Archive for: July, 2011

The Supreme Court's Cocaine Problem

Jul 07 2011 Published by under Uncategorized

Figure 1

Ask a chemist the difference between cocaine and crack, you’ll likely hear about acid-base chemistry.  Ask the other type of chemist and you’ll likely hear “about 5 years”.  It is mainly the sentencing differences, rather than the chemical differences, that dominate discussions on cocaine and crack.  Those sentencing differences were kicked-off by The Anti-Drug Abuse Act of 1986 (eventually Public Law No: 99-570), which resulted in vastly different mandatory sentences for federal cocaine versus crack crimes (US Code § 841).

How different?  It took 500 grams of cocaine to get a nickel in the Big House, but only took 5 grams of crack to land you in the clink for the same time (see A, B & C).  Clearly, it was legally advantageous to do and deal in blow rather than rocks.  Based on this 100-to-1 sentencing difference, belies how chemically similar these compounds are.

Figure 2

Cocaine is often thought of as that white powder Scarface planted his face in (Figure 2).  That powder is actually cocaine hydrochloride (chemical formula [C17H22NO4]+ Cl-), a salt of the alkaloid compound cocaine (Figure 1).

Like other salts, cocaine hydrochloride is the result of reacting an acid (hydrochloric acid, HCl) and a base (cocaine).

Cocaine hydrochloride has a melting point (mp*) of 190-192 ˚C and decomposes at high temperatures, making it far better suited for insufflation rather than smoking.

Crack, however, seems made for smoking with a mp* of 96-97 C.  Crack is easily prepared by heating an aqueous solution of cocaine hydrochloride and the base sodium bicarbonate (baking soda), then collecting the precipitate.  So... crack is cocaine and what we think of as cocaine is actually cocaine salt.  Oh, and freebase is also cocaine. Freebase cocaine is prepared much the same way as crack, swapping ammonia for baking soda, with the additional steps of ether extraction to yield ‘freebase’.  Like crack, freebase is typically smoked.  While cocaine hydrocloride has that powdery appearance (Figure 3A), crack and freebase look like rocks (Figure 3B).

While members of the US Congress likely tossed around the words 'coke', 'crack' and 'freebase' during floor debates, hearings, committee meetings and whatever else occurred to bring us Public Law No: 99-570, you won't find those words in US Code § 841 (excerpt below).

(B) In the case of a violation of subsection (a) of this section involving—

  • (i) 100 grams or more of a mixture or substance containing a detectable amount of heroin;
  • (ii) 500 grams or more of a mixture or substance containing a detectable amount of—
  • (I) coca leaves, except coca leaves and extracts of coca leaves from which cocaine, ecgonine, and derivatives of ecgonine or their salts have been removed;
  • (II) cocaine, its salts, optical and geometric isomers, and salts of isomers;
  • (III) ecgonine, its derivatives, their salts, isomers, and salts of isomers; or
  • (IV) any compound, mixture, or preparation which contains any quantity of any of the substances referred to in subclauses (I) through (III);

(iii) 5 grams or more of a mixture or substance described in clause (ii) which contains cocaine base;

.
.
.

such person shall be sentenced to a term of imprisonment which may not be less than 5 years...

In US Code § 841, cocaine hydrochloride fell under (B) (ii), crack under (B) (iii) as “cocaine base”, and the disparate sentences came under attack.  What was the motivation for 100-10-1 sentencing difference? Race, pharmacological differences, drug war politics, some or none of the above?  This disparity debate bounced around the country and returned to the US Congress in 2009 with the introduction of the Fair Sentencing Act.

Various individuals and groups showed their varying-levels of support (see D, E, F & G) for this act.  Why the varying levels of support?  The Fair Sentencing Act didn't make the sentences equal.  Instead of a 100-to-1 difference in sentencing, it was now a (roughly) 18-to-1 difference.  As of August 2010, when the Fair Sentencing Act became law , 500 grams of cocaine or 28 grams of crack will get you five in the joint.

