26 May 2022

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Oxycodone the Molecule for OxyContin

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Academic level: University

Paper type: Research Paper

Words: 1882

Pages: 7

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Discovery and History of OxyContin 

OxyContin is a drug that is classified under opiates and was discovered in Germany in 1916. The designers expected the drug to perform better than other opiates in the market such as morphine, heroin, and codeine. Before its discovery, several people were getting addicted to heroin, and many more were suffering from the side effects due to its abuse ( Jones, Muhuri, & Lurie, 2017) . During that period, oxycontin was not taken seriously as the consequences from the use of the drug were not yet evident. Today, not only the government but also physicians and the general public have realized the harm associated with the drug, and many are raising their concern over its use and prescription. 

The drug is derived from Oxycodone and found its way into the US market around 1939 where it got is a fair share of ups and downs in the prescription category until in the 1990s when Purdue Pharma began its manufacture. Oxycodone is gotten from either codeine or thebaine. When made from thebaine, hydrogen peroxide is oxidized to form hydroxycodeinone, but better results are from the reaction of acetic acid with m -chloroperoxybenzoic acid ( Brennan et al., 2017) . In 1995, the Food and Drug Administration in the U.S. legitimatized its formula and thereby making the drug readily available for the drug stores and users due to its increased production. By 2001, the drug was a hit and was the leading pain reliever in the US market. It was during the same period that many people began misusing the drug for uses other than medication while others used it excessively. 

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In 2007, a series of lawsuits were brought against not only the drug but the manufacturer too. Purdue Pharma was charged and forced to pay fines for promoting the drugs aggressively using marketing strategies that were not appropriate for the drug ( Brennan et al., 2017) . Many associates the increase in addiction of oxycontin to the aggressive marketing of Purdue that promoted the drug even in pedometers and beach hats ( Brennan et al., 2017) . Moreover, the company was encouraging people to overdose on the drug by creating advertisements that suggested that it had lesser possibilities for addiction and abuse. These promotions are contrary to the Center for Substance Abuse Research that explains the drug to alter the brain in a manner that makes it hard to quit if it is used extendedly. 

Biological Function of OxyContin 

Oxycodone as a molecule is used biologically as it has medicinal value that is associated with the treatment of pain that is severe or moderate. Oxycontin can be consumed orally or used through intravenous injection and is available in structured release designs and instant release. When used with instant release design, the drug provides relief from pain after fifteen minutes and takes up to six hours before its effects subside. Moreover, the drug can also be found as combination product available in drugs such as aspirin or acetaminophen. 

The drug has several mild side effects which are tied to its use, and they comprise sweating, itching, sleepiness, dry mouth, constipation, dizziness, and nausea. Some of the severe side effects from the use of oxycontin comprise low blood pressure, a reduced effort to inhale and exhale connected to respiratory depression, and addiction. The molecule could also lead to allergic reactions especially to those who are allergic to codeine ( Brennan et al., 2017) . If the use of oxycodone is rapidly stopped, its effects may include opioid withdrawal. Even though oral consumption is averaged to be one and half times more effective than morphine of a similar amount, the drug is relatively safe for consumption in the early stages of pregnancy. 

In the structured release design, the oxycontin tablet is prescribed for use after every twelve hours and the time taken for its effective action is in between 10 and 12 hours. Moreover, the structured release tablet has similar results but with lesser side effects in comparison to immediate release morphine when used in the managing of pain in cancer especially when it is severe ( Jones, Muhuri, & Lurie, 2017) . Therefore, the structured release tablet is used widely as the preferred treatment for the pain in cancer and the oral intake is advocated more than the oral intake of morphine for the same condition. 

The United States has authorized the use of Oxycontin in the relief of pain related to major surgery, cancer or trauma and has further approved the extended-release use in minors from age 11. For kids who are undergoing treatment using opioids, the extended release design of the drug is the best alternative compared to fentanyl. The drug was first released through structured design; the molecule oxycodone was gradually released into the patient so that they took it twice daily ( Coplan et al., 2016) . But, the patients realized that when the drug was crushed oxycodone was all released at once and hence had a high feeling. Therefore, they began crushing it for the aim of abusing it through dilution in water, injection or snorting. 

