Drug info - What are DOx compounds?

Discussion in 'Phenethylamines' started by Dalfir, Mar 13, 2007.

  1. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    I've seen the term quite a bit, Erowid doesn't point to DOx specifically, but rather to derivatives like DOB, DOI etc etc...Are these basically synthetic phenethylamines or is it something else?

    LSD is a synthetic tryptamine, right? So is phenethylamine a different type of neurotransmitter?

    Do all of these chemicals, tryptamine, phenethylamine, etc occur naturally in the brain, and consuming drugs with these as active ingredients just increases their presence? DMT is a naturally occuring hallucinogen secreted by the brain, correct?
     
    Last edited by a moderator: Sep 18, 2010
  2. Psych0naut

    Psych0naut Platinum Member

    Reputation Points:
    2,229
    Messages:
    2,250
    Joined:
    Feb 27, 2006
    from The Netherlands
    The DOx compounds are 2,5-dimethoxyamphetamines, with a added molecule on the 4th position if I'm not mistaken, and they are indeed synthetic phenethylamines.
     
  3. Bildo

    Bildo Silver Member

    Reputation Points:
    23
    Messages:
    42
    Joined:
    Feb 2, 2007
    from ireland
    There are a few tryptamines found naturally in the body. Serotonin being one of them. Tryptamine is just a chemical structure that can be the main functional part of a molecule or the structural backbone of the molecule.
    DOXs are amphetamines (dimethoxy). the X beit I, B, etc usually stands for a substitution atom or molecule. DOB - bromine, DOI - Iodine.(the same occurs for many chemical series such as 2cX)
    I believe the precursor to these molecules is DOH where the substituted molecule is Hydrogen.
    According to Shulgin the heavier the substitution (in molecular weight) the more potent the chemical.

    I don't believe that many tryptamines and phenethalamines occur naturally in the brain.
     
  4. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    So the original tryptamine molecule is just a C10H12N2 amine that is pretty ineffective on its own? Is it only effective when there's substitution? I believe psilocybin is tryptamine with a substitute atom on the R3, R4 and R5 position?

    The same question of phenethylamines, are they relatively subtle on their own, and only effective when modified? I know that LSD has a very basic tryptamine framework, but it's too different to technically be referred to one? It's also not a phenethylamine, so where does it fit in with the two, if at all?
     
  5. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    Sorry, mixed up the mescaline modified phenethylamine with psilocybin, which is the R4, RN1 and RN2 position.
     
  6. Nagognog2

    Nagognog2 Iridium Member

    Reputation Points:
    1,936
    Messages:
    7,017
    Joined:
    Feb 1, 2005
    The actual nucleus of tryptamines is indole. This holds true for LSD as well. The phenethylamines do not have an indole nucleus, per say. But their shape mimics such - allowing it to, in laymen's terms, fit the key into the lock. Explaining more would require paper and a pen. Suffice to say - they, phenethylamine and tryptamine psychedelics, work along the same pathways.
     
  7. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    Don't worry, my brother has a PhD in chemistry, I spent the day with pen and paper so I understand the key/lock scenario and how LSD mimics certain chemicals, causing feedback. Niether of us are sure exactly how it works, other than simply binding to seretonin, Erowid doesn't seem to have the answer of what exactly LSD does that causes its effects.

    I understand that phenethylamine is a neurotransmiter, but what does tryptamine do on its own?
     
  8. Nagognog2

    Nagognog2 Iridium Member

    Reputation Points:
    1,936
    Messages:
    7,017
    Joined:
    Feb 1, 2005
    Tryptamine by itself has no psychoactivity. One way used to describe the action of these substances is by viewing serotonin as an electrical-relay. Impulse travels through serotonin and is directed across the junction into the appropriate receptor. Replace serotonin with, say, psilocin - and it fires the impulse across to a multitude of receptors at once. An imperfect analogy - but it gets the basic idea across.
     