Actually, if we're being specific, 28 grams of "cocaine base" will get you a nickel.  By now, it seemed clear that "cocaine base", though redundant, includes crack, freebase and anything else with cocaine (Figure 1) in it.  Not so, argued Frantz DePierre.

In 2005, DePierre got caught selling drugs and charged with distributing 50 grams or more of "cocaine base".  Now DePierre didn't try to argue that the stuff he was caught selling was cocaine hydrochloride, thus lessening any possible prison time.  Let's face it, that argument would have been absurd.  No, DePierre argued that "cocaine base" was crack - and only crack.

DePierre asked the District Court to instruct the jury that, in order to find him guilty of distribution of cocaine base, it must find that his offense involved “the form of cocaine base known as crack cocaine.” App. in No. 08–2101 (CA1), p. 43. His proposed jury instruction defined “crack” identically to the Guidelines definition. See id. , at 43–44; see also USSG §2D1.1(c), n. (D). In addition, De-Pierre asked the court to instruct the jury that “hemi-cal analysis cannot establish a substance as crack because crack is chemically identical to other forms of cocaine base, although it can reveal the presence of sodium bicarbonate, which is usually used in the processing of crack.” App. in No. 08–2101, at 44. [excerpt^ from Franz DePierre v. United States]

Figure 4

You can almost see DePierre's (or his lawyer's) train of thought...  "If the court says "cocaine base" is only crack, but chemical analysis can't tell crack from freebase from other stuff with cocaine in it, then I've got a get out of jail free card."

Well, the District court didn't do as DePierre requested.

Instead, the District Court told the jury "..the statute that’s relevant asks about cocaine base. Crack cocaine is a form of cocaine base, so you’ll tell us whether or not what was involved is cocaine base … ”.

During DePierre's trial, a government chemist testified that the drug DePierre was caught selling was "cocaine base" and that no sodium bicarbonate was identified.  DePierre was convicted and he took his argument to the next level, i.e. the United States Court of Appeals for the First Circuit (CA1).  The CA1 sided with the District Court and...

...reject[ed] DePierre’s argument that §841(b)(1)(A)(iii) should be read only to apply to offenses involving crack cocaine....holding that “ ‘cocaine base’ refers to ‘all forms of cocaine base, including but not limited to crack cocaine.’ ” Id. , at 30–31 (quoting United States v. Anderson , 452 F. 3d 66, 86–87 (CA1 2006)).  [excerpt from Franz DePierre v. United States]

Essentially, CA1 takes "cocaine base" in US Code § 841 to mean the alkaloid compound cocaine (Figure 1) and stuff containing said alkaloid (e.g. crack, freebase, coca paste).  Once again, DePierre took it to the next level and Supreme Court of the United States (SCOTUS) granted certiorari "..to resolve the longstanding division in authority among the Courts of Appeals on this question."

To SCOTUS, DePierre made 5 arguments “...that the term ‘cocaine base’ in clause (iii) is best read to mean ‘crack cocaine.’  SCOTUS was not convinced by any of them.  Sure, SCOTUS agreed that ‘cocaine base’ was redundant, discussed how the language of the law could be fixed, and what Congress could have meant by "cocaine base", but in the end…

That we may rue inartful legislative drafting, however, does not excuse us from the responsibility of construing a statute as faithfully as possible to its actual text. 11 And as noted earlier, there is no textual support for DePierre’s interpretation of “cocaine base” to mean “crack cocaine.”  [excerpt from Franz DePierre v. United States]

“Textual support”?  SCOTUS seems to mean that since "cocaine base" not "crack cocaine" appears in the relevant statue(s) and congressional records, ‘cocaine base’ isn’t only crack.  Plus, it appears that SCOTUS found that swapping "crack cocaine" for "cocaine base" made no sense in some sections of the relevant statue.

