Bluelight

Synthetic Cannabinoids Study

Thread: The Big & Dandy 25I-NBF Thread

Page 1 of 2 12 LastLast
Results 1 to 25 of 47
  1. Collapse Details
    The Big & Dandy 25I-NBF Thread 
    #1
    Bluelight
    Welcome to the Big & Dandy 25I-NBF Thread



    EDIT: (the structural formula on the right is supposed to say: (N-(4-fluoro)-benzyl-2,5-dimethoxy-4-iodo-phenethylamine) since the fluorine position is changed from ortho to para)

    IUPACs:
    for '2-fluoro = 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(2-fluorophenyl)methyl]ethanamine
    for '4-fluoro = 2-(4-iodo-2,5-dimethoxyphenyl)-N-[(4-fluorophenyl)methyl]ethanamine



    Apparently a product represented under the name 25I-NBF was meant to be the left 2-F isomer compound (25I-NB2F) but at least some of the material available right now is the right 4-F isomer (25I-NB4F). Right now there is virtually no bioassay available on either of these compounds so this only adds to the confusion. Nevertheless let this thread be about all 'simple' fluoro substituted N-benzyl PEAs.

    25X-NBOMe, 25X-NBOH, 25X-NBF SAFETY MESSAGE




    This is a newly discovered group of chemicals, with little history of human use.
    It has already become clear that these substances carry substantial risks that must be highlighted.

    Examples of chemicals belonging to this family include 25i-NBOMe, 25c-NBOMe, 25i-NBOH, 25c-NBOH.
    Nicknames include "25i", "25c", N-bomb, N-bome etc.

    Some facts you should know about The 25X - NBOMe series which must also be considered to apply to the NBF compounds:

    25x NBOMe chemicals have killed at "normal" recreational doses.
    • We don't know how it kills.
    • People have died from doses that are smaller than ones they've taken in the past.
    • We don't know the reasons why it is so unpredictable yet.

    Doses can lead to psychotic episodes and ER visits
    • If you or people around you must take these drugs, avoid combinations and advise others to avoid it as well.
    • If someone appears to be overdosing, it is important to get medical attention quickly to minimize chance of death or injury.

    These chemicals are sometimes mislabeled and sold as LSD or "acid"
    • If in doubt about your drugs, learn how to test them using testing kits/reagents. Don't have blind faith in the reputation of your source.
    • A good rule of thumb these days is "if it's bitter it's a spitter"
    • If you take blotters sold as LSD, swallowing them may render NBOMe type compounds inactive while swallowing LSD will work just as well!

    25x is difficult to dose properly
    • Tolerance builds quickly, but toxicity may still occur.
    • Doses can often be unpredictable and uneven, even from the same sheet.
    • There is an unknown but narrow margin between a fun dose, and an overdose.
    • Reactions may vary wildly between individuals, but can also be inconsistent for the same person. Previous successful experiences offer no guarantees.


    NBOMe substances are cheap and widely available, however they are not well understood, and have caused a number of deaths. There are safer and (arguably) better substances to begin with than these. Know your drugs, do your research, and spread the word!


    And finally information for people pushing the dosage with NBOMe's:


    The NBOMe series is known to be more dangerous than other psychedelic drug families. High doses can easily result in severe reactions such as seizures and HPPD. It is possible to get away with high doses because the mental component of the trip is mild so it may not feel as intense as other psychedelics even though there are powerful visuals. In order to try and overcome this some users take several doses to get a more intense/spiritual experience. While this does work for some, for others this is where the serious side-effects emerge.

    As a result of this it is recommended that if you are seeking an intense experience, something more than eye candy, you select a different psychedelic with a higher natural intensity and better safety record such as 2C-E or LSD.

    It is strongly advised that users do not take more than 1.5 doses of this drug, with one dose generally agreed to be x.x mg (xxxxu g).

    Insufflating doses further increases the risk.

