• Neuroscience & Pharmacology Discussion Welcome Guest
    Posting Rules Bluelight Rules
    Recent Journal Articles Chemistry Mega-Thread
    FREE Chemistry Databases! Self-Education Guide

  • N&PD Moderators: Skorpio

JWH-171 - Hydrocarbon CB1 agonist

Think of that one as being the hydrocarbon analog of JWH-018. The typical alkylaminoindoles (ones with O and N in them too, based on indole) can have a better affinity (probably because polar interactions help in getting better affinity) but it does show that just intermolecular forces excluding polar interactions can satisfy binding conditions for that receptor by themselves - pretty cool I reckon. CB1 & CB2 are pretty promiscuous :D !
 
Looked at it and thought 'polycyclic aromatic hydrocarbon'... no polar handle to facilitate excretion, so probably a good candidate for epoxidation to open one of the aromatic rings by adding in an oxygen. Now this is how the likes of benzene etc are metabolized and also the mechanism by which they are fuck off nasty carcinogens as the intermediate epoxide compound will alkylate DNA as soon as look at it.

An interesting compound for cannabinoid receptor research, but I wouldn't let it get within 10 feet of my body...
 
interesting in that it proves no hydrogen bonding capacity is needed, but also i am not surprised that is so....and indeed not even remotely on the list of items in this class to consider tasting
 
Yep, F&B has it correct, I'd avoid any large cyclic compounds consisting only of hydrocarbons. As my highschool chemistry teacher always told me, "Hydrocarbons make for some neat bioactive compounds, however most of them also cause cancer."
 
Pretty amazing you can take out what most would have considered to be crucial elements and be left with an active compound.

I wonder how well this would work with the other unique cannabinoids.
 
With strategic placement of an -OH or -OCH3 group, one could probably create a more favorable metabolic profile. I'm convinced that a similar JWH-type compound is present in this "Spice Gold" legal smoke, vaporizes easily, partial agonist with low-to-moderate affinity for CB1.
 
I've heard reports of JWH-018, JWH-073 and JWH-200 all being available, and apparently they are all smokable and can be rather pleasant. None of them seem to have hit the "mainstream" RC scene yet, although I'd imagine its only a matter of time.

However I'm not sure that any of these is the active in Spice, simply because the Spice products have been around for quite a number of years now, since long before I heard of these JWH compounds cropping up. Phase_dancer has been dropping hints that his contacts have analysed the Spice and found what is in it, but are not yet ready to reveal their results, I will be most interested to see what they have found...
 
^he is saying it may not really be a cannabinoid but via GABA modulation it agonises CB1, I think is the latest (in spice)
 
I've heard reports of JWH-018, JWH-073 and JWH-200 all being available, and apparently they are all smokable and can be rather pleasant.
Click to expand...

As long as you don't make a pig of yourself with them as at higher doses they can produce some pretty intense symptoms of anxiety. They differ from THC in that they produce their peak effect almost instantaneously, unlike the 10-15 minute delay with cannabis/THC as they are not metabolized to a more active compound (THC is metabolized to the more active 11-hydroxy THC).

Rather than bother with the hydrocarbon , which is purely a research curio in my opinion, anyone interested in trying this group would be best advised to stick with the 1-alkyl-3-naphthoylindoles as they have a nice oxygen & nitrogen atom in their structure which allows the body to deal with them without the need for nasty routes like epoxidation
 
fastandbulbous said:
As long as you don't make a pig of yourself with them as at higher doses they can produce some pretty intense symptoms of anxiety. They differ from THC in that they produce their peak effect almost instantaneously, unlike the 10-15 minute delay with cannabis/THC as they are not metabolized to a more active compound (THC is metabolized to the more active 11-hydroxy THC).

Rather than bother with the hydrocarbon , which is purely a research curio in my opinion, anyone interested in trying this group would be best advised to stick with the 1-alkyl-3-naphthoylindoles as they have a nice oxygen & nitrogen atom in their structure which allows the body to deal with them without the need for nasty routes like epoxidation
Click to expand...

with 081, I think it was, I always found it to creep up on me. Of those listed, I've only tasted 018, and that did seem to come on much quicker (or maybe I have this backwards).
 
I can vouch for intense anxiety with too high doses of the 018. It's pretty tricky. Even at doses around 5 mg.
 
Sorry to dig this up from the dead, but I am trying to determine the structure of two compounds, JWH-171 and JWH-176 in order to understand implications of statements made by legislative bodies here in Australia.

The confusion I'm experiencing is that the structure posted on the Wikipedia article, claimed to be JWH-171, is identical to the structure claimed to be JWH-176 from this article in Bioorganic & Medicinal Chemistry.

I can't be bothered to extract the image manually; besides I'm a bit frustrated that ChemDraw is crashing on my computer constantly and I can't get it to draw a single carbon. :\

Anyway, the structure can be found on the third page (page number 541 in the top right hand corner), with the identifier 26 underneath. The pentyl chain has been abbreviated, and the text above identifies the compound as JWH-176. The numerous authors of the paper include Huffman himself, lending an air of credibility.

I'm not a cannabinoid user, synthetic or otherwise, but there has been a recent scheduling decision made by the advisory authority here in Australia, and in this text they claim that JWH-171 does not fit into any of the eight* classes of cannabinoids they are scheduling, which would mean that under our incredibly vague analogue act the only way they see it being illegal is via the pharmacologically similar clause. Since the specifics of the analog act aren't well defined, and they aren't exactly throwing examples of compounds that escape the structurally similar analogue laws, I'd like to know exactly what it is about this compound that makes it so different. If what they are calling JWH-176 is actually what has been posted here as JWH-171, then correct me if I'm wrong, as my phD is in swing and not chemistry (yet), but that compound does not seem that structurally different to some others that would be considered illegal. I understand that this is a fairly unique structure that was designed specifically to eliminate hydrogen bonding from it's action at the receptor, but there don't seem to be huge structural differences that would put it above the analogue laws.

Any help would be appreciated, I can provide more information from the actual paper if needed. :)
 
I guess it's a mistake on wiki, unless there's another Huffman article that references the compound as JWH-171?

I'd think the lack of heteroatoms qualifies it as structurally dissimilar, it would be something like calling isobutylbenzene an analog of amphetamine...
 
You know... I wonder about about the psychoactivity of this compound. It seems like it should be so lipid soluble that once it entered the cell membrane it would have a hard time leaving it. Also, due to the planarity, I'm curious if it can complex with DNA a la Benzo[a]pyrene.

The confusion I'm experiencing is that the structure posted on the Wikipedia article, claimed to be JWH-171, is identical to the structure claimed to be JWH-176 from this article in Bioorganic & Medicinal Chemistry.
Click to expand...

Almost certainly an error on wikipedia's part, someone should correct it.
 
Corrected it. As it turns out JWH-171 is the (Z)-isomer while JWH-176 is the more active (E)-isomer.

What's really interesting to me is how much potency a morpholinylethyl tail imparts for this particular compound, it goes from 26.0nM with the pentyl tail down to 2.7nM with the morpholinethyl. (see example 35 from this paper: http://www.scribd.com/doc/79822377/Structural-Requirements-for-Cannabinoid-Receptor-Probes)

Does this suggest that aromatic stacking could play more of a role when the northern ketone is not present? Or is it more likely that this is related to the indole-Nitrogen (or lack thereof)? I wish I could find data on the methylpiperdinyl variation..
 
You must log in or register to reply here.
Top