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New High Potency Eugeroics - Beyond Modafinil

modafinil armodafinil cephalon eugeroic research chemical

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#1 3AlarmLampscooter

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Posted 06 December 2013 - 04:54 AM


stponkey made an interesting post a couple days ago linking to some research correspondence between Cephalon (the makers of Modafinil) and the Journal of Chemical Biology and Drug Design about the former's work on finding a successor compound to Modafinil.

Wake-promoting agents: Search for next generation modafinil: Part I
Wake-promoting agents: Search for next generation modafinil: Part II
Wake-promoting agents: Search for next generation modafinil: Part III
Wake-promoting agents: Search for next generation modafinil: Part IV

From the last publication, it looks like they've selected two fairly promising successors to Modafinil for further investigation, namely "Compound 2" and "Compound 16"

Here's a chart of their properties, versus Modafinil and Control:
Assay_____________________________________Modafinil___(-)-16_______(+)-16_______(-)-2_______(+)-2_______Control
DAT_binding_(rat_IC50_μM)_________________3.70________0.0216_______0.037________0.40________4.20________–
NET_binding_(rat_Ki_μM_or_%_inhibition)___N/A_________10___________13___________16%_@10μM___12%_@10μM___–
SERT_binding_(rat_Ki_μM_or_%_inhibition)__N/A_________39%_@30μM____5.5__________3%_@10μM____4%_@10μM____–
CYP2C19_(IC50_μM_or_%_inhibition)_________11__________29%_@100μM___42%_@100μM___174_________112_________-
CYP3A4_(IC50_μM_or_%_inhibition)__________<10%_@10μM__<10%_@100μM__<10%_@100μM__139_________159_________-
CYP2D6_(IC50_μM_or_%_inhibition)__________<10%_@10μM__16%_@100μM___<10%_@100μM__177_________151_________-
Rat_wake_time_over_4h_(100_mg⁄kg_ip)______117_±13_____175.7_±2.9___157.2_±12.8__238.5_±0.8__227.1_±7.8__67.8_±4.5
Average_%_of_time_awake_versus_control____173%________259%_________232%_________352%________335%________100%
Relative_Eugeroic_Potency_to_Modafinil____100%________150%_________134%_________203%________194%________58%

"Compound 2"
aka CHEMBL1956397 aka SureCN1195760
IUPAC name: 2-[[2-(4-chlorophenyl)phenyl]methylsulfinyl]acetamide
Posted Image

"Compound 16"
aka SureCN2206684
IUPAC name: 2-[[2-(1-benzothiophen-2-yl)phenyl]methylsulfinyl]acetamide
Posted Image

Running a structure search on Pubchem based off these two also yields many more interesting very recent results of similar compounds with unknown properties, presumably a few of which could be even more potent. Cephalon also has a lot of recent patent filings and other research I haven't had a chance to look through yet, there may be some other gems hidden in there.

Edit: fixed table formatting

Edited by 3AlarmLampscooter, 06 December 2013 - 04:56 AM.

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#2 MasterHerb

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Posted 06 December 2013 - 05:06 AM

Very interesting! The half life must be crazy in some of those new compounds

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#3 Reformed-Redan

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Posted 06 December 2013 - 05:16 AM

Let's get a racemix Compound 2. Good lord 2x modafinil potency, helluva time working. Chew chew!
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#4 MasterHerb

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Posted 06 December 2013 - 05:19 AM

Let's get a racemix Compound 2. Good lord 2x modafinil potency, helluva time working. Chew chew!


I am down for a group buy!
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#5 Reformed-Redan

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Posted 06 December 2013 - 05:25 AM

Already sent an e-mail to supplier. Guys but BPAP is the thing! Shit is awesome.

#6 3AlarmLampscooter

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Posted 06 December 2013 - 07:45 AM

Already sent an e-mail to supplier. Guys but BPAP is the thing! Shit is awesome.


