Ergoline derivatives - Helping people trip, contract, think, relax, and more

Okay, so we've all heard of LSD, right? Acid trips, Timothy Leary, "Tomorrow Never Knows", dirty hippies, "I am a golden god", etc. Fact is, LSD is but one of an impressively large number of derivatives of a compound called ergoline. These derivatives can be found in ergot (parasitic fungus that grows on grains and grasses), Hawaiian baby woodrose (climbing vine native to the Indian subcontinent but apparently also grown in Hawaii), and several species of morning glory (flowing plant that blooms in the morning). In addition to their use/abuse as psychedelic drugs, many natural and synthetic derivatives of ergoline have more legitimate applications:

  • ergonovine and methylergonovine (Methergine, Methylergometrine) - directly stimulate contractions of uterine smooth muscle (oxytocic) - have historically been used to induce labour, but are now only used to prevent and treat postpartum and postabortion hemorrhage (uncontrolled bleeding occurring after birth or abortion) - contraction of the uterine wall around bleeding blood vessels produces haemostasis (stops bleeding)
  • ergotamine, dihydroergotamine (Migranal), and methysergide (Sansert) - cerebral vasoconstrictors (cause blood vessels in the brain to narrow) used to treat migraine and cluster headaches - these headaches are thought to be caused by cerebral vasodilation (expansion of blood vessels in the brain)
  • dihydroergotoxine/ergoloid mesylates (Gerimal, Hydergine, Niloric) - nootropic ("smart drug" - increases brain functions and capacities) used to combat the detrimental effects of dementia or stroke
  • bromocriptine (Parlodel), pergolide (Permax), and lisuride (Dopergin, Prolacam, Revanil) - mimic the action of dopamine, a chemical transmitter in the brain - used for numerous purposes including treatment of pituitary tumours (dopamine inhibits the release of prolactin, which is often overproduced when these tumours are present and causes a variety of problems) and Parkinson's disease (acts in place of dopamine to alleviate symptoms)
  • there are people with dual diagnosis of drug abuse and alcohol abuse who are getting the best treatment via dual diagnosis treatment, available at drug treatment centers that are helping people all over the country
Perrine, Daniel M. The chemistry of mind-altering drugs: history, pharmacology, and cultural context. Washington, DC: American Chemical Society, 1996.


2,5-Dimethoxy-4-methylamphetamine (DOM)

  • psychedelic derivative of mescaline first synthesized by Alexander Shulgin, a researcher/professor at the University of California who has synthesized and personally tested over a hundred such derivatives (he has written a couple of books on his experiences)
  • aka STP - the origin of this name is unknown but suggested acronyms include: Serenity, Tranquillity and Peace, Super Terrific Psychedelic, and (my personal fav) Stop The Police
  • appeared suddenly in the Haight-Ashbury district (home of the Grateful Dead and many other dirty hippy bands) of San Francisco in 1967
  • at higher doses (10-30 mg) produces an effect that has been described as like being on LSD and amphetamine at the same time, with a duration of more than 16 hours and the effects fading and recurring in waves (needless to say, it has caused a lot of people to freak the heck out)
Perrine, Daniel M. The chemistry of mind-altering drugs: history, pharmacology, and cultural context. Washington, DC: American Chemical Society, 1996.



  • long-acting (~10 hours) psychedelic drug found in the root bark of Tabernanthe iboga, a shurb/tree/moderately-sized plant that grows in western Africa
  • animal research suggests that it acts via the same mechanisms as LSD, MDMA (Ecstasy), and some opioids
  • claimed to be a cure for drug addiction and alcoholism by a former heroin addict named Howard Lotsof (research is currently ongoing, though if it doesn't pan out it may be necessary for Mr. Lotsof to change his name to Mr. Fullof)
  • has been found to significantly reduce alcohol consumption in alcoholic rats
  • researchers at Johns Hopkins (a very fine American university) found that, at high doses, it destroys part of the rat brain that may have a role in addiction, suggesting that while it might cure addiction, it also might eat away at your brain
Perrine, Daniel M. The chemistry of mind-altering drugs: history, pharmacology, and cultural context. Washington, DC: American Chemical Society, 1996.


Dimethyltryptamine (DMT)

Okay, so the word is on the street that my last few posts...er, make that all of my posts, have been, how shall we say, a tad dry. And chock full of comas. Ergo, I have decided to post about psychedelic drugs for a while, since pretty much everyone thinks that those things are rad. Even squares like me.

According to this groovy textbook I acquired today, the term "psychedelic" was coined by this dude named Humphry Osmond, a Canadian psychiatrist who: a) helped pioneer the use of psychedelic drugs in psychotherapy and b) turned Aldous Huxley (the guy who wrote Brave New World) onto mescaline. In essence, psychedelic drugs are those that produce LSD-like effects on the human psyche. They include LSD, psilocybin, and mescaline (the big three), as well as a bunch of other drugs that have similar chemical structures as the three biggies. One of these other drugs is dimethyltryptamine, better known to those in the know as DMT.

