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This is the second half of

PiHKAL: A Chemical Love Story

, by Alexander Shulgin and Ann Shulgin

.Please forgive any typos or misprints in this file; further, because of ASCII limitations, many of the typographical symbols in the original book could notbe properly represented in this file.If you are seriously interested in the chemistry contained in these files, you should order a copy of the book PiHKAL. The book may be purchased for $22.95 ($18.95 + $4.00 postage and handling) from Transform Press, Box 13675, Berkeley, CA 94701. California residents please add $1.38 Statesales tax.nAt the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern effortsto obtain legal approval to do work with these compounds in human beings.... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruinationof a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs describedherin, without being familiar with that drug's action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsiblyand immorally, whether or not he is doing so within the bounds of the law.A SHORT INDEX TO THE PHENETHYLAMINESThis short index to the phenethylamines lists the 179 entries thatfollow in alphebetical order. The abbreviation PEA is for phenethylamine, and A is for amphetamine. The long index includes allsynonyms and is in Appendix A.CodeCompact chemical name1AEMa-Ethyl-3,4,5-trimethoxy-PEA2AL4-Allyloxy-3,5-dimethoxy-PEA3 ALEPH4-Methylthio-2,5-dimethoxy-A4 ALEPH-24-Ethylthio-2,5-dimethoxy-A5 ALEPH-44-Isopropylthio-2,5-dimethoxy-A6ALEPH-64-Phenylthio-2,5-dimethoxy-A7ALEPH-74-Propylthio-2,5-dimethoxy-A8ARIADNE2,5-Dimethoxy-a-ethyl-4-methyl-PEA9 ASB3,4-Diethoxy-5-methoxy-PEA10 B4-Butoxy-3,5-dimethoxy-PEA11BEATRICE2,5-Dimethoxy-4,N-dimethyl-A12 BIS-TOM2,5-Bismethylthio-4-methyl-A13 BOB4-Bromo-2,5,beta-trimethoxy-PEA14 BOD2,5,beta-Trimethoxy-4-methyl-PEA15 BOHbeta-Methoxy-3,4-methylenedioxy-PEA16 BOHD2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA17BOM3,4,5,beta-Tetramethoxy-PEA18 4-Br-3,5-DMA4-Bromo-3,5-dimethoxy-A19 2-Br-4,5-MDA2-Bromo-4,5-methylenedioxy-A20 2C-B 4-Bromo-2,5-dimethoxy-PEA213C-BZ 4-Benzyloxy-3,5-dimethoxy-A22 2C-C4-Chloro-2,5-dimethoxy-PEA23 2C-D 4-Methyl-2,5-dimethoxy-PEA24 2C-E4-Ethyl-2,5-dimethoxy-PEA25 3C-E4-Ethoxy-3,5-dimethoxy-A26 2C-F4-Fluoro-2,5-dimethoxy-PEA27 2C-G3,4-Dimethyl-2,5-dimethoxy-PEA28 2C-G-33,4-Trimethylene-2,5-dimethoxy-PEA29 2C-G-43,4-Tetramethylene-2,5-dimethoxy-PEA30 2C-G-53,4-Norbornyl-2,5-dimethoxy-PEA31 2C-G-N1,4-Dimethoxynaphthyl-2-ethylamine32 2C-H2,5-Dimethoxy-PEA33 2C-I 4-Iodo-2,5-dimethoxy-PEA34 2C-N4-Nitro-2,5-dimethoxy-PEA35 2C-O-44-Isopropoxy-2,5-dimethoxy-PEA36 2C-P4-Propyl-2,5-dimethoxy-PEA37 CPM4-Cyclopropylmethoxy-3,5-dimethoxy-PEA38 2C-SE4-Methylseleno-2,5-dimethoxy-PEA39 2C-T4-Methylthio-2,5-dimethoxy-PEA40 2C-T-24-Ethylthio-2,5-dimethoxy-PEA412C-T-44-Isopropylthio-2,5-dimethoxy-PEA42 gamma-2C-T-4 4-Isopropylthio-2,6-dimethoxy-PEA43 2C-T-74-Propylthio-2,5-dimethoxy-PEA44 2C-T-84-Cyclopropylmethylthio-2,5-dimethoxy-PEA45 2C-T-94-(t)-Butylthio-2,5-dimethoxy-PEA46 2C-T-134-(2-Methoxyethylthio)-2,5-dimethoxy-PEA47 2C-T-15 4-Cyclopropylthio-2,5-dimethoxy-PEA48 2C-T-174-(s)-Butylthio-2,5-dimethoxy-PEA49 2C-T-214-(2-Fluoroethylthio)-2,5-dimethoxy-PEA

