Morphine and codeine are called opiates and are found naturally in the opium pop
ID: 1067517 • Letter: M
Question
Morphine and codeine are called opiates and are found naturally in the opium poppy plant Papaver somniferum. Morphine and codeine are medications used to treat pain (analgesic). Morphine is the drug of choice for severe pain control, while codeine is used to treat mild to moderate degrees of pain and is used in prescription cough medicine. Morphine can be chemically converted into two other semi-synthetic opioids, oxycodone and heroin. Oxycodone, also called oxycotin, is a moderately potent opioid, use in treatment of moderate to severe pain. Heroin, is an illegal, highly addictive drug that is both the most abused and the most rapidly acting of the opiates. Nearly 300,000 persons receive treatment for heroin abuse annually. When heroin was originally synthesized from morphine in 1874 it was first perceived as morphine's replacement. Unfortunately, heroin proved to be even more addictive titan morphine and has found little legitimate medical use. Heroin, a is a prodrug - a substance that isn't a drug but is converted into a drug by normal metabolism; heroin becomes morphine once it crosses the blood-brain harrier, where it hits with approximately 3 times the potency per measure of morphine. In criminal investigations, infrared spectroscopy and mass spectrometry can be used to distinguish among various opiates. Using the following spectra, can you tell if this sample is morphine, codeine, ocycodone or heroin?Explanation / Answer
IR spectrum of the sample indicates a broad band between 3500-3300 cm-1 indicating the presence of a hydroxyl group in the molecule. The band between 3050-3000 indicate aromatic C-H str, 2850-2950 indicate -C-H str, 1640-1600 indicate -C=C (alkene and aromatic). The band between 1500-1400 is due to -C-H bending and a band at 1260 indicates aromatic ether group.
Out of the four molecules, Heroin does not contain a hydroxyl group. So it can be eliminated.
Oxycodone contains a keto group in its structure which should give a characteristic absorption between 1680-1720 cm-1 but it is absent in the given spectrum. Hence, oxycodone can be eliminated.
Therefore, the two options remaining are codeine or morphine. The molecular weight of codeine is 14 amu higher than morphine because of methylation of phenolic hydroxyl making it 299g/mol.
The given mass spectrum shows a base peak at m/z 299 which indicates that the given sample contains codeine.
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