endlessness said:
He is talking about the test I made, posted in the acacia analysis thread, I suppose.
Thanks for the clarification, endlessness! I guess you are referring to
this acacia analysis thread ? Could that also incidentally be the undeclared source of wikipedia's numbers?
endlessness said:
One acuminata broad leaf var had a lot of mthbc (not 2-mthbc).. Either way, notice it was extracted with DCM, very likely that substance would not come across if simply extracting with naphtha or any of the typical non-polar solvents we use.
A reaction with dcm would have resulted in a chlorine bearing product molecule, it would have attached a chloromethyl group to the nitrogen atom. 1-mthbc could not logically be the result of an interaction with dcm. In the other case 2-chloromethyl-thbc would be seen instead of 2-methyl-thbc. For reference,
here (1) and
here (2) are links to the articles by Simon Brandt et al. describing these chlorinated solvent interactions with dmt.
Anyway, 1-mthbc cannot be oxidized into a potentially toxic quaternary metabolite cf. mppp+, so the whole scare is moot for that case. Regarding 2-mthbc, in the the acacia analysis thread I found
a post referencing
an article that details 2-mthbc as "in vivo constituents of rat brain and adrenal gland"(3)
endlessness said:
I wholeheartedly agree. These wonderful kits are a great help to amateurs everywhere!
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(1)
http://www.sciencedirect.com/science/article/pii/S0731708507007820?via=ihub
N,N-Dimethyltryptamine and dichloromethane: Rearrangement of quaternary ammonium salt product during GC–EI and CI-MS–MS analysis
Brandt SD, Martins CP, Freeman S, Dempster N, Wainwright M, Riby PG, Alder JF.
Journal of Pharmaceutical and Biomedical Analysis Volume 47, Issue 1, 12 May 2008, Pages 207-212
Abstract:
N,N-Dimethyltryptamine (DMT) 1 is a simple tryptamine derivative with powerful psychoactive properties. It is abundant in nature and easily accessible through a variety of synthetic routes. Most work-up procedures require the use of organic solvents and halogenated representatives are often employed. DMT was found to be reactive towards dichloromethane, either during work-up or long term storage therein, which led to the formation of the quaternary ammonium salt N-chloromethyl-DMT chloride 2. Analysis of this side-product by gas chromatography ion trap mass spectrometry (GC-MS), both in electron and chemical ionisation tandem MS modes, gave only degradation products. For example, 2 could not be detected but appeared to have rearranged to 3-(2-chloroethyl)indole 3 and 2-methyltetrahydro-beta-carboline 4, whereas HPLC analysis enabled the detection of 2. GC-MS is a standard tool for the fingerprinting of drug products. The identification of a particular synthetic route is based on the analysis of impurities, provided these side products can be established to be route-specific. The in situ detection of both 3 and 4 within a DMT sample may have led to erroneous conclusions with regards to the identification of the synthetic route.
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(2)
http://www.fsijournal.org/article/S0379-0738(08 )00133-3/fulltext
Halogenated solvent interactions with N,N-dimethyltryptamine: Formation of quaternary ammonium salts and their artificially induced rearrangements during analysis
Brandt SD, Martins CP, Freeman S, Dempster N, Riby PG, Gartz J, Alder JF.
Forensic Science International Volume 178, Issues 2-3, 4 July 2008 Pages 162–170
Abstract:
The psychoactive properties of N,N-dimethyltryptamine (DMT) 1a are known to induce altered states of consciousness in humans. This particular attribute attracts great interest from a variety of scientific and also clandestine communities. Our recent research has confirmed that DMT reacts with dichloromethane (DCM), either as a result of work-up or storage to give a quaternary N-chloromethyl ammonium salt 2a. Furthermore, this was observed to undergo rearrangement during analysis using gas chromatography–mass spectrometry (GC–MS) with products including 3-(2-chloroethyl)indole 3 and 2-methyltetrahydro-β-carboline 4 (2-Me-THBC). This study further investigates this so far unexplored area of solvent interactions by the exposure of DMT to other halogenated solvents including dibromomethane and 1,2-dichloroethane (DCE). The N-bromomethyl- and N-chloroethyl quaternary ammonium derivatives were subsequently characterised by ion trap GC–MS in electron and chemical ionisation tandem MS mode and by NMR spectroscopy. The DCE-derived derivative formed at least six rearrangement products in the total ion chromatogram. Identification of mass spectrometry generated by-products was verified by conventional or microwave-accelerated synthesis. The use of deuterated DCM and deuterated DMT 1b provided insights into the mechanism of the rearrangements. The presence of potentially characteristic marker molecules may allow the identification of solvents used during the manufacture of controlled substances, which is often neglected since these are considered inert.
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(3)
http://www.sciencedirect.com/science/article/pii/0006295281902781
Identification and quantification of 1,2,3,4-tetrahydro-β-carboline, 2-methyl-1,2,3,4-tetrahydro-β-carboline, and 6-methoxy-1,2,3,4-tetrahydro-β-carboline as in vivo constituents of rat brain and adrenal gland
Steven A. Barker, Robert E.W. Harrison, John A. Monti, George B. Brown, Samuel T. Christian.
Biochemical Pharmacology Volume 30, Issue 1, 1 January 1981, Pages 9-17
Abstract:
The identification and quantification of three 1,2,3,4-tetrahydro-β-carbolines as normal constitutents of rat brain and adrenal gland, using combined gas chromatographic/mass spectrometric techniques, are reported. Qualitative analyses of these tissues led to the identification of 1,2,3,4-tetrahydro-β-carboline (THBC), 2-methyl-THBC (2-MTHBC) and 6-methoxy-THBC (6-MeOTHBC), as determined by observed peak retention times, mass fragments and ion mass ratios. Quantitative analyses, using deuterated internal standards, gave the following results: THBC (ng/g wet wt) in brain = 17.5 ± 4.86, adrenal = 500.3 ± 163. 6-MeOTHBC (ng/g wet wt) in brain = 35.6 ± 16.6, adrenal = 1113.7 ± 300. Mechanisms for the formation of these β-carbolines as well as their possible function in vivo are discussed.