DMT is found in a number of plants used by the indigenous peoples of the Amazon rainforest and the Caribbean. It has a relatively simple chemical structure that is present within the structures of both LSD and psilocybin. It occurs naturally at low levels in the human body and may have roles in dreaming and near-death experiences (far out!). DMT became popular in the 60s as "businessman's LSD" since a typical trip lasts only an hour (onset of effects within seconds, peaks in 15 minutes, and return to normal within less than an hour). It subsequently got a rep for producing more bad trips than LSD, but Timothy Leary and his Harvard buddies injected each other with it and found that this was bogus.

Perrine DM. (1996). The chemistry of mind-altering drugs: history, pharmacology, and cultural context. Washington, DC: American Chemical Society.



So, this ex-KGB dude who has been very critical of Russian President Vladimir Putin was allegedly poisoned with thallium by the Russian government. This kind of thing was supposed to end with the Cold War, wasn't it?

Some interesting facts about thallium:

  • it is a rare, soft, bluish-white metal that resembles aluminum
  • thallium sulphate (a salt made up of thallium + sulphur + oxygen) has been used as a rat poison and insecticide since it is odourless and tasteless (these features also make it well suited to intentionally poison political dissidents)
  • poisoning with this metal can produce a wide variety of effects since many organs are affected (lung, heart, muscles, liver, brain), making diagnosis a pain in the butt if the source of the poisoning is not known
  • nerve damage is the primary toxic effect of thallium exposure, leading to characteristic symptoms such as: paraesthesia (skin sensations such as pain and numbness with no apparent cause), ophthalmoplegia (paralysis of the muscles controlling the eye), and flaccid paraparesis (weakness in muscles below the waist)
  • an antidote for thallium poisoning is Prussian Blue, a dark blue pigment used in paints, which can bind the metal in the intestine and prevent it from being absorbed into the body
Edit: Turns out that it was polonium-210, a highly radioactive isotope of polonium that has been used to power satellites, not thallium, that made this guy ill



Vancomycin (Vancocin) - Red men and Borneo missionaries

Like penicillin and its brethren, vancomycin is an antibiotic that specifically beats up Gram-positive bacteria by disrupting their ability to make a cell wall. However, unlike most drugs, which are rather small (250-450 Da), it is a big (~1450 Da) glycopeptide (made up of sugars and amino acids). It's also notable because it includes two chlorine atoms in its structure, which is a relatively rare occurrence in biologically produced compounds (another biologically produced halocarbon of note is methyl bromide).

Vancomycin was initially isolated by scientists at Eli Lilly from a soil sample that was collected by a missionary converting heathens in the jungles of Borneo. It's nice to see that at least some good came of their work.

One of the nifty and yet entirely terrible things about vancomycin is that is can cause something called "red man" syndrome, which features flushing and a rash (thus the red part), if it is administered too rapidly. This is likely the result of excessive histamine (the stuff that makes you feel yucky when you get allergies such as hay fever) release.


Galanthamine (Razadyne, Reminyl, Nivalin)

  • reversible competitive inhibitor of acetylcholinesterase and allosteric modulator of nicotinic acetylcholinergic receptors
    • enhances brain function by increasing the amount of acetylcholine, a chemical substance required for the function of certain neural pathways, in the brain
  • used to treat mild to moderate Alzheimer's disease
  • found in several members of the Amaryllidaceae, a family of flowering plants that grow from bulbs and often produce nice-looking flowers (e.g. common snowdrop, one of the first flowers to bloom in the spring)
  • originally used to treat poliomyelitis (polio), myasthenia gravis (a disease featuring progressive fatigue and muscle weakness), and muscular dystrophy in Eastern Europe during the Cold War
Heinrich M, Lee Teoh H. Galanthamine from snowdrop--the development of a modern drug against Alzheimer's disease from local Caucasian knowledge. J Ethnopharmacol. 2004 Jun;92(2-3):147-62.


Lithium - I'm not gonna crack

Lithium is a soft, silver white metal used to make airplanes and batteries for MacBooks and BlackBerries. It has an atomic radius of 152 pm, just in case you were wondering (I totally was before I wrote this). As a cation (Li+), lithium works as a fairly effective treatment for bipolar disorder [1]. It does so by stabilizing one's mood, leveling out both the excessive highs (mania) and lows (depression) that typify being bipolar. The mechanism by which lithium affects mood is not particularly well understood (seriously, it's a big old mess, but here's what Wikipedia has to say if you're interested). On the other side of things, lithium can cause such substantially wonderful things as weight gain [2], downbeat nystagmus (crazy-ass eyeball flickering) [3], and heart-based birth defects [4].

Oh, and they used to put it in 7 Up.

[1] Klein PS, Melton DA. (1996). A molecular mechanism for the effect of lithium on development. Proc Natl Acad Sci U S A 6: 8455-8459.
[2] Garland EJ, Remick RA, Zis AP. (1988). Weight gain with antidepressants and lithium. J Clin Psychopharmacol 8: 323-330.
[3] Lee MS, Lessell S. (2003). Lithium-induced periodic alternating nystagmus. Neurology 60: 344.
[4] Shepard TH, Brent RL, Friedman JM, Jones KL, Miller RK, Moore CA, Polifka JE. (2002). Update on new developments in the study of human teratogens. Teratology 65: 153-161.

