My favorite drug structures to draw, that I've learn this summer, 2023

 Hey team,

Today I will draw out all the drugs I've learned and memorized this summer. After taking organic chemistry, both 1 and 2, this past year at university I learned how to use skeletal structures as a way to understand the structure of different organic (carbon based) chemicals. Though we didn't have to learn any specific compounds in this class, I started to dive more into the specific drugs I found interesting around me. These are drugs for common health conditions, psychiatric conditions, recreational purposes, plant derived and so on. There isn't a need to know the structure of these drugs unless you are an organic chemist synthesizing them, so for me it's kynda just for fun and a fun challenge that happens to align well with my education and career path. Over this summer I have lots of books of psychiatry and pharmacology and have also read many papers and looked up individuals drugs as well to learn and indulge in that which I find interesting and learn new structures as a fun challenge. I then like to try to memoize the structure by drawing it over and over and eventually it sticks. It's gotten significantly easier each time I learn a new one. Before it would take me a day to learn 1 structure however now I can learn countless a day through a few glances and analysis. 

Let me briefly explain how these structures work. Each point represents a new carbon, sense it is so so abundent chemists realized it could be the default and we could draw the other elements in. So if you see an O in the mix of lines, that represents an atom of oxygen. If you see an N, that represents a nitrogen. We can also assume that every carbon has a proper amount of hydrogens attached so those are also not drawn in. Each carbon can have 4 attachments, this can be 4 bonds or something like 2 double bonds, 1 triple bond and 1 single bond, ect. As long as there are 4 total lines, that's all that matters. The first picture is shown right, hopefully it makes sense. 

Okay, into the meat and potatoes. 

To the right I have some different alkaloids meaning compounds with a basic nitrogen in them. The top two compounds, ibogenic acid and muscimol come from the Amanita Muscaria mushroom (fly agaric) and are some of the first psychoactive drugs ever used my native peoples. Ibogenic acid is stimulating and muscimol is sedating/ calming.

Below that we see Atropine and Scopolamine, nearly identical compounds from the Atropa Belladonna plant that block the neurotransmitter acetylcholine (shown at the very bottom) from doing its job. The name Belladonna means beautiful woman and is called that as women used to put these compounds in their eyes as they act as pupil dilators, giving a traditionally beautiful appearance.  They have many other effects outside of pretty eyes, and are rarely used for this goal.

Nicotine is below that which acts on the acetylcholine system as well. It activates a subtype of the acetylcholine receptors known as (get this) nicotinic receptors. 

Next page! At the top is ibogaine, the active chemical from the Tabernanthe iboga plant. It acts at the Kappa opioid receptor, which is not associated with traditional opioids. It also blocks the reuptake of serotonin which allows more free serotonin to effect the post synaptic neuron (exactly like the antidepressants referred to as SSRIs).

Below that is Resperine, which is the largest compound I've learned. It comes from Rauwolfia serpentina (also known as Indian snakeroot). It was used to calm down psychotic patients and even had some success in western medicine as well and helped lead to further advances. 

And then there is cocaine, from the coca plant native to South America. Natives used to chew these leaves and had lots of stamina and reduced appetite. When chewed it has a very gradual and relatively weak onset, comparable to coffee. When isolated and snorted or smoked it's exponentially stronger. It works by blocking the reuptake of dopamine which leads to more dopamine available to synapse with more neurons. It also has a weak mechanism of blocking reuptake on serotonin and norepinephrine neurons. ALSO, it is a great local anasethetic (like when you get cavities filled) which led to the discovery of more local anesthetics like lidocaine and procaine.

Here are some opioid agonists (and gabapentin) with activity at different subtypes of receptors which produce significantly different psychological effects. Morphine comes directly from the opium poppy and can be easily made into heroin (diacetylmorphine) and enters the brain easier but is quickly turned back into morphine to produce its effects. 

Below those two is the compound salvinorin A, from the Salvia Divinorum plant native to the Oaxaca area of southern mexico. It effects the kappa opioid receptor, like ibogaine!

And for fun gabapentin is below that. Although named after the neurotransmitter GABA, gabapentin does NOT act on the GABA system but instead helps precent calcium from entering a neuron which is needed to "activate" a neuron and have it release its chemicals to the next neuron. 

Antihistamines!! The top one is diphenhydramine, better known as benedryl. It was one of the OG drugs in this class and led to the discovery on fluoxetine! Below that is Hydroxyzine, which also has strong anxiolytic effects (kills anxiety) from its effects on serotonin. And cetirizine (zyrtec) is below that. Apparently hydroxyzine is metabolized into certizine in the body, but I'm skeptical, they look too different. 

Fun ones ahead! At the top is LSD aka Acid. Works but agonizing (binding with effect) to the subtype of serotonin receptor known as 5HT 2A which shuts down your default mode network which is home to the idea of self and ego, which is made up and you should let go of, but thats for next time. 

Below that is olivelic acid which is the precursor to the CBGA, which itself is a precursor to compounds like THC, CBD and CBC. These are known as phytocannabinoids  meaning cannabinoids from a plant. 

The structure of cannabichromic acid (CBCA) is below that which is a lesser known cannabinoid.

Andddd below that are the two most abundent endocannabinoids. This means cannabinoids that your body makes. They are aptly named after the cannabis plant even though the endocannabinoid system was apart of nature far before the cannabis plant even came about. These compounds are released and bind to the receptors called CB1 and CB2. They serve important roles in pain, inflammation and more. 

 

 Terpenes!!! Terpenes are simple hydrocarbon (hydrogen and carbon) based structures that are found throughout the plant kingdom. They contribute heavily to the unique smell of plants and have unique roles and effects of their own as well. Unlike most plants which produce maybe 1 or a few terpenes, the cannabis plant produces a TON! However in commercial cannabis (both high THC and CBD dominant "hemp") the following terpenes are all you'll really see in abundence. 

Myrcene is in like very strain of cannabis ever but if it's the dominant terpene is will make you SLEEPY. It's also known to be good for pain as well!

Linalool is also sedating and especially good for anxiety. It's found in lavender in high levels and is more common in more purple colored strains of cannabis (like lavender). 

Beta-caryophyllene is the terpene that can give that gas/ fuel/ rubber smell. Fan favorite for sure. Its a strong anti inflammatory because it can actually act on CB2 receptors, like THC and the endocannabinoid. Alpha humelene is very similar to caryophyllene and you'll almost always find them is similar concentrations. They look very similar.

The right side of the paper contains the stimulating terpenes. Terpinolene smells amazing and is distinct. Terpinolene, along with pinene,  are partial cholinesterase inhibitors. Let me explain why this is good. Cholinesterase is an enzyme that breaks down acetylcholine, mentioned earlier, a bunch of annoying side effects like dry mouth and dry eyes, are due to low acetylcholine (called anticholinergic effects). If we prevent the breakdown of it we get more acetylcholine in your system available to keep things moisturized and ready to party! 

Limonene is also shown and is found in lemons and can be stimulating, think about the shock of eating a sour lemon and how it gives you some energy.

That is all for now, thank you!