Comet Lovejoy Spewed Alcohol and Sugar: an Interview

MilamI created a transcript of a  Quirks and Quarks’ Bob McDonald- interview with NASA’s Stefanie Milam. It’s been slightly edited, and in brackets are my own detailed additions for those interested in learning a little more chemistry. Milam is a chemist by profession with a specialty in rotational spectroscopy. In the recorded interview, her enthusiasm for her research is apparent and contagious.

Bob: Comets can be pretty spectacular objects in the night sky, and they can also provide important clues to the formation of our solar system. But most comets orbit far from the sun where they and the secret storm within them remain frozen. On occasion though a gravitational disturbance will bring one closer, where the heat of the sun melts away the comet’s signature–components which can then be analyzed by scientists.Comet_Lovejoy

Well that’s what happened to Comet Lovejoy, which recently ventured close to the sun and gave scientists, including Dr. Stefanie Milam of the NASA Goddard Space Flight Center in Greenbelt Maryland, cause to celebrate. In fact when they discovered its composition, they have even raised a glass or two. Dr. Milam, welcome to Quirks and Quarks.

Stefanie: Thank you very much.

Bob: Tell me about Comet Lovejoy.

Stefanie:  Comet Lovejoy was a great comet for us astronomers. Comets are very few and far between whenever we get a nice bright one in the sky. Comet Lovejoy was only discovered a few months before we actually started observing it. It’s from the outer, outer edges of the solar system, way past Neptune, Pluto and New Horizons. So when it came in and all the icy material was melting, its activity was detected by Terry Lovejoy, an amateur, who discovered the comet. He notified the proper channels so larger telescopes could begin observing it.

Bob: When did the comet go by?

Stefanie: The comet reached its peak activity from mid to late January this year (2015).

Bob: Comets are called dirty snowballs , but in general what are some of the things that come off a comet when it gets close to the sun?

Stefanie: So water is the dominant molecule that you see in  comets, but there are lot of other things like hydrogen cyanide (HCN); things that everyone should know about like formaldehyde (H2CO), which preserves people when they pass away, methanol(CH3OH), carbon monoxide(CO), carbon dioxide(CO2), and we’ve also detected ethylene glycol (HOCH2CH2OH), which is used in antifreeze… ( Glycine, an amino acid, has also been found in comets.)

Bob: Boy, that’s outstanding!

Stefanie: …giggles…. It is really exciting because it’s showing us that we have a rich, organic chemistry in comets.

Bob: Now when you say “peak activity”, what do you mean by that?

Stefanie: The closer the comet gets to the sun, the more ice that actually starts melting, which is not officially melting because it actually does not form a liquid but goes from ice directly to gas. (The ice sublimates due to the low pressure in space.) So the hotter it is and the closer it gets to the sun, the more the ices sublimates.

Bob:  When you examined Comet Lovejoy, what was different about it?

Stefanie: At first there didn’t seem to be much different; it wasn’t even one of the most spectacular comet we’d had. It was not as bright as Comet Hale Bopp that appeared in the mid to late 1990s (1995 to 1997; it was visible for 18 months), but it’s been the best comet we’ve had in the last decade or so.

Bob:  So what kind of things did you see this time that were surprises?

glycoaldehyde
Glycoaldehyde is technically a sugar because it contains both an aldehyde group and a hydroxyl group. It was found sublimating from Comet Lovejoy.

Stefanie: So now we’ve had a fantastic detection of sugar and ethanol. So ethanol is the same alcohol that we have in our drinks. (The sugar found was the  simplest monosaccharide sugar, known as glycolaldehyde. Ethanol and glycolaldehyde ‘s abundance relative to methanol and water  is somewhat higher than what’s measured in solar-type protostars.)

 

F2.largeBob: Drinking-alcohol coming off a comet?

Stefanie: …giggles…. Yes, and a significant amount actually.

Bob: How much?

Stefanie: Since the campaign was led by a French group, we correlated it to wine. So there’s enough to produce 500 bottles of wine per second. (Assuming 1.0 L wine bottles, and 12 % content by volume, that’s 500 L*(12 L alcohol/100 L wine)* 789 kg of alcohol/1000L) = about 47 kg of ethanol spewed out every second.)

Bob: Holy cow! that’s quite a party!

Stefanie: …giggles…. Oh yeah!

Bob: Were you surprised by that?

