylamine (DMAA), due to its potential ill effect on health. MHRA advocates medicine controls for such products declaring it an unlicensed medicinal product which is in continuum with Australia's Therapeutic Goods Association banning DMAA following reports of death due to its alleged purchase from internet and its subsequent use. The possible ill effects of the use of DMAA are constriction of the arteries (vasoconstriction) and increase in palpitation (bradycardia), which can lead to breathlessness or myocardial infarction. World Anti-Doping Agency's list of banned substances also includes DMAA. (Steve Down, 2012).

Nuclear Magnetic Resonance-

Nuclear Magnetic Resonance- The initial description and measurement of Nuclear Magnetic Resonance was done by Isidor Rabi in the year 1938, for which he was honored with Nobel Prize in Physics for his outstanding contribution. In 1946, two physicists, namely, Felix Bloch and Edward Mills Purcell went further to use this on liquids and solids. They were feted with Nobel Prize in Physics for their stellar work in 1952. (Rabi, J.R. et al 1938).

Isidor Rabi made the observation that a nucleus is said to be being in resonance when RF energy bearing a certain frequency which was specific to the identity of the nuclei of the molecule facilitates absorption by magnetic nuclei, 1H and 31P of RF energy within magnetic field. In magnetic field strength bearing same strength, there are a number of atomic nuclei and these various atomic nuclei in a molecule resonate at different radiofrequencies. This epoch making discovery can be used to find important structural composition and chemical information pertaining to molecules by observing magnetic resonance frequencies of the nuclei inherent in a molecule. (Rabi, J.R. et al 1938).

NMR is widely used in analytical chemistry and biochemistry, which spiraled the development of advanced electronics and electromagnetic technology and set the stage for its use by civilians. NMR is a physical phenomena, magnetic nuclei in magnetic field absorbs and re-emits electromagnetic radiation. The magnetic properties of the isotope of the atoms and the strength of the magnetic field, decides the specific resonance of frequency of the energy so emitted. It is akin to the frequency found in practical applications of daily life like VHF and UHF television broadcasts (60-1000MHz). This technology permits observation of mechanical magnetic properties of the atomic nucleus. NMR phenomena are nowadays widely used in many scientific methods in the study of various materials ranging from molecular, crystals to non-crystalline substances through NMR spectroscopy. In medical sciences, it is this path breaking technology which is daily used in superior imaging techniques as in MRI (magnetic resonance imaging). (Edwards, J.C. 2009)

Certain Isotopes comprise an odd number of neutrons and/or of protons which have a nonzero spin which is otherwise explained as an intrinsic angular momentum and magnetic moment. On the other hand, nuclides with even number of protons and/or neutrons have zero total spin. NMR spectroscopy is also used to study nuclei from isotopes of 2H, 6Li, 10B, 11B, 14N, 15N, 17O, 19F, 23Na, 29Si, 31P, 35Cl, 113Cd, 129Xe, 195Pts pin while 1H and 13C are the most studied nuclei.

The most striking characteristic of NMR is that the strength of the applied magnetic field makes the resonance frequency directly proportional to it. Imaging techniques like magnetic resonance imaging uses this feature in the following manner: the resonance frequencies emanating from the sample's nuclei depends on the location of the field in which they are located, in case of a sample which is placed in a magnetic field of non-uniform nature. Efforts are on to use superconductors to increase the strength of the field because magnitude of the magnetic field gradient decides the resolution of the image. However, hyper polarization, and/or using two-dimensional, three-dimensional and higher-dimensional multi-frequency techniques can be used to enhance the effectiveness of NMR.

The following is the sequence of steps in the principle of NMR:

In an applied constant magnetic field H0, alignment (polarization) of the magnetic nuclear spins

Using radio frequency (RF) pulse which is an electro-magnetic pulse, this alignment of nuclear spins is disturbed. Static magnetic field as denoted by H0 and the nuclei of observation decides the required frequency to create disturbance among the alignment of nuclear spins.

