Some Simple Tryptamines 2nd ed. PDF with addendum

311 Pages·2013·26.82 MB·English

by  Keeper Trout

“More than you need to know?”
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“More than you need to know?”
Some Simple Tryptamines
2nd Edition
A brief overview & resource compendium
Trout’s Notes #FS-X7 Revised 12-2006 with minor revisions 5-2007.
Created & edited by Keeper Trout with a lot of help from many friends.
Copyright ©2007 by Trout’s Notes & Mydriatic Productions
Revises, updates, merges & replaces ALL FS-X material. (©1993-2004)
ISBN 0-9770876-5-4 (softcover); 0-9770876-6-2 (hardcover)
Produced by MydriaticProductions; a division of Better Days Publishing
Photographs are by Keeper Trout unless indicated otherwise.
All photos copyrighted by the photographers & reproduced here with permission.
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Cover design by Mulga.
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Unauthorized commercial reproduction and distribution of Trout’s Notes is prohibited.
However: Trout’s Notes strongly encourages the dissemination of any and all factual information contained within
these pages so long as proper acknowledgment of the authorships and original sources of data origin are maintained.
No one owns facts or factual data.
Page 1 images:
Psilocybe semilanceata (The Liberty Cap*): Photo by Dr.
P.C. Hickey; * The common name of “Liberty Cap” is believed due
DMT crystals: Photo T. Greif & S. Czolowski; to a rough resemblance to a “Phrygian cap”.
Acacia cultriformis flowers;
DMT crystal packing: after Falkenburg (rendering by This soft pointed cap, gen-
Trout); erally with a peak falling to
Photo collage by Trout. one side, was given to freed
slaves to publicly
denote their restored citizen-
ship and, much later, was
La Liberté image is from made famous as a symbol of
Museum of the French Revolution: the French Revolution.
Vizelle, France [83.314] La Liberté
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Trout’s Notes on Tryptamines
Dedicated with Love to the One
Long may we live & prosper; wherever & whoever we are.
IMPORTANT C S R
AUTIONARY TATEMENTTO EADERS
All information is contained strictly for informational and educational purposes and should not be construed as
advocacy for anyone to violate state or federal laws.
Depending on where a person lives, the following material contains techniques and procedures that might place
one in direct violation of state and federal laws if they were put into practice.
Several (four or five) of these substances are currently regarded as dangerous drugs.
Despite a lack of human fatalities and their known safety records exceeding that of many commonly prescribed
& over-the-counter pharmaceuticals, they are, in fact, at least potentially, quite dangerous substances, not for their
pharmacological or toxic properties but due to the potential actions that may arise from those who quixotically
consider them to be dangerous and who are dedicated to MAKING them dangerous.
These zealous peoples’ extremely serious and ever-present threat of very real danger should never be underes-
timated.
Failure to comply with state or federal laws can result in lengthy imprisonment, excessive fines, terroristic home
invasions, deliberate terrorism of your family & friends, wanton destruction & vandalism of personal belongings,
infliction of immense mental anguish on you & your loved ones, savage beatings & other physical injury, intimida-
tion or harassment of friends or casual acquaintances or even the targeting of them for similar fates, attempted or
successful sabotage of careers or business reputation with malicious attacks upon and slanderous accusations
against personal character being presented to employers, friends, family or business acquaintances, deliberately
brutal murder or injury of pets, eviction from rental properties and/or a complete loss of assets, checking &
savings accounts, vehicles, computers, other possessions & real property, child custody; or even worse. Even if you
are completely uninvolved and merely the owner of a desirable enough piece of real estate, you may still find
yourself being shot in the middle of the night by automatic weapons carrying, night-vision goggled home-invaders
as you are trying to put on your pants.
There is no example mentioned above which has not already occurred in the efforts being directed against drug
users.
While seemingly unthinkable in any free and democratic society, this is presently the very serious state of
reality produced by the current illegality of several of these substances.
Readers should operate under no illusions when reflecting upon the reality of this state-sponsored social purge
& cultural cleansing.
The contained information is intended to serve as a reference tool to better enable future research into this
important and fascinating area of human consciousness and pharmacognostic science.