While we're on the stimulant topic, I was looking through an old paper on Modafinil-Nocaine Hybrids and came across "Compound 9" aka CHEMBL365227. It is an NDRI which is reasonably selective for DAT in a 12:42:2183 nM Ki DA:NE:5-HT ratio. For comparison, dexmethylphenidate has a DA:NE Ki of 161:206 nM. So you're look at a 3.5 vs a 1.27 selectivity for dopamine over norepinephrine of CHEMBL365227 vs Dexmethylphenidate. My money would be on this being a better stimulant than Focalin by a good bit.

There were a couple other mildly interesting ones, like the somewhat less selective NDRIs CHEMBL192801 and CHEMBL192801. CHEMBL373108 was a very selective NRI and CHEMBL190173 was a reasonably balanced TRI.

CHEMBL365227
2-[[4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfinyl]ethanol
Posted Image

I've got a lot of free time tonight, so I'll probably keep diving deeper into the literature on modafinil derivatives. After reading that nocaine paper, I'm starting to brainstorm about modafinil-phenmetrazine hybrids on the stimulant side... :cool:

#7 Reformed-Redan

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Posted 06 December 2013 - 08:02 AM

My supplier wont deal with stimulants. Focalin is weak for ADD from what I've heard. Plus it has a short half life.

If your goal is to get high there are plenty of other RCs I've see.

#8 p3x888

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Posted 06 December 2013 - 10:49 AM

Let's get a racemix Compound 2. Good lord 2x modafinil potency, helluva time working. Chew chew!


I am down for a group buy!


Roger that. Me too.

#9 3AlarmLampscooter

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Posted 06 December 2013 - 02:03 PM

My supplier wont deal with stimulants. Focalin is weak for ADD from what I've heard. Plus it has a short half life.

If your goal is to get high there are plenty of other RCs I've see.


Oh that sucks. Is it just a general stimulant policy, or specifically things that might fall under the analog act? In the case of these Modafinil derivatives you're getting pretty far aware from anything remotely schedule 1/2. Remember even alpha-ethyltryptamine didn't even count as a DMT analog before it was specifically scheduled (from the US v. Forbes case).

As far as CHEMBL365227, I've been looking for a reasonably selective DRI with higher potency than Modafinil for a while. Not so much for getting high, as for being productive. Focalin is indeed fairly well garbage, but CHEMBL365227 shows every indication on paper of being significantly better. CHEMBL365227 probably has a decently long half life, considering Modafinil primarily undergoes decarboxylation. CHEMBL365227 is also ~13.4 times as potent as a DRI as Focalin, but only ~5 times as potent an NRI. I'd think it would be subjectively similar in stimulant effect to taking Modafinil and Selegiline with a low dose of Dexedrine.

Now moving back across the blurry line between stimulants and eugeroics, I've dug up a few more interesting things.

Cephalon's third paper had a real oddball in it. They accidentally discovered "Compound 3" was responsible for the effects of some of the others, and tested it at 139% the eugeroic potency of Modafinil with 2.4x less affinity for the dopamine transporter. Now that's strange enough in and of itself, but take a look at the structure:
Posted Image
It's Fluorenol aka 9-Hydroxyfluorene! TIL Fluorenol is a fairly potent eugeroic, I guess :|?

It metabolizes into Fluorenone. I haven't looked too extensively into safety, although acute toxicity does not seem to be an issue. Sure would make an odd nootropic, huh? :laugh:

Interestingly Cephalon's old site mentions a drug called CEP-16233 as an "atypical-psychostimulant" and CEP-26401 as an H3 antagonist. Going through other publications by some of the authors on the "Search for the next generation modafinil" series has yielded a few interesting results including a new series of 5-HT6 antagonists. I highly suspect CEP-16233 is either of the compounds mentioned in my original post, more likely "compound 2" and that the structure was only publicized as a eugeroic last year. Looks like CEP-26401 is probably in here too.

This looks like a very interesting article on more modafinil derivatives from the english abstract, although unfortunately I can't read Chinese: http://www.ncbi.nlm....pubmed/23724650
I tried plugging it into google translate, and it makes absolutely no sense. All I can gain is mice move around more on "compound 6h" than Modafinil. :-D
Anyone who can read chinese care to give a quick summary of what compounds they made, and with what effect?