    [original post:]

    I did not find much about this compound besides the wikipedia article (http://en.wikipedia.org/wiki/25I-NBF).

    In which way is the 2-fluorogroup changing the activity in comparison to the 2-methoxygroup?

    I will start with a sub 100microgram dose and will slowly up the dose from there on.
    But it would be nice to gather some additional information before I start testing this substance.
    Last edited by Solipsis; 22-02-2016 at 20:38.
    Reply With Quote
     

  2. Collapse Details
     
    #2
    Bluelight Crew Jesusgreen's Avatar
    Join Date
    May 2010
    Location
    Poland
    Posts
    4,591
    Wise decision on looking for more info before testing it, and a very responsible idea with starting at < 100mic dosage.

    I don't have anything to offer but I'd also be curious if anyone has any experiences or more info.

    When Googling the substance I found this:
    http://molpharm.aspetjournals.org/co...28720.full.pdf

    It seemed to mention something about 25I-NBF and 5ht2a receptor interaction, possible with comparisons to other similar compounds, so it might be useful - unfortunately it's not loading for me, so I just left the link here in case it works for you or anyone else.
    Reply With Quote
     

  3. Collapse Details
     
    #3
    Moderator
    Psychedelic Drugs
    Solipsis's Avatar
    Join Date
    Mar 2007
    Location
    NL
    Posts
    14,487
    The 2-fluorogroup is not that much bigger than a hygrogen group in that place in the case of N-benzyl-2C-I or 25I-NB or 25-NBz. In Ralf Heim's article you can see that these compounds are slightly less potent than the corresponding NBOMe's so in this case 25I-NBOMe. The 2-F group is pretty electronegative though so it may be more like an NBOH in that respect.

    I have a very brief overview of known subjective properties of N-substituted phenethylamines but there are no NBF in the list.

    The article JG linked to in the post above mine actually shows something I had not expected namely that 25I-NBF is not that great of an agonist when looking at PI turnover, but only a partial agonist. This might be expected to lead to higher doses needed (although you should still start super super low and work your way up, always!!!!!), this is a problem. High doses with these sorts of compounds can bring more side-effects even if the psychedelic effects are not that strong at used doses. But all this is far from conclusive since PI turnover is not necessarily associated with psychedelic effects. But I'd say it does not really bode very well - as in it is probably not as strong as 25I-NBOMe but I have no reason to suspect it is not active at all.

    Be very careful with these compounds and do your research, they should be handled with extreme care and you need to know what equipment and materials to use to be able to dose accurately. If you cannot meet these expectations do not experiment with them!
    Trippers, please start at the Beginners FAQ - Read the PD Rules and BLUA - Use the Psychedelic Index and/or the advanced search engine
    Reply With Quote
     

  4. Collapse Details
     
    #4
    Bluelighter kingme's Avatar
    Join Date
    Jul 2010
    Location
    Europe
    Posts
    4,938
    it really is a wonder how some of these compounds surface "in the wild" with only a couple of articles about them online... the internet never seemed to be such a small place before.

    seriously dude, take care and dont do anything to jeopardize your health in the name of supposed science. and be sure to report the bad with the good, if it is the case...
    Reply With Quote
     

  5. Collapse Details
     
    #5
    Bluelighter fly-'s Avatar
    Join Date
    Dec 2010
    Location
    Amsterdam
    Posts
    418
    Quote Originally Posted by kingme View Post
    it really is a wonder how some of these compounds surface "in the wild" with only a couple of articles about them online... the internet never seemed to be such a small place before.

    seriously dude, take care and dont do anything to jeopardize your health in the name of supposed science. and be sure to report the bad with the good, if it is the case...
    word!
    Reply With Quote
     