The Line Structure of the Molecule 

Functional Organic groups 

Chiral Centers 

R and S Configuration 

The arrangements of atoms of a chiral molecule are the absolute configuration together with the stereochemical description such as the Rectus (R) or Sinister (S). The use of X-ray crystallography mostly obtains these configurations, dichroism in circular vibration, the explosion of coulomb imaging, rotatory optical dispersion, and use of shift reagents ( Coplan et al., 2016) . After obtaining the absolute configuration, the determination of the R or S is founded on the rules of Cahn-Ingold-Prelog priority. Moreover, the characterization of the molecules is also crucial in the absolute configuration. Earlier in the 1940s, chemists had no way of determining the absolute configuration, and thus scientists unanimously agreed to use glyceraldehyde as the enantiomer (R). Therefore, sequences of chemical reactions by glyceraldehyde were then related to other chiral compounds to determine their configuration. 

The empirical derivation of a name can be communicated by the optical activity (+/-). Present are also protein building blocks and carbohydrates as biochemical conventions. Molecules were assigned the handedness through an unambiguous method derived by C. Ingold, R. S. Cahn, and V. Prelog and that eventually adopted their names ( Cicero, & Ellis, 2015) . Hence, for purposes of determining the configuration out of the lab, the R-S system is extremely critical. Even though the rotatory optical dispersion has two different enantiomers of a molecule of a chiral, is not meaningful in the establishment of the absolute configuration even at the same temperature. The main reason is that the dispersion of optical rotation can easily be modified with alterations of the temperature for specific enantiomer. 

The rules of priority (Cahn-Ingold-Prelog) are founded on the atoms that are generally of interest. Hence, the atoms that are joined by carbon bonds are the atoms of interest for chirality. Therefore, the atom that has the highest atomic number is given the highest consideration such as O>N>C>H. Similarly, in the comparison of isotopes, the highest consideration is given to the atom with the highest mass number like 15 N> 14 N or 18 O> 16 O or 13 C> 12 C ( Jones, Muhuri, & Lurie, 2017) . Whenever there is a similarity between in the comparison of isotopes, relative consideration is established by shifting to the subsequent atom along with the series until observation of the initial variance made. In the case of multiple bonds, they are considered as though individual bonds are attached to a distinct atom. 

Enantiomer 

The “clockwise” and “anticlockwise” nomenclature is essential in identifying the enantiomers of chirality. Thus, the chiral centers are identified as R or S. Hence, in determining the configuration for the stereo-chemical of the enantiomer above, using the bonds to the stereocenter, hydrogen is the 4 th priority. Nitrogen is the first and the carbonyl group the second and the methyl group the third ( Jones, Muhuri, & Lurie, 2017) . Thus, the hydrogen is directing away from our direction; hence the consideration of the molecules takes a right-hand course. This way points to the enantiomer for oxycodone is R. therefore, the R-side of Oxycodone could have the desired impacts on the treatment of ailments when used for medical purposes while the S-side is the undesired effects used by the majority to abuse the drug Oxycontin. 

3D structure of an Oxycodone 

Commercial names of Oxycontin 

For a very long time, the drug has been abused within the US, and as early as in the 1960s its related effects have been in the desire for many. It has always been used to ease the withdrawal syndrome of the opiates by street urchins. An amount of ten to eighty milligrams of the drug present in the structured release of the design for the drug an attraction addicted opiate users and abusers ( Jones, Muhuri, & Lurie, 2017) . The IUPAC name of the Oxycontin is (4 R ,4 aS ,7 aR ,12 bS )-4 a -hydroxy-9-methoxy-3-methyl-2,4,5,6,7 a ,13-hexahydro-1 H -4,12-methanobenzofuro[3,2-e]isoquinolin-7-one ( Coplan et al., 2016) . But it also has several brand names including Roxicet, Percodan, Percocet, Endodan, Endocet, and Roxipirin, and shares similar deleterious impacts on the nervous system as morphine. Furthermore, the excessive use of these drugs poses a potential risk associated with accumulations of toxic substance within the liver. 

