Bagseed
Bluelighter
here we go again...
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N&PD Moderators: Skorpio | someguyontheinternet
I Like to Draw Pictures of Random Molecules
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little known Cannabis molecules:
Cannabisativine (isolated from roots bark of sativa not the buds!):
Looks (remotely) like anandamide (endogenous cannabinoid receptor ligand) could be CB agonist or antagonist.. anybody knows anything about this compound??
Here is Anandamide :
Cannabisativine (isolated from roots bark of sativa not the buds!):
Looks (remotely) like anandamide (endogenous cannabinoid receptor ligand) could be CB agonist or antagonist.. anybody knows anything about this compound??
Here is Anandamide :
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I doubt that macrocyclic compound would have any endocannabinoid-like activity as it lacks any double bonds, which are necessary for activity. I posted structures here of simpler compounds that would have activity, including one that has been isolated from an evergreen shrub's seeds. Interestingly, those seeds are a brisk selling item on eBay.
I haven't studied the SAR for these but the key portions are the multiple double bonds, which both act to fold the chains to mate with the receptor & to act in binding. The terminal end can be either an amide or either a 2-gylyceryl ester or ether.
I haven't studied the SAR for these but the key portions are the multiple double bonds, which both act to fold the chains to mate with the receptor & to act in binding. The terminal end can be either an amide or either a 2-gylyceryl ester or ether.
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Alpha-Linolenic Acid for your cardiac health
In a break from the usual posts in this forum I'd like to talk about a recent discovery of mine that is actually good for you: omega-3 fatty acids & in partiuular alpha-linolenic acid.
Lipids are fats produced in the body & that circulate in the blood stream. These, in general, occur as 2 types: lipoproteins that carry cholesterol & triglycerides, which are similar to natural animal fats in that they consist of glycerol esterified by 3 molecules of fatty acids. Both Low-Density Lipoprotein (LDL) & triglycerides, if present at high levels, can bind to the walls of arteries and result in the formation of atherosclerotic plaque. IOW, hardening of the arteries. This is a bad thing as these plaques build up they can lead to heart attacks & strokes.
Big pharma is introducing a number of products intended to lower high triglyceride levels. These are in the form of 1 gram enteric capsules filled with highly purified omega-3 fatty acids or their ethyl esters. Omega-3 acids are thought to be effective in lowering triglyceride levels. But these products are in the form of big capsules that I have difficulty swallowing & they are expensive, as all new drug products tend to be.
I am concerned about both LDL & triflycerides. I take Lipitor, a so-called statin, a sterol biosynthesis inhibitor to keep my LDL levels in the right range. So I grew concerned about managing my triglycerides & started reading some articles on the net.
I found that walnuts contain high levels of an omega-3 fatty acid called alpha-linolenic acid. In fact, 1 ounce of walnut meat contains 2.5 grams of it. So I am now taking an ounce a day of tasty walnuts. Even my doctor thought that this was a good idea. And an inexpensive as well as tasty solution to my triglyceride problem.
In a break from the usual posts in this forum I'd like to talk about a recent discovery of mine that is actually good for you: omega-3 fatty acids & in partiuular alpha-linolenic acid.
Lipids are fats produced in the body & that circulate in the blood stream. These, in general, occur as 2 types: lipoproteins that carry cholesterol & triglycerides, which are similar to natural animal fats in that they consist of glycerol esterified by 3 molecules of fatty acids. Both Low-Density Lipoprotein (LDL) & triglycerides, if present at high levels, can bind to the walls of arteries and result in the formation of atherosclerotic plaque. IOW, hardening of the arteries. This is a bad thing as these plaques build up they can lead to heart attacks & strokes.
Big pharma is introducing a number of products intended to lower high triglyceride levels. These are in the form of 1 gram enteric capsules filled with highly purified omega-3 fatty acids or their ethyl esters. Omega-3 acids are thought to be effective in lowering triglyceride levels. But these products are in the form of big capsules that I have difficulty swallowing & they are expensive, as all new drug products tend to be.
I am concerned about both LDL & triflycerides. I take Lipitor, a so-called statin, a sterol biosynthesis inhibitor to keep my LDL levels in the right range. So I grew concerned about managing my triglycerides & started reading some articles on the net.
I found that walnuts contain high levels of an omega-3 fatty acid called alpha-linolenic acid. In fact, 1 ounce of walnut meat contains 2.5 grams of it. So I am now taking an ounce a day of tasty walnuts. Even my doctor thought that this was a good idea. And an inexpensive as well as tasty solution to my triglyceride problem.
