1.In allergy sufferers, histamine causes runny noses, red eyes, and other symptoms. Here is its structural formula.
a.Give the chemical formula for this compound
Ans:C5H9N3
b.Circle the amine functional groups in histamine
c.Which part (or parts) of the molecule make the compound water-soluble.
Ans:The amine groups
2.Antihistamines are widely used drugs for treating symptoms of allergies caused by reactions to histamine compounds. This class of drug competes with histamine, occupying receptor sites on cells normally occupied by histamine. Here is the structure for a particular antihistamine.
a.Give the chemical formula for this compound
Ans: C16H21N3
b.What similarities do you see between this structure and that of histamine (shown in the previous question 1) that would allow the antihistamine to compete with histamine?
Ans:
The similarities in structure between histamine and the antihistamine are marked in color on the structures below:
The similarities are a two-carbon chain with a nitrogen at the end (marked in red), and a three-atom sequence of N-C-N (marked in blue). The spatial placement of these pieces seems similar as well. One might also consider the flat 5-ring of histamine to be similar to the flat 6-ring of the antihistamine.
Given the similarities in structure, we might guess that the antihistamine would bind to histamine receptor sites on cells more tightly than histamine itself, thus blocking histamine action.
Q3. Into which class does each of these drugs fall?
Aspirin – Inhibits growth of substances that cause infections
Morphine – Physiological response
(Keflex) antibiotic – Inhibits growth of substances that cause infections
Estrogen – Physiological response
Amphetamine – Physiological response
Penicillin – Inhibits growth of substances that cause infections
Q4. (a) What do you think is the evidence from herbal supplement manufacturers that address these issues?
But since they became widely available in 1994, the FDA and some independent researchers have found problems with some dietary supplements. Products like herbs are sometimes tainted with germs, pesticides, or toxic heavy metals. Other supplements do not contain what’s listed on the label. Still others contain more or less than the amount of the herb listed on the label. And many have ingredients that aren’t listed on the label at all.
This problem extends beyond the supplement makers and sellers. Some herbal suppliers (those who grow, harvest, or sell the crops) may mix or even substitute their crops with less expensive or more readily available plants. There’s also the problem of accidental contamination, when one plant grows in with others, as well as cases of mistaken identity (when one plant looks like another). Given the global market, all of these problems can make it harder for a company to be sure that what they thought they were buying to make supplements is actually the herb they wanted.
In 2013 researchers in Toronto published a report in which they sampled and analyzed 44 herbal supplements. The supplements were sold in both the US and Canada, and labeled as containing single herbs. Using DNA bar coding analysis, less than half the supplements (48%) contained any of the herb listed on the label. More than half of the supplements contained something that wasn’t on the label (substitutions or fillers). Even among the samples that contained the herb on the label, many also contained fillers or contaminants.
(b) Do you know anything about Singapore’s legislation on the topic?
All Chinese Proprietary Medicines (CPM) i.e. products in the finished dosage forms (e.g. tablet, capsule, liquid) are regulated by the Health Sciences Authority (HSA) and must comply with a set of safety and quality criteria before they are allowed to be sold in Singapore. In addition, CPM dealers (importers, wholesale dealers and manufacturers) are also required to be licensed by HSA.