I'll be getting some sleep now, as I still haven't found a powerful enough eugeroic to fully eliminate my need for it, but I'll pick up my search tomorrow and dig deeper into literature. "Compound 2" is looking like a real winner thus far. I still bet there are even more potent ones out there, from what I've seen the surface has barely been scratched on the 2-substituted modafinil derivatives.

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#10 Metagene

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Posted 06 December 2013 - 02:28 PM

I need this in my life.


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#11 Reformed-Redan

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Posted 06 December 2013 - 04:13 PM

My supplier indicated he can produce Compound 17 with relative ease. Let me know what you guys think.

#12 Reformed-Redan

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Posted 06 December 2013 - 04:18 PM

Compound 17 from here, Is the same as Compound 2 up in the post by 3AlarmLampscooter.

#13 Reformed-Redan

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Posted 06 December 2013 - 04:36 PM

Already sent an e-mail to supplier. Guys but BPAP is the thing! Shit is awesome.


While we're on the stimulant topic, I was looking through an old paper on Modafinil-Nocaine Hybrids and came across "Compound 9" aka CHEMBL365227. It is an NDRI which is reasonably selective for DAT in a 12:42:2183 nM Ki DA:NE:5-HT ratio. For comparison, dexmethylphenidate has a DA:NE Ki of 161:206 nM. So you're look at a 3.5 vs a 1.27 selectivity for dopamine over norepinephrine of CHEMBL365227 vs Dexmethylphenidate. My money would be on this being a better stimulant than Focalin by a good bit.

There were a couple other mildly interesting ones, like the somewhat less selective NDRIs CHEMBL192801 and CHEMBL192801. CHEMBL373108 was a very selective NRI and CHEMBL190173 was a reasonably balanced TRI.

CHEMBL365227
2-[[4-(4-chlorophenyl)-1-methylpiperidin-3-yl]methylsulfinyl]ethanol
Posted Image

I've got a lot of free time tonight, so I'll probably keep diving deeper into the literature on modafinil derivatives. After reading that nocaine paper, I'm starting to brainstorm about modafinil-phenmetrazine hybrids on the stimulant side... :cool:

I'll see what my supplier can do about this. It seems highly functional. Though I'm not sure about addictive characteristics or the FAA. On the other hand have you found any good 5-HT6 inverse agonists or just antagonists? Also wondering about alpha7nicotininc PAM's or agonists.

#14 MasterHerb

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Posted 06 December 2013 - 04:38 PM

My supplier indicated he can produce Compound 17 with relative ease. Let me know what you guys think.


My money is ready

#15 Q did it!

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Posted 06 December 2013 - 06:48 PM

I am game for what ever we decide on & can handle the shipping for non US residents if need be / if we have any who jump on board.

#16 chung_pao

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Posted 06 December 2013 - 07:09 PM

I'm interested if it's a eugeroic with shorter half-life. Doesn't need to be more potent than moda, just shorter lasting.

#17 baronjpetor

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Posted 07 December 2013 - 12:36 AM

I'm in

#18 3AlarmLampscooter

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Posted 07 December 2013 - 01:50 AM

I'm interested if it's a eugeroic with shorter half-life. Doesn't need to be more potent than moda, just shorter lasting.


Compound 16 looks to only have a 2-3h half life from the literature. Also worth pointing that the (+) enantiomer probably has fairly significant stimulant activity, the DAT IC50 is 37nM, which is around 4x more potent than dexmethylphenidate as a DRI assuming they have the same downstream effects (still reading up on this). The (-) enantiomer is marginally less potent than dexmethylphenidate in the DRI department. Given they both display fairly negligible affinity for NET, they are probably very "smooth" stimulants in comparison to dexmethylphenidate.