50 4-D4-Trideuteromethyl-3,5-dimethoxy-PEA51beta-D beta,beta-Dideutero-3,4,5-trimethoxy-PEA52 DESOXY4-Methyl-3,5-Dimethoxy-PEA53 2,4-DMA2,4-Dimethoxy-A54 2,5-DMA2,5-Dimethoxy-A55 3,4-DMA 3,4-Dimethoxy-A56 DMCPA 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine57 DME3,4-Dimethoxy-beta-hydroxy-PEA58 DMMDA2,5-Dimethoxy-3,4-methylenedioxy-A59 DMMDA-2 2,3-Dimethoxy-4,5-methylenedioxy-A60 DMPEA3,4-Dimethoxy-PEA61 DOAM4-Amyl-2,5-dimethoxy-A62 DOB4-Bromo-2,5-dimethoxy-A63DOBU4-Butyl-2,5-dimethoxy-A64 DOC4-Chloro-2,5-dimethoxy-A65 DOEF4-(2-Fluoroethyl)-2,5-dimethoxy-A66 DOET4-Ethyl-2,5-dimethoxy-A67 DOI4-Iodo-2,5-dimethoxy-A68 DOM4-Methyl-2,5-dimethoxy-A69gamma-DOM 4-Methyl-2,6-dimethoxy-A70 DON 4-Nitro-2,5-dimethoxy-A71 DOPR4-Propyl-2,5-dimethoxy-A72 E4-Ethoxy-3,5-dimethoxy-PEA73 EEE 2,4,5-Triethoxy-A74EEM2,4-Diethoxy-5-methoxy-A75 EME2,5-Diethoxy-4-methoxy-A76EMM2-Ethoxy-4,5-dimethoxy-A77ETHYL-JN,a-diethyl-3,4-methylenedioxy-PEA78 ETHYL-KN-Ethyl-a-propyl-3,4-methylenedioxy-PEA79 F-2Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)80 F-22Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)81FLEA N-Hydroxy-N-methyl-3,4-methylenedioxy-A82 G-33,4-Trimethylene-2,5-dimethoxy-A83G-4 3,4-Tetramethylene-2,5-dimethoxy-A84 G-53,4-Norbornyl-2,5-dimethoxy-A85 GANESHA3,4-Dimethyl-2,5-dimethoxy-A86 G-N1,4-Dimethoxynaphthyl-2-isopropylamine87HOT-2 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA88 HOT-72,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA89 HOT-172,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA90 IDNNA2,5-Dimethoxy-N,N-dimethyl-4-iodo-A91IM2,3,4-Trimethoxy-PEA92 IP 3,5-Dimethoxy-4-isopropoxy-PEA93 IRIS5-Ethoxy-2-methoxy-4-methyl-A94 Ja-Ethyl-3,4-methylenedioxy-PEA95 LOPHOPHINE3-Methoxy-4,5-methylenedioxy-PEA96 M3,4,5-Trimethoxy-PEA974-MA4-Methoxy-A98 MADAM-6 2,N-Dimethyl-4,5-methylenedioxy-A99 MAL3,5-Dimethoxy-4-methallyloxy-PEA100 MDA 3,4-Methylenedioxy-A101 MDALN-Allyl-3,4-methylenedioxy-A102 MDBUN-Butyl-3,4-methylenedioxy-A103MDBZN-Benzyl-3,4-methylenedioxy-A104MDCPMN-Cyclopropylmethyl-3,4-methylenedioxy-A105 MDDM N,N-Dimethyl-3,4-methylenedioxy-A106 MDEN-Ethyl-3,4-methylenedioxy-A107 MDHOETN-(2-Hydroxyethyl)-3,4-methylenedioxy-A108 MDIP N-Isopropyl-3,4-methylenedioxy-A109 MDMA N-Methyl-3,4-methylenedioxy-A110 MDMC N-Methyl-3,4-ethylenedioxy-A111 MDMEON-Methoxy-3,4-methylenedioxy-A112 MDMEOET N-(2-Methoxyethyl)-3,4-methylenedioxy-A113 MDMPa,a,N-Trimethyl-3,4-methylenedioxy-PEA114 MDOHN-Hydroxy-3,4-methylenedioxy-A115 MDPEA3,4-Methylenedioxy-PEA116 MDPHa,a-Dimethyl-3,4-methylenedioxy-PEA117MDPLN-Propargyl-3,4-methylenedioxy-A118 MDPRN-Propyl-3,4-methylenedioxy-A119 ME 3,4-Dimethoxy-5-ethoxy-PEA120 MEDA3,4-Ethylenedioxy-5-methoxy-A121 MEE 2-Methoxy-4,5-diethoxy-A122 MEM 2,5-Dimethoxy-4-ethoxy-A123 MEPEA 3-Methoxy-4-ethoxy-PEA124 META-DOB5-Bromo-2,4-dimethoxy-A125 META-DOT5-Methylthio-2,4-dimethoxy-A126 METHYL-DMAN-Methyl-2,5-dimethoxy-A127 METHYL-DOB 4-Bromo-2,5-dimethoxy-N-methyl-A