We agree with the Government that the most natural reading of the term “cocaine base” is “cocaine in its base form”— i.e. , C 17 H 21 NO 4 , the molecule found in crack cocaine, freebase, and coca paste. On its plain terms, then, “cocaine base” reaches more broadly than just crack cocaine. [excerpt from Franz DePierre v. United States]

SCOTUS’ final word?

We hold that the term “cocaine base” as used in §841(b)(1) means not just “crack cocaine,” but cocaine in its chemically basic form. We therefore affirm the judgment of the Court of Appeals.

It is so ordered.

Figure 5

What does this mean for cocaine hydrochloride?  Absolutely nothing, it’s not a “cocaine base” – something SCOTUS states at the start of its opinion.

Chemically, therefore, there is no difference between the cocaine in coca paste, crack cocaine, and freebase—all are cocaine in its base form. On the other hand, cocaine in its base form and in its salt form (i.e. , cocaine hydrochloride) are chemically different, though they have the same active ingredient and produce the same physiological and psychotropic effects. See id. , at 14–22. The key difference between them is the method by which they generally enter the body; smoking cocaine in its base form—whether as coca paste, freebase, or crack cocaine—allows the body to absorb the active ingredient quickly, thereby producing a shorter, more intense high than obtained from insufflating cocaine hydrochloride.  [excerpt from Franz DePierre v. United States]

So where are we at now?  An 18-to-1 sentencing difference between cocaine hydrochloride and “cocaine base” crimes, with “cocaine base” not limited to crack.  In Franz DePierre v. United States, SCOTUS did not directly address the validity of cocaine hydrochloride and “cocaine base” sentencing differences.  If anything, SCOTUS seemed to say “Congress had its reasons and it’s up to Congress to deal with it" - but, I'm no legal scholar (though I did watch Law & Order for 20 years).   Nope, I'm just a chemist happy to see little chemistry in the courts.

____________

Figure image attributions:
Figure 1: Image from http://read.bi/lN9hQk
Figure 3: Images from http://bit.ly/n8r1Uw (cocaine hydrochloride) and  http://bit.ly/pctx5C (crack)
Figure 4: Image from http://bit.ly/oGcmWr
Figure 5: Image from http://bit.ly/nLqwIF
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Special notes
*The mp values listed are from a single publication, but these values are in-line with values listed in the SciFinder compound properties feature.  The mp values of 180 ˚C for cocaine hydrochloride and 80 ˚C for crack are also found in literature (see X and Y).
^All Franz DePierre v. United States excerpts are from the majority opinion.  The concurring opinion can be found here.

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Unfortunately, I'm your guest blogger for the next 2 weeks

Jul 04 2011 Published by under Uncategorized

original image from http://bit.ly/jQG0uC

Let me be the first to apologize for Scientopia having me serve as their guest blogger for two weeks.  The next two weeks might well be the most frivolous two weeks on the Scientopia Guest Blogge.  Not that I'm a frivolous person, mind you.  I am an analytical chemist focused on separation methods, small molecule mass spectrometry and chemometrics.

As further proof of my non-frivolity, I read a gratuitous amount of non-fiction, listen to NPR and watch PBS.  But I'm a bit of a class clown, a trait most evident in my science blogging (see JAYFK).  I am more likely to write about trebuchet toting traffickers than trace chemical analysis.

During my two weeks as Scientopia guest blogger, you'll be subjected to posts on the SCOTUS' cocaine problem and threatened nuts, along with an episode of Bunsen Burner & Hooch.  Hopefully, this two weeks will be fun for you readers.  Unfortunately, I'm not sure you'll actually learn anything sciency.

