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Fundamentals of General, Organic, and Biological Chemistry

John McMurry, David S. Ballantine, Carl A. Hoeger

Chapter 28

Chemical Messengers: Hormones, Neurotransmitters, and Drugs - all with Video Answers

Educators

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Chapter Questions

03:11

Problem 1

While thinking about how a messenger molecule and receptor molecule interact, list three possible intermolecular forces that involve noncovalent interations.

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01:47

Problem 2

Look at the structure of epinephrine in Section $28.3 .$ Is it a steroid, an amino acid derivative, or a polypeptide?

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01:57

Problem 3

Review the structure of thyroxine in Section 28.4 . Which amino acid could be biochemically altered to synthesize thyroxine? Review the amino acid structures in Chapter 18 for assistance.

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02:41

Problem 4

Review the structure of thyrotropin-releasing hormone (TRH) in Section 28.4 . This chemical messenger has one chiral carbon, which happens to be an alpha carbon of an amino acid. Which amino acid is part of TRH?

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02:36

Problem 5

A phosphorus-containing anion is removed from ATP in its conversion to cyclic AMP, as shown in Figure $28.3 .$ The anion is often abbreviated as $\mathrm{PP}_{i} .$ Which of the following anions is represented by $\mathrm{PP}_{i}$ ?
(a) $\mathrm{P}_{3} \mathrm{O}_{10}{ }^{5-}$
(b) $\mathrm{P}_{2} \mathrm{O}_{7}^{4-}$
(c) $\mathrm{PO}_{4}^{3-}$
(d) $\mathrm{H}_{2} \mathrm{PO}_{4}^{-}$

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03:16

Problem 6

Caffeine and theobromine (from chocolate) act as stimulants. They work by altering the cAMP signal. Refer to Figure 28.3 and decide how these molecules might interact with an enzyme in the cAMP pathway to enhance the effect of cAMP.

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02:16

Problem 7

Examine the TRH structure and identify the three amino acids from which it is derived. The $N$ -terminal amino acid has undergone ring formation, and the carboxyl group at the $C$ -terminal end has been converted to an amide.

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02:16

Problem 7

Examine the TRH structure and identify the three amino acids from which it is derived. The $N$ -terminal amino acid has undergone ring formation, and the carboxyl group at the $C$ -terminal end has been converted to an amide.

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02:34

Problem 8

Look at the structure of thyroxine shown earlier in this section. Is thyroxine, an amino acid derivative, hydrophobic or hydrophilic? Explain.

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02:28

Problem 9

Nandrolone is an anabolic, or tissue-building, steroid sometimes taken by athletes seeking to build muscle mass (it is banned by the International Olympic Committee as well as other athletic organizations). Among its effects is a high level of androgenic activity. Which of the androgens shown on page 867 does it most closely resemble? How does it differ from that androgen?

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02:28

Problem 9

Nandrolone is an anabolic, or tissue-building, steroid sometimes taken by athletes seeking to build muscle mass (it is banned by the International Olympic Committee as well as other athletic organizations). Among its effects is a high level of androgenic activity. Which of the androgens shown on page 867 does it most closely resemble? How does it differ from that androgen?

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02:49

Problem 10

Which of the following transformations of amines in Figure 28.6 is (1) an acetylation,
(2) a methylation, and (3) a decarboxylation?
(a) 5-Hydroxytryptophan to serotonin
(b) Serotonin to $N$ -acetylserotonin
(c) $N$ -Acetylserotonin to melatonin

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02:49

Problem 10

Which of the following transformations of amines in Figure 28.6 is (1) an acetylation,
(2) a methylation, and (3) a decarboxylation?
(a) 5-Hydroxytryptophan to serotonin
(b) Serotonin to $N$ -acetylserotonin
(c) $N$ -Acetylserotonin to melatonin

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02:36

Problem 11

Propranolol (trade name Inderal) is an antagonist for certain epinephrine receptors and is a member of the class of drugs known as beta blockers (because they block what are known as beta receptors). Circle the functional groups in propranolol and name them. Compare the structure of propranolol with the structure of epinephrine and describe the differences.

