Fentanyl – A Primer

Fentanyl is an extremely potent drug, whose legitimate uses include pain relief for cancer patients. It is one of the most potent drugs in the pharmacopeia. A usual dose of 100 micrograms or less does the trick; it would take about 10 milligrams of morphine to achieve the same result. For those who are metric challenged, a milligram is equal to 1,000 micrograms. If you do the math, fentanyl is about 100 times more powerful than morphine.

Fentanyl was first synthesized in 1960, and made its way into legitimate medicine a few years later. It is listed in Schedule 2 of the Controlled Substances Act (CSA), owing to its extreme potency, making it highly prone to abuse. During my career with DEA, I never encountered the stuff until I had been “off the bench” for several years.

The CSA, along with state drug laws, has been on the books since 1970. Most of the listed drugs were “grandfathered” into it from earlier statutes. Obviously, there needs to be a mechanism for adding new substances. To do so, one needs to elucidate the correct chemical structure (not always easy), demonstrate that it has been “abused”, and then, DEA (part of the Department of Justice) can propose it for addition to the Act. The law, however, requires concurrence of the Department of Health and Human Services. Once this has been achieved, the drug can be added to the list. This can easily take months.

Unfortunately, fentanyl is relatively easy to make. Moreover, fentanyl “analogues” are also easily synthesized. As a consequence, there are numerous clandestine “laboratories” making these substances. The Internet describes several “one pot” procedures. There are at least a dozen or so of these analogues out there in the traffic. They are closely related structurally to fentanyl, and have the same effects. Only fentanyl, itself, was illegal. If someone was busted for trafficking in an analogue which was not on the list, no prosecution was possible under the CSA. What is a narc to do? Even back in the day, in my early career in the 1960’s, there were clever chemists who made analogues which were not listed (as the saying went they were staying “one carbon atom” ahead of the feds).

By now, you might be wondering what an “analogue” is. If a molecule such as fentanyl is represented by a Christmas tree, each ornament might be likened to an organic functional group. For example, a methyl functional group consists of a single carbon atom bonded to three hydrogen atoms. If the fentanyl tree is decorated with a methyl group, an analogue is formed. This is a different organic compound from fentanyl. Its effect on the human body may be the same as fentanyl, be totally different, or, in many instances, much more potent. The position where the group is bonded to the fentanyl molecule is indicated by a number, or a greek letter. Thus, an additional methyl group may be 3-methyl fentanyl or alpha-methyl fentanyl, each of which are compounds distinct from fentanyl itself.

This issue came to a head in the late 1970’s when a new, more powerful “synthetic heroin” appeared on the West Coast, sold as “China White”. The stuff, however, caused some fatalities, always bad for business. Some of the material was submitted to the DEA Special Testing and Research lab. At first, the sample was found to contain nothing but lactose, a harmless cutting agent. When the chemists concentrated the mixture, however, they were able to detect miniscule amounts of a new (to us, anyway) substance which appeared to be similar to fentanyl. It was later found to be alpha-methyl fentanyl. (“Later” took several weeks during which many more might have overdosed).

Clearly, a speeded-up process to add stuff like this to the CSA had to be devised. Congress did pass a law, the Controlled Substances Analogue Act, in 1986. This pretty much said that if a substance was “chemically similar” to a controlled drug (if it looked like a duck…) it was illegal. This helped somewhat, but with the plethora of illegal substances flooding the market during the 2010’s, it was not adequate. In 2018, Congress passed legislation to permit DOJ to list substances by class, rather than specific name. Fentanyl analogues could be regarded as a “class” of drugs, and included in the CSA. Unfortunately, the legislation was to specified expire in two years. Congress has passed legislation to extend this provision when the current law expires on February 8th of 2020. Stay tuned…….

Happy Endings

Ever wonder where the happy endings to our children’s nursery stories, to Hollywood pictures and other types of prose, have gone? Well, many of the nursery stuff (particularly ones from our English culture) were somewhat gory, when you think about it (think of the unfortunate Humpty Dumpty, Jack with Jill on the hill and others). Happy endings still do exist, if only on our TV drug commercials.

These art forms feature adults, for the most part, suffering from health issues. They take the medication, and, presto! They seem miraculously cured, or symptoms are magically alleviated. They all get better!

Back in the day, we went to the doctor, who would prescribe something. Under this model, we become more proactive (“ask your doctor if ____________________ is right for you”). How could it be wrong? Just watch the commercial. We do need to pose some questions, however guided by the voiceover:

-Have you been to places where certain fungal infections are common…..What? What are these? Where are these?

