We all know that drugs like heroin, meth and cocaine have ruined a lot of lives. That isn’t (or shouldn’t) be news. And yet despite their dire effects, the science and the stories behind these drugs is sort of fascinating nonetheless. They’re sort of like a vast unplanned neuroscience experiment that reveals some interesting things about how the human brain works.
So forget about the politics of the drug war and the future of American drug policy for now… we’ll leave that for the pundits and the politicians to debate. Instead, let’s talk about the chemistry and biochemistry of illegal drugs. We’ll find out why people smoke crack and snort cocaine; what LSD does inside the brain, and why it glows under a black light; what chemists and crackheads mean by “freebasing”; why the DEA tracks sales of iodine; and why Bayer used to sell heroin as a cough suppressant. Because this is the interesting stuff.
There’s a scene in the movie Traffic where Catherine Zeta-Jones’ character approaches the head of the Obregon cartel. Her husband, a major distributor for Obregon in the US, is about to go on trial in San Diego and she wants to offer Obregon a deal. Forgive her husband’s debts and kill the lead witness for the prosecution, she tells him, and in exchange she’ll give him…a new way to smuggle cocaine into the states. A doll.
Obregon: “If you want to smuggle narcotics in Senore Espastic Jacobo, that is nothing new, Senora.”
C Z-J: “No, not in. The doll IS cocaine. High-impact, pressure-molded cocaine. It’s odorless. Undetectable by the dogs. Undetectable by anyone…”
Obregon: “I don’t believe you, Senora.”
A wise move on his part, because the solid-pure-cocaine doll that no one can detect isn’t a very plausible plot element. The movie doesn’t bother to explain, although in order to demonstrate her doll is legit C Z-J dissolves some of it in water. Which is interesting, because it comes back to some basic chemistry.
The structure of the cocaine molecule is like this:
–shamelessly borrowed from Wikipedia because their structure is accurate and borrowing is faster than drawing my own in ChemDraw. (Lazy, I know.) One of the first few things you should notice about this structure is the nitrogen or “amine” up on top of that boat-shaped ring. Amines are in general somewhat basic, meaning they can pick up a hydrogen ion. (A base is something that wants to accept a hydrogen ion, whereas an acid is something that wants to give a hydrogen ion away.) Once the nitrogen has a hydrogen or H attached to it in addition to the three bonds it’s formed already, it will have a positive charge.
If I take cocaine, which is a base, and mix it with an acid like HCl, I end up with a salt — positively charged cocaine ions and negatively charged Cl ions. If I take this salt and mix it with a base, I’ll remove the hydrogen ion back from the amine group so we end up back with the structure you see above, the “freebase” structure because the amine is “free” — it doesn’t have a hydrogen ion attached to it. And this is where freebasing comes in.
What most people call cocaine is actually the hydrochloride salt, cocaine HCl. Crack cocaine, by contrast, is the freebase form. When crackheads cook up their
narcotic drug of choice, they’re mixing some cocaine HCl with a weak base in water, and so they end up with pure freebase cocaine (aka crack) which forms an oily slick.
So why are they doing that? is it just ’cause they’re crackheads? No, it’s ’cause they know some science, that’s why. (Well, maybe that’s why. More likely they’re just doing it because somebody told them to do it that way.)
Why do some things play well with water and others don’t? You can mix water and ethanol just fine, for example, but try mixing water and dichloromethane or water and MTBE and you get something that looks like this:
Notice how there are two separate layers — layers that don’t mix. You can force them to mix by picking up the funnel and shaking it, but put it back down and before you know it they’ll separate again.
The reason why some things dissolve in water and others don’t is a little complicated, but there’s an easy general rule of thumb you can use to figure out what dissolves in what. It goes like this:
Like dissolves like.
