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Possible CNS activity of a major methoxetamine synthesis impurity?

K

klfiend

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Jun 28, 2011
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I have been trying to get to the bottom of the subjective difference many users report between the so called "UK methoxetamine" and "chinese methoxetamine" or the fluffy white methoxetamine and sandy off-white to yellow methoxetamine. My previous theory was different synthesis routes may result in differing enantiomer ratios and the subjective difference was caused by differing pharmodynamics of the enantiomers. However, I was reading the DEA microgram journal article on methoxetamine and the DEA chemists identified a major synthesis impurity in the methoxetamine sample they had analyzed. The isolated impurity was identified as 1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone.

1-(ethylamino)cyclopentyl](3-methoxyphenyl)methanone structure:





Just by looking at the structure of this impurity I am assuming its CNS active and is likely responsible for the differing subjective effects of the "chinese" or sandy yellow methoxetamine. I suppose I was wondering if this pure compound has been ingested by any humans before? I'm rather curious to know what its effects are as I have had methoxetamine from numerous different sources which are supposedly of high purity and myself have noticed differing effects with the white "uk methoxetamine" seeming to have less after effects and generally feels "cleaner" than the off white to yellow sandy methoxetamine.

Here is a link to the DEA journal article the structure of the methoxetamine synthesis impurity is on page 15 and the chemical analysis can be found a on the previous few pages

http://www.justice.gov/dea/pr/microgram-journals/2012/mj9-1_3-17.pdf
 
I'd suspect with a cyclopentane ring instead of cyclohexane, london forces would be smaller meaning less bonding affinity with the receptor and thus a drop in potency or CNS activity.
 
The Methoxetamine I was getting at the start of 2010 was significantly different to the mxe thats about now. Way less aftereffects.
 
The beginning of the article states it was 200mg of unknown powder seized in the northwest united states. I don't know what "type" of methoxetamine they analyzed I was just hypothesizing that the impurity found in their sample could be the cause for the subjective difference reported between certain varieties of methoxetamine. If someone has some of the sandy yellow methoxetamine they should do a comparison pre and post acetone wash, for science!
 
An acetone wash won't remove that. Maybe recrystallisation from EtOH or iPrOH.
 
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p.17:
A significant amount of a by-product (impurity) was
produced during the synthesis of methoxetamine. The FTIR
(Figure 12a) of the synthesis impurity indicated that a carbonyl
was present and its mass spectrum (Figure 12b) indicated a
molecular weight of 247. The impurity was easily isolated
from methoxetamine HCl by its solubility in acetone.
Click to expand...
 
This looks like a simple acid-catalyzed rearrangement of methoxetamine. It probably happens if it is heated too much while forming an acid salt. The possible mechanism is shown below.
 
Hm... That's incredibly interesting.

That certainly looks like an active monoamine reuptake inhibitor. Perhaps a serotonin / dopamine releaser.

Extremely interesting though!
 
doppelgänger said:
Can anybody gess from the spectra how big the percentage of this is in their methoxetamine?
I'm wondering if this might be responsible for the mania some users report with mxe.
Click to expand...

They haven't included any information about the purity of their crude or final product, but I would assume their final product was very pure if they were using it as a standard for analytical purposes.

I wouldn't go so far as to blame this particular impurity for the poor quality of most "street" methoxetamine. About a year and a half ago I analyzed two separate purchases and found them to be very impure as a result of deliberate cutting. One of the samples even contained about 20% tiletamine which really made me cringe.

I am also very interested in what Hammilton said about the impurity discussed being psychoactive. Can your possibly explain what leads you to believe this could be a monoamine reuptake inhibitor/releaser? I have a decent chemistry background but not much pharmacology or biochem so I'd love to get more info about this.
 
It looks vaguely similar to an a,a-disubstituted N-ethyl cathinone.
 
It's basically a ring-closed cathinone derivative of phentermine.

Cathinones differ a surprising amount from their amphetamine relatives. Has bk-phentermine been made?
 
I have some off white sandy mxe i got about 8 months ago, and some white powdery mxe i got a a few months after that from a different source.

Gonna do a dry acetone wash on 50mg of each to see if theres any difference in whats pulled off in weight after evap.

Edit-

Negligible losses on both (2-3mg's each). Guess both of them are from a good synth.
 
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Why not TLC both samples on the same plate, that would be much more useful...
 
Ceres said:
Why not TLC both samples on the same plate, that would be much more useful...
Click to expand...

Don't have access to TLC, and i wouldn't know how to do it anyway, I'm far from a chemist. Just a dude who deals with alkaloid extractions and happened to have some dry acetone on hand. .5ml of acetone, for ~45 sec, then decant, dry, and weigh again.

Not really useful, but others should at least do this if they can, and have two different color/consistency's of mxe on hand. TLC definitely is the only way to really know though. The impurity could be anything, not specifically the one in question, after an acetone wash, and thats not all that scientific. At most it that theres not specifically that impurity in your mxe by washing it.
 
Hammilton said:
That's 94-96% pure.

I wouldn't call that quality material.
Click to expand...

Well it was done rather hastily and a few mgs may have been lost in handling between washes. In retrospect i should have washed them on the weighing dish, rather than another surface.

Might try it again tomorrow with a larger amount and see how it goes.
 
All that's really happened here is you've lost some of the material to the solvent. Off-white colour could indicate the presence of anything from organic impurities to a diluent like lactose. The hydrochloride salt of the 5-membered ring version of methoxetamine pictured above would still very likely be colourless/white to the naked eye when pure.
 
It's not a "5 membered ring version of methoxetamine" however. It's not even an analogue. I don't think this effects it's coloring though. Pretty much all of these compounds are more or less white when pure.


While it's pharmacology may be interesting, unless someone takes their methoxetamine and purposely converts it to this compound (not much work, fwiw) we're probably not going to see human bioassays. I'd be real surprised if it was all that potent. Phentermine itself is fairly weak (37.5mg starting dose, IIRC) and cathinone analogues are generally less potent. An N-ethyl doesn't really help or hurt. I think n-ethylamp was equipotent with amphetamine proper so that substitution may be a wash. The 3-methoxy may increase sertonergicity, but I'm not certain. 4-methoxy certainly would.

One word of caution- there's a chance this compound could be an MAOI. It's not that different from tranylcypromine, but it's not that close either. Close enough that I'd be concerned and take necessary precautions for initial testing!
 
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