Author Topic: 5-methoxy-tryptamine  (Read 7855 times)

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Ace99

  • Guest
5-methoxy-tryptamine
« on: October 21, 2002, 10:34:00 PM »
Is 5-methoxy-tryptamine cas#608-07-1 chemical formula: c11h14n2o a psycoactive compound with any sort of recreational value?

Lilienthal

  • Guest
No, sorry. A combination with beta-carbolines ...
« Reply #1 on: October 22, 2002, 12:05:00 AM »
No, sorry. A combination with beta-carbolines might result in something like 5-MeO-DMT (but I wouldn't count that as something of recreational value).

Ace99

  • Guest
Could this be synthesized into 5-meo-dmt?
« Reply #2 on: October 22, 2002, 02:28:00 PM »
Could this be synthesized into 5-meo-dmt?

Rhodium

  • Guest
Yes, see my page for various tryptamine ...
« Reply #3 on: October 22, 2002, 03:18:00 PM »
Yes, see my page for various tryptamine methylations, and I believe that many of them has been posted in the tryptamine forum if you UTFSE.

thethethe

  • Guest
Is there any way...
« Reply #4 on: October 23, 2002, 11:13:00 AM »
...to de-methylate a compound, such as 5-MeO-DMT?

TTT

Rhodium

  • Guest
Demeth(ox)ylation
« Reply #5 on: October 23, 2002, 11:20:00 AM »
Yes, you can demethylate it (probably with BBr3), forming 5-Hydroxy-DMT (Bufotenine). You can not demethoxylate it (forming DMT) though.

Kinetic

  • Guest
What if?
« Reply #6 on: October 23, 2002, 01:21:00 PM »

You can not demethoxylate it (forming DMT) though.


What if you were to peform a HI/red phosphorus reduction as I asked in

Post 356523

(Kinetic: "Hmm", Tryptamine Chemistry)? Just wondering, as I didn't get any responses to that post and I don't understand why it wouldn't work.


Rhodium

  • Guest
Cleaving methoxy groups with HI will leave you ...
« Reply #7 on: October 23, 2002, 01:29:00 PM »
Cleaving methoxy groups with HI will leave you with CH3I and the corresponding phenol. It won't remove the methoxy group from the ring, only the methyl group from the oxygen.

dmitri

  • Guest
demethoxylation in three steps...
« Reply #8 on: October 24, 2002, 06:49:00 PM »

Yes, you can demethylate it (probably with BBr3), forming 5-Hydroxy-DMT (Bufotenine). You can not demethoxylate it (forming DMT) though.




Almost. After demethylation, you can tosylate the phenol with TsCl, then reduce it with a hydride like LiAlH4 to yield DMT. It's not exactly a sensible route to DMT, but it is technically feasible.


No1CockSucker

  • Guest
5-MeO-T.
« Reply #9 on: October 27, 2002, 12:47:00 PM »
5-MeO-T guards against nuclear radiation, but that's about it.

scarmani

  • Guest
Reconsidering Mexamine
« Reply #10 on: March 31, 2003, 02:22:00 AM »
In addition to mentioning research on 5-MeO-T as a guard against radiation, Shulgin also mentions it was investigated as "a potentiator to centrally active drugs" in TiHKAL.

There is also a very interesting statement made in:

"Binding of Indolylalkylamines at 5-HT2 Serotonin Receptors: Examination of a Hydrophobic Binding Region"
Richard A. Glennon et al
J. Med. Chem. 1990,33, pg. 2777-2784

"[3H]Ketanserin labels both the high- and low-affinity states of 5-HT2 receptors whereas [3H]DOB labels only the high-affinity state; thus, for an anticipated agonist, the use of [3H]DOB as radioligand may give more meaningful information.  For this reason, the affinities of [3f-3i] were determined for [3H]DOB-labeled 5-HT2 receptors and compared with the affinities of 5-methoxy-[alpha]-methyl-tryptamine and its desmethyl derivative 5-methoxy-tryptamine."

"Typically, 5-HT2A agonists [[ psychedelics ]] bind with about a 50-fold higher affinity at [3H]DOB-labeled receptors relative to their affinity at [3H]ketanserin-labeled receptors; whereas antagonists show little difference in affinity regardless of which radioligand is employed.  Both 5-methoxy-alpha-methyltryptamine (Ki = 7 nM) and 5-methoxytryptamine (Ki = 5 nM) bind at tritiated DOB-labeled receptors with about a 50-fold higher affinity than they display for [3H] ketanserin-labeled 5-HT2 receptors. A similar result is noted for the 5-methoxy-1-propyl derivative (Ki = 12 nM), suggesting that it too is most likely an agonist."

According to those numbers, 5-MeO-T should be an active psychedelic, slightly more potent than 5-MeO-aMT  :o .  Maybe 5-MeO-T can't cross the blood brain barrier well enough to be active ... maybe it's metabolized too quickly to be active ... or perhaps nobody has tried IV'ing enough of it to check!


Rhodium

  • Guest
Tryptamines in high yields from indoles
« Reply #11 on: July 26, 2003, 11:27:00 PM »
The synthesis of 5-Hydroxytryptamine (Serotonin) and Related Tryptamines
E.H.P. Young

J. Chem. Soc. 3493-96 (1958)

(https://www.thevespiary.org/rhodium/Rhodium/pdf/indoles2tryptamines.pdf)

Abstract

A new route to 5-hydroxytryptamine (Serotonin) and related substituted tryptamines is described. 3-2'-Nitrovinylindoles, readily prepared by the condensation of substituted indole-3-aldehydes and nitroparaffins, are reduced with lithium aluminium hydride to the corresponding substituted tryptamines. An improved method of preparation of the indole-3-aldehydes, which are now obtained in 85-95% yield, is also described.