The Cactus Alkaloids

386 Pages·2017·10 MB·English

by  Keeper Trout

““More than YOU need to know?”
Sacred cacti Fourth Edition
Part C: Cactus Chemistry: Section 1
Trout’s Notes on
The Cactus Alkaloids
Nomenclature, Physical properties,
Pharmacology & Occurrences
Assembled by
Keeper Trout
& friends
A Better Days Publication
“More than you need to know?”
C13-2013 PDF generated 3 December, 2013 updated to fix bad links Jan. 2018
Working Draft Version
Trouts Notes
Still In-Editing & Proofing
on
The Cactus Alkaloids
Copyright ©2013, 2007 by MydriaticProductions
Copyright ©1997, 1998, 2003 by Trout’s Notes & Mydriatic Productions
(where applicable).
Originally published in part as Appendix A to Sacred Cacti (first edition) in 1997 and again in 1998 as Trout’s
Notes #C-9 Cactus Alkaloids, other than Mescaline; Reported from Mescaline Containing Cacti; (including
Coryphantha alkaloids)
Now retitled as“The Cactus Alkaloids” it has been expanded to encompass all of the known cactus alkaloids.
It also now includes what formerly were several chapters concerning Mescaline in Sacred Cacti Part A.
This illustrated version merges, updates, corrects and replaces all previous versions.
All rights reserved.
Produced by Mydriatic Productions; a division of Better Days Publishing
© Photos by K. Trout except where specified otherwise.
All other photos remain copyrighted by the photographer(s) credited.
Reproduction without express written authorization is prohibited.
MydriaticProductions
Unauthorized commercial reproduction, distribution and/or sales of Trout’s Notes is
prohibited.
However:
This series of works is intended to serve the reader as reference material for further
research and study.
Trout’s Notes therefore strongly encourages the dissemination of any and all factual
information contained within these pages so long as proper acknowledgment of author-
ships as cited herein are maintained.
No one owns facts or factual data.
Cactus Alkaloids
This is an editing copy of a work that is ongoing.
Much of this work is as complete as was possible for me in 2007. Acquiring and processing
the references needed for its completion has continued to delay the planned release to such an
unacceptably uncertain future date that it was deemed of value to make the in-proofing version available
even though work is still actively ongoing. Despite the larger work Sacred Cacti now including more
than 2900 references there is still a stack of hundreds more papers presently being processed and at least
as many that are still being sought. By the time that a thorough treatment of Hylocereus and Opuntia is
completed I anticipate that more than a thousand additional titles could be added on those two alone.
Several more recent chapters from Sacred Cacti are also now included. Some of that is almost unchanged
from the 2001 edition but many portions are either new or updated. The chapters on mescaline, its
physical data, occurrences and pharmacology were moved to this book as it has always been an
arbitrary call which work the mescaline entries best belonged and where to draw the lines. While they
belong with the alkaloid entries their much greater size makes them a lumpy fit.
Part A itself is now focused mainly on the plants and to a lesser degree on their politics.
To simplify keeping track of references it was decided to create a master reference section for the work
Sacred Cacti. That will be found in the pages of this book.
Sacred Cacti Fourth Edition (revised yet again) [now online at sacredcacti.com]
Part A The Mescaline Containing Cacti (Current PDF to come; much new material.)
Part B San Pedro [3rd edition PDF version online]
Part C Cactus Chemistry
Section 1 The Cactus Alkaloids [4th edition PDF version online]
Section 2 Cactus Chemistry By Species [4th edition PDF version online]
Please let me know if you spot errors or know of additions or if you have suggestions on how to make
this a better work. I also welcome any contributions of images; especially in habitat.
Periodically this work will be replaced whenever progress merits it. When that occurs the index and
table of contents pagination will shift and so may elements of the layout or any aspect of its imagery.
When the new edition is completed, it will replace this PDF version online and hopefully see print.
Check my webpage for contact information, new uploads and updated versions:
http://troutsnotes.com/
“More than you need to know?”
This work is dedicated to the smiling jaguar deity of the Chavin
and to all humans who still know what sacred truly means.
iMPOrtaNtdiSclaiMer & cautiONary StateMeNt tO readerS

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.
Mescaline and some similar substances are currently regarded as dangerous drugs.
Despite a complete lack of human fatalities and a proven safety record in humans exceeding that of many com-
monly prescribed & readily available over-the-counter pharmaceuticals, they are, in fact, at least potentially, quite
dangerous substances. This is not due to their their pharmacological or toxic properties but rather is entirely the
direct result of the potential actions that may arise from those who quixotically consider them to be dangerous and
who are dedicated to MAKING them dangerous.