128 METHYL-JN-Methyl-a-ethyl-3,4-methylenedioxy-PEA129 METHYL-KN-Methyl-a-propyl-3,4-methylenedioxy-PEA130 METHYL-MA N-Methyl-4-methoxy-A131 METHYL-MMDA-2N-Methyl-2-methoxy-4,5-methylenedioxy-A132 MMDA3-Methoxy-4,5-methylenedioxy-A133 MMDA-22-Methoxy-4,5-methylenedioxy-A134 MMDA-3a 2-Methoxy-3,4-methylenedioxy-A135 MMDA-3b4-Methoxy-2,3-methylenedioxy-A136 MME 2,4-Dimethoxy-5-ethoxy-A137 MP3,4-Dimethoxy-5-propoxy-PEA138 MPM2,5-Dimethoxy-4-propoxy-A139 ORTHO-DOT2-Methylthio-4,5-dimethoxy-A140 P3,5-Dimethoxy-4-propoxy-PEA141 PE 3,5-Dimethoxy-4-phenethyloxy-PEA142 PEA PEA143PROPYNYL4-Propynyloxy-3,5-dimethoxy-PEA144 SB3,5-Diethoxy-4-methoxy-PEA145 TA2,3,4,5-Tetramethoxy-A1463-TASB4-Ethoxy-3-ethylthio-5-methoxy-PEA147 4-TASB3-Ethoxy-4-ethylthio-5-methoxy-PEA148 5-TASB 3,4-Diethoxy-5-methylthio-PEA149 TB 4-Thiobutoxy-3,5-dimethoxy-PEA150 3-TE 4-Ethoxy-5-methoxy-3-methylthio-PEA151 4-TE3,5-Dimethoxy-4-ethylthio-PEA152 2-TIM2-Methylthio-3,4-dimethoxy-PEA153 3-TIM 3-Methylthio-2,4-dimethoxy-PEA154 4-TIM4-Methylthio-2,3-dimethoxy-PEA1553-TM3-Methylthio-4,5-dimethoxy-PEA1564-TM4-Methylthio-3,5-dimethoxy-PEA157 TMA 3,4,5-Trimethoxy-A158 TMA-22,4,5-Trimethoxy-A159 TMA-32,3,4-Trimethoxy-A160 TMA-42,3,5-Trimethoxy-A161 TMA-5 2,3,6-Trimethoxy-A162 TMA-62,4,6-Trimethoxy-A163 3-TME4,5-Dimethoxy-3-ethylthio-PEA1644-TME3-Ethoxy-5-methoxy-4-methylthio-PEA165 5-TME3-Ethoxy-4-methoxy-5-methylthio-PEA166 2T-MMDA-3a 2-Methylthio-3,4-methylenedioxy-A167 4T-MMDA-2 4,5-Thiomethyleneoxy-2-methoxy-A168 TMPEA 2,4,5-Trimethoxy-PEA169 2-TOET4-Ethyl-5-methoxy-2-methylthio-A1705-TOET4-Ethyl-2-methoxy-5-methylthio-A171 2-TOM 5-Methoxy-4-methyl-2-methylthio-A172 5-TOM2-Methoxy-4-methyl-5-methylthio-A173 TOMSO2-Methoxy-4-methyl-5-methylsulfinyl-A174 TP4-Propylthio-3,5-dimethoxy-PEA175 TRIS3,4,5-Triethoxy-PEA176 3-TSB3-Ethoxy-5-ethylthio-4-methoxy-PEA177 4-TSB3,5-Diethoxy-4-methylthio-PEA178 3-T-TRIS4,5-Diethoxy-3-ethylthio-PEA179 4-T-TRIS 3,5-Diethoxy-4-ethylthio-PEAPHENETHYLAMINES