To maximize the signal strength of NMR, usually, the two fields are perpendicular to each other. Magnetic resonance imaging (MRI) and NMR spectroscopy exploits this phenomenon of the resultant response by total magnetization (M) of the nuclear spins. To get dispersion and very high stability to deliver spectral, MRI and NMR spectroscopy use intense applied magnetic fields (H0). Chemical shifts, the Zeeman Effect, and Knight Shifts in metals are some of the ways in which they can be described.

Infrared spectroscopy-

Infrared spectroscopy- In the 1950s, it was Wilbur Kaye who started using infrared spectroscopy. He came up with the theory to elaborate the results of his study on testing the near-infrared spectrum with the help of a machine specially designed for the purpose by him. Thereafter, Karl Norris started using IR Spectroscopy in the 1960s in the analytical world. Hence, IR Spectroscopy evolved as a much accepted technique. Improvements in the field of IR Spectroscopy have been numerous, of which the most noticeable was the application of Fourier Transformations. This led to creation of an IR method, in the late 1960s, which had a higher resolution and reduced in noise levels.

In other words, Infrared Spectroscopy concerns with the spectroscopy of infrared area in the electromagnetic spectrum. As compared to visible light, this light has a longer wavelength and lower frequency. IR encompasses a range of techniques concerned on absorption spectroscopy. Fourier transform infrared (FTIR) spectrometer is one such laboratory instrument which uses this technique.

The following are the three divisions of infrared portion of electromagnetic spectrum: the near infrared, mid infrared, and far infrared. They are given these names on the basis of their relation to the visible spectrum. The three regions of IR can put to numerous uses like the higher-energy near-IR has approximately 14000-4000 cm−1 (0.8-2.5 μm wavelength), overtone and harmonic vibrations can be excited using this higher-energy near-IR. The mid-infrared has approximately 4000-400 cm−1 (2.5-25 μm) is useful to study the fundamental vibrations and associated rotational-vibration structure. Rotational spectroscopy uses the far-infrared of approximately 400-10 cm−1 (25-1000 μm), has low energy, which lies adjacent to the microwave region. The relative molecular or electromagnetic properties form the basis of names and classifications of these sub regions, and are treated as conventions.

Molecules absorb specific frequencies which are unique to their structure, and it is this fact that infrared spectroscopy uses to enhance its utility. The frequency of the absorbed radiation matches the frequency of the vibrating group or bond, which makes these absorptions as resonant frequencies. The shape of the molecular potential energy surfaces, the masses of the atoms, and the associated vibronic coupling together determined the energy expended. To be more specific, when Hamiltonian molecule corresponding to the electronic ground state is approximated using a harmonic oscillator within the vicinity of the molecular equilibrium geometry, specifically as in the Born-Oppenheimer, the normal modes corresponding to molecular electronic ground state potential energy surface determines the resonant frequencies. At both the end of the bond, the resonant frequencies can be related to its strength, which makes it possible to associate frequency of the vibrations of a specific type of bond.

Gas chromatography and Mass spectrometry-

Gas chromatography ("GC") and mass spectrometry ("MS") together make a worthy and effective combination for chemical analysis. (GC-MS) works with the help of gases like Helium, Nitrogen and Hydrogen. Thus, (GC-MS) is a method which combines the characteristics of gas-liquid chromatography and mass spectrometry and is employed to identify and segregate various substances within a given test sample. Its applications invariably include drug detection, fire investigation, analysis of environment analysis, investigation of explosives, and to identify unknown samples. Also, it can be used to identify trace elements in such materials that were previously thought to have disintegrated beyond identification.