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you right, it might not .. altho I was thinking the macrocycle might mimic the pseudo-carbocycle of anandamide: the double bonds of anandamide and related arachidonic merely restrict the molecule into a pseudocyclic conformation .. but who knows?.... was just curious about these sativa alkaloids like these others:
Cannabisin A:
Cannabisin B:
or Grossamide:
may or may not have cannabinoid psychoactivity.. .. may be opioids.. but who knows?? (I couldnt find any biological data on those)
could you repost structures again when you have the chance??.. are they alkaloids or fatty acids...
I take 145 mg of
![O-isopropyl-2-[4-(4-chlorobenzoyl)phenoxy]-2-methyl-propanoic%20acid.png](/community/proxy.php?image=https%3A%2F%2Fopsin.ch.cam.ac.uk%2Fopsin%2FO-isopropyl-2-%5B4-%284-chlorobenzoyl%29phenoxy%5D-2-methyl-propanoic%2520acid.png&hash=031cbcfa358679d4cac4577a67c545f3)
TRICOR (fenofibrate)
every AM for high blood triglycerides.
I looked at the fibrates as one option along with niacin (nicotinic acid) & the omega-3 fatty acids. The expense as well as the side effects with both the fibrates & niacin did not turn me on. When I found the natural source for the linolenic acid it was an easy choice. My doctor liked the omega-3 choice & did not suggest either a fibrate or niacin. This was yesterday when I had my annual Medicare physical so she took her time with me. Even though she is a DO & not an MD, she's very sharp & I value her opinions.
While my LDL & triglycerides are normal, I recently had an echocardiogram to compare against one I had taken 4 years ago & there were enough negative differences in plaque build-up in my ascending aorta for my doctor to suggest I see a cardiologist. I drink more than I should (vodka at ice temp, Russian style) & ethanol is one of the factors that drives triglyceride production. So my choice of adding linolenic acid was defensive. The cardiologist (2 months to get an appointment!) may have other thoughts. I'm planning to get my blood tested for lipids before I see him so we both know what we're talking about.
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you right, it might not .. altho I was thinking the macrocycle might mimic the pseudo-carbocycle of anandamide: the double bonds of anandamide and related arachidonic merely restrict the molecule into a pseudocyclic conformation .. but who knows?.... was just curious about these sativa alkaloids like these others:
Cannabisin A:
Cannabisin B:
or Grossamide:
may or may not have cannabinoid psychoactivity.. .. may be opioids.. but who knows?? (I couldnt find any biological data on those)
could you repost structures again when you have the chance??.. are they alkaloids or fatty acids...
There are only 2 species in the plant family Cannabinaceae: Cannabis (marijuana, hemp) & Humulus (hops). There are a lot of interesting secondary metabolites in hops that you might want to take a look at. Who knows what you're ingesting when you have a beer?
FYI I am using ChemDraw 17 Professional to draw structures & the free image posting app PostImage. The ChemDraw is a hoot as it is a lot of fun & very easy to use once you get the hang of it. The downside is that it costs something like $1,500 for the whole ChemOffice bundle from Perkin-Elmer but I got my copy free for participating in one of their new release beta-test.
Nagelfar
Bluelight Crew
Rather fanciful structures that combine both pharmacophores of morphine but avoids the fused ring system of that alkaloid. They appear to be difficult molecules to approach synthetically. The 6-methyl should have been drawn as being in a chiral center.
Interestingly, as far as the EPA is concerned, the racemic form of this aminoindene is a known compound (CAS [FONT=&]78950-87-5).
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Further reducing the fanciful structures in order to obtain morphine analogs with simpler structures, I came up with this:
These are great empirical studies from a purely abstract starting/standpoint. This thread needs more of the above style and ambition.
(then again, it may just be the fantasy of the compound in question in my present state)
reminds me of the benzomorphan class, like Dezocine:
Thanks for the reply. Interesting that you should bring up dezocine, as the bonding pattern between the phenolic atomatic ring & the nitrogen atom is different from the examples I have presented in prior posts. It's also interesting that the nitrogen atom in dezocine is primary as compared to the tertiary atom in morphine. These differences may help to explain its mixed agonist/antagonist activity.
There appears to be more possibilities for dreaming up biologically active opioid molecules than I had thought if this alternate bonding scheme is adopted, though my principal focus has been on pure agonists modeled after morphine.
I had not intended to do a thorough analytical survey of the morphine analogs. Most of my books on drugs, such as Lednicer's survey, are still hidden in boxes that remain unpacked since I moved nearly 4 years ago! Just as well, as I don't have the shelf space for them since we downsized. The internet & Google have replaced the need for most of my books, luckily.
Here is the Wikipedia article on dezocine: https://en.wikipedia.org/wiki/Dezocine. It is no longer sold or used outside of China.
