“More than you need to know?” y sem 1 D “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. Contact us: Cover design by Mulga. http://troutsnotes.com [email protected] Sales & Distribution: M k h P MydriaticProductions 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 2 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. 3 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 4 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 8