Gas Chromatography (GC): This technique is employed to segregate drugs that might have a presence in the sample provided. Gas Chromatography involves injecting the sample into a long tubular column, known as the chromatography column. Helium gas is used to sweep the given drugs through the column. Since some drugs take longer time to pass through the column when compared to others, drugs in the given sample get separated in the process. The whole process is just like a race where initially all the racers are huddled together in a group but finishing line sees the fastest one ahead of others, as they get distanced/separated from each other owing to their respective speed. The time taken by the respective drug to go through the tubular column is determined by the individual chemical feature/characteristic endemic to that particular drug. Thus retention time (RT) is the time taken by any drug to travel the long tubular column, which makes RT as an distinguishing characteristic for any given drug.

Mass Spectrometry (MS): Mass Spectrometry (MS) detector is the detector for Gas Chromatography. After traveling the tubular column of GC, when the drug leaves the column, it is divided or disintegrated by ionization. These fragments are segregated by mass which gives a certain fragmentation pattern. This pattern is unique for the provided drug just like its retention time (RT), which is another identifying feature of the drug. The fragmentation pattern is also called molecular fingerprint which is specific for any given drug.

Internal standard-

Internal Standard (I.S.): A drug with same chemical features as the one which is assayed is called as an Internal Standard (I.S). To prepare and analyze the given drug which is assayed, I.S. is added to the given sample. Then, the signal given by I.S. is compared to that signal which is produced by the given drug. This analysis is done to measure the drug and so that it qualifies the assay. The isotope of hydrogen with a mass of 1 atomic unit more than hydrogen can be found in Deuterium. The deuterated version of the drug is the ideal I.S. To manufacture the deuterated drug, one or more hydrogen atoms are substituted with an atom of deuterium. Same chemical characteristics and retention time (RT) during GC analysis are shown by the deuterated I.S. during the preparation of the sample similar to a non-deuterated drug. The only way to differentiate is to use the MS detector to study the pattern of fragmentation. A deuterated I.S. can only be used by a GC/MS.

Figure 2. Schematic diagram of a GC-MS (Murray, K. 2006)

Gas chromatography uses mass spectrometer as the detector, which was developed in 1950s. Its use was started by Roland Gohlke and Fred McLafferty. These devices are extremely sensitive. Initially, due to nature of these devices as being bulky, fragile, its use was limited to laboratory setting. (Gohlke, R; McLafferty, Fred W.)

The change came when analysis of fire accelerants was done in less than 90 seconds by top-of-the-line high-speed GC-MS in 1996. This was spectacular when compared to first-generation GC-MS which would have had a timing of at the least 16 minutes for the same exercise. By 2000s, quadrupole technology assisted computerized GC/MS instruments had become pivotal for chemical research. This began to be used as one of the chief instruments for organic analysis. In the present scenario, GC/MS instruments are used in monitoring of environmental elements like water, air, and soil. It is even used to regulate agriculture practices and food safety. Most importantly, they are widely used to discover and produce medicine.

GC-MS are being extensively used in the field of sports by officials to check whether athletes are using contraband substances to enhance their performance. For this purpose, the urine sample of athletes is run in the GC-MS which identifies the drug ingested by the athletes, the traces of which could be determined easily by GC-MS in the urine sample. Due to this technology, the Chinese Olympic team had to reduce 27 members from its Olympic contingent for failing doping tests in the 2000 Olympic Games in Sydney. This was followed by expelling Romanian and Bulgarian weight-lifting squads for alleged use of diuretics, and failing the tests, some weeks later. The diuretics helped these athletes to shed weight and conceal the presence of steroids in their body. German freestyle wrestler, Alexander Leopold had to give away his gold medal in November, after he tested positive for a banned steroid, nandrolone. (Aguilera, R. et al).

Doping is banned in Games arena but some athletes still are pursuing the intake of contraband substances to enhance their performance, despite its ill effect on human health. The utility of GC-MS cannot be negated in the light of the above stated facts. Its essentiality can be underscored from the various civilian uses it can be put to.

