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    5 Methyl MDA 
    #1
    A friend recently mentioned 5 methyl MDA to me, the compound sounds fascinating, it was described as a more potent MDMA, possibly with a psychadelic edge.
    A wikipedia page regarding the substance : -

    http://en.wikipedia.org/wiki/3-Methy...oxyamphetamine

    It states that 5 methyl MDA is more selective to 5HT than NA or DA, I was under the impression that part of the dopamine release mechanism of MDMA is due to the vast 5HT release influencing dopamine release, as opposed to the actual compound inspiring the release, can anyone educate me as to whether this is true or not?

    Does anyone have any experience with this compound?

    The methyl addition on the main ring falls under UK phen analogue laws (making this compound class A) doesn't it?

    I apologise if this should have been posted elsewhere.
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    #2
    Awesome, I want some!

    As for the UK Analogue Act, I couldn't tell you; just don't get caught with it, and you'll be fine.

    I have a feeling 3-Cl-4,5-MDA would be shinier, though.
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    #3
    Could the various neuropharmacological experts on here give an opinion as to the activity of BK 5 methyl MDA.

    http://img138.imageshack.us/my.php?i...thylmdaps2.jpg

    Would I be right in thinking it would be very unstable due to the primary amine and beta ketone?

    Any idea if MADAM-5 (3-methyl-4,5-methylenedioxy-N-methylamphetamin) would be to MDMA, what 5 methyl MDA (3-Methyl-4,5-methylenedioxyamphetamine) is to MDA?
    Have there been any studies regarding this analogue of MDMA?
    What about other alkyl substitutions like butyl or propyl analogues?
    How would Cl, I, and B at the 5 position affect the activity?

    The beta ketone of MADAM-5 would be far more stable due to a secondary amine (as is methylone), I wonder if it would have any activity.
    Last edited by IlostaMadge; 25-05-2008 at 17:21.
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    #4
    Cathinone (beta-ketoamphetamine) from the African khat plant, for example, may be somewhat unstable, but certainly, beta-keto primary amine cathinones / amphetamines are chemically possible. They are far from "very unstable," in fact.

    I know this because I read the link on the recent thread "Interesting Article on Cathinones" posted by morningloryseed, I think. The authors of the referenced scientific study synthesized 3,4-methylenedioxycathinone (MDC) starting with 3,4-MD-propiophenone plus butyl nitrite followed by catalytic hydrogenation of the resulting oxime (R=N-OH) to yield MDC, which they then injected into rats and observed their resulting behavior, so no, it's not a chemical impossibility by any stretch of the imagination. Also, I have heard reports of people getting high on MDC ("hydrolone") which they made for themselves; how they did it, I couldn't tell you.

    Bk-5-methyl-MDA might be a decent serotonin releaser / agonist, but its proficiency at stimulating the dopamine (DA) system, which is responsible for learning, memory, pleasure drugs, and addictive behaviors, would probably be mediocre at best. I would say 100 mg might be an optimal dose, but would probably start at 20 mg just to be safe.

    And finally, yes, 3-fluoro-MDA, 3-chloro-MDA, 3-bromo-MDA and 3-iodo-MDA can all be made and tested just like with the 2c's and DOx's, but you would be trying out a new drug with the halogen on the 3rd (or meta-) postion to the aliphatic carbon nitrogen side chain instead of the 4th (or para-) position. Another interesting possibility is the introduction of an ethyl group either place.

    From what I've read (Shulgin), N-methyl-TMA, N-methyl-MMDA, and N-methyl-TMA-6 are all inactive whereas N-methyl-DOB and N-methyl-DOM are of 10 fold reduced potency. Thus, it would appear that the 3,4,5-trisubstituted amphetamine family is not amenable to
    N-methylation and neither is the 2,4,6-family. Then again, the MD ring might make a difference. But like I said, I think bk-5-methyl-MDA is probably plenty stable enough already based on the examples of hydrolone / MDC (published literature) and cathinone, a natural plant product.
    Last edited by <pyridinyl_30>; 25-05-2008 at 17:40.
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    #5
    Thank you for that.

    I would of thought that MADAM 5 would be active, 5-methyl MDA is far more potent than MDA, and I wouldn't of thought (even though I am the pharmacological equivalent of Jacqui Smith on cannabis) that the extra methyl on the amine would make such a vast difference.

    If Beta ketone primary amines are stable, what would be the result of chucking a beta ketone group on 2c's or DO's, does the BK group reduce/deny 5HT2a agonism?

    It's fairly obvious I am trying to find UK legal compounds, I have a friend who is an organic chemist willing to synth things, but he can't go near anything illegal.

    Are there any legal compounds you could recommend? Either psychadelic or stimulatory?
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    #6
    Obviously, the methylamine would be the way to go. The alpha ketone cannot then dimerize. Oh, you could make the hydroxylamine as well, but that's not totally stable...
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    #7
    I can think of a lot of things that I'd like to try, but since I don't know the laws in your country, you'll have to check out the legality aspect for youself.