-Am I allergic to ______ or any of its ingredients? How would I know? What about some of the excipients used to make the tablets? Am I allergic to lactose, corn starch, D&C Red#1 used to color the tablets?

Then we have all the possible things which could go wrong (may lead to death….). Maybe some of these things have really happened, which begs the question why any sane person would take this stuff, anyway

The voiceover, is, of course, primarily intended to cover the drugmaker’s posterior. It is probably written by lawyers and, I guess, a necessary evil, but it casts a shadow over the spirit of good news (Well, we can’t have everything). Fortunately it is delivered quite rapidly, and there s no quiz afterwards. We are redirected to the optimistic wrapup (“going for my best. For Eliquis!”).

And so it goes. The good news is not completely free, of course. These commercials cost about 4.5 billion dollars annually, industrywide, which could be used for, maybe, R&D, or lowering the cost for these expensive meds. Maybe this is “why we science”!

The Seaman’s Exam

Fresh out of 90-day wonder school, I reported to my first duty station, line officer, USS Aeolus (ARC-3). (I always will remember when they passed out these assignments. My company chief told me where I was going, then took a beat “Mr. Canaff, what the hell is an ARC?”) The ship, converted from a Navy cargo ship, layed SOSUS cable to track Soviet nuclear submarines on the North Atlantic. Among the modifications was the complete removal of all gunnery from the ship, to allow for specialized cable laying gear (this becomes important later). I was made the Deck Division officer (Ship’s Bosun), with approximately 40 enlisted men under my command (who knew a lot more about what the ship did for a living than I did).

I was lucky to have excellent senior enlisted people, including a Chief Boatswain’s Mate and a First Class of the same specialty. Evidentally the Navy made sure to staff these ships with the best deck rigging types possible to perform the ship’s mission, oriented as it was toward complicated tasks involved in laying cable.

The remainder of my charges consisted of young seamen with limited experience. These men were almost all “seaman apprentice”, Pay Level E-2. Few, if any, had been promoted to E-3, “seaman”. In my limited experience, E-1’s (Seaman Recruit) were promoted to Seamen Apprentices upon completion of naval boot camp, then sent to their first duty stations. Within a year or so, they usually were promoted to Seaman, E-3. By contrast, my people seemed mired as E-2’s, even 2-3 years later. Why? They all seemed competent enough. What was holding them back? In 1963, when all this took place, monthly E-1 pay was $78 monthly, E-2’s drew $85, and E-3’s about $95.

It seems the problem was the sailors’ inability to pass a Navy-Wide written exam. Many of the exam questions concerned gunnery topics, which were all but impossible to train people about on a ship with no guns! I did do some bureautic research, and found that the “Navy-Wide” exam was merely a suggestion, not a requirement.

Each command could make up its own test, based on the ship’s mission. Ship’s command just assumed the test was a requirement, and nobody had bothered to challenge it.

After I had convinced them, I got with my senior enlisted folks and had them modify the exam to pretty much eliminate the gunnery questions, and substitute stuff most pertinent to laying cable. The test was taken shortly afterward, and most every SA passed and got promoted to Seaman. About $10 more in the monthly pay envelope.

No big deal, but even I, not having an MBA or any experience in management, had learned that a vital function of a supervisor is to look after your people. They will then, in the current idiom, in some manner, have your back.

Caveat Emptor (what you see is (often not) what you get…….)

We seem to be hearing a lot of Latin these days (quid pro quo and all that). In a past career with DEA, I was editor, for a time, of a newsletter and journal we called Microgram. We received a never ceasing flow of mail concerning bait-and-switch in the drug trade (caveat emptor, buyer beware). Here are a couple of examples.

During the 1980’s, we began to see drugs which mimicked common ones such as heroin. Many of these were not listed as controlled (illegal) under federal or state law. They became known, collectively, as “designer drugs”, mostly synthesized by “chemists” working in clandestine labs (think of meth labs nowadays). These people ranged in qualifications from college professors to barely literate folks who followed a recipe. One such drug went by “MPPP” (1-methyl-4-phenyl-4-propionoxypiperidine if you’re into formulas). This substance was first synthesized in the 1940’s as a potential competitor of meperidine, aka demerol, but was never approved by FDA. It is listed as a Schedule 1 drug, with effects similar to heroin.