#1 AEM; a-ETHYLMESCALINE;2-AMINO-1-(3,4,5-TRIMETHOXYPHENYL)BUTANE;1-(3,4,5-TRIMETHOXYPHENYL)-2-AMINOBUTANE

SYNTHESIS: To a solution of 45 g 3,4,5-trimethoxybenzaldehyde in 1.2 L IPA, there was added 125 g nitropropane and 67.5 g t-butylammoniumacetate and the reaction mixture was held at reflux for 16 h. This was poured into 6 L H2O, and extracted with 2x250 mL hexane. The pooled extractswere stripped of solvent under vacuum giving a residue that slowly set to a crystalline mass. On filtering, there was obtained 9.4 g of a crude yellowproduct which, on recrystallization from hexane provided 8.7 g of slightly sticky bright yellow crystals of 2-nitro-1-(3,4,5-trimethoxyphenyl)butene-1, witha mp of 71-73 deg C. A second recrystallization from hexane gave fine yellow crystals with a mp of 72-73 deg C. Attempts at the preparation of thisnitrostyrene by the more conventional methods with ammonium acetate in acetic acid led either to the formation of a white product C23H30N2O8 whichwas composed of a molecule of the nitrostyrene, one of the benzaldehyde itself, and a molecule of ammonia, or to 3,4,5-trimethoxybenzonitrile, fromreaction with the decomposition products of nitropropane.A stirred suspension of 5.9 g LAH in 310 mL anhydrous Et2O was held at a gentle reflux in an inert atmosphere. A solution of 8.5 g 2-nitro-1-(3,4,5-trimethoxyphenyl)butene-1 in 125 mL Et2O is added drop-wise over the course of 0.5 h. The reaction was maintained at reflux for 6 h, then cooled, andthe excess hydride destroyed by the cautious addition of 300 mL 1.8 N H2SO4. The phases were separated, and the aqueous phase brought to a pH of 6 by the addition of a saturated Na2CO3 solution. The neutral solution was brought to a boil, and clarified by filtration through paper. To the hot filtratethere was added a solution of 8.9 g picric acid in 100 mL boiling EtOH. The mixture was stirred and cooled, with the formation of a heavy yellowcrystalline mass. After standing in the ice tub for several hours the mixture was filtered, providing 8.0 g of the picrate salt with a mp of 176-181 deg Cfrom H2O. A solution of this salt in 300 mL boiling H2O was treated with 60 mL concentrated HCl. On cooling, there was a deposition of picric acid,