  6. Collapse Details
     
    #6
    Additionally, it would be wise to determine whether the degradation products are toxic or not. I'm certainly no expert in that field so I sadly can't provide more information regarding this than bringing up that issue.
    Pure speculation: it should be metabolized to 2-Fluorobenzoic acid, I think. I don't know how toxic that is. Due to the small dose of the administered substance it shouldn't be much of a problem, but better to be safe.
    Last edited by sn23; 04-12-2011 at 21:17.
    Reply With Quote
     

  7. Collapse Details
     
    #7
    Moderator
    Psychedelic Drugs
    Solipsis's Avatar
    Join Date
    Mar 2007
    Location
    NL
    Posts
    14,487
    Well N-dealkylation yielding 2-fluorobenzaldehyde would not be expected to be more toxic than regular old benzaldehyde - I THINK - and remember we are talking quite small amounts anyway, but I will check the MSDS for you. Well after checking it seems there isn't really much toxicological information on it either way. Aldehydes tend to cause nausea, headaches, irritation and vomiting but the body can oxidize it into the acid and get rid of it. Acetaldehyde which is produced in absolutely copious amounts when you drink alcohol is responsible for a lot of the hangover effects but I imagine you would have to eat ridiculous amounts of N-benzylic 2C-X compounds to come close to such a hangover. There would be a lot of other things too worry about if you ingest that much of one of these superpotent drugs, like lethal vasoconstriction and maybe cardiotoxicity.

    Benzaldehyde which is closely related to 2-fluorobenzaldehyde is indeed an irritant and not very healthy but it is still considered a safe food additive because it is so quickly metabolized into benzoic acid.

    Another metabolite would be 2C-I, and other than that O-demethylation would surely occur - of the parent compound and the 2C-I metabolite.
    Last edited by Solipsis; 04-12-2011 at 21:40.
    Trippers, please start at the Beginners FAQ - Read the PD Rules and BLUA - Use the Psychedelic Index and/or the advanced search engine
    Reply With Quote
     

  8. Collapse Details
     
    #8
    Alright thanks for your input Solipsis. Since my interest in pharmacology is at the time more or less a spare time activity I don't feel fit enough to give any qualified advise, but my ideas about the matter are about the same as yours.

    The metabolic degradation of the 2C-I part of the molecule should be considered safe, because 2C-I is a pretty established psychedelic plus the doses of the N-(2-Fluorobenzyl) variant would be expected to be lower than 2C-I. The degradation of the fluorobenzyl group results in the new product, so that pathway may be worth a closer look. I think it would be a good idea to check the toxicity profile of fluorobenzaldehyde and fluorobenzoic acid very well, maybe ask in the ADD forum for further input. Just to be sure
    Reply With Quote
     

  9. Collapse Details
     
    #9
    thanks @ Solipsis and all the others for the nice and well informed answers...

    I will report back when I tried this substance but this is going to take some time...
    Reply With Quote
     

  10. Collapse Details
     
    #10
    This was already discussed briefly in ADD, with a bioassay: http://www.bluelight.ru/vb/threads/598403-25F-NBOMe
    Bioassay: http://www.bluelight.ru/vb/threads/5...1#post10129779

    The metabolism of o-fluorobenzoic acid in humans appeared to have been studied very little, this is the only paper I found - http://www.jbc.org/content/243/20/5374.short. I suspect it is not particularly dangerous because of it's high water solubility which means it will be excreted quickly, the study indicates that it is defluorinated and hydroxylated (and sometimes the carboxylic acid replaced too, leaving you with catechol), and with what little substrate that escapes that fate (making it harmless salicylic acid, or catechol) the structure indicates its unlikely to gum up any particularly important cellular process like the citric acid cycle.
    Same goes for the benzaldehyde.
    Last edited by MattPsy; 06-12-2011 at 22:13.
    Reply With Quote
     

  11. Collapse Details
     
    #11
    The thread in ADD is about 25F-NBOMe, not 25I-NBF.
    Reply With Quote
     

  12. Collapse Details
     
    #12
    Hilarious. This is why I shouldn't post late at night. My bad.
    Though i'm a bit put out that 25F doesn't work now!
    Anyway, the metabolism comments I made still stand. Now we wait for a bioassay...