Unfortunately, the manufacture method used by the bad guys produced an impurity, which was nicknamed “MPTP” (1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine). Since clandestine labs are not into quality control, the mixture was put out on the street, and, as it happened, MPTP caused Parkinson-like symptoms in numerous users. Unfortunately, the symptoms were not reversable.

During that same decade, we encountered several analogs of fentanyl, a legally produced narcotic. This stuff is, dosewise, about 100 times more potent than morphine or heroin. Some of these analogs were estimated to be five times more potent than fentanyl. Numerous overdose fatalities resulted, since the substances were handled by distributors in much the same manner as the cutting of heroin. Who knew??? Fentanyl, itself, is now mass-produced or trans-shipped through Mexico. It poses a significant threat to police or other first responders who have to handle it.

Only two of caveat emptor situations out of countless others. Buyer beware!

Marijuana Species……..What’s in a name?

The Controlled Substances Act of 1970 defines marijuana, in part, as “All parts of the plant Cannabis Sativa L…….”. Many of us learned that biological classification of living things follow a sequence in order of specificity:

Kingdom, Phylum, Class, Order, Family, Genus, Species, Variety

Skipping over the obvious. Marijuana is a plant, not an animal. It essentially falls into the genus Cannabis, Species Sativa. The capital letter “L” probably stands for Linneaus, the botanist who published the classification a long time ago. Sometime early in the last century, the definition became part of the Marijuana Tax Act, and was lifted word for word into the 1970 statute, the one used today.

Like most plants, there are numerous agronomic varieties in existence, some of which enter the legal lexicon without too much attention to detail, an example being Cannabis Indica, having something to do with regulation of hemp, a variety of the Cannabis plant having considerable tensile strength (good for making rope), but not good for getting high. This ambiguity led in the 1980’s toward some legal mischief.

I was working at DEA headquarters at the time. A major case (probably involving tons of pot) was argued in federal court for the Eastern District of New York, before Judge John R. Bartels, Sr. The defense had hired Professor Richard E. Shultes as an expert witness. Shultes was a Harvard professor (Ever wondered about the plethora of

o Harvard professors

o Kentucky colonels

o New York Times best-selling authors

out there? I have. But I digress).

Anyway, Shultes advanced an opinion that the law proscribes C. Sativa, but not species such as C indica or C. ruderalis. Further, the correct species can only be determined on intact plants (which never happens in a forensic setting).

Shultes did not advance any theories about any of the other “species” not containing psychoactive substances.

To better understand the far-reaching implications of this interpretation, here is a short description of forensic identification of marijuana plant material. After measurement of exhibit weight, a few simple chemical tests are run, to confirm the presence of delta-9-tetrahydrocannabinol (THC), which gets one high. The stuff is then examined under a low powered microscope to examine morphology of the plant material. The examiner typically looks for cystolithic hairs and other such features, and based on their appearance, identifies the stuff as marijuana. All of this can be done within an hour or less by an experienced analyst.

Shultes’ take was challenged by an expert retained by the prosecution, one Dr. Ernest Small, who, basically, stated that the taxonomic world agreed with the current classification of the marijuana plant. What was Judge Bartels to do?

The judge retained the services of Dr. Arthur Cronquist of the New York Botannical Gardens, who agreed with Dr. Small. Case closed.

Although probably coincidental, Judge John R. Bartels, Sr. was the father of John R. Bartels, Jr., the first Administrator of DEA. Bartels was no longer in that post when these events unfolded.

Chicken of the Sea

Shortly before reporting for duty on my first ship in 1963, she was involved in a collision in San Francisco Bay. According to my shipmates, the captain (a well politically connected naval reserve commander) was heard to say to the exec as collision was imminent,”Well, John, there goes my fourth stripe”. As the Navy cliché goes, a collision can ruin your day. To make matters worse, the captain had just taken command, and this was his first voyage, from Adak, Alaska to San Franscisco.

I reported to the USS Aeolus (ARC-3) as a boot ensign, fresh from 90-day wonder school (Naval OCS) in March 1963. In a few months time, I qualified as OOD.

As an Officer of the Deck, one basically drives the ship on a watch, typically four hours. Obviously, the CO has to sleep (for example), or has other things to do. As OOD we were required to keep the captain informed of any threats to the ship’s well being, threats such as another ship which might collide with us on the open ocean, or worsening weather. On this particular night, my standing orders were to notify (awaken) the skipper if another ship was projected to pass within three miles or so, or the barometer had fallen by a certain amount. Both of these circumstances occurred. I called down the voice tube to his stateroom to report them.