Compound 2 on the other hand looks like more a pure eugeroic with a long half life (not exactly sure what, but I think we're talking modafinil range). Although the (-) enantiomer still displays around half the DAT potency of methylphenidate, while the (+) one is around 26x lower, a bit under regular modafinil.

And I wouldn't discount Fluorenol yet either if you don't prefer DRIs.

Overall I'm thinking CEP-16233 = CHEMBL1956397 and leaning towards (-)-2-[[2-(4-chlorophenyl)phenyl]methylsulfinyl]acetamide as Nunuvigil, if you will :laugh:
I noticed the corresponding author (Chatterjee) was apparently in charge of the CEP-16233 project at Cephalon, I'm wondering if he might be able to shed any light their progression of Nunuvigil to humans, or if he's still under NDA. Just throwing ideas out there.

I've still got my head buried in pubmed and pubchem pouring over variations of sulfinylacetamides for the next little while, I'll be posting a few more interesting compounds later on.
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#19 Reformed-Redan

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Posted 07 December 2013 - 05:55 AM

SB-742,457 looks interesting. CHEMBL365227 also looks intersting; but, could be highly addictive.

Wondering what more you've got that is conceivably doable for a lab without cost overrun, 3AlarmLampscooter

#20 3AlarmLampscooter

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Posted 07 December 2013 - 01:56 PM

Few more interesting ones:

An old paper similar to Zhou's Nocaine-Modafinil work, "Novel 3 alpha-(diphenylmethoxy)tropane analogs: potent dopamine uptake inhibitors without cocaine-like behavioral profiles." by Newman et. al identified SureCN6676047 as a very high potency DRI modafinil derivative which is probably similar to Amofonelic Acid in expected effects. Assayed at 11.8nm for diplacing WIN-35428 binding in rat caudate-putamen. It came out of the same series that ultimately produced Vanoxerine. Definitely one of those chems pretty far down the DRI rabbit hole. Discussed further in this paper.
3-[bis(4-fluorophenyl)methoxy]-8-methyl-8-azabicyclo[3.2.1]octane
Posted Image

"Structure-Activity Relationships at the Monoamine Transporters for a Novel Series of Modafinil (2-[(diphenylmethyl)sulfinyl]acetamide) Analogues"
Is some more recent work by Cao et. al, also with Newman. They identified "Compound 9a" as a 1:5:11 DA:5-HT:NE reuptake inhibitor, making a decently selective SDRI, probably some decent potential as an anti-depressant.
N-(2-diphenylmethanesulfinylethyl)-N-propylaniline
Posted Image

And they've now apparently filed a patent for clinical uses, but the application doesn't mention exactly what compounds.

Cephalon's recent (nearly incomprehensible) patent filings seem to indicate they've taken a real interest in tricyclic compounds as eugeroics, even though there isn't much in literature on them beyond what I already posted:
https://www.google.c...s/US20080070956
https://www.google.c...s/US20120295882
https://www.google.c...s/US20130310389

I finally sort of muddled my way through understanding "Synthesis and biological evaluation of novel diphenyl methane sulfinyl and diphenylthio-acetamide derivatives"

They measured "Inhibition rate of independent activity (after administration)", and after 3h the control mice scored -50.4 and the Modafinil mice scored 69.1.

They describe it as "Effect of the target compounds on independent activities of mice within 5 minutes. Inhibition rate of independent activity (%) = (The number of activities after administration – The ones before administration) / The number of activities before administered × 100%. Data are expressed as the mean from each group of mice (n = 8). *P < 0.05 vs control"

One of the compounds beat modafinil at 3h, scoring 81.5, apparently being 118% as powerful as Modafinil by whatever measure this is exactly. Seems to me more a measure of stimulant potency than eugerocity, so this one may be a more powerful eugeroic than they are giving it credit for. It's another funky tri-phenyl halogenated version of Modafinil (that isn't on pubchem yet):

Zhu et al. "Compound 6h"
N-(3-chlorophenyl)-2-diphenylmethanesulfinylacetamide
Posted Image

Starting to notice a pattern here? :laugh:

Whipping out 30 seconds worth of rational drug design, I hybridized Zhou 6h/CHEMBL1956397 (OP Compound 2/Chatterjee 2). I call it "Chlortriafinil" from being a chlorinated tri-phenyl modafinil derivative.