  9. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
  10. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    And just to get this straight; when a phenethylamine has an alpha-methyl group added to it, it becomes an amphetamine. Then when dimeoxy is added to that with an hydrogen atom, it's Dimeoxyamphetamine hydride(?) (DOH)

    That H can then become the x, which is replaced with B (DOB) or I (DOI)

    Also, am I correct basically with the above post regarding neurotransmitter mimics?
     
  11. Nagognog2

    Nagognog2 Iridium Member

    Reputation Points:
    1,936
    Messages:
    7,017
    Joined:
    Feb 1, 2005
    Close enough for basic reference.
     
  12. snapper

    snapper Gold Member

    Reputation Points:
    2,208
    Messages:
    2,136
    Joined:
    Sep 30, 2005
    from U.S.A.
    While on the topic, what about DOF andd DOMF ?
     
  13. Nagognog2

    Nagognog2 Iridium Member

    Reputation Points:
    1,936
    Messages:
    7,017
    Joined:
    Feb 1, 2005
    To my knowledge neither has been tested. By the standard scale, a fluoro is the least powerful. And fluorine compounds are toxic. Much more so than Cl, Br, I. So may well be not a good idea to go there - unless you hate your monkey.
     
  14. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    Aha...So is Dimeoxyamphetamine by itself, with out the H or the x effective at all as a stimulant?
     
  15. turkeyphant

    turkeyphant Gold Member

    Reputation Points:
    613
    Messages:
    506
    Joined:
    Oct 12, 2005
    from U.K.
    Well it has to have a hydrogen there, but yes, 2,5-dimethyoxyamphetamine is active. Shulgin calls it DMA or 2,5-DMA and reckons it's active in the 80-160 mg range.

     
    Last edited by a moderator: Sep 18, 2010
  16. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    Haha, forgive me, I never did science in school :p

    So DMA is dimoxy added to amphetamine? (Which is a substituted phenethylamine.)

    If
    DOI and DOB are created by substituting the H with an I or B

    When does this I believe the precursor to these molecules is DOH where the substituted molecule is Hydrogen. occur?
     
  17. Rush

    Rush Titanium Member

    Reputation Points:
    146
    Messages:
    155
    Joined:
    Nov 30, 2006
    from switzerland
    really fluorine compounds are so toxic?even fluoxetine?


    something made swim think that fluorine compounds, like fluoxetine,fluoro tryptamines, 4-fluoro-alpha-PEA(which seems to have lots of his action on serotonin),TFMPP (that is pure serotonin euphoria) have some kind of particular and interesting pharmacologichal effect on serotonin systems...

    and I was thinking how interesting should be experimenting on DOF and 2C-F.
    oh i see there is DOEF(ethyl-fluorine) cool!
     
    Last edited: Mar 15, 2007
  18. turkeyphant

    turkeyphant Gold Member

    Reputation Points:
    613
    Messages:
    506
    Joined:
    Oct 12, 2005
    from U.K.
    Yes, you are broadly correct. Take phenethylamine. Add the alpha methyl group. You have amphetamine. Add one methoxy group to the 2 carbon and one to the 5 carbon to make dimethyoxyamphetamine or DMA. DOI is made by substituting an I at the 4 position.

    I'm sorry but I don't understand what your last question is...
     
  19. Dalfir

    Dalfir Titanium Member

    Reputation Points:
    196
    Messages:
    222
    Joined:
    Mar 9, 2007
    from Colorado, U.S.A.
    The last question was when does DMA become the inactive DOH precursor?

    Also, going a bit off topic, but what is then added to amphetamine to make it methamphetamine? Adding a methoxy group to just one carbon?
     
  20. Psych0naut

    Psych0naut Platinum Member

    Reputation Points:
    2,229
    Messages:
    2,250
    Joined:
    Feb 27, 2006
    from The Netherlands
    No, another methyl group on the nitrogen atom. That's why you sometimes see methamphetamine named as N-methylamphetamine.
    The N stands for nitrogen, and the extra methyl group is attached to the nitrogen atom of the amine group.

    A methoxy group is a methyl group, linked by an oxygen atom, hence meth(yl)oxy(gen).