““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. 4 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 66 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 7 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 8 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 9 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 10
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