10-methoxy-harmalan ,an anti-serotonin chemical?

Mauritio

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Danny roddy and georgi dinkov discussed 10-methoxy-harmalan on the latest podcast ,which seems to be as anti-serotonin as LSD ,but without any hallucination effects .
Anybody heard of it or knows where to get it?
Let's compile some info!

 

Mauritio

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Found this on a DMT forum:

"Although some of the compounds of this group occur in plants used as hallucinogens for millenia by the aborigines of South America and elsewhere, very little scientific work has been done on them. The Homa of Asia Minor appears to be syrian rue (Peganum harmala) from which harmaline was first isolated. Harmaline (1-methyl-7-methoxy-3,4-dihydro-beta-carboline) is about three times less potent than the 6-methoxy isomer, and very probably the 5-methoxy isomer will be even more active. The 6-methoxy isomer is also called 10-methoxy-harmalan. Activity appears to be greater when the methoxy group is replaced by a longer chain alkoxy group. If a double bond is also placed in the 3-4 position of harmaline, one obtains harmine. These compounds are active at about 200 mg orally. Most of these compounds are probably legal."
 

Mauritio

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I think this is the study georgi talked about. Would love to see the full text!

"10-Methoxyharmalan, an alkaloid obtained by the cyclodehydration of melatonin, itself a derivative of serotonin, is a more potent serotonin antagonist than harmaline and is only slightly less active than lysergic acid diethylamide. It has a similar, yet slightly greater, effect on behavior as that of harmaline and is the most potent serotonin derivative, so far tested, that affects the avoidance-escape behavioral reflex"

 

Mauritio

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So its seems harmaline and 6methoxyharmalan are hallucinogenic ,but only at higher doses , so maybe similar as LSD.

One more substance, 6-
methoxyharmalan, has been shown to derive, at least in vitro, from melatonin (9), which in turn results from
the methylation of acetylserotonin. The enzyme which makes this methylation possible,
hydroxyindole-0-methyltransferase (HIOMT), has only been found in the pineal body. (See Fig. 1.)
6-Methoxyharmalan is an isomer of harmaline differing in the position of the methoxy group, which is attached
to the same point of the ring as the phenolic group in serotonin or the methoxy group in ibogaine, a
demonstrated hallucinogen (10). (See Fig. 2.)
As will be seen in the rest of the paper, I have found both synthetic 6-methoxyharmalan and 6-
methoxytetrahydroharirnan to be hallucinogenic (11), a fact which invites speculation on the possible role of
the metabolites on the psychoses. It is suggestive that the highest concentrations of serotonin have been
found in the pineal glands of schizophrenics, and that 6-methoxyharmalan is a powerful serotonin antagonist.

The only compound in this chemical group reported to have hallucinogenic properties, to my knowledge, is
harmine (15), which may be regarded as identical to telepathine, yageine, and banisterine, and constitutes
most of the alkaloid content in the Banisteriopsis extracts. Yet the question poses itself as to whether the
qualitative similarity of harman derivatives, as evidenced by many pharmacological effects, would also apply to
the psychological syndrome produced. For instance, Gunn finds that harmaline is twice as active as harmine,
judging from the lethal doses of both compounds for the rabbit, and from their toxicity to protozoa. I have
indeed found harmaline to be hallucinogenic at dosage levels above 1 mg./kg. i.v. or 4 mg./kg. by mouth,
which is about one half the thresh-old level for harmine. It may be interesting to note at this point that the
onset of effects of harmaline or other derivatives is about one hour after ingestion by mouth, but almost
instantaneous after intravenous injection, if circulation time from elbow to brain is taken into account. In this,
harmaline resembles the chemically related tryptamines and differs from the slow-acting phenylethylamines

6-Methoxyharmalan was indeed
shown to be hallucinogenic, as was anticipated, subjective effects becoming apparent with approximate oral
dosages of 1.5 mg./kg. The ratio between threshold doses of harmaline and its 6-methoxy analog is 3:2,
6-methoxyhannalan being the more active.

the 6-methoxy compounds happened to be of a less hallucinogenic
nature in the strict sense of the word, their
effect being more akin to a state of inspiration and heightened introspection. Among the 7-methoxy
compounds, harmaline seemed to cause more withdrawal and lethargy than harmine, but both substances
showed a highly hallucinogenic quality in the visual domain.

 

Mauritio

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The standard oxytocic response to
0.2 ju,g of serotonin was completely
blocked by the addition of 0.5 jmg of
lysergic acid diethylamide, 2.0 pg of 10-
methoxyharmalan (Fig. 2), 50 fig of
harmaline (Fig. 3), or 50 fig of harmine
to a 10-ml muscle bath 5 min before
addition of the serotonin. At higher
dose levels, the harmala alkaloids fre-
quently caused contractions, and it was
noted that if a contraction was elicited
the subsequent serotonin antagonism
was decreased.

Rats given 10-methoxyharmalan at
doses greater than 2 mg/kg exhibited
tremor
which lasted for approximately
1 hour, but were well able to walk at
dose levels as high as 10 mg/kg.

Bromo-lysergic
dcid diethylamide, for example, is a
potent serotonin antagonist, yet has lit-
tle psychotomimetic action.
(anybody heard about that one ??? )




It is, how-
ever, significant that the compound, 10-
methoxyharmalan, is a potent antagonist
of the myotropic action of serotonin
and probably is a competitive antagonist.
It is also the most potent derivative of
serotonin, so far tested, that causes con-
ditioned animals to malte mistakes in
~u avoidance-escape schedule
 

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James b

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Would love to be able to get hold of this. If anyone has access to Sigma and wants to get a group together.
 

Mauritio

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Some vendors that offer harmaline or harmine:



 

Mauritio

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Interestingly this chemical is only 2 steps away from serotonin and only 1 step away from melatonin ,but seems to have quite different properties.
Plus it's also structurally very close to serotonin/melatonin .
Unfortunately you dont see into what 6methoxyharmalan metabolizes.
Screenshot_20210110-160846_Drive.jpg
 

MeatOrchid

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Found this on a DMT forum:

"Although some of the compounds of this group occur in plants used as hallucinogens for millenia by the aborigines of South America and elsewhere, very little scientific work has been done on them. The Homa of Asia Minor appears to be syrian rue (Peganum harmala) from which harmaline was first isolated. Harmaline (1-methyl-7-methoxy-3,4-dihydro-beta-carboline) is about three times less potent than the 6-methoxy isomer, and very probably the 5-methoxy isomer will be even more active. The 6-methoxy isomer is also called 10-methoxy-harmalan. Activity appears to be greater when the methoxy group is replaced by a longer chain alkoxy group. If a double bond is also placed in the 3-4 position of harmaline, one obtains harmine. These compounds are active at about 200 mg orally. Most of these compounds are probably legal."

1610306719583.png
 

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Mauritio

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View attachment 21131
You want to say that they're the same chemical I guess?

I said that already in my third post . But it's good to highlight that once more 👍
 

jmojo

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Georgi said he's soon releasing this as an IdeaLabs product right? So we can soon order from there.
 
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