    I expect this to be pretty lacklustre as it will be a partial agonist.
    Last edited by MattPsy; 06-12-2011 at 22:12.
    Reply With Quote
     

  13. Collapse Details
     
    #13
    Quote Originally Posted by MattPsy View Post
    Anyway, the metabolism comments I made still stand. Now we wait for a bioassay...
    Thanks for your input too, much appreciated. I am looking forward to the assay too, I'm fairly interested in the results of further modifying the N-Benzyl
    Reply With Quote
     

  14. Collapse Details
     
    #14
    Moderator
    Psychedelic Drugs
    Solipsis's Avatar
    Join Date
    Mar 2007
    Location
    NL
    Posts
    14,487
    Quote Originally Posted by MattPsy View Post
    Hilarious. This is why I shouldn't post late at night. My bad.
    Though i'm a bit put out that 25F doesn't work now!
    Anyway, the metabolism comments I made still stand. Now we wait for a bioassay...

    I expect this to be pretty lacklustre as it will be a partial agonist.
    Haha, I guess you were too F'd to post?

    Anyway I have been confused about full 5-HT agonists vs partial agonists. The definition of a partial agonist is that it has relatively less efficacy compared to the full agonist that is used in the assay. If you compare to serotonin, all of these compounds are partial agonists. If your assay employs another ligand categorized or defined as a full agonist then this can be different. At least I think this is how these definitions work.

    I realize there is some subjectivity to it but the synthetic cannabinoid phenomenon made me suspicious of full agonists. I'm not sure if you can expect problems to arise when you use drugs that have efficacies that are very close to or even above that of the endoligand used in the body or if it is just some imaginary line that varies, that you probably should not cross. I don't have enough understanding of this to say more useful things about this but I am just trying to say that high potency can be nice with the clean aspect of high selectivity that these drugs may also have but there might be such a thing as 'too potent', not only because it becomes dangerous to handle the chemical but also because it has too much of a pervasive disruptive effect on the neurotransmitter system it affects. My understanding is that with cannabinoids you should avoid what are called full agonists like JWH-018 because of the consequences of them acting 'too well' and I would be happy for someone to enlighten me about whether this should be feared with serotonergic agents as well or not.
    An example would be that it would not surprise me if use of superpotent serotonin agonists like NBOMe's and analogues bring a larger risk of HPPD over time compared to less potent agonists. Isn't LSD suspected to have more risk of HPPD than mushrooms? Maybe I am way off here but the potency could be the reason.
    Trippers, please start at the Beginners FAQ - Read the PD Rules and BLUA - Use the Psychedelic Index and/or the advanced search engine
    Reply With Quote
     

  15. Collapse Details
     
    #15
    There is some data on 25I-NBF in Nichols' paper: Mol Pharmacol 70:19561964, 2006. It has about the same affinity for 5HT-2a receptors as the unsubstituted N-benzyl, and is about 3-6-fold weaker than 25I-NBOMe, depending on the assay. The efficacy for activation of PI hydrolysis at human 5HT-2a is comparable to 25I-NBOMe, 87%.
    Reply With Quote
     

  16. Collapse Details
     
    #16
    PI hydrolysis isn't necessarily a great correlate for psychedelic activity, there are good reasons for thinking a decent HBA (hydrogen bond acceptor) is necessary for a key interaction for another signalling pathway so a halogen may not work since it is a donor instead. The 4-MeO-thiophen-3-yl derivative works well with similar properties to 25I (also a good HBA, whichever way the thiophene ring is flipped, as it can accept via either the S or O), NBOH derivative doesn't work so well (not an HBA) despite having otherwise good affinity and efficacy at PI hydrolysis, O-cyclized derivatives such as the dihydrofuran,dihydrobenzofuran, and NBMD work well (all HBAs) - and then there's LSD's amide.