Shortly aferward, the captain appeared on the bridge. I briefed him on the other ship in the vicinity; he appeared not to be listening. The better part of a minute went by with silence. Then, he said to me in a shaky voice, “Mr. Canaff. Right full rudder”. I barked the order to the helmsman, and the ship began to turn. After what seemed a long time, he said, “Steady on 180” which was, basically, returning to port in Kittery, Maine. His short explanation? The drop in barometer portended a hurricaine!

The captain, who had spent most of his career in the (relatively calm) Pacific, was deathly afraid of the climate in the North Atlantic. To prepare himself, he had enrolled in a correspondence course on weather, and had learned that a sudden drop in air pressure often portended a tropical storm, nor’easter, or worse. He wanted no part of that!

After a couple of other instances of aborting missions because of (not so) foul weather, the type commander relieved him, and he was given command of a naval training center in the Midwest, safely far from salt water. Not before, however, the crew labelled him King Tuna, Chicken of the Sea.

War Story

One afternoon as I toiled as a forensic chemist in DEA’s Northeast Lab in New York, two agents came in, quite excited. They were getting a large amount of cocaine “just off the boat”, a big deal in the early 70’s. Could I hang around past quitting time so I could analyse some stuff they were getting on consignment? Sure.

A short time later, they arrived with a baggie of white powder. I ran some tests; yes, it was coke, all right, but had been “stepped on” (cut), and only assayed maybe 30% or so. They were not happy, to say the least. They asked me if I’d stay around, while they went back to the seller. Again, a short time went by, and they were back. This time, I told them the stuff wasn’t pure as the driven snow, but assayed about 75% . They said this was fine, and were about to go back and complete the purchase and subsequent bust. Thanks, Rog! I said wait a minute- what are you telling this creep? How are you testing purity? The reply: “We tell him we feed the stuff to the house junkie, and if he keels over, it’s good stuff”. You’ve got to be kidding me- would anyone fall for that? One of them, special Agent Howie Safir, told me, “you got to understand, Roger, that drug dealers are greedy and stupid”. Words to live by. I had only been with DEA a short time. What did I know?

By the way, in the fullness of time, Howard Safir went on to be a higher-up in the U.S. Marshalls Service, then became Police Commissioner in New York, during Rudy Guiliani’s term as mayor (I guess this was just before Tom Selleck got the job….). His partner, Ron Mockler, became a manager in the DEA New York office.

How “legal” should pot be?

About 21 states have adopted some form of “decriminalization” of marijuana to date. The legality is, at best, confused. Under current federal law, pot is a Schedule I controlled substance (it has a high potential for abuse, and has no accepted medical use). This is stated in the Controlled Substances Act of 1970, and is the law of the land, so to speak. The 21 states and the District of Columbia have “legalized” it, though. Of these, seven have approved it for “recreational” use by adults. Is this a good idea?

Despite a 25 year stint with DEA as a forensic chemist and lab manager, I’m not really a hard liner. I am pretty convinced that pot should be available for medical treatment, if desired. Although there is no “hard evidence” (clinical studies) of its efficacy for conditions such as epilepsy, or nausea brought on by chemotherapy, as examples, there seems to be enough anectodal evidence to suggest it might alleviate these conditions. Lack of clinical evidence is likely caused by, as much as anything else, the lack of profitability, and the difficulty of procuring the stuff for research by Big Pharma in the first place. If you have a child who suffers from multiple daily seizures which is alleviated by pot in some form, who am I to tell you it’s prohibited?

My difficulties with recreational weed lie mainly in that we have not done our homework. We really do not know much about it. For one thing, the stuff available for sale these days is not your father’s or mother’s pot. THC (delta-9-tetrahydrocannabinol, if you’re into chemical names) potency, the usual oversimplified measure, has increased sharply since the eighties. Street level THC has gone from less than one percent to 5-10% currently. What could have been a pleasant high back then might be a toxic (bad trip) reaction today, particularly in children (or teens). I realize that the laws specify availability to adults only; how has that worked for us keeping alcohol, for instance, away from kids?

To further complicate matters, is THC the only psychoactive substance? Cannabis sativa, to use its biological name, contains about 80 different chemicals. Do any of these make you high? We really don’t know. By comparison, alcohol is extremely simple- we know only too well how much gets you loaded. We can give you a breath test and easily define how impaired you are. Alcohol, being water soluble, is easily excreted within a short time. By contrast, THC, being fat soluble, can take months to be totally excreted. How does one measure impairment on the road? We just don’t know.