We do not advocate the use of illicit —or for that matter, any— drugs by uninformed or underinformed individu-
als.
However, we also recognize that many people will choose to use drugs whether they are informed or not.
We do not intend to encourage or promote drug use. We do want those who are already determined to use these
substances, regardless of current legal status, whether planned as sacrament, ‘recreation’ or experimental mate-
rial, to be able do so in an informed, knowledgeable and responsible manner.
Our hopes and intentions are that, through education and awareness, more informed choices can be made,
thereby minimizing the risks often associated with substance use.
It is with this in mind that we present the following.
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Trout’s Notes FS-X7: Comments
ALL Alkaloid Summaries are perennially Incomplete and and is indeed applicable to the vast majority of snuffs but
In Progress. many exceptions exist and these designations are not agreed
Non-bold face species names in the occurrence lists denote a upon by all who use them. Science may define the terms for
conflict, error or lack of proper publication. itself but in light of the ambiguous use by native users, strict
This may variously indicate: 1) questions exist; 2) we are un- definition of the names, as proposed, cannot reflect reality and
able to locate any verifiable references to support the claim; 3) may instead serve to introduce even more confusion to an al-
that the entry represents as-yet unconfirmed preliminary re- ready confused area. If those who use the snuffs do not follow
sults; or, 4) that it is an erroneous entry published in a second- the proposals of scientists this presented convention, however
hand listing in the literature. See comments included in each rational, seems of dubious usefulness.
entry for exact details. Any reference in the bibliography or entry within the occur-
All results of TLC (most graciously performed by my friend rence listings that are incomplete was obtained from second-
Mr. Johnny Appleseed) must be considered to be tentative as hand sources due to the primary paper being unavailable to us
results were based entirely on co-tlc with known reference (for one of various reasons).
standards and color reactions with Ehrlich’s reagents and/or
Xanthydrol.
Abbreviations: ml = milliliter
Pure reference material was only available for DMT and 5-
bp= boiling point mM = milliMolar
Methoxy-DMT.
cm = centimeter mm = millimeter
All potential positive assays for N-Methyltryptamine re- gc = gas chromatography mmp = mixed melting point
lied on comparison of chromatographic behavior with isolates gm = gram mp = melting point
of plants known to contain (or sometimes contain) MMT (like im = intramuscular ms = mass spectroscopy
Acacia maidenii, Desmanthus illinoensis, Desmanthus ip = intraperitoneal na = not available/applicable
leptolobus and Psychotria viridis. In all cases the probable iden- ir = infrared nd = not detected
tity of MMT was assigned to a particular one of the dark iv = intravenous nm = nanometer
kg = kilogram RT = room temperature
bands that were present at a lower Rf than DMT (intermediate
kV = kilovolt sc = subcutaneous
value). Of the bands sometimes seen at a lower Rf than DMT,
LD100 = Lethal dose 100% sp. = species
the band we suspected of being MMT was the only one ob- LD50 = Lethal dose 50% TLC = thin-layer chroma-
served in ALL the species just mentioned. Other low Rf bands ma = milliamp tography
sometimes present were never shared by all species. We in- mao = monoamine oxidase uv = ultraviolet
clude our observations here not as proof of MMT’s occurrence maoi = mao inhibitor v = volt
in any of the plants we mention but rather to stimulate those in
a more tenable position to look closer.
It must be emphasized that both alkaloid concentration and Acacia maidenii flowers
composition may vary substantially from one plant to the
next, from one part to another within the same plant, and they
can also vary by season, or by time of day. Environmental
factors, water availability, degree of sun and nutritional factors
are also known to affect alkaloid concentration. When a per-
cent is listed, this simply represents what was reported in the
literature.
Plant sources for snuffs are highly variable, occasionally
ambiguous, and we merged their entries with the probable bo-
tanical source. Some of these entries may be erroneous as vouch-
ers were lacking. Botanical sources for Yopo, Paricà and Epéna
should be regarded as tentative unless preparation was ob-
served and vouchers made. The presented notions that pres-
ence of bufotenine indicates Anadenanthera as the source is
probably correct but discounts the possibility that other plants
may be involved. The paired idea that absence of bufotenine
and presence of 5-MeO-DMT indicates Virola as the source is
also probably correct in most cases but Anadenanthera
peregrina seeds have been analyzed that showed the presence
of 5-MeO-DMT and absence of bufotenine.