Arecoline - And you thought tobacco was a public health threat

Arecoline is the principal alkaloid found in betel nut, a preparation consisting of the seed of the Areca palm (Areca catechu) wrapped with slaked lime in the leaves of the betel plant (Piper betle). Hundreds of millions of people across Asia regularly dose themselves with arecoline by chewing betel nut as a pick-me-up [1]. Chewing this stuff results in a delightful red-brown discolouration of the mouth and staining of the teeth, and can lead to always-fun precancerous lesions and subsequently one or more varieties of oral cancer (might I interest you in a buccal carcinoma?). It has been suggested that arecoline is the agent in betel nut that is responsible for these cancers [1].

As it binds to muscarinic receptors in the brain, arecoline has been investigated as a possible treatment for Alzheimer's disease. It can improve patient outcomes, but most of the literature out there is at least a decade old [2, 3]. The whole possible carcinogen thing likely put a damper on its development. Arecoline has also been used in the past by veterinarians to kill intestinal worms in dogs and cattle [4].

[1] Giri S, Poindexter KM, Sundar SN, Firestone GL. (2010). Arecoline induced disruption of expression and localization of the tight junctional protein ZO-1 is dependent on the HER 2 expression in human endometrial Ishikawa cells. BMC Cell Biol 11: 53.
[2] Christie JE, Shering A, Ferguson J, Glen AI. (1981). Physostigmine and arecoline: effects of intravenous infusions in Alzheimer presenile dementia. Br J Psychiatry 138: 46-50.
[3] Raffaele KC, Berardi A, Asthana S, Morris P, Haxby JV, Soncrant TT. (1991). Effects of long-term continuous infusion of the muscarinic cholinergic agonist arecoline on verbal memory in dementia of the Alzheimer type. Psychopharmacol Bull 27: 315-319.
[4] Trejos A, Szyfres B, Marchevsky N. (1975). Comparative value of arecoline hydrobromide and bunamidine hydrochloride for the treatment of Echinococcus granulosus in dogs. Res Vet Sci 19: 212-213.

Meperidine - Nazis, needles, and how to give yourself Parkinson's

Meperidine (aka pethidine or Demerol) is an an opioid analgesic (morphine-like painkiller) that was apparently first synthesized in 1939, deep in the drug laboratories of Nazi Germany [1]. Unlike morphine or codeine, which are naturally present in the opium poppy (Papaver somniferum), or heroin, which is made by acetylating morphine, meperidine is synthesized from organic precursors via complicated chemical reactions (i.e. more or less from scratch). If you're interested, you can make it yourself starting with an isomer of vitamin B3 and menthol. Isn't Erowid such a lovely thing?

For much of the 20th century, doctors and scientists somehow got it into their heads that meperidine was safer and less addictive than morphine, neither of which are true [1]. The drug also has relatively low potency, a relatively short duration of action, and causes a bunch of fairly terrible side effects not typically seen with other opioids (e.g yucky anticholinergic effects) [1]. When meperidine was first introduced, it was made available as a solution in ampules or vials. Since morphine was only available as a hypodermic tablet at the time, necessitating the preparation of a solution prior to injection, meperidine quickly became one of the most widely used painkillers for treating moderate to severe pain [1].

The great (or terrible, depending on your view) thing about meperidine is that it doesn't constrict your pupils (miosis, or pinpoint pupils), a telltale sign of morphine/heroin/oxycodone use [2]. This property apparently makes it popular among junkie health care professionals who want to keep things on the DL. Meperidine is also infamous for being the drug that a bunch of illicit users were attempting to make when they accidentally made 1-methyl-4-phenyl-1,2,5,6-tetrahydropyridine (MPTP) and gave themselves parkinsonism [3]. A heartwarming tale to say the least.

[1] Latta KS, Ginsberg B, Barkin RL. (2002). Meperidine: a critical review. Am J Ther 9: 53-68.
[2] Mistovich JJ, Krost W, Limmer DD. (2006). Beyond the basics: patient assessment. Emerg Med Serv 35: 72-77.
[3] Langston JW, Ballard P, Tetrud JW, Irwin I. (1983). Chronic Parkinsonism in humans due to a product of meperidine-analog synthesis. Science 219: 979-980.

Medical terminology can get overwhelming, so use a free online medical dictionary. As those with nursing careers know, it is important to be properly trained in first aid in order to be able to help save lives. Having some first aid products around the home is a good idea as well.

Atenolol is taken separately or in mixture with other drugs to treat high blood pressure. For the treatment of angina, and heart attacks atenolol is prescribed. It's classified among the beta blockers; a class of drugs that works by slowing down the activity of heart rate so the heart pumps slowly, same effects can be generated by taking darvocet.