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02:36

Problem 11

Propranolol (trade name Inderal) is an antagonist for certain epinephrine receptors and is a member of the class of drugs known as beta blockers (because they block what are known as beta receptors). Circle the functional groups in propranolol and name them. Compare the structure of propranolol with the structure of epinephrine and describe the differences.

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03:18

Problem 12

The $\mathrm{LD}_{50}$ values (lethal dose in $\mathrm{mg} / \mathrm{kg},$ for rats) for the three organophosphorus insecticides listed in this section are parathion, $3-13 \mathrm{mg} / \mathrm{kg}$; diazinon, $250-285 \mathrm{mg} / \mathrm{kg} ;$ and malathion, $1000-1375 \mathrm{mg} / \mathrm{kg}$. (a) Find the molecular structures using the Internet.
(b) Which would you choose for use in your garden and why?
(c) Thinking about hydrophobic and hydrophilic, which is most dangerous for mammals to ingest? Why?

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03:18

Problem 12

The $\mathrm{LD}_{50}$ values (lethal dose in $\mathrm{mg} / \mathrm{kg},$ for rats) for the three organophosphorus insecticides listed in this section are parathion, $3-13 \mathrm{mg} / \mathrm{kg}$; diazinon, $250-285 \mathrm{mg} / \mathrm{kg} ;$ and malathion, $1000-1375 \mathrm{mg} / \mathrm{kg}$. (a) Find the molecular structures using the Internet.
(b) Which would you choose for use in your garden and why?
(c) Thinking about hydrophobic and hydrophilic, which is most dangerous for mammals to ingest? Why?

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03:05

Problem 13

Some drugs are classified as agonists, whereas others are classified as antagonists.
(a) Sumatripan, sold as Imitrex, is effective in treating migraine headaches. It acts as an agonist at the serotonin receptor. Explain the effect Imitrex has on the serotonin receptor.
(b) Ondansetron, sold as Zofran, acts on a subclass of serotonin receptors to inhibit nausea and vomiting; it is frequently prescribed to patients in chemotherapy. It acts as an antagonist at these receptors. Explain the effect Zofran has on these receptors.

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03:10

Problem 14

Identify the functional groups present in THC. Is the molecule likely to be hydrophilic or hydrophobic? Would you expect THC to build up in fatty tissues in the body, or would it be readily eliminated in the urine?

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02:58

Problem 15

Predict which of the following compounds is an antihistamine and which is an antidepressant.

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04:02

Problem 16

In many species of animals, at the onset of pregnancy, $\mathrm{LH}$ is released; it promotes the synthesis of progesterone- a major hormone in maintaining the pregnancy.
(a) Where is LH produced, and to what class of hormones does it belong?
(b) Where is progesterone produced, and to what class of hormones does it belong?
(c) Do progesterone-producing cells have LH receptors on their surface, or does $\mathrm{LH}$ enter the cell to carry out its function?
(d) Does progesterone bind to a cell-surface receptor, or does it enter the cell to carry out its function? Explain.

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02:38

Problem 17

The "rush" of epinephrine in response to danger causes the release of glucose in muscle cells so that those muscles can carry out either "fight-or-flight." Very small amounts of the hormone produced in the adrenal gland cause a powerful response. To get such a response, the original signal (epinephrine) must be amplified many times. At what step in the sequence of events (Section 28.3 ) would you predict that the signal is amplified? Explain. How might that amplification take place?

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04:24

Problem 18

Diabetes occurs when there is a malfunction in the uptake of glucose from the bloodstream into the cells. Your friend's youngest brother was just diagnosed with type I diabetes, and she has asked you the following questions. How would you answer them?
(a) What hormone is involved, and what class is it?
(b) Where is the hormone released?
(c) How is this hormone transported to the cells that need it to allow glucose to enter?
(d) Would you expect the hormone to enter the cell to carry out its function? Explain.

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01:45

Problem 19

Give two mechanisms by which neurotransmitters exert their effects.

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02:46

Problem 20

When an impulse arrives at the synapse, the synaptic vesicles open and release neurotransmitters into the cleft within a thousandth of a second. Within another ten thousandth of a second, these molecules have diffused across the cleft and bound to receptor sites in the effector cell. In what two ways is transmission across a synapse terminated so that the neuron's signal is concluded?

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02:43

Problem 21

What is the significance of dopamine in the addictive effects of cocaine, amphetamines, and alcohol?