Additionally harmine has been found one sample of Paricà
co-occurring with DMT, bufotenine and 5-MeO-DMT and in
another co-occurring with harmaline and tetrahydroharmine.
Similarly a sample of Epéna was reported to contain harmine
and tetrahydroharmine.
The frequently presented proposal that Yopo be used to
refer only to Anadenanthera originating snuffs and Epena be
reserved for the Virola based snuffs is a sane one in principle
Diplopterys cabrerana
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Trout’s Notes on Some Simple Tryptamines
Table of Contents
3 56
IMPORTANT Baeocystin
Cautionary Statement to Readers 59
9-50 Psilocin
Tryptamines Lacking Ring Substitution 62
11 4-Methoxy-DMT
Gramine 64
13 4-Acetoxy-DMT
Tryptamine 65
17 Psilocybin
N-Methyltryptamine 87
22 Aeruginascin
N,N-Dimethyltryptamine 88
38 1-Methyl-psilocybin
DMT-metho cation 88
38 CZ 74
N,N-DMT-N-oxide 90
40 4-Acetoxy-DET
DET 91
44 CEY 19
DPT 93-138
46 The 5-Substituted Tryptamines
Lespedamine 95
51-92 5-Bromotryptamine
4-Substituted Indoles 95
53 5,6-Dibromotryptamine
4-Hydroxyindole 95
53 5,6-Dibromo-N-methyltryptamine
4-Acetoxyindole 95
53 5-Bromo-DMT
4-Chloro-indole acetic acid methyl ester 96
53 5,6-Dibromo-DMT
4-Hydroxytryptophan 97
54 Serotonin
4-Hydroxytryptamine 102
55 5-OH-N-Methyltryptamine
Norbaeocystin 103
55 Bufotenine
4-Hydroxy-MMT 111
Bufotenine-N-oxide
5
Trout’s Notes FS-X7
112 197-222
Bufotenidine Tryptamines from plants
114 212
Bufoviridine A Simple Alkaloid Volatizer
114 214
Bufothionine Conversion of a Salt to the Free Base
115 218
Dehydrobufotenine Useful Properties of Some Solvents
116 Commonly Used in Chromatography
5-Methoxytryptamine 223-224
118 Indolic Structural table
5-Methoxy-N-methyltryptamine 225-236
121 Endnotes & Commentary
5-Methoxy-N,N-dimethyltryptamine 228
135 Extreme-Condition Hostilis Extraction
5-MeO-DMT-N-oxide 229
136 Questions concerning the Efficacy of
O-Methyl-nordehydrobufotenine Methanol vs. Optimized Methanol vs.
139-186 Ethanol
Assays for Some Indoles 230
141 Hotknives
Color Reactions & Chromophoretic 231
Reagents Tolerance & Cross-tolerance
153 233
Chromophoretic Reagents: Preparations Drug Interactions. Potentiation &
& Assays Synergy
162 237-265
Potassium iodoplatinate References
162 267-286
To recover alkaloids from tlc plates Index
after using Potassium iodoplatinate 289-291
163 Amphibian Common Names
Rapid Field Test for Alkaloids 291-303
163 Information Resources & More Images
Several Useful Techniques for Crude 304
Estimations of Alkaloid Content Acknowledgements
169
Reported Rf Values for Some Selected
Tryptamines
179
Reported Chromatographic Assay Data

and Alkaloid Tests
187
Abstracted Isolations of Some Indoles
6
Some Simple Tryptamines
Rock art from the Tassili Plateau in southern Algeria (~5500 years old)
Rendering by Kat Harrison; reproduced with permission
7
Trout’s Notes FS-X7
DMT freebase crystals (Photo T. Greif & C. Czolowsky; courtesy of Nick Sand)
DMT crystal packing
(After FALKENBERG)
Mesquite
Left & Below
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