Chlortriafinil
N-(3-chlorophenyl)-2-{[2-(4-chlorophenyl)phenyl]methanesulfinyl}acetamide
Posted Image

Anyone have some narcoleptic rats to feed it to, and see if it works? :-D (of course it could be totally non-bioactive, or lethal too! rational drug design has limits)
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#21 Reformed-Redan

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Posted 07 December 2013 - 05:15 PM

Apart from compound 2 the rest look like short half lives with potent DRI properties. Little nootropic value here, just getting high. I'm going to see what my supplier has to say about compound 2.

#22 chung_pao

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Posted 07 December 2013 - 08:54 PM

I'm interested if it's a eugeroic with shorter half-life. Doesn't need to be more potent than moda, just shorter lasting.


Compound 16 looks to only have a 2-3h half life from the literature. Also worth pointing that the (+) enantiomer probably has fairly significant stimulant activity, the DAT IC50 is 37nM, which is around 4x more potent than dexmethylphenidate as a DRI assuming they have the same downstream effects (still reading up on this). The (-) enantiomer is marginally less potent than dexmethylphenidate in the DRI department. Given they both display fairly negligible affinity for NET, they are probably very "smooth" stimulants in comparison to dexmethylphenidate.

Compound 2 on the other hand looks like more a pure eugeroic with a long half life (not exactly sure what, but I think we're talking modafinil range). Although the (-) enantiomer still displays around half the DAT potency of methylphenidate, while the (+) one is around 26x lower, a bit under regular modafinil.

And I wouldn't discount Fluorenol yet either if you don't prefer DRIs.

Overall I'm thinking CEP-16233 = CHEMBL1956397 and leaning towards (-)-2-[[2-(4-chlorophenyl)phenyl]methylsulfinyl]acetamide as Nunuvigil, if you will :laugh:
I noticed the corresponding author (Chatterjee) was apparently in charge of the CEP-16233 project at Cephalon, I'm wondering if he might be able to shed any light their progression of Nunuvigil to humans, or if he's still under NDA. Just throwing ideas out there.

I've still got my head buried in pubmed and pubchem pouring over variations of sulfinylacetamides for the next little while, I'll be posting a few more interesting compounds later on.


Tell us in case you do find such a substance!
With Modafinil I usually finish all my work in 25-50% of the normal time, enjoy a couple of hours of hypomania, then neuroticism and insomnia ensues. And the next day, I feel hypogonad and miserable.
In other words, the half-life makes the poison in this case.

Edited by chung_pao, 07 December 2013 - 08:56 PM.


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#23 3AlarmLampscooter

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Posted 07 December 2013 - 09:54 PM

Tell us in case you do find such a substance!
With Modafinil I usually finish all my work in 25-50% of the normal time, enjoy a couple of hours of hypomania, then neuroticism and insomnia ensues. And the next day, I feel hypogonad and miserable.
In other words, the half-life makes the poison in this case.


"Compound 16" is basically what you are after, it looks to only have a 2-3h half life. Half lives on a lot of the others are still unknown. Probably a fairly potent stimulant though.

Apart from compound 2 the rest look like short half lives with potent DRI properties.


16 definitely has a short half life. Flurenol is actually the least DAT of all of them (including regular modafinil) and is probably a bit shorter on the half life side. Zhu's "Compound 6h" looks to be fairly long half-lived, at least a bit longer than regular modafinil, given their marginal improvement was testing stimulant activity versus eugerocity, I'd be highly inclined to investigate it further. Most of the others are pretty unknown on half life, but DRI does not automatically equal short half life, take DBL-583 for example!

Little nootropic value here, just getting high. I'm going to see what my supplier has to say about compound 2.