C:\Users\Jobin\Dropbox\Camera Uploads\2012-07-25 13.23.54.jpg

Figure 3. GC-MS DEVICE

2. Materials And Methods

2.1 Chemicals -

Capsule and powder of dimethylamylamine (DMAA)

Cyclohexanone 100ml

2 Aminoheptane 200ml

Tert-Butyl methyl ether 400ml (TBME)

Methanol 2 lit


Cyclohexanone 99.8%

Figure 4: Cyclohexanone (Sigma Aldrich, 2012)

Know as an organic compound and its molecular formula is (CH2)5CO it contain a ketone group and six carbon of cyclic molecules. It's Molecular Weight 98.14. This colorless oil has an odor reminiscent of peardrop sweets as well as acetone. Over time, samples assume a yellow color due to oxidation. Cyclohexanone is slightly soluble in water (5-10 g/100 mL).


Molecular formula


Molar mass

98.14 g/mol


Colorless, liquid


0.9478 g/mL, liquid

Melting point

−16.4 °C

Boiling point

155.65 °C

2 Aminoheptane-

2-Aminoheptane purum, ≥98.0% (GC)

Figure 5 : 2 Aminoheptane (Sigma Aldrich, 2012)

Aminoheptane also know as a Tuaminoheptane. It is a nasal decongestant drug which is a sympathomimetic stimulant and vasoconstrictor. However, it can cause skin irritation, which limits its usefulness as a nasal decongestant. Oral preparations were once available, but are no longer produced. Side effects associated with the use of Tuaminoheptane can include shortness of breath, tachycardia and hypertension.


Molecular formula


Molar mass

115.22 g mol−1


Colourless liquid


766 mg mL−1

Boiling point

142 °C, 415.2 K, 288 °F

Tert-Butyl methyl ether- (TBME)

Methyl tert-butyl ether analytical standard

Figure 7: Tert-Butyl methyl ether (Sigma Aldrich 2012)

Tert-Butyl methyl ether is an organic compound with molecular formula (CH3)3COCH3. TBME is a volatile, flammable, and colorless liquid that is sparingly soluble in water. It has a minty odor vaguely reminiscent of diethyl ether, leading to unpleasant taste and odor in water.


Molecular formula


Molar mass

88.15 g mol−1


0.7404 g/cm³

Melting point

-109 °C, 164 K, -164 °F

Boiling point

55.2 °C, 328 K, 131 °F

Methanol -

Figure 8: Methanol (Sigma Aldrich, 2012)

Methanol is a chemical with the formula CH4O. Methanol is the simplest alcohol, and is a light, volatile, colorless, flammable liquid with a distinctive odor very similar to, but slightly sweeter than, ethanol (drinking alcohol). At room temperature, it is a polar liquid, and is used as an antifreeze, solvent, fuel, and as a denaturant for ethanol. It is also used for producing biodiesel via transesterification reaction.


Molecular formula


Molar mass

32.04 g mol−1


Colorless liquid


0.7918 g cm−3

Melting point

−98--97 °C, 175-176 K, -144--143 °F

Boiling point

65 °C, 338 K, 149 °F

Dimethylamylamine (DMAA) -


Figure 9: Dimethylamylamine (Sigma Aldrich, 2012)

Dimethylamylamine is an organic compound with the formula C7H17N and its molecular weight is 115.22 g mol−1 which is commonly known as 1,3-dimethylamylamine or Methylhexanamine. Though it is popular in the consumer market in many names, its use and safety has been always doubted. Also, it is used as a simple aliphatic amine to treat nasal decongestion and to correct hypertrophied or hyperplasic oral tissues. It can be administered nasally by inhalation which exerts influence on the nasal mucosa. It is also used as a popular vasoconstrictor.


Molecular formula


Molar mass

115.22 g mol−1

All the chemicals were taken as GC-MS grade. All the above chemicals were purchased from Sigma Aldrich UK.

