Chemistry
The primary active ingredients of Psilocybe mushrooms are
(surprise!) psilocybin and psilocin, and to a lesser extent
baeocystin and norbaeocystin. The ratio of psilocybin to psilocin
varies from species to species. The primary difference is
that psilocin is unstable and it breaks down when the mushroom
is dried, while psilocybin lasts much longer (a 115-year old
mushroom sample was found to contain some). The two are equally
psychoactive, since one molecule of psilocybin breaks down
into one molecule of psilocin. But in terms of weight, we
find that:
molecular weight of psilocybin 284.3
------------------------------ = ----- = 1.391
molecular weight of psilocin 204.3
So by weight psilocin is around 1.4 times more
potent. The formula for calculating total potency, ignoring
[nor]baeocystin, is thus:
(psilocybin) + (1.4 * psilocin) = total potency in 'psilocybin units'
Now, here's the structural diagram for psilocybin:
N
/ \ PSILOCYBIN
/ \
______/ \ C H N O P
/ / \ \ || 12 17 2 4
/ / \ \ ||
/ / \ \ || 4-OPO -DMT
\/ \/___|| C C 4
\________/ \ / \ /
\______/ \ / \ / 4-Phosphoryloxy-N,N-dimethyltryptamine
\ \ / \ /
\ C N 1H-Indol-4-ol, 3-[2-(dimethylamino)-
\ (+) | ethyl] dihydrogen phosphate ester
O |
| C CAS #: 520-52-5
____| (-)
O____P____O DEA #: 7437
|
|
O
In the body, the phosphorus part is chopped off ("dephosphorylated")
by the enzyme alkaline phosphatase, turning it into our other
friend:
N PSILOCIN
/ \
/ \ C H N O
______/ \ 12 16 2
/ / \ \ ||
/ / \ \ || 4-OH-DMT
/ / \ \ ||
\/ \/___|| C C 4-Hydroxy-N,N-dimethyltryptamine
\________/ \ / \ /
\______/ \ / \ / 1H-Indol-4-ol, 3-[2-(dimethylamino)
\ \ / \ / ethyl]
\ C N
\ | CAS #: 520-53-6
O |
C DEA #: 7438
Psilocybin and psilocin are part of the tryptamine family
(indole C8H7N & ethylamine side chain). They bear close resemblance
to the neurotransmitter serotonin. How these substances work
is, I have come to believe, still quite obscure. Primary effect
seems to be the inhibition of neurotransmitter serotonin (5-hydroxytryptamine
aka 5-HT), i.e. a 5-HT2A post-synaptic agonist that mimics
the effects to 5-HT to put it in jargon. This is the working
hypothesis for LSD-25 at the moment and it's probably true
for psilocybin as well. These substances also present some
cross-tolerance.
As a good psychedelic should, psilocybin, psilocin and psilocybian
mushrooms have low toxicity - in tests with mice, doses up
to 200 mg of psilocybin/kg of body (in average human terms
(65 kg) 13 grams) have been injected intravenously without
lethal effects. The ED50:LD50 ratio is 641 according to the
NIOSH Registry of Toxic Effects; compare this with 9637 for
vitamin A, 4816 for LSD , 199 for aspirin and 21 for nicotine.
Poisoning, at least physically, is thus not a problem.
Then we have the two other significant indole alkaloids:
N
/ \ BAEOCYSTIN
/ \
______/ \ C H N O P
/ / \ \ || 11 15 2 4
/ / \ \ ||
/ / \ \ || 4-OPO -MT
\/ \/___|| C 4
\________/ \ / \
\______/ \ / \ 4-Phosphoryloxy-N-methyltryptamine
\ \ / \
\ C N 1H-Indol-4-ol, 3-[2-(methylamino)-
\ (+) | ethyl] dihydrogen phosphate ester
O |
| C CAS #: 21420-58-6
____| (-)
O____P____O DEA #: None
|
| The monomethyl analogue of psilocybin
O
Unlike psilocybin, baeocystin is somewhat unstable,
and decays noticeably with age. And then we have baeocystin's
close chemical cousin:
N
/ \ NORBAEOCYSTIN
/ \
______/ \ C H N O P
/ / \ \ || 10 13 2 4
/ / \ \ ||
/ / \ \ || 4-OPO -T
\/ \/___|| C 4
\________/ \ / \
\______/ \ / \ 4-Phosphoryloxytryptamine
\ \ / \
\ C N 1H-Indol-4-ol, 3-[2-aminoethyl]
\ (+) dihydrogen phosphate ester
O
| CAS #: 21420-59-7
____| (-)
O____P____O DEA #: None
|
| The demethyl analogue of psilocybin
O
In other words, baeocystin and norbaeocystin
are just psilocybin with one methyl and two methyls respectively
lopped off. And unfortunately for all you synthesis experts,
while baeocystin and norbaeocystin do not have DEA control
numbers they do both come under the Controlled Substance Analogue
Act.