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03:39

Problem 22

What do the terms chemical messenger, target tissue, and hormone receptor mean?

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03:17

Problem 23

What is a hormone? What is the function of a hormone? How is the presence of a hormone detected by its target?

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01:45

Problem 24

What is the main difference between a hormone and a vitamin?

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01:29

Problem 25

What is the main difference between a hormone and a neurotransmitter?

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01:57

Problem 26

Is a hormone changed as a result of binding to a receptor? Is the receptor changed as a result of binding the hormone? What are the binding forces between hormone and receptor?

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02:12

Problem 27

How is hormone binding to its receptor more like an allosteric regulator binding to an enzyme than a substrate binding to an enzyme?

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03:44

Problem 28

What is the purpose of the body's endocrine system?

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03:40

Problem 29

Name as many endocrine glands as you can.

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01:40

Problem 30

List the three major classes of hormones.

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01:44

Problem 31

Give two examples of each of the three major classes of hormones.

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01:38

Problem 32

What is the structural difference between an enzyme and a hormone?

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02:06

Problem 33

What is the relationship between enzyme specificity and tissue specificity for a hormone?

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01:41

Problem 34

Describe in general terms how a peptide hormone works.

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01:39

Problem 35

Describe in general terms how a steroid hormone works.

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03:15

Problem 36

In what gland is epinephrine produced and released?

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03:32

Problem 37

Under what circumstances is epinephrine released?

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01:51

Problem 38

How does epinephrine reach its target tissues?

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01:12

Problem 39

What is the main function of epinephrine at its target tissues?

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02:06

Problem 40

In order of their involvement, name the three membranebound proteins involved in transmitting the epinephrine message across the cell membrane.

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02:29

Problem 41

What is the "second messenger" inside the cell that results from the epinephrine message? Is the ratio of epinephrine molecules to second messenger less than 1: 1,$1: 1,$ or greater than $1: 1 ?$ Explain.

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03:40

Problem 42

What role does the second messenger play in a cell stimulated by epinephrine?

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01:55

Problem 43

What enzyme catalyzes hydrolysis of the second messenger to terminate the message? What is the product called? (Hint: Consult Figure $28.2 .)$

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01:55

Problem 44

Epinephrine is used clinically in the treatment of what lifethreatening allergic response? (Hint: Think about the use of the EpiPen.)

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02:39

Problem 45

People susceptible to anaphylactic shock due to insect stings or certain food allergies must be prepared to treat themselves in case of exposure. How are they prepared and what must they do?

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02:14

Problem 46

Give an example of a polypeptide hormone. How many amino acids are in the hormone? Where is the hormone released? Where does the hormone function? What is the result of the hormone message?

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02:54

Problem 47

Give an example of a steroid hormone. What is the structure of the hormone? Where is the hormone released? Where does the hormone function? What is the result of the hormone message?

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01:34

Problem 48

What do the three major classes of steroid hormones have in common?

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01:44

Problem 49

What molecules are the steroid hormones derived from? How does that make the physical properties of steroid hormones different from the other hormones?

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01:36

Problem 50

Name the two primary male sex hormones.

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02:00

Problem 51

Name the three principal female sex hormones.

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01:52

Problem 52

Until relatively recently, the use of androgens by athletes was a common, legal practice. What are the advantages of using androgens during athletic training and competition?

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01:42

Problem 53

The use of androgens during athletic training and competition has been banned in national and international sports. What are the disadvantages of using androgens during athletic training and competition?

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02:21

Problem 54

List two hormones that also function as neurotransmitters.

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01:52

Problem 55

Explain why epinephrine can act as both a neurotransmitter and a hormone without "crossover" between the two functions.

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03:38

Problem 56

Identify the class to which each of these following hormones belongs:

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03:19

Problem 57

Identify the class to which each of these following hormones belongs:

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02:03

Problem 58

What is a synapse, and what role does it play in nerve transmission?

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02:39

Problem 59

What is an axon, and what role does it play in nerve transmission?

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02:35

Problem 60

List three cell types that might receive a message transmitted by a neurotransmitter.

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01:51

Problem 61

What kinds of cellular or organ actions would you expect to be influenced by neurotransmitters?

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01:35

Problem 62

Describe in general terms how a nerve impulse is passed from one neuron to another.