Stefanie: We’ve reached a level of technology where we can start looking for things on a very fine level, and we could this now with comets because we could recover a large number of “fingerprints”. Compared to 20 years ago when we could recover 1 fingerprint at at time, now we could look for 50 molecules at the same time.

Bob: How do you do that?

F1.large
The “fingerprints” of molecules detected in Comet Lovejoy

Stefanie: Every molecule has a unique fingerprint, corresponding to a different frequency. We aim the radio telescope at an area , and we start looking for spectral signatures that correspond to given molecules. The flux of each fingerprint is proportional to the quantity of the specific molecule.  (Gas molecules rotate. If they have a dipole caused by unequal sharing of electrons by  atoms, the molecules emit energy when they go from a high quantized rotational state to a lower one. As the comet approached the sun and molecules were being released from the comet’s surface, an IRAM 30m radio telescope in the 211–272 GHz band on Earth picked up the characteristic frequencies of ethanol and other molecules.)

Bob: So how would alcohol end up on a comet?

Stefanie: That’s an excellent question. Umm.. we’re striving to see how much chemistry is happening on the surface of a comet when the solar system actually formed. Was it highly processed or was it frozen material that’s never been altered since the formation of the sun–that’s representative of the same cloud, dust and ice that formed other solar systems?  If that’s the case, then that chemistry has been preserved and it’s remnant from when the sun and other systems formed, which would mean that the chemistry is ubiquitous.

Bob: Boy!

Stefanie: So that means that there could be other solar systems producing “wine”.

Bob:  So you’re saying,  either this alcohol is very well-aged or it was “fermented” along the way.

Stefanie: Yeah, that’s a great way to think of it.

Bob: Well if these comets are spewing out alcohol and sugar, what effect does this have on our solar system?

Stefanie: Well as the organic material is being spewed out, some of it actually survives the harsh environment of space. So we’re distributing organic material in the solar system, and the more complex that organic material is, the more exciting this is for us. It means that there is really a rich chemistry, a prebiotic one that’s so pristine coming from interstellar space. It would be the same mixture raining on other planets in other solar systems.

Bob: Where is Comet Lovejoy now? _Comet_Lovejoy_

Stefanie: It’s well on its way out of the system.

Bob: Will we ever see it again?

Stefanie: Yeah, in about 9000 years!

 

 

 

 

 

 

 

 

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Drugs: Simple Solutions Won’t Cut It

The legality of a substance of misuse is not correlated with its perceived harm.

This was the conclusion of a 2012 study published in the British Medical Journal. The data was based on consultations with 292 addiction specialists and psychiatrists working with substance misuse across Scotland.  DrugsHArm

The “combined harm” includes damage to both the individual drug user and society at large. Class A drugs carry the highest legal penalties for possession and trafficking, Although the classification includes the 3 most harmful substances on the chart, the danger of half of Class A drugs is below average, and alcohol, a legal substance, is nestled in between cocaine and crystal meth. Furthermore alcohol along with tobacco and solvents, which are also legal, do more harm than any Class B or C substance.

drugUseThe study was inspired by the fact that drug and alcohol-related deaths in Scotland are among the highest in Europe and have doubled between 1997 and 2012. Globally, over the past century, we have seen that avoiding prohibition (as in the case of alcohol) or aggressive punishments (as in the case of heroin and crack) don’t solve the plethora of social problems associated with the misuse of substances. Legislation is too simple a solution to such a complicated issue. But why is the problem complex? We will use cocaine as an example of how harmless leaves from a tropical plant Erythroxylum coca have led to a substance that wreaks so much havoc.

  1. The Difference Between a Compound and its Source.
cocaleaf
Erythroxylum coca , not just the source of cocaine, but the main ingredient of the relatively innocuous acullico.

The source of cocaine, the coca leaf, has been chewed and brewed for tea traditionally without problems for centuries among its indigenous peoples in the Andean region.  Acullico, consists of keeping a saliva-soaked ball of coca leaves mixed with quinoa ashes in the mouth. When ingested in this manner, coca numbs the mouth slightly but basically acts as a mild stimulant and suppresses hunger, thirst, pain, and fatigue. Coca also helps in overcoming altitude sickness. The innocuous leaf is even considered sacred within some indigenous cultures.

cocaine
The structure of cocaine. The tropane ring, common to other drugs such as scopalamine, is on the right. It has a heptagonal carbon-ringed structure with an alkaline “hat” carrying a methyl group.

