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2-MTHBC - 2-methyl-1,2,3,4-tetrahydro-β-carboline - information project

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Boundary condition
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There are so many unanswered questions about 2-MTHBC that I've decided to get this effort rolling to consolidate knowledge and techniques relating this widespread secondary alkaloid. I'll be building up an index of links below in this post, so anything anyone can bring to this discussion would be very welcome.

An early discussion was here:

Work in progress - more to follow!
 
This post covers links within the Nexus which make any meaningful reference to MTHBC at all.

Again, a work in progress, feel free to contribute!


 
This post will be covering details of chemistry relating to MTHBC and its close derivatives (perhaps), such as 6-MeO-2-MTHBC.

Usual rules apply :)

2-MTHBC - DMT-Nexus Wiki - plenty of room for updates and improvements here too!

this betacarboline is associated with DMT containing species and is the betacarboline analog of DMT itself
One should be able to produce this chemical by employing a Pictet Spengler reaction on DMT, something typically requiring heat, a Lewis acid and aldehyde.

This betacarboline might be an artifact of hot acidic extractions, or perhaps it is present in the plant, however it might not be as soluble as DMT, typical exactions that result in traces of this alkaloid may not be ideal for it and may only be recovering a small portion of the molecule present in the basic or caustic solution.

This betacarboline may also oxidize.
It should have a glow under uv, unlike DMT, so if it did occur in DMT the material would glow in a visible spectrum under a black light. DMT is fluorescent, but not in a visible spectrum.

I would expect that this alkaloid, 2MTHbC, would also be colored, and would discolor DMT if it occurred in it.
I wish there was more data about central effects of this molecule. It occurs in nature in DMT containing plants and has been known as a contaminant product in DMT synthesis.

What are the sizes of the breakdown products of this molecule, what does it fracture into and how does it's molecular weight and melting point differ from DMT?
edited to add this :
2-Methyl-1,2,3,4-tetrahydro--carboline (4), white
shiny needle crystals (MeOH) (50 mg), mp 213 ∞C,
UV λmax (MeOH) nm 290, 294. EIMS, m/z (rel.
int.): [M+] 186 (26), 171 (6), 144 (100), 143 (63),
115 (10), 94 (5), 77 (4), 42 (4).
Here

 
Thank you for providing informations on this important topic.

2-Me-THBC and 2,9-diMe-THBC are protoxins that are oxidized by heme peroxidases into 2-Me-DHBC+/2-Me-BC+ and 2,9-diMe-DHBC+/2,9-diMe-BC+. These oxidized forms are suspected neurotoxins. Elevated levels of 2-Me-BC+ cations have been found in the lumbar cerebrospinal fluid of individuals with Parkinson's disease. Although a causal relationship has not yet been proven, THBCs may be involved in neurodegeneration as slow-acting neurotoxicants.

We have added some relevant papers to the discussion.
  • Hannu Komulainen; Jouko Tuomisto; Mauno M. Airaksinen; Ilkka Kari; Pekka Peura; Liisa Pollari (1980). Tetrahydro-β-carbolines and Corresponding Tryptamines: In Vitro Inhibition of Serotonin, Dopamine and Noradrenaline Uptake in Rat Brain Synaptosomes. , 46(4), 299–307. doi:10.1111/j.1600-0773.1980.tb02458.x
  • Youdim, M.B.H.; Oppenheim, B. (1981). The effect of tryptolines (1, 2, 3, 4-tetrahydro-β-carbolines) on monoamine metabolism and the platelet aggregation response in human platelets. , 6(4), 801–810. doi:10.1016/0306-4522(81)90163-9
  • Kazuo Matsubara; Michael A. Collins; Atsushi Akane; Jun Ikebuchi; Edward J. Neafsey; Masato Kagawa; Hiroshi Shiono (1993). Potential bioactivated neurotoxicants, N-methylated β-carbolinium ions, are present in human brain. , 610(1), 0–96. doi:10.1016/0006-8993(93)91221-d
  • Matsubara, K., Kobayashi, S., Kobayashi, Y., Yamashita, K., Koide, H., Hatta, M., … Kimura, K. (1995). beta-Carbolinium cations, endogenous MPPplus analogs, in the lumbar cerebrospinal fluid of patients with Parkinson’s disease. Neurology, 45(12), 2240–2245. doi:10.1212/wnl.45.12.2240
  • Alexander Storch; Yu-I Hwang; Debra A. Gearhart; J. Warren Beach; Edward J. Neafsey; Michael A. Collins; Johannes Schwarz (2004). Dopamine transporter-mediated cytotoxicity of β-carbolinium derivatives related to Parkinson's disease: relationship to transporter-dependent uptake. , 89(3), 685–694. doi:10.1111/j.1471-4159.2004.02397.x
  • Tomás Herraiz; Hugo Guillén; Juan Galisteo (2007). N-Methyltetrahydro-β-carboline analogs of 1-methyl-4-phenyl-1,2,3,6-tetrahydropyridine (MPTP) neurotoxin are oxidized to neurotoxic β-carbolinium cations by heme peroxidases., 356(1), 0–123. doi:10.1016/j.bbrc.2007.02.089
 

Attachments

  • Herraiz 2007.pdf
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  • Komulainen 1980.pdf
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  • Matsubara1993.pdf
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  • Matsubara1995.pdf
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  • Storch 2004.pdf
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  • Youdim 1981.pdf
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