Also, for what it’s worth, the US of A is a signatory to the Single Convention on Psychotropic substances, since 1972. Marijuana is on the list, as it were. Were we to legalize it, we would be the only United Nations member to do so. Pot was legal in many Mideastern countries, probably since ancient times. One by one, these nations chose to make it illegal. Many did so because marijuana use appeared to make people apathetic and cognitively impaired. Did they seem to know something we didn’t (or don’t)? Since the early seventies mental health researchers have defined something labelled “amotivational syndrome”, believed to be caused by excessive marijuana use, particularly by teens. Do we really need to have this added to our plates? Don’t forget, it’s not your parents’ weed anymore, but something much more potent.

My First Blog Post

The Biden crime bill and Crack

— Oscar Wilde.

In the late 1980’s, cities in this country were confronted with a new drug fad involving cocaine; namely, “freebasing”. Traditionally, cocaine is abused by “snorting”; the user inhales the powder up the nose. This can be somewhat uncomfortable, In that the individual crystals are rather sharp, and repeated use can damage the septum, the membrane between the nostrils.

I hate to do this, but we need to consider some chemistry here. Cocaine, along with most other drugs, fall into a category called “nitrogeneous bases”, substances that contain nitrogen in the molecule. These are frequently messy, smelly liquids (think of ammonia). As such their physical properties render them unfit for ingestion. What is generally done about this is to convert them chemically to acid salts, usually the hydrochloride (HCl). This dramatically alters them to a more suitable form for use in the body. For instance, the conversion makes them dissolve better I n water, which makes up most of us. Another property which changes is the melting point; it is much lower in the freebase form. One can smoke the stuff, which gives a quicker high, and avoids damage to the nose. Win-Win!

In a pervious life, I worked in DEA forensic labs. I was once called upon to do a dog-and-pony show for agency higher-ups. I took a gram of cocaine HCl , added an ounce or so of water and a teaspoonful of baking soda, stirred briefly, and a white solid dropped to the bottom of the beaker. I poured out the water, and voila! Crack cocaine!!

In so doing, however, I increased the penalty for dealing the mere gram of coke (as the HCl salt) to what it would have been for a kilo. Talk about value added!

Evidentally, Joe Biden, then a senator, had some responsibility for drastically increasing penalties for trafficking on crack, vis a vis cocaine as the HCl salt. This had the unintended consequence of filing jails with low level druggies, mostlyminorities, with no effect to speak of on cocaine trafficking by the organized crime cartels, who rarely fooled with crack.

The crack epidemic was a crisis in many large cities at the time. Whether this did any good to deal with the problem is well above my pay grade. The law was modified in 2010 to reduce the sentencing disparity from 1,000 to 18. It is probably still too great, but a baby step in the right direction, maybe.

Introduce Yourself (Example Post)

This is an example post, originally published as part of Blogging University. Enroll in one of our ten programs, and start your blog right.

You’re going to publish a post today. Don’t worry about how your blog looks. Don’t worry if you haven’t given it a name yet, or you’re feeling overwhelmed. Just click the “New Post” button, and tell us why you’re here.

Why do this?

  • Because it gives new readers context. What are you about? Why should they read your blog?
  • Because it will help you focus you own ideas about your blog and what you’d like to do with it.

The post can be short or long, a personal intro to your life or a bloggy mission statement, a manifesto for the future or a simple outline of your the types of things you hope to publish.

To help you get started, here are a few questions:

  • Why are you blogging publicly, rather than keeping a personal journal?
  • What topics do you think you’ll write about?
  • Who would you love to connect with via your blog?
  • If you blog successfully throughout the next year, what would you hope to have accomplished?

You’re not locked into any of this; one of the wonderful things about blogs is how they constantly evolve as we learn, grow, and interact with one another — but it’s good to know where and why you started, and articulating your goals may just give you a few other post ideas.

Can’t think how to get started? Just write the first thing that pops into your head. Anne Lamott, author of a book on writing we love, says that you need to give yourself permission to write a “crappy first draft”. Anne makes a great point — just start writing, and worry about editing it later.

When you’re ready to publish, give your post three to five tags that describe your blog’s focus — writing, photography, fiction, parenting, food, cars, movies, sports, whatever. These tags will help others who care about your topics find you in the Reader. Make sure one of the tags is “zerotohero,” so other new bloggers can find you, too.