There appears to be more possibilities for dreaming up biologically active opioid molecules than I had thought if this alternate bonding scheme is adopted, though my principal focus has been on pure agonists modeled after morphine.
I had not intended to do a thorough analytical survey of the morphine analogs. Most of my books on drugs, such as Lednicer's survey, are still hidden in boxes that remain unpacked since I moved nearly 4 years ago! Just as well, as I don't have the shelf space for them since we downsized. The internet & Google have replaced the need for most of my books, luckily.
Here is the Wikipedia article on dezocine: https://en.wikipedia.org/wiki/Dezocine. It is no longer sold or used outside of China.
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C12H16N2O-OH-OH-YE
Greenlighter
- Joined
- Jul 27, 2018
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*read my SN*
OP: I just went ahead and changed my legal name as well , since (instead of wrighting danger fantastic I'd written the chemical formula out on the application already.. The OH-OH-YE was simply flashback and a turret happening simultaneously. I decided to keep it. It bonds we'll
Im glad to know I'm not alone!! ��
OP: I just went ahead and changed my legal name as well , since (instead of wrighting danger fantastic I'd written the chemical formula out on the application already.. The OH-OH-YE was simply flashback and a turret happening simultaneously. I decided to keep it. It bonds we'll
Im glad to know I'm not alone!! ��
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You're in the wrong forum.
Interesting recent article on the effect of a wide range of natural product molecules as GABA(A) receptor modulators. Available full text as pdf download at:
http://www.mdpi.com/1420-3049/23/7/1512.
http://www.mdpi.com/1420-3049/23/7/1512.
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https://en.wikipedia.org/wiki/Apigenin
Interesting molecule, available online & in health food stores. Possibly a true 'mellow yellow.' Likely acts as an antioxidant beside it's listed biological effects.
From the Wikipedia article:
Apigenin acts as a monoamine transporter activator, one of the few chemicals demonstrated to possess this property.[8] Apigenin is a weak ligand for central benzodiazepine receptors in vitro and exerts anxiolytic and slight sedative effects in an animal model.[9] Apigenin shows second-orderpositive modulatory activity at GABAA receptors.[10][11] It has also effects on adenosine receptors[12] and is an acute antagonist at the NMDA receptors (IC50 = 10 μM).[11] In addition, like various other flavonoids, apigenin has been found to possess nanomolar affinity for the opioid receptors (Ke = 410 nM, 970 nM, and 410 nM for the μ-, δ-, and κ-opioid receptors, respectively), acting as a non-selective antagonist of all three opioid receptors.[13]
A note of caution from the same article:
In vitro studies have shown that apigenin may be toxic to red blood cells.[14]
Interesting molecule, available online & in health food stores. Possibly a true 'mellow yellow.' Likely acts as an antioxidant beside it's listed biological effects.
From the Wikipedia article:
Apigenin acts as a monoamine transporter activator, one of the few chemicals demonstrated to possess this property.[8] Apigenin is a weak ligand for central benzodiazepine receptors in vitro and exerts anxiolytic and slight sedative effects in an animal model.[9] Apigenin shows second-orderpositive modulatory activity at GABAA receptors.[10][11] It has also effects on adenosine receptors[12] and is an acute antagonist at the NMDA receptors (IC50 = 10 μM).[11] In addition, like various other flavonoids, apigenin has been found to possess nanomolar affinity for the opioid receptors (Ke = 410 nM, 970 nM, and 410 nM for the μ-, δ-, and κ-opioid receptors, respectively), acting as a non-selective antagonist of all three opioid receptors.[13]
A note of caution from the same article:
In vitro studies have shown that apigenin may be toxic to red blood cells.[14]
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^ Interesting.. Best source of apigenin tho is Passion Flower extract. Contains more apigenin than Chamomille + other more potent GABAergic flavonoids like vitexin ie 8-(6-glycosyl)-apigenin .. the ultimate "yellow mellow" really..
Here is vitexin structure:
As well as oxazepam? no wonder FDA tried to ban it.. anyway very interesting compounds..thanks for posting..
Here is vitexin structure:
Hereis an interesting review of passion flower extract: https://www.webmd.com/vitamins/ai/ingredientmono-871/passionflower. Seems useful, for a number of things but according to them it was taken off the market in 1978. Here is the Wikipedia article on vitexin, though it doesn't give anything on biological activity: https://en.wikipedia.org/wiki/Vitexin. It's the flavone glucoside if apegenin & would be expected to have similar effects.
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Meptazinol, a very simple opioid analgesic. Mixed agonist/antagonist activity. I screwed up when I drew the receptor binding correlation. There is only a 2-carbon bridge between the phenol group & the tertiary amine in morphine. I'll post a new analog of this that may have pure agonist activity.
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