When dephosphorylated, they turn into 4-hydroxy-N-methyltryptamine
and 4-hydroxytryptamine. All 4 substances are presumed hallucinogenic,
but less so than psilocin or psilocybin. Very little work
seems to have been done on them (Chemical Abstracts averages
a cite a year, with most of them of the variety "baeocystin
found in Psilocybe totallyobscuralis"). There has been
some speculation on the 'net about them, and a possible correlation
between nausea and the amount of baeocystin has been found.
We hope to be able to investigate the question further for
the next version.
These are just the four "biggies". A whole truckload of
other indoles are known to exist in Psilocybe mushrooms. Here's
a sample of what was found in a batch of Psilocybe baeocystis,
excluding the ones mentioned above:
| Indole derivative |
Amount (ug) |
| 5-Benzyloxy-3-indole acetic acid |
2 |
| N,N-Dimethyltryptamine hydrogen-oxalate [aka DMT] |
4 |
| Gramine |
40 |
| 3-Hydroxyethyl indole |
2 |
| 5-Hydroxy-3-indole acetic acid |
2 |
| 5-Hydroxyindole |
4 |
| 3-Hydroxymethylindole |
2 |
| 5-Hydroxytryptamine creatine sulfate [aka Serotonin] |
4 |
| 5-Hydroxytryptophane |
2 |
| Indole |
4 |
| 3-Indoleacetamide |
2 |
| 3-Indole acetic acid |
2 |
| 3-Indoleacetic acid ethyl ester |
2 |
| 3-Indoleacetonitrile |
2 |
| 3-Indolealdehyde |
40 |
| 3-Indoleacetaldehyde |
2 |
| 3-Indolecarboxylic acid |
4 |
| 3-Indolelactic acid |
2 |
| gamma-(Indole)-N-butyric acid |
4 |
| beta-Indole-3-acrylic acid |
2 |
| beta-(Indole-3)-propionic acid |
4 |
| Indoxylacetate |
2 |
| Indoxylbutyrate |
2 |
| Isatin |
2 |
| 5-Methoxy-2-carboxyindole |
2 |
| 5-Methoxydimethyltryptamine monooxalate [aka Bufotenine] |
4 |
| 5-Methoxyindole |
4 |
| 2-Methylindole |
2 |
| 3-Methylindole |
4 |
| 5-Methylindole |
4 |
| 5-Methyltryptophane |
2 |
| N-Methyltryptophane |
2 |
| Tryptamine hydrochloride |
4 |
| L-Tryptophane |
0.8 |
| From: A.Y. Leung, A.H. Smith & A.G. Paul,
"Production of Psilocybin in Psilocybe baeocystis Saprophytic
Culture" J Pharm Sci 54: 1576 (1965) |
Yes, Psilocybe mushrooms contain DMT, but in microscopic
amounts. DMT is not orally active anyway, so it doesn't do
anything.
The effects of psilocybin can be potentiated (made stronger)
by taking them with a monoamine oxidase inhibitor (MAOI).
The potency is roughly doubled, according to most reports.
The best known MAOIs are harmine and harmaline from the plant
Peganum harmala (Syrian rue). Combining MAOIs and tryptamines
is an unsafe activity; not only are there are number of substances
you must avoid during use to prevent a serious hypertensive
crisis (see: Foods to Avoid When Using MAO-Inhibitors), but
the long-term health effects are unknown. If you wish to know
more, consult the Tryptamine FAQ. Personally, I doubt it's
worth the risk, if you pick or grow shrooms it's easy to get
enough shrooms for a double dose. |