PiHKAL

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PiHKAL
Pihkal.jpg
Book Information
Book Name Pihkal: A Chemical Love Story
ISBN-13 9780963009609
ISBN-10 0963009605
Author Alexander Shulgin, Ann Shulgin
Publisher Transform Pr
Published September 1991

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin which was published in 1991. The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. The main title is an acronym that stands for "Phenethylamines I Have Known and Loved".

The book consists of two parts: the first is a fictionalised autobiography of the authors which introduces the couple's background, working lives and relationships. The second part contains detailed instructions for the synthesis of 179 psychedelic phenethylamines which were mostly discovered by Shulgin himself. For each substance, there is an account of the bio-assays he conducted as well as a suggested effective dosage, duration, and commentary on the subjective effects the couple experienced.

The second part of the book was made available for free and can