Coca contains alkaloids, which are plant-produced organic compounds containing at least one alkaline nitrogen atom. Cocaine is specifically a tropane- alkaloid, meaning that its basic nitrogen atom bridges over a heptagonal ring.  Unlike the tropane alkaloids of the nightshade family, coca alkaloids are not produced in the roots but are biosynthesized directly in the leaf. The cocaine content in coca leaf ranges between only 0.5 and 1.0 percent, and in wild varieties, the fraction is even lower. Aside from having a diluted concentration of the drug, the coca leaf has other alkaloids and natural products that I speculate might alter the physiological response to cocaine when it’s chewed.

But since the 1850s, chemists have learned how to extract cocaine and purify it from coca leaves. A common method used today and, which is at the root of the drug trade, involves macerating leaves and employing several sulfuric acid extractions , followed by filtrations and pH-increases to precipitate a cocaine paste.  To further purify it, kerosene is used as a solvent followed by re-extraction with acid and more precipitation with lime. A 3rd major extraction is done with acetone or ether, followed by a precipitation with a mixture of acetone and hydrochloric acid. The product,cocaine hydrochloride, is filtered with bed sheets and dried with microwaves or in sunlight.

In Cubism the artist depicts the subject from a multitude of viewpoints to represent the subject in a greater context. Cocaine's several modes of action force us to examine its several mdoes of action.
In Cubism, the artist depicts the subject from a multitude of viewpoints to represent the subject in a greater context. Cocaine’s several modes of action lead us to examine several molecular mechanisms.

In this purified and therefore concentrated form, cocaine, unlike coca, acts as a local anesthetic, vasoconstrictor, stimulant and euphoriant. The pure drug’s anesthetic and vasoconstrictive properties drew the interest of doctors and surgeons in the late 1800s. Eventually, cocaine’s other properties were exploited by typically absorbing its powdered form through the nasal membranes—by “snorting it”. In the early 1980s, an alternate method of intake surfaced in U.S urban areas. Cocaine was heated with baking soda, and the product, “crack” was smoked to deliver even more intense highs. Cocaine defies classification due to its ability to interact with at least three different nerve cell channels or receptors. It blocks both the reuptake of dopamine and of norepinephrine. These mechanisms also play a role in its desirability and in its potential for addiction.

cocaine3
Cocaine can also act like as an anesthetic like xylocaine (lidocaine). Both drugs block sodium channels, preventing polarization and therefore transmission of pain signals. A surprising number of dentists who all use lidocaine have forgotten the theory behind this mechanism!

cocaine1 cocaine2

2. Why Is There Addiction?

In the Biology of Desire, neurobiologist Marc Lewis bucks the trend and argues that addiction is not a disease. He convincingly demonstrates that although the brain indeed changes over the course of addiction, the modifications are parallel to those experienced by sports aficionados, passionate lovers or people obsessed by a hobby. But bad habits such as addiction form deeper connections between the dopamine-releasing midbrain, and the accumbens and dorsal striatum. The pathways of these brain structures, which play central roles in desires and compulsions, override good judgment from the prefrontal cortex because of reinforcing feedback loops.

With regards to cocaine, after repeated use, genetic expression of proteins acting as dopamine receptors slows down in the accumbens. In the addict then, without cocaine, neurons in the limbic system become less sensitive to dopamine. Cocaine is needed to bring concentrations merely back to levels that existed prior to addiction.

Yet not everyone who experiences a few rushes from cocaine becomes an addict. People become more vulnerable to repeated use of a drug and its damaging consequences if in their youth, their personalities accumulated many unmet needs and goals and if they suffered repeated anxiety and depression. In a society where vast numbers of people are directed towards materialistic goals there is widespread dissatisfaction; there is neglect of human warmth and disconnections with the rest of our natural environment. This can only increase the need for self-medication.