    That said I'm interested whether a halogen can work anyway, it might even be more interesting if it can.

    Yeah full agonists definitely have their problems, though in particular the combination of high affinity and efficacy is a recipe for receptor internalisation or at the very least downregulation; this can be observed in the tachyphylaxis following the use of these NBOMe compounds and to a slightly lesser extent by LSD, and for other examples, in the superpotent fentanyls (alpha-methylfentanyl, 3-methylfentanyl, Ohmefentanyl, carfentanil, etc) and other opioids, and the very potent cannabinoids (HU-210, AM-2201, etc).
    Also I expect that the higher affinity ligands are more specific for one mode of signalling and so will show less complex effects, I guess you'd describe the high as being one-dimensional. LSD is a bit of a wildcard here since it manages to bind to such a diverse range of targets with reasonable affinity anyway. and, yeah, too f'ked
    Last edited by MattPsy; 10-12-2011 at 23:32.
    Reply With Quote
     

  17. Collapse Details
     
    #17
    Bluelighter
    Join Date
    Jan 2010
    Location
    Poland
    Posts
    142
    I tried 2 mg intransally , It was threeshold dose without any special effects , the feeling of strangeness , quite euphoric , without visuals .Next time maybe I will trying 2 or 4 mg with cyclodextrine.
    Last edited by Thorns Have Roses; 06-01-2012 at 02:11. Reason: de-SWIMified
    Reply With Quote
     

  18. Collapse Details
     
    #18
    Bluelight Crew Jesusgreen's Avatar
    Join Date
    May 2010
    Location
    Poland
    Posts
    4,591
    ^ Interesting to hear an experience. Remember we don't use SWIM here though, doesn't protect anyone and makes your posts harder to read
    Reply With Quote
     

  19. Collapse Details
     
    #19
    Quote Originally Posted by MattPsy View Post
    LSD is a bit of a wildcard here since it manages to bind to such a diverse range of targets with reasonable affinity anyway.
    We don't know how selective the NBOMe analogs are either, probably not as broad as LSD but maybe some like 25I-NBF with its fluorine atom are more broad than 2CI.

    Can anyone find the supplemental data for Mol Pharmacol 70:19561964, 2006?
    Reply With Quote
     

  20. Collapse Details
    Human Application & NMR 
    #20
    Greenlighter
    Join Date
    Dec 2011
    Location
    Germany
    Posts
    26
    It seems I have sort of bad news. Some days ago I finally decided to take a shot at this chemical. It has waited in my drawer for too long.
    So I prepared a 10% suspension in caffeine using a analytical balance by adding some methanol, mixing the slurry thoroughly and then drying in high vakuum.
    Yesterday night I finally tried, starting with 20 mg of the cut chemical (2 mg of the active compound). After about 10 min I felt some threshold effects but nothing more, so I snorted another 20 mg (2 mg). I noticed a some color enhancement and maybe light visual effects but nothing special. There was definitely a feeling that something is going on but it was very hard to pin down. There was also some entactogenic effect, reminiscent of 2C-B. I was very clearheaded throughout the whole time, though. After 2 hours I felt the effects weaken even more so I took another 50 mg (5 mg) expecting to get more defined effects then. I was disappointed, though. The effects did not exceed what I had after the first two doses...
    All in all I found this rather disappointing, so I started looking into the NMR again to check if I had missed something.



    I compared the aromatic peak pattern with 2-FA and 4-FA and found it looked pretty much like substitution in the 4-position!