The drug has been marred by several controversies mainly due to its benefits and abuse that has stirred mixed reactions regarding its use. Products that contain oxycodone can be found in three forms that are liquid, capsule, or tablet and come in different colors. In the streets, the drug is known by the pseudo names OC, Blues, Oxy, Hillbilly heroin, and Kickers ( Cicero, & Ellis, 2015) . The combination of oxycodone has been used in the production of several combination products such as xolox, oxycet, taxadone,roxicet, lynox, narvox, Percocet, tylox, endocet, perlox, and magnacet. These are among the many combinations that oxycodone and acetaminophen have been successfully combined to produce the brand names in the medical field. Oxycontin has also been produced under the commercial names of Roxicodone, Dazidox, Percolone, Oxecta, Oxyfast, Endocodone, and Oxaydo among other names. 

Physical Properties 

Oxycodone has a molecular weight of 315.369 g/mol and an experimental melting point of 219 °C. Oxycontin has the same monoisotopic masses of 315.147 g/mol while the heavy atom count is 23. It has no formal charge and is found in a solid physical description which also includes long rods derived from ethanol. My prediction is that the drug is partially soluble in cold water, but when the water is warmed, the rate of reaction is catalyzed. Moreover, the molecule is soluble in ethanol and is not readily soluble in sodium hydroxide, ether, and potassium. 

Discussion of Downloaded Paper 

Based on a survey carried out by the agency on health, drug use and a national survey, sixteen million residents within the United States from the age of 12 and above have been reported to use products that have the oxycodone molecule for non-medical uses. The agency proceeds to note that the figures of Oxycontin users keep on increasing every year ( Brennan et al., 2017) . Further research from the American Association of Poison Control Centers indicates that each year the number of deaths related to the abuse of the drug has been rising with the last recorded figures at 43 deaths. The consumption of the drug goes all the way to schools where several studies show 8 th , 10 th , and 12 th graders were found to abuse the drug. 

In 2011, the Drug Abuse Warning indicated that approximately 151,000 patients reported at the emergency department with Oxycodone related cases. Each year reports are received of deaths associated with the condition while some states such as Florida have been successful in decreasing the death rate from the drug every year ( Brennan et al., 2017) . Generally, the prevalence of oxycontin availability has affected the masses cutting through all ages and races as most consider it as a white collar addiction. The drug floods the streets from robberies and break-ins of drug stores and nursing homes, fake prescriptions, professional misconduct through corrupt physicians, dentists, doctors, and nurses. 

The Drug Enforcement Agency through their reports indicates that a milligram of the drug in the street trades at one dollar and the most common or most available is the forty-milligram tablet. Through their investigations, the drug that was the most frequent that was found readily in use by addicts ( Brennan et al., 2017) . Additionally, every other year the drug is categorized as the top pharmaceutical drug readily available in the street. The forensic laboratories stand to prove the agency that claims between 2012 and 2013 over 50,000 exhibits was positively identified as Oxycodone the molecule used in the manufacture of Oxycontin. 

References 

Brennan, M. J., Kopecky, E. A., Marseilles, A., O'Connor, M., & Fleming, A. B. (2017). The comparative pharmacokinetics of physical manipulation by crushing of Xtampza® ER compared with OxyContin®.  Pain management 7 (6), 461-472. 

Cicero, T. J., & Ellis, M. S. (2015). Abuse-deterrent formulations and the prescription opioid abuse epidemic in the United States: lessons learned from OxyContin.  JAMA Psychiatry 72 (5), 424-430. 

Coplan, P. M., Chilcoat, H. D., Butler, S. F., Sellers, E. M., Kadakia, A., Harikrishnan, V., & Dart, R. C. (2016). The effect of an abuse ‐ deterrent opioid formulation (OxyContin) on opioid abuse ‐ related outcomes in the postmarketing setting.  Clinical Pharmacology & Therapeutics 100 (3), 275-286. 

Jones, C. M., Muhuri, P. K., & Lurie, P. G. (2017). Trends in the nonmedical use of OxyContin, United States, 2006 to 2013.  The Clinical journal of pain 33 (5), 452-461. 

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StudyBounty. (2023, September 14). Oxycodone the Molecule for OxyContin.
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