3. The War on Drugs Amplifies Alienation

From the Economist Mar 5th 2009
Where coca is grown, from the Economist, Mar 5th, 2009

Tougher prison sentences for drug possession incarcerates too many people who are not necessarily dangerous. The illegality of distribution does not cut the supply of illicit substances; it creates an underground economy where only a tiny elite are raised above poverty. The leaders typically have a talent for extreme violence and bribing of officials, which are used to maintain the status quo. According to Tom Blickman, a specialist in International Drug Control Policy and Organised Crime, aggressive strategies have been applied to try to eliminate coca cultivation in the Andean region. While the strategy has failed, it has led to clashes between coca-producers (cocaleros) and local military, resulting in deaths and human right violations. The environment has also suffered in Colombia where spraying with herbicides (fumigation) is used to kill coca plants, which has only succeeded in displacing more coca production to Peru and Bolivia . Uncontrolled growth of crops encouraged by the underworld also creeps into ecologically sensitive tropical areas.

calabria
While Italian authorities concentrated on fighting the Sicilian Mafia, the Ndragheta, based in Calabria, surreptitiously became the country’s most powerful criminal organization. Their profits exceed those of all but four of Italy’s largest corporations.

Writer Roberto Saviano, still living under police protection since 2006, penned Zero Zero Zero in 2013, the title referring to cocaine of the highest purity. The Calabrese Mafia known as the Ndragheta has a monopoly over the importation of cocaine and heroin into Europe from Latin America and Southeast Asia, respectively. Their counterparts are the Cartels of Mexico who supply the United States with most of its drugs, including cocaine. Americans, who have 4.5% of the world’s population, consume 25% of the planet’s cocaine. In Mexico, over 47,000 people were killed by violence associated with the drug trade between 2006 and 2011. Saviano points out that Cartel and Ndragheta drug profits have infested the legal economy. The most dramatic example of this occurred in 2008. During the world financial crisis, cash-strapped banks lowered their guards, allowing hundreds of billions of drug dollars to get laundered.

The poverty of Latin America and Southern Italy is in no way disconnected to the problem of organized crime. Those who get a higher education often leave the small villages, and some of those left behind get lured towards gangs or remain within privileged criminal families. The rest of the villagers are intimidated into passivity and silence, allowing either cartels or mafias to operate without opposition. Moreover, as humans, we have the unfortunate habit of subjectively judging people’s actions based on how they treat us. Thus favors and donations by powerful mobsters in poor towns severely distort the perception of what they are doing worldwide. Similarly, most drug users and the rest of us participating in an infested economy don’t realize how we are all part of the problem.

Plant Chemistry Quiz

Unless they’re food on the table or part of captivating scenery, plants are under-appreciated. Even fewer people care for the intricacy of their biochemistry or realize how in tune they are with their environment. Here’s a short quiz written for nonspecialists who nevertheless have a curiosity for what goes on below the surface of leaves and flowers. Especially since there are no student grades at stake, if one can anesthetize the ego, one can trade in a little time for precious botanical knowledge. By clicking on “explanation” below each question, you will find the answer with more insight into the topic.

1.  Which of these compounds do plants assemble “from scratch”—- in other words just from water, carbon dioxide and ions from the soil?

(A) glucose

(B) amino acids

(C) flavonoids (used as a “sunscreen”, pigments and have many other functions)

(D) defence compounds

(E) all of the above

(F) none of the above

Explanation


2. What compound, found in willow bark, can be reacted with acetic anhydride in the presence of mineral acid to make aspirin?

(A) paracetamol
(B) ibuprofen

(C) salicylic acid

(D) caffeine

Explanation


3. Which of these plants, a member of the buttercup family, has one of the most poisonous roots due to 3 nasty alkaloids(aconitine, mesaconitine & jesaconitine)?

(A) monkshood (B) mountain ash

(C) opium poppy

(D) milkweed

Explanation


4. Fermentation often occurs inside a cantaloupe. Small volumes of which alcohols are produced?

(A) butanol and ethanol

(B) ethanol and benzyl alcohol

(C) methanol and benzyl alcohol

(D) methanol and butanol

 

Explanation


5. The glandular hairs of wormwood leaves, Artemisia annua , yields the important drug artemisinin? What disease does the drug treat?

(A) malaria (B) sleeping sickness

(C) elephantiasis

(D) ebola

Explanation


6. At least 400 compounds contribute to its beautiful scent including these:

Which flower are we referring to? (look carefully at the structures!)

(A) iris

(B) peony

(C) rose

(D) violet

Explanation


7. Compounds like tomatin make the leaves poisonous to many insects. Solanine makes the leaves of related plants also toxic to many insects. Compared to tomatin, solanine is considerably more toxic to humans. What plants are we referring to, respectively?