2.2 Instruments -

There are 3 instruments which were used in my whole project and they are as follows.

GC-MS - (Gas Chromatography and Mass Spectroscopy)

IR - (Infrared)

NMR - (Nuclear Magnetic Resonance)

1. GC-MS -

C:\Users\Jobin\Dropbox\Camera Uploads\2012-07-25 13.23.54.jpg

Figure 10. GC-MS

Samples were measured on Agilent 7890A GC-MS system equipped with Agilent 7693 auto-sampler and MSD-5975C VL-MSD with triple axis detector with the serial number CN10041134. The system was equipped with a Hewlett Packard packed column of stainless steel with dimensions- 30m in length with 0.25 mm internal diameter and 0.25 μm film thickness. The column stationary phase was of HP5MS type composed of 5% diphenyl and 95% dimethyl polysiloxane. The column is capable of operating and separating materials from mixtures from +4̊C - 450̊C with ramp rates at a maximum rate of 120̊C/ min (Agilent 2011). The MS detector employed was the Agilent 5975C VL-MSD triple axis detector consisting of a diffusion pump that could perform ionization in electron impact mode/ EI mode (Agilent 2012). 1 µl of reference standard, internal standard and their mixture thereof were injected in split less mode. The oven temperature was set initially at 40̊C for 1 minute and subsequently increased at 25̊ C/minute to 310̊ C and held there for 1.5 minutes. The flow rate of carrier gas, hydrogen was set at 2ml/min. The injection temperature was set at 200̊ C. The quadrupole and ion source temperatures were set at 150 ̊C and 230 ̊C respectively. The instrument was operated in full scan and SIM mode with scan data obtained at the rate of 5 scans/second with the scan range set from m/z 40-300 and the ionization mode of the instrument set at 70eV.

2. IR -

3. NMR -

2.3 Methods -

Experiment 1

GC-MS analysis of capsule and powder with derivatizating agent.

20.7 mg capsule and powder sample were taken and then added 100 ml of methanol in 250 ml of volumetric flask after that added 10 µl of 2 amino heptanes then kept the both sample for sonication for about 10 minutes and after 10 minutes of sonication make up the volume of 250ml of volumetric flask my methanol. After adding methanol in that take 20 µl, 50 µl and 100 µl of sample dry it from nitrogen gas that will take around 3-4 minutes after dry add 250 µl of Tert-Butyl methyl ether- (TBME) and after that add 20 µl of cyclohexanone. After adding all this sample needs to be heated 20 minutes for 20̊ C. And after that take the remaining samples in the GC-MS vials and inject it to the GC-MS in full scan mode.

Experiment 2

GC-MS analysis of capsule and powder without derivatizating agent.

20.7 mg capsule and powder sample were taken and then added 100 ml of methanol in 250 ml of volumetric flask after that added 10 µl of 2 amino heptanes then kept the both sample for sonication for about 10 minutes and after 10 minutes of sonication make up the volume of 250ml of volumetric flask my methanol. After adding methanol in that take 20 µl, 50 µl and 100 µl of sample dry it from nitrogen gas that will take around 3-4 minutes after dry add 250 µl of Tert-Butyl methyl ether- (TBME). After adding all this sample needs to be heated 20 minutes for 20̊C. And after that take the remaining samples in the GC-MS vials and inject it to the GC-MS in full scan mode.

Experiment 3

IR analysis of capsule and powder.

Pure 1gm of capsule and powder sample were taken without adding any additive in that and kept it in the detector which is made up of diamond. After putting there within 1minutes if will show the graph of the sample which is placed there.

Experiment 4

NMR analysis of capsule and powder.

1gm of capsule and powder sample was taken in a thin and narrow tube and mixes it with the methanol and put that sample in the NMR device that will count the number of hydrogen bond in the given sample. And the same process is done in this device but with the carbon, this will tell you how many carbon atoms are present in the sample. By which we can determine that given sample is pure or not.

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