    4-Cl-DMT
    3-MeO-MA
    3,4-dimethyl-MA
    3-MeO-IAP
    4-(n)-pentyl-3,5-di-MeO-PEA
    MET
    3-Cl-MA
    3,4-di-Cl-MA
    3,4-di-MeO-MA
    3-methyl-MA
    2-Bz-piperidine
    beta-CO2Me-(meth)amphetamine
    3-Bz-morpholine
    2-piperonylpiperidine
    3-piperonylmorpholine
    pyrrolidinoamphetamine
    MD-pyrrolidinoamphetamine
    indazolic DMT
    indazolic 4-OH-DMT
    beta-3,4-MD-phenyl-alphamethylfentanyl
    3-chloro-4-methoxyamphetamine
    4-chloro-3-methoxyamphetamine
    etc.

    As you are probably beginning to imagine, I could continue with my list but as for me, mainly, I just want some speed: Methylphenidate, amphetamine, cocaine, or methamphetamine each does the trick for me.
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    #8
    ^Then you want phenmetrazine, fencamfamine or 4MAR... the standout stimulants.
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    #9
    Unfortunately the majority of those are illegal .

    http://www.erowid.org/psychoactives/...e_phen_4.shtml

    Essentially any pea (or N-alkylphenethylamine, alpha-methylphenethylamine, an N-alkyl-alpha-methylphenethylamine, alpha-ethylphenethylamine, or an N-alkyl-alpha-ethylphenethylamine) skeleton with ring substitutions of alkyl, alkoxy, alkylenedioxy or halide is class A within the UK. Copy and paste rules .

    If you shove a halogen in place of an alkyl group, say chloro in place of an alkyl, does it change the nature of the drug drastically?
    Comparing 2ce and 2cp to 2ci and 2cb I would hazard a guess at no.

    For example, what would 4 chloro methcathinone be like in comparison to 4 methyl methcathinone?
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    #10
    Do these count?

    2-phenyl-1-oxa-4-azolane
    2-(3,4-methylenedioxyphenyl)-1-oxa-4-azolane
    2-(3,4-dichlorophenyl)-1-oxa-4-azolane
    1-methylamino-2-phenylcyclohexane
    1-(3,4-methylenedioxyphenyl)-2-methylamino-cyclohexane
    1-(3,4-dichlorophenyl)-2-methylamino-cyclohexane

    None of them are pea's or amp's, strictly speaking.

    As for the aromatic halogen versus alkyl question, the halogenated compounds will tend to be more potent, more metallic, yield shinier colors, and be more stimulating, rather than more sedating; that is, until you extend the chain above a one carbon (methyl) group, and then the substituent will have enough electron density to donate that all bets are off and new theories have to be formulated (but even those are still not particularly stimulating--think THC).
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    #11
    Is there a specific order of the halogen potency?
    From your comment I guess it depends on electron density and thus would run down the periodic table with fluorine being the least potent and iodine being the most potent?
    This fits in with the 2CI > 2CB > 2CC > 2CF pattern of potency.

    Thanks for the list, unfortunately my chemistry knowledge (or lack of) means I will have to sit down and draw out those compounds, I can't visualise them. Would you mind awfully putting a basic description of what they would be like alongside them?
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    #12
    the halogenated compounds will tend to be more potent, more metallic, yield shinier colors, and be more stimulating, rather than more sedating;
    I find it hard to believe that there's any connection between the color of visuals and alkyl vs. halogen as a groups- though maybe for some of the halos and some of the alkyls will be this way, and some of the alkyls and some of the halos another.
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    #13
    yeah but that order of potency doesn't apply to thier amphetamine counterparts, and thier subjective fx seem to differ alot aswell, doi/2ci is kindof a lame psychedelic IMO not very magical and doesn't seem to increase in intensity unlike br/cl...not familiar with fl
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    #14
    Hmm, it is DOI that is out of line, doesn't that sit in the lung for 3 hours before moving to the brain? I wonder if that is to do with it's reduced potency compared to the other chems.
    2C-F produced nothing at 250mg according to Shulgin.
    I found 2CI and DOI very enjoyable but pretty shallow compounds.