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02:00

Problem 63

What are the two methods for removing the neurotransmitter once its job is done?

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02:04

Problem 64

List the three steps in chemical transmission of the impulse between a nerve cell and its target.

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02:14

Problem 65

Write an equation for the reaction that is catalyzed by acetylcholinesterase.

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01:38

Problem 66

Why are enkephalins sometimes called neurohormones?

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02:25

Problem 67

Outline the six steps in cholinergic nerve transmission.

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03:07

Problem 68

Describe the difference between drugs that are agonists and those that are antagonists.

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02:18

Problem 69

Give an example of a drug that acts as an agonist for acetylcholine receptors and one that acts as an antagonist for these receptors.

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01:58

Problem 70

Give an example of a drug from each family in Problem $28.69 .$

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02:10

Problem 71

Give examples of two histamine antagonists that have very different tissue specificities and functions.

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01:59

Problem 72

Name three families of drugs used to treat depression.

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01:24

Problem 73

Name the "big three" monoamine neurotransmitters.

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02:21

Problem 74

What is the impact and mode of action of cocaine on dopamine levels in the brain?

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02:10

Problem 75

What is the impact and mode of action of amphetamines on dopamine levels in the brain?

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01:50

Problem 76

How is the THC of marijuana similar in action to heroin and cocaine?

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01:58

Problem 77

Why do we have brain receptors that respond to morphine and other opium derivatives from plants?

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02:05

Problem 78

In schizophrenia, the neurons affected by dopamine are overstimulated. This condition is treated with drugs like chlorpromazine (Thorazine), which bind to the affected receptors and inhibit the dopamine signal. Does chlorpromazine act as an agonist or antagonist?

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02:14

Problem 79

Methamphetamine "highs" often are accompanied by behavioral changes that resemble schizophrenia. Does methamphetamine act as an agonist or antagonist?

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02:35

Problem 80

What are endorphins? Where in the body are they found?

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02:16

Problem 81

Enkephalins and endorphins are referred to as "nature's opiates." Explain this saying.

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01:54

Problem 82

Why might it be an advantage for an animal to produce its own pain-suppressing molecules?

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04:16

Problem 83

Suppose you are hiking in the Alaskan wilderness when your path crosses that of a bear. What hormone is responsible for your immediate response?

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01:59

Problem 84

How do curare-treated arrows work?

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02:00

Problem 85

What characteristics in their mechanism of action does thyroxine share with the steroid hormones?

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02:12

Problem 86

List and describe the functions of the three types of proteins involved in transmission of a hormone signal.

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02:19

Problem 87

The cyclic AMP (second messenger) of signal transmission is very reactive and breaks down rapidly after synthesis. Why is this important to the signal-transmission process?

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02:31

Problem 88

We say that there is signal amplification in the transmission process. Explain how signal amplification occurs and what it means for transmission of the signal to the sites of cellular activity.

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02:25

Problem 89

Compare the structures of the sex hormones testosterone and progesterone. What portions of the structures are the same? Where do they differ?

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02:09

Problem 90

When you compare the structures of ethynyl estradiol to norethindrone, where do they differ? Where is ethynyl estradiol similar to estradiol? Where is norethindrone similar to progesterone?

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01:59

Problem 91

Identify the structural changes that occur in the first two steps in the conversion of tyrosine to epinephrine (Figure 28.4). To what main classes and subclasses of enzymes do the enzymes that catalyze these reactions belong?

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02:24

Problem 92

Look at the structures of the two male sex hormones shown on page 867 . Identify the type of functional group change that interconverts testosterone and androsterone. To which class of chemical reactions does this change belong?

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02:02

Problem 93

Look at the structures of the three female sex hormones shown on page 867 . Identify the type of functional group change that interconverts estradiol and estrone. To which class of chemical reactions does this change belong?

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02:06

Problem 94

Anandamides have been isolated from brain tissues and appear to be the natural ligand for the receptor that also binds THC. Anandamides have also been discovered in chocolate and cocoa powder. How might the craving for chocolate be explained?

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02:44

Problem 95

The phosphodiesterase that catalyzes hydrolysis of cyclic AMP is inhibited by caffeine. What overall effect would caffeine have on a signal that is mediated by cAMP?

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