(A) tomatoes and red peppers

(B) tomatoes and potatoes/eggplant

(C) potaotes and red peppers

(D )potatoes or eggplant/ tomatoes

Explanation


8. What common substance is crucial to photosynthesis because it is the ultimate source of electrons, which must be returned to excited chlorophyll?

(A) potash fertilizer

(B) nitrate fertilizer

(C) water

(D) carbon dioxide

Explanation


9. Which plant’s roots provides sugars and leghemoglobin to bacteria in exchange for ammonium ion?


(A) bean

(B) radish

(C) tomato

(D) lettuce

Explanation


10. What are the most common elements in a plant?

(A) N, C, H, O, P and Mn

(B) N, C, H, O and S

(C) C, H, O, N and Mg

(D) C, H, O, P, N and K

Explanation


whitespace#Answer1 –E–Plants don’t eat. They only absorb water and ions from the soil and carbon dioxide from the air. With these substances they produce not only glucose but all of the amino acids, nucleic acids and secondary compounds that they require.

whitespace#Answer2 –C– The first two are tylenol and advil. Salicylic acid, upon reacting with acetic anhydride in the presence of a catalyst(acid), will create acetylsalicylic acid, which is aspirin.

Caffeine is an alkaloid, whose structure is unrelated to aspirin.

whitespace#Answer3 –A– If one is familiar with the buttercup family(Ranunculacae), one realizes from the shape of the leaves of the four plants shown, that only the monkshood is related to the buttercup. The opium poppy produces morphine in its pod. The fruits of the mountain ash in large amounts can cause stomach irritation and pain, vomiting, queasiness, diarrhea, kidney damage, and other side effects. Finally the milkweed concentrates its poison in the above ground parts.

whitespace#Answer4 –B– Technically an alcohol is any compound in which the oxygen atom is sandwiched between a hydrogen and a carbon atom from a hydrocarbon group. Cantaloupe produces small amounts of ethanol (CH3CH2OH), the same alcohol produced from fermentation of apples, hops and grapes to make cider, beer and wine. According to this source benzyl alcohol (C6H5CH2OH) can also be produced.  The latter is not at all toxic in low doses and has a sweet, pleasant odor. Not surprisingly, it is also found in hyacinth and jasmine flowers.

whitespace#Answer5 –A– Notice that malaria and one form of sleeping sickness are directly caused by protozoans(Plasmodium and Trypanosoma respectively), but in both cases the microorganism needs a vector, another organism that carries it from one victim to the next. Elephantiasis has no vector, and ebola is the only one out of the four above diseases to be caused by a virus.

From Center of Disease Control http://www.cdc.gov/malaria/about/biology/
From Center of Disease Control http://www.cdc.gov/malaria/about/biology/

 

For more on the use of artemesin and its “green” extraction, see this Periodic Table Video: artemisinin , which is sparingly produced by Artemisia annua and also difficult and expensive to artificially make from scratch.

whitespace#Answer6 –C– The name of the first compound gives it away, cis-rose
oxide.

whitespace#Answer7 –B–
The name tomatin gives away the 1st part of the answer. Potatoes and eggplant leaves are toxic to humans becuase of solanine. Those of tomatoes are free of solanine and since tomato leaves have low concentrations of a much milder alkaloid, they are not toxic, contrary to popular belief. In fact tomatin is also found in green tomatoes.

whitespace#Answer8 –C–
Plants need water for a variety of reasons but especially to release electrons after sunlight ejects electrons from the photosystems of chloroplasts. Oxygen is produced when water dissociates, and the hydrogen ions that are also released set up a +/- gradient and thus a voltage that provides the chloroplast with the energy it needs to incorporate carbon dioxide.

whitespace#Answer9 –A–
From the list only the bean is a legume, which thanks to mutualism, can get ammonium ion from Rhizobium bacteria, which use nitrogen from the air to produce it.

whitespace#Answer10 –D– Along with N, C, H, O, and P,  sulfur is one of the six most common elements of life. Sulfur is part of four amino acids and is also key to many biochemical reactions. Having said that, S only makes up 0.1% of dry plant matter. From recalling the components of industrial fertilizer (N-P-K) one could correctly surmise that potassium(K) would be more common than sulfur in plants. And that would be correct. It makes just under 1% of plant dry matter, on average. Plants need potassium ion for proper transcription of many genes and to control the activity of many enzymes.

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