    I might get the opportunity to try 5 methyl MDA over the next few weeks, I will post my findings if so.
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    #15
    the order of potency with the 2,5-dimeo 4-halo PEAS and AMPs goes: I more potent than Br more potent than Cl and F is essentially inactive. the pseudohalogen CF3 is more potent than I by a small margin. the correlation is pretty much to do with size and lipophlicity of the 4 substituent. 1,1,1,trifluoromethoxy f3c-o- is a sure fire potent compound too with different electronic properties to the trifluoromethyl f3c-

    The colours in the visuals produced are to do with the fact halogens are colored and methane isn't, iodine producing more purple visuals.
    what the fuck!!
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    #16
    Quote Originally Posted by vecktor
    iodine producing more purple visuals.
    what the fuck!!
    Heh! Is that ironically or really :P ?
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    #17
    you can probably figured that out... lol
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    #18
    the order of potency with the 2,5-dimeo 4-halo PEAS and AMPs goes: I more potent than Br more potent than Cl and F is essentially inactive. the pseudohalogen CF3 is more potent than I by a small margin. the correlation is pretty much to do with size and lipophlicity of the 4 substituent. 1,1,1,trifluoromethoxy f3c-o- is a sure fire potent compound too with different electronic properties to the trifluoromethyl f3c-
    Only with the 2,5 dimetho-4-halo series?
    It wouldn't apply to 4-halo substitutions on pea or amp skeletons, or 3-halo substitutions on MDA/MDMA?

    Sorry I am bouncing all over the place here, but has anyone seen anything regarding 4-halo/alkyl pea's? Basic pea is pretty much inactive, but a 4 subsitution should stop it being chewed up by MAO B shouldn't it?
    Just checked in pihkal and it had no activity at 500mg, would the other halogens or alkyls in the 4 position prevent it being munched by MAO B?
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    #19
    Quote Originally Posted by IlostaMadge
    Only with the 2,5 dimetho-4-halo series?
    It wouldn't apply to 4-halo substitutions on pea or amp skeletons, or 3-halo substitutions on MDA/MDMA?

    Sorry I am bouncing all over the place here, but has anyone seen anything regarding 4-halo/alkyl pea's? Basic pea is pretty much inactive, but a 4 subsitution should stop it being chewed up by MAO B shouldn't it?
    Just checked in pihkal and it had no activity at 500mg, would the other halogens or alkyls in the 4 position prevent it being munched by MAO B?
    yes the same order of potency applies for the 4 halo amphetamines the 4-halo phenethyamines appear inactive. the 4 haloamphetamines are potent stimulants and even more effective neurotoxins, the iodo and bromo being more potent toxins than the chloro, the fluoro seems to be mostly devoid of neurotoxicity,

    substitution at the 4 position doesn't protect from MAO AFAIK unless it is really bulky.
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    #20
    yes the same order of potency applies for the 4 halo amphetamines the 4-halo phenethyamines appear inactive. the 4 haloamphetamines are potent stimulants and even more effective neurotoxins, the iodo and bromo being more potent toxins than the chloro, the fluoro seems to be mostly devoid of neurotoxicity,
    Is this neurotoxicity due to them being more potent 5HT agonists/releasers?
    This would sort of explain why Fluoro is minimally neurotoxic as it doesn't seem to have much 5HT agonism in that position, hence the incredibly weak nature of 2C-F, again, I am merely guessing and basing this on no knowledge whatsoever.

    Thank you for your replies by the way Vektor, you have been incredibly helpful and informative over a wide range of threads and topics.
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    #21
    Electronegativity is a useful concept when considered alongside with atomic size in both organic chemistry and pharmacology.

    F is the most electronegative (electron withdrawing) halogen, but it is only about the size of a H atom. All attached halogens have three pairs of lone pairs of electrons. F is basically useless by itself; for example, 4-FA is only about a 1/3rd as good as regular amphetamine. Next, is Cl; Cl is you best bet as far as the halogens go. Take a perusal of the Physician's Desk Reference and you will find Cl aplenty represented in psychoactive drug structures. Br is heavier than Cl and is too toxic; bromazepam, for instance, is the one of the few benzodiazepines that causes liver damage. I is the largest/heaviest and most electropositive halogen, but it makes for weak psychedelics.

    3,4-dichloroamphetamine has shown the most potential in animals studies as far as level of self-administering, a measure of addiction potential. Addiction potential is related to the dopamine neurotransmitter system. I would suggest
    3,4-dichlormethcathinone perhaps. I say 3,4-dichloro over plain 4-chloro because the former is a closer analogue to dopamine. Reinforcing dopamine is the whole point of addictive drug design. An aromatic Cl functional group is somewhat similar to a hydroxy but crosses the blood brain barrier a lot better. Cl is basically
    non-toxic.
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    #22
    So what is the consensus on this and/or has anyone performed any testing? Being that it affects primarily serotonin by weight ratio comparison to mda would we expect it to be primarily psychedelic and slight empathenogenic?

    Would this be considered an analogue?

    I have access to this and I am wondering what to expect and what would be a good starting dosage. I weigh 160lbs.
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    #23
    Even if no one has direct experience, is there a report anywhere out there on it's activity?
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    #24
    Im shocked that noone has anything at all to add. Lol. Yall are hidin it huh? Lol. jk.
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    #25
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    Seem to have found a way to get it, perhaps for free even. Hardly any experiences with this yet but it sounds awesome.
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