I definitely wouldn't knock selective DRIs. These compounds are a lot less likely to act as releasing agents then Methylphenidate or Amphetamine. Remember, a lot of Selegiline's nootropic effects are thanks to increses in extracellular dopamine! As with everything, the key is moderation.

Overall I'm for pushing forward on compound 2 the most for a group buy at the moment, but I think some of the others may warrant further exploration too. There are definitely some really "smooth" stims in there that likely possess at least decent nootropic activity.
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#24 Reformed-Redan

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Posted 08 December 2013 - 03:37 AM

Hey, 3ArmLampscooter

Let me know what you think is worth getting:
WAY-317,538
SB-742,457
compound 2

Do you think tolerance will build up quickly with WAY-317,538?

Of all the above I think WAY-317,538 could easily be obtained or rather synthesized.

#25 3AlarmLampscooter

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Posted 08 December 2013 - 08:26 AM

Hey, 3ArmLampscooter

Let me know what you think is worth getting:
WAY-317,538
SB-742,457
compound 2

Do you think tolerance will build up quickly with WAY-317,538?

Of all the above I think WAY-317,538 could easily be obtained or rather synthesized.


All of the above look pretty promising to me. The former two definitely aren't the absolute most potent in their class (example: I linked Chatterjee's new 5-HT6 antagonist), but would be first in class to hit the nootropics market, and are great candidates given they've already been in human trials (cough cough IDRA-21, I'm glaring at you :-D). I think receptor desensitization will be an issue to some degree with any nicotinic agonist, but it's nothing that doesn't reverse itself fairly quickly. We've got a few of them progressing in clinical trials, so the issue can't be that bad. A paper I saw a while ago talked about combining PAMs/agonists on a7 nicotinic receptors to prevent that, but I don't think any PAMs are in clinical trials yet.

Overall I'd be inclined to push forward on all three (and perhaps 16 also) as long as they don't cost an arm and a leg, and also continue to explore more modafinil derivatives for new eugeroics+stims (I'm sure some of the others in this thread are in fact uber-"clean" stims).

And from here on in, we should at least refer to "Compound 2" and "Compound 16" elsewhere by their identifiers on pubchem to avoid confusion with other studies.
Compound 2 = CHEMBL1956397
Compound 16 = SureCN2206684
I'll even go so far as to uncreatively name them based off structure:
Compound 2 = CHEMBL1956397 = Orchlorafinil (from Ortho-(para-chlorophenyl) Modafinil derivative)
Compound 16 = SureCN2206684 = Orbenzthiafinil (from Ortho-(1-benzothiophen-2-yl) Modafinil derivative)

Or maybe Nunuvigil 2 and Nunuvigil 16. I'd make a terrible pharmaceutical marketer :laugh:

#26 Metagene

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Posted 12 December 2013 - 07:35 PM

Any developments?

#27 MasterHerb

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Posted 18 December 2013 - 01:50 AM

Hey, 3ArmLampscooter

Let me know what you think is worth getting:
WAY-317,538
SB-742,457
compound 2

Do you think tolerance will build up quickly with WAY-317,538?

Of all the above I think WAY-317,538 could easily be obtained or rather synthesized.


Updates from your supplier?

#28 stponky

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Posted 18 December 2013 - 06:28 AM

Wow, just saw this now. Great work 3AlarmLampscooter! I was hoping someone would be able to make heads or tails of those articles. Way over my head.
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#29 3AlarmLampscooter

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Posted 21 December 2013 - 10:23 AM

So any luck with synthesis quotes on any of these yet?

I'm not too in the loop on reputable labs at the moment, but I could send off quotes to a couple I know produce for large nootropics vendors.

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#30 Reformed-Redan

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Posted 21 December 2013 - 04:49 PM

So any luck with synthesis quotes on any of these yet?

I'm not too in the loop on reputable labs at the moment, but I could send off quotes to a couple I know produce for large nootropics vendors.

I'm pretty sure Compound 2 is in the works.





Also tagged with one or more of these keywords: modafinil, armodafinil, cephalon, eugeroic, research chemical

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