These peoples’ extremely serious and ever-present threat of very real danger should never be underestimated. This
is not a rational issue for them and no amount of logical persuation can be expected to sway their emotionally and/
or religiously based opinions.
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, intimi-
dation or harassment of friends or casual acquaintances or even the targeting of them for similar fates, attempted
or successful sabotage of career or business reputation with malicious attacks upon and slanderous accusations
against personal character being deceptively presented to employers, friends, family or business acquaintances with
deliberate pejorative intent, 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.
You may even 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 currently the very serious state of reality
produced by the current illegality of an increasing number of these substances and the existence of a well-funded
and powerful modern-day Inquisition that is dedicated towards our eradication via a brutal reign of terror and
violent suppression.
Readers should operate under no illusions when reflecting upon the reality of this as yet another attempted
state-sponsored social purge & cultural cleansing.
The information contained in these pages is intended to better enable future research into this important and
fascinating area of consciousness and science.
We do not advocate the use of illicit —or for that matter, any— drugs by uninformed or underinformed individuals.
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, to be able
do so in an informed, knowledgeable and responsible manner; whether this is planned as sacrament, ‘recreation’
or experimental material.
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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Cactus Alkaloids
The identifications of the species pictured in this work Unless we had questions which are noted or altered the
are as accurate as possible. However, in some cases we name to come into line with other images of the same
are not qualified to judge accuracy of the labels so in the species we present them as they were labeled.
event of mislabeled plants grown from seed we could
have inaccuracies.
Trichocereus peruvianus (Bob Wallace)
5
Notice the cool horn-shaped leaves.
5
Trout’s Notes on Cactus Chemistry
Trouts Notes on Cactus Chemistry
Photograph by
Joylene Sutherland.
Mixed cactus planting in Victoria. Trichocereus vollianus is in the center flowering.
Fat ones on the right are Trichocereus sp. “WK”; named after the Australian who collected it.
Xcoahuilense (center row)
Xcapricorne (bottom row)
Astrophytum cv. Superkabuto hybrids
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Cactus Alkaloids
Table of Contents
IMPORTANTDisclaimer & Cautionary Statement to Readers 4
Some opening comments 13
Comments on the occurrence & distribution of mescaline 15
Distribution of alkaloids within cacti 17
Chapter One: Phenethylamines Reported from the cactaceae
Phenethylamine — Demethylmescaline 19
Phenethylamine 21
N-Methylphenethylamine 22
N,N-Dimethylphenethylamine 24
(+) Coryphanthine 26
Tyramine 26
m-Tyramine 32
Octopamine 33
N-Methyltyramine 34
Synephrine 38
beta-O-Methylsynephrine 39
Candicine 46
Leptodactyline 48
4-Methoxyphenethylamine 49
4-Methoxy-beta-hydroxyphenethylamine 50
N-Methyl-4-methoxyphenethylamine 50
(–)-N-Methyl-4-methoxy-beta-hydroxyphenethylamine 51
N,N-Dimethyl-4-methoxyphenethylamine 51
N,N-Dimethyl-4-methoxy-beta-hydroxyphenethylamine 52
O-Methylcandicine 52
Dopamine 52
Norepinephrine 54
Epinine 56
Epinephrine 57
N-Methyladrenaline 58
Coryneine 59
3-Hydroxy-4-methoxyphenethylamine 59
3-Methoxytyramine 60
Normetanephrine 61
N-Methyl-3-methoxytyramine 61
Metanephrine 62
NAMT 62
N,N-Dimethyl-3-methoxytyramine 62
3,4-Dimethoxy-beta-hydroxyphenethylamine 67
3,4-Dimethoxy-N-methylphenethylamine 67
(–)-Normacromerine 69
beta-Methoxy-3,4-dimethoxy-N-methylphenethylamine 71