    Aromatic peak pattern of 2-FA (left), the 25I-NBF (center) and 4-FA (right):


    The outer peaks (singlets at 7.44 and 6.89 ppm) are attributed to the H-atoms of the 2C-I core. Would you agree that it seems I'm right about this? I'll need to get some more of the pure material to measure 13C NMR to confirm this.
    Since there is not much 25I-NBF available yet, there's a high chance that the material you have is the "25I-NB4F" isomer. Please keep that in mind, especially when trying new batches that should be the same compound!
    Reply With Quote
     

  21. Collapse Details
     
    #21
    Greenlighter
    Join Date
    Dec 2011
    Location
    Germany
    Posts
    26
    I downloaded the paper and searched the site hour 15 minute - nothing! It's a linking loop that just brings you back to where you started, so I give up!
    Reply With Quote
     

  22. Collapse Details
     
    #22
    Bluelighter Erny's Avatar
    Join Date
    Sep 2008
    Location
    Mordor
    Posts
    168
    Quote Originally Posted by MattPsy View Post
    NBOH derivative doesn't work so well (not an HBA) despite having otherwise good affinity and efficacy at PI hydrolysis
    What is meant by "working well" here? They are just as potent as NBOMes when being tested in vivo.

    O-cyclized derivatives such as the dihydrofuran,dihydrobenzofuran work well
    What is the source of your confidence in this? Our empirical data says the opposite. And there have been no real proof of 2-OMe hydrogen bonding with anything in the active site as far as I am aware.

    That said I'm interested whether a halogen can work anyway, it might even be more interesting if it can.
    There is a way to work for it. Not by hydrogen bonding, but by activating the benzene ring it is attached to, and its hydrogens at 5 and 6 positions. For a better interaction with Phe339.
    Reply With Quote
     

  23. Collapse Details
     
    #23
    If you are looking for an extensive summary of human, rat, 5HT2A/2C, and 5HT2A mutant receptor binding affinities and IP activities/efficacies for a number of agents, you might want to check out the appendices of the dissertation of the first author of that Mol. Pharm. paper:

    Towards a biophysical understanding of hallucinogen action
    by Braden, Michael Robert, Ph.D., Purdue University, 2007 , 176 pages; AAT 3287241

    The following is a ProQuest link which should allow you to download a pdf for free, but you may have to be on a university or other library subscribing IP address to access it:

    http://proquest.umi.com/pqdweb?did=1...=309&VName=PQD

    No synthesis information, only pharmacology.

    aloha
    dr.psilo
    Reply With Quote
     

  24. Collapse Details
     
    #24
    Bluelighter Erny's Avatar
    Join Date
    Sep 2008
    Location
    Mordor
    Posts
    168
    I've seen it. There, in this paper, they wrote they did not found 2-OMe to form an H-bond with Asn343 like they expected. And some of their ligands proved to be inactive in human animal. They're writing about some binding affinities etc they have measured in vitro, I am talking about testing this in vivo.
    Reply With Quote
     

  25. Collapse Details
     
    #25
    Bluelighter Erny's Avatar
    Join Date
    Sep 2008
    Location
    Mordor
    Posts
    168
    I'll cite what is related to our discussion from that dissertation

    If the hypothesis is valid that N6.55(343) interacts with the amide oxygen of ergolines and the polar ortho-substitution of the N-Benzyls, one would expect a marked decrease in binding affinity and/ or functional activity at the h5-HT 2A/N343A mutant receptor for these compounds. Surprisingly, this effect was not observed. As indicated in Figure 4.8, the affinity for LSD actually increased slightly, the other ergolines and half of the N-Benzyls were indistinguishable from wild type, and the remaining N-Benzyls had only slight decreases; the potencies for the ergolines and most of the N-Benzyls were decreased, but only slightly. As with affinity, the changes of intrinsic activity were either slight or indistinguishable from wild type, with the exception of LS D, where there was a -25% shift, and 25I-NB, which actually increased slightly.
    - p. 71
    Reply With Quote
     

Page 1 of 2 12 LastLast

Posting Permissions

  • You may not post new threads
  • You may not post replies
  • You may not post attachments
  • You may not edit your posts
  •