Bear in mind, that doesn’t mean “like” in terms of color or scent. Electron density in a molecule can be evenly distributed (nonpolar) or unevenly distributed (polar). Water is a very polar molecule — so polar, in fact, that water molecules can form weak interactions with each other called hydrogen bonds. So water is very good at dissolving things that are polar and can form lots of hydrogen bonds (like dissolves like). It’s very good at dissolving ionic compounds like table salt, because these are formed from ions that have + and – charges on them (because having a charge is like being extremely super-polar if you want to think about it like that). And it’s very bad at dissolving things that are mostly or completely nonpolar, like the molecules in oils and fats.
If we stick a hydrogen ion onto the cocaine molecule by mixing it with acid, we end up with ions that are much more soluble in water than the original compound. That’s why cocaine HCl dissolves in water and crack cocaine doesn’t. If you wanted to dissolve crack cocaine, you’d just mix it with some acid (e.g. lemon juice), and that would do the trick just fine.
The same thing is true for lots of other big ugly organic (carbon-based) compounds that contain amine groups. Make a salt out of them by mixing them with acid and they dissolve pretty well in water; remove the hydrogen ion by mixing them with base and they dissolve much better in some other more nonpolar solvent like dichloromethane. Next time you go down the OTC drug aisle in the pharmacy or the supermarket, take a look at the ingredient list and see if you spot any compounds with “HCl” on the end. These are hydrochloride salts. The manufacturer used the hydrochloride salt of the drug rather than the freebase form.
So why does anybody want the freebase form of cocaine? The answer has to do with vaporization. At pretty much any temperature above absolute zero, molecules are moving around. In a solid they’re held together by tight bonds, so they’re fidgety but they stay put. In a liquid they’re held together but have some more freedom to move, and in a gas they’re flying around like ping-pong balls. So to turn something from a solid into a liquid or a liquid into a gas, we have to overcome the forces that hold these molecules together, and that takes energy. The stronger those forces, the more energy it takes, and the higher the melting point (or boiling point) of the solid or liquid.
Solid cocaine HCl contains positively charged cocaine ions and negatively charged Cl ions. They’re held together by the attraction between opposite charges, which is very strong, so vaporizing cocaine HCl isn’t easy. In fact, you’d have to heat it high enough you’d kickstart some chemical reactions that would destroy your cocaine, and now you just defeated the whole purpose of the experiment. So that’s why people don’t smoke coke.
In crack cocaine, on the other hand, the molecules don’t have any charge, so the forces that hold the crack cocaine molecules together are much weaker and you can vaporize it at a reasonable temperature. Inhaling the vapor puts it into circulation much more rapidly and the maximum blood concentration or Cmax is generally higher.
Once you have the cocaine in your system, your body will get rid of it by chemically altering (metabolizing) it and by excreting it (filtering it out of the bloodstream into the urine), just like any other drug. The way the body metabolizes it is just about what you’d expect: by breaking down (hydrolyzing) those esters. If you look at the structure again, you have two C-O-C=O groups that look a little like legs on the boat-shaped ring, and these are called esters. When you break them down, you wind up with the junk you see below (depending on what gets hydrolyzed):
These reactions are spontaneous and happen of their own accord in water, but enzymes in your blood and liver catalyze these reactions or speed them up so they happen very rapidly, and cocaine doesn’t actually last very long in your bloodstream. Your liver also converts a small fraction of the cocaine into another metabolite called norocaine by yanking the CH3 group off of the nitrogen in the boat-shaped ring.
Ultimately, the three molecules you see above end up in your urine, together with a tiny amount of unaltered cocaine*. So if you’re a drug testing lab, your best bet is to look not for cocaine itself, which is only going to be present in trace amounts, but for the metabolites; and in fact, drug testing labs look for the second molecule down from the top in urine samples. But cocaine is eliminated so rapidly from your system that labs can only confirm its presence for a fairly limited period of time — unlike THC, which is eliminated much more slowly.
Coming up in the next post: Meth (which gives me an excuse to talk about the awesomeness that is Breaking Bad.) Stay tuned.
*(See this paper for a more complete discussion of cocaine pharmacokinetics).
Jatlow P (1988). Cocaine: analysis, pharmacokinetics, and metabolic disposition. The Yale journal of biology and medicine, 61 (2), 105-13 PMID: 3043924
Pingback: Contagions Round-up 24: The Links of Summer « Contagions
Love it! Looking forward to the rest!
Excellent article, I love all the detail you include. When you get to methamphetamine, I hope you explain the difference between a pseudo cook and Mr. White’s Blue.
methamphetamine has one chiral center, pseudoephederine has this center set correctly. The Blue method gives you racemic methamphetamine because there is no way to set that chiral center correctly, so it is really only 50% active.
I don’t think 50% active is the right way to put it; It may not increase your euphoria much, but the L isomer provides a different, smoother–preferable to many–high.
Pingback: The Scienceblogging Weekly (July 27th, 2012)
Pingback: The Scienceblogging Weekly (July 27th, 2012) | Stock Market News - Business & Tech News
Pingback: The Scienceblogging Weekly (July 27th, 2012) | Seniors & Boomers News
dude this is my new favorite blog. awesome man. i can’t wait to read what else is next. plus i’m studying ochem so this shit is sooo rad man.
Reblogged this on Mark Solock Blog.
need more of the product visit this website i got quality here
Chemistry is cool……
Pingback: The New Digg Debuted a Day Early | Con Games
Pingback: The New Digg Debuted a Day Early - Nlyten.com
“The reason why some things dissolve in water and others don’t is a little complicated; it has to do with the Second Law of Thermodynamics” – This is not true!!
Think back to your basic chemistry. For something to dissolve in water, the Second Law dictates that the net change in entropy (i.e. sum of change in entropy of the system plus change in entropy of the surroundings) associated with that process must be positive. For a constant-temperature constant-pressure process (which are the conditions we usually care about), we can restate this as ΔG < 0, where ΔG = ΔH – T ΔS.
What are you saying "is not true"? Explain yourself.
Looking forward for the next one! Good read!
But just a note, Cocaine and Crack aren’t narcotics, both are stimulants (Narcotics being defined as a drug which induces sleep in the user)
Arrrgh, my bad; you’re absolutely right about that. I feel like I hear it used a lot of the time as a catchall phrase for “illegal drug”, though, and so that’s how I used it — technically though that’s not correct. i’ll change it. Thanks.
Pingback: The Chemistry Of Cocaine | The Penn Ave Post
My understanding is that the original “freebasers” were coke smokers, then it morphed into crack smokers. I also know for a fact that people smoke coke, although its not the common method for intake.
How would one extract the cocaine from crack cocaine disolved in lemon juice in order to obtain pure cocaine? I would like to know hte chemistry behind it.
This is really interesting – thanks for the explanation! I work at a syringe exchange program and we give out absorbic acid to help break down the crack instead of lemon juice or vinegar, which can be harmful. So cool that I now know WHY crack won’t dissolve just in water! I just wanted to point out that lots of people who use crack aren’t “crackheads”, just as many “addicts” are just drug users who are labelled based on assumptions.
Looking forward to reading your next one!
cocaine molecule itself is polar right ?
Polar isn’t really an all-or-nothing thing. I mean, yeah, it’s more polar than, say, hexane, but it’s also less polar than, say, ethanol.
Reblogged this on chemistry is the answer !.
Pingback: Drugs: Imported From Detroit | MADE IN MICHIGAN | TAKIN' A BITE OUTTA MICHIGAN.
regardless they are synthetic drugs and ultimately second best to nature and what is grown in nature
Nature provided the leaf and the brain. “Synthetics” are just the mixture of these. Natural + Natural = Natural
would it possbile to disolve cocaine HCl in a mix of propylene glycol (PG)/vegetable glycerin (VG) and then use a Personal vaporiaser ( eectronic cigarette) to vaporise it?
Pingback: Your Brain on Crack Cocaine | AdzVillage Online Tv
Pingback: All The Things You’ve Never Heard About Crack Cocaine | Click here for latest music news (full color articles)
Pingback: Your Brain on Crack Cocaine - World MysteriesTV | World MysteriesTV
Pingback: Your Brain on Crack Cocaine | O.M.G Network
Pingback: Your Brain on Crack Cocaine | O.M.G Network
Pingback: Your Brain on Crack Cocaine | Te Platim Sa Publici Anunturi
Pingback: Your Brain on Crack Cocaine | MiNDFOOD
Pingback: Your Brain on Crack Cocaine | Social Sounder
Pingback: Your Brain on Crack Cocaine | Secret of Entertainment Videoblog
Pingback: Your Brain on Crack Cocaine | Cockroach TV
So this is what the Rock has been cooking all this time. When’s dinner!?
Pingback: Your Brain on Crack Cocaine - Best Video Clips
Pingback: Your Brain on Crack Cocaine | FanMedia
Pingback: Your Brain on Crack Cocaine science video clip - Life Sciences Discovery - All Sciences Discovered
Pingback: Your Brain on Crack Cocaine | Knowledge
Pingback: Your Brain on Crack Cocaine | Software
Pingback: Your Brain on Crack Cocaine | Padsoc Tube
Pingback: Your Brain on Crack Cocaine - Skeptic.live | Skeptic.live
Pingback: Your Brain on Crack Cocaine | Biyoloji Günlüğü
Pingback: Your Brain on Crack Cocaine - Alcohol-Detox-Drugs.com
Pingback: Addiction Website – Your Brain on Crack Cocaine
Pingback: Crack Side Affects
Pingback: Your Brain on Crack Cocaine – Efeito Bumerang
Pingback: Your Brain on Crack Cocaine
I’m a bio major in chemistry and my secrets go with me to my grave Mr Derham Alwyn Paul because the use of all these chemicals I made in the periodic table are highly addictive and illegal all the best the best high is living well and eating properly and exercise everyday and hobbies and the love of music art and culture have a lovely day or evening 🌃 we all have 1 life like mine not 2
Pingback: Your Brain on Crack Cocaine - www.usadetoxcenter.com
all the drugs containing nitrogen are not basic it is not true..explain plz???
Pingback: Your Brain on Crack Cocaine #DidYouKnow #Science #learn #fun #Asap - LGBT 2
Pingback: Your Brain on Crack Cocaine - ClipTrends
People love chemistry oh good try this 1 ok get your friends around for a hello 👋 boys party 🎉 open the fridge door 🚪 put in a candle light the candle before putting it in your freezer shut the door and let the modern Olympiad if of not if google this is crazy I can’t back space my writing I’ll go on thought thorough see it’s crazy not thought though so just put a lit candle if you dare in your freezer shut the door and run but it may not work but will is I can’t say because it will kill you in a second um I’m not allowed to say the chemical damn lol I can’t
Just imagine Sheldon cooper his secrets all of them holy molybdenum penny penny lol
Pingback: Your Brain on Crack Cocaine | i love 1080p
Pingback: Your Brain on Crack Cocaine | who is 2d
Pingback: Your Brain on Crack Cocaine | Wordpress Wiki
Pingback: Your Brain on Crack Cocaine – Very funny Video
Pingback: Your Brain on Crack Cocaine | Allergies News
Pingback: Your Brain on Crack Cocaine — This TV Knows – Tools & More Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Maureen Smith Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Nike Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – QuickBooks Desktop
Pingback: Your Brain on Crack Cocaine — This TV Knows – Air King Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Wireless Cloud Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Amerzam Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Pop Out Pets
Pingback: Your Brain on Crack Cocaine — This TV Knows – Bounce Balls
Pingback: Your Brain on Crack Cocaine — This TV Knows – JBW Products
Pingback: Your Brain on Crack Cocaine — This TV Knows
Pingback: Your Brain on Crack Cocaine — This TV Knows – Veronica Yang Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Windows XP Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Solo Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Corel Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Coffee Brewers
Pingback: Your Brain on Crack Cocaine — This TV Knows – Nintendo Products
Pingback: Your Brain on Crack Cocaine — This TV Knows – Dominique Thomas Products
Pingback: Your Brain on Crack Cocaine – Good Medic
Pingback: Your Brain on Crack Cocaine - MegaClip
Pingback: Your Brain on Crack Cocaine | AndroidTut.Net
Pingback: Your Brain on Crack Cocaine | Wordpress Tutorials
Pingback: Your Brain on Crack Cocaine – ATAK NEWS
Pingback: Your Brain on Crack Cocaine – 420life.info
Pingback: Update, Your Brain on Crack Cocaine - Blogger Indonesia
Pingback: Your Brain on Crack Cocaine » Dancehall Dancehall
I have noticed you don’t monetize your site, but you can earn extra cash
every day. It’s very easy even for noobs, if you are
interested simply search in gooogle: pandatsor’s tools
Pingback: Your Brain on Crack Cocaine – Canada Videos Overflow
Pingback: Your Brain on Crack Cocaine (Video) | Journal TV
Pingback: Your Brain on Crack Cocaine | USAVideoNews
Pingback: Your Brain on Crack Cocaine - Review
Pingback: Your Brain on Crack Cocaine – insomnia
Pingback: Your Brain on Crack Cocaine – medical-weeds
Pingback: Your Brain on Crack Cocaine | No Smoking Tips
Pingback: Your Brain on Crack Cocaine – CBD Oil
Pingback: Your Brain on Crack Cocaine – HEALTHY ENVIRONMENTS, A DIV. OF CYBERMARK SOLUTIONS
Pingback: Your Brain on Crack Cocaine – Hungoin
Good article. I’m dealing with a few of these issues as well..|
Pingback: indonesian gambling and betting
Pingback: virtual office setup
Pingback: Best Youtube Music Downloader
Pingback: best tumblr videos for free download
Pingback: google youtube downloader
Pingback: best poker game android
Pingback: micro switches supplier
Pingback: mbbs study in russia
Pingback: cbd oil at best price
Pingback: best poker game site
Pingback: online image compression tool
Pingback: zynga poker
Pingback: tips for cleaning a house
Pingback: limit switch manufacturers in chennai
Pingback: air purifier
Pingback: the best luxury watch in instagram
Pingback: laptop charger tips
Pingback: agen slot online
Pingback: muay thai shorts womens
Pingback: instant delivery of RuneScape gold
Pingback: convert m4a to mp3 google drive
Pingback: automatic screw fitting machine
Pingback: company information
Pingback: advanced aesthetics med spa
Pingback: hydraulic car washing lift price
Pingback: loa contracting
Pingback: amazon seo services
Pingback: Your Brain on Crack Cocaine | | cannabisq4h.com
Pingback: Your Brain on Crack Cocaine | | medicannastore.com
Pingback: cocomo submodels
Pantai Wae Rana mempunyai udara yang fresh dan disokong oleh pasir putih yang halus. Mempunyai panorama yang molek dan jauh dari hingar bingar keramaian kota, pantai ini pas buat kalian yang https://jelajah-indonesia.net/ pengin nikmati berlibur dengan tenang. Kalian bisa juga bermain sepak bola atau voli saat bertandang ke pantai ini.
Pingback: olansi hydrogen water bottle
Pingback: ocean recovery project
Pingback: best digital marketing institute in india with placement
Pingback: financial advisory services
Pingback: add a device windows 10
Pingback: Read more
Pingback: pg slot easy
Pingback: olansi hydrogen water bottle
Pingback: san francisco registered agent
Pingback: the best poker gambling
Pingback: ss g profile
Pingback: uses of honey
Pingback: backwoods hoodie purple
Pingback: air purifier price in india
Pingback: bandarq pkv
Pingback: snowflake training coursera
Pingback: poker online with friends
Pingback: sodium hyaluronate eye drops side effects
Pingback: Your Brain on Crack Cocaine - Cannabis News
Pingback: [idnreader] Your Brain on Crack Cocaine 2022 | idnreader.com
Pingback: AsapSCIENCE: Your Brain on Crack Cocaine - Social Chatter Watch