N-Acetyl DMPEA 71
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Trouts Notes on Cactus Chemistry
3,4-Dimethoxy-N,N-dimethylphenethylamine 72
Macromerine 72
beta-Methoxy-3,4-dimethoxy-N,N-dimethylphenethylamine 75
phenethylamine 75
3-Nitrotyramine 75
3,4,5-Trihydroxyphenethylamine 75
3,4-Dihydroxy-5-methoxyphenethylamine 76
3-Hydroxy-4,5-dimethoxyphenethylamine 76
N-Methyl-3-hydroxy-4,5-dimethoxyphenethylamine 77
N-Formyl-3-hydroxy-4,5-dimethoxyphenethylamine 77
N-Acetyl-3-hydroxy-4,5-dimethoxy-
phenethylamine 77
N,N-Dimethyl-3-hydroxy-4,5-dimethoxyphenethylamine 77
4-Hydroxy-3,5-dimethoxyphenethylamine 78
Chapter 2: Mescaline 81
Physical Data & Toxicity 83
Some Rf values reported for Mescaline 93
Some Color Reagents and Reactions Reported For Mescaline 94
Mescaline Endnotes 97
The reported occurrences of mescaline 99
Chapter 3: Pharmacology & Metabolism of Mescaline 105
Physical & psychological effects in humans 107
Mescaline pharmacology endnotes 141
Chapter 4: Phenethylamines Reported from the cactaceae
N-Methylmescaline — 2,6-Dichloromescaline 147
N-Methylmescaline 149
N-Formylmescaline 150
N-Acetylmescaline 150
beta-Hydroxymescaline 151
Mescaloxylic acid 152
Mescaloruvic acid 152
N,N-Dimethylmescaline 152
Peyonine 154
Mescaline succinamide 155
Mescaline malimide 155
Mescaline maleimide 155
Mescaline citrimide 155
Mescaline isocitrimide lactone 155
3,4,5-trimethoxyphenylalanine 155
Peyoglunal 155
Peyoglutam 156
Mescalotam 156
2-Chloro-mescaline 156
2,6-Dichloromescaline 156
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Cactus Alkaloids
Chapter 5: Isoquinolines reported from the Cactaceae 157
Isoquinolines 157
Longimammatine 159
Weberidine 159
Longimammosine 160
Longimammidine 160
?-Methoxy-1-methyl-THIQ 161
(–) Longimammamine 161
Arizonine 161
Heliamine 162
Dehydroheliamine 163
Backebergine 163
Lemaireocereine 163
Dehydrolemaireocereine 164
Isobackebergine 164
Uberine 164
Corypalline 164
Salsolinol 165
Salsoline 166
Isosalsoline 167
(±)-Salsolidine 168
Dehydrosalsolidine 169
Isosalsolidine 169
N-Methylheliamine 169
N-Methyl-6,7-dimethoxyisoquinolinium chloride 170
N-Methylisosalsoline 170
N-Methylisosalsoline 170
Lophocerine 171
Carnegine 173
Tepenine 174
Anhalamine 174
N-Formylanhalamine 176
N-Acetylanhalamine 176
Isoanhalamine 176
Anhalinine 177
N-Methylanhalinine 178
N-Formylanhalinine 178
O-Methylanhalinine 179
Dehydronortehuanine 179
5,6,7-Trimethoxy-isoquinoline 179
Isoanhalonidine 179
Anhalonidine 180
N-Formylanhalonidine 182
Isoanhalidine 182
Anhalidine 183
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Trouts Notes on Cactus Chemistry
S-(+)-O-Methylanhalonidine 184
N-Formyl-O-methylanhalonidine 185
O-Methylanhalidine 185
? Tri-MeO-1-methyl-1,2,3,4-tetrahydro-isoquinoline 186
Tehuanine 187
Tehuanine-N-oxide 187
Anhalotine 188
6,7-Dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt 188
6,7-Dimethoxy-8-hydroxy-3,4-dihydroisoquinoline 188
1-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinoline 188
2-Methyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt 188
S-(+)-Gigantine 189
Isopellotine 190
Pellotine 190
O-Methylpellotine 193
N-Acetyl-anhalonine 196
(–)-1-Hydroxymethyl-2-methyl-5-hydroxy-6,7-dimethoxy-1,2,3,4-tetrahydroisoquinoline
196
Deglucopterocereine-N-oxide 197
Pterocereine 197
1,2-Dimethyl-6,7-dimethoxy-8-hydroxy-3,4-dihydroisoquinolinium inner salt 197
Peyotine 198
Peyoxylic acid 198
Peyoruvic acid 198
O-Methylpeyoxylic acid 198
O-Methylpeyoruvic acid 199
Mescalotam 199
Anhalonine 199
N-Formylanhalonine 201
(+)-N-Acetylanhalonine 201
N-Ethylanhalonine 202
Lophotine 202
? Mono-OH-tri-MeO-2-Methyl-isoquinoline 202
Norweberine 203
Isonorweberine 203
Pachycereine 203
Dehydropachycereine 203
Weberine 204
N-Methylpachycereine 204
Pilocereine 204
Piloceredine 206
Lophocine 206
Chapter 6: Imidazoles reported from the Cactaceae 207
Dolichotheline 209
N,N-Dimethylhistamine 210
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