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Half a Decade of Happiness

Jul 02 2011 Published by under Uncategorized

In what will probably be my last post here at Scientopia, I'd like to take things in a slightly different direction and wear my heart on my sleeve for a change. I've spent a lot of time in the past writing as best as I can about the wonders of our universe, life's fleeting existence on this planet as well as the possibility that billions of other life-bearing worlds may exist out in the cosmos. As you can imagine, comprehension of space and time on this enormous scale is initially quite discomforting. As organisms evolved to deal with relatively small areas of grassland and savannah, and with medically extended lifespans of only 70 years or so, we lack the innate ability to visualise and properly grasp the true magnitude of the distances and time-spans associated with the study of astronomy and extra solar planets. Consider, for example, the fact that there are estimated to be 9 sextillion (9 x 1021) stars in the observable universe, most with the potential to harbour one or more planets. That's 9 with 21 zeroes. It is impossible to genuinely appreciate the enormity of this number; we lack the relevant mental computational ability and it can be quite psychologically distressing to attempt to do so.

Any rudimentary perspective that I have managed to gleam from these humble posturings and my barely appreciable understanding of this area of science has required that I approach the subject with as much rational objectivity as is possible, and I have always sincerely attempted to do so. This area of science is evolving rapidly and every new discovery of another 'Super Earth' or 'Hot Jupiter' brings with it a smorgasbord of new puzzles, excitement and hypotheses. However, I am often concerned that immersing myself in space and time on these magnitudes, even at my amateurish level, may eventually erode or distort my limited perspective on my own place in the world. I am very aware of the fact that I am unlikely to ever even properly appreciate my own ignorance, or to begin to understand how little I actually know about the intricate complexity of our journey through space and time.

Carl Sagan once wrote that "...astronomy is a humbling and character-building experience." Whilst I wholeheartedly agree, I also sincerely appreciate and am genuinely grateful for the opportunity to continue to study in this important area of contemporary science and hope that I continue to do so for many years to come. This contrast between the humbling, occasionally distressing appreciation of the futility of our own efforts to survive, persist and understand, and the life-affirming, almost indescribable enthusiasm to learn and understand presents a slight problem. Is it possible, within the context of our enormous, ancient universe to extract meaning from our short, insignificant lives? I would like to dedicate this article, as well as all that have come before and all that will follow after, to my personal solution to this juxtaposition. I'm sure other scientists and philosophers have various other means of dealing with the problem of grey objectivity and its potentially damaging psychological affects; from religion to alcohol, meditation to psychology. But for me, the reason I feel that I can remained focussed and enthusiastic, is because of the unconditional support, love and dedication afforded to me by my wonderful girlfriend and companion, Hannah. Her caring demeanour, warming smile and gentle caress provides me with calming perspective to a degree that I am unaware she appreciates. She is the reason that I wake up with a smile, go to bed happy and dream contentedly about our joint and happy future.

Scientists know a lot about the chemical basis of love, the subtle interplay between chemical messengers and the architecture of our brain that forms the basis of our lust, attraction and attachment, but the psychological expression of love is a powerful emotion. It is for this reason, like the study of the stars, that love is difficult to objectively analyse. I for one, and in a marked departure from my general philosophy, am happy for the effects of love to remain a personal, subjective experience. Love is not a rational emotion, but it is exactly for this reason that it is consoling. Objectivity is important if we want to understand, in any meaningful way, the workings of our planet and the mysteries of the universe. However, we are borne of the dust of stars and shaped by the subjective comprehension of our experiences of this world. The illogical fact that the love of one person is able to mitigate the distress that can be caused by the comprehension of the scale of our universal insignificance provides me with confidence that objective rationality is not always the best lens with which to view our existence. Evolution has provided us with the emotional equipment to abate the negative repercussions of our superlative intelligence, and we should use it as such. I may be a short-lived, tiny organism, one of 6 billion clinging to a tiny planet around one of 9 sextillion stars, but I have the warm and comforting embrace of loving company along the way, and that is enough for me.

Dedicated with love to Hannah, on the anniversary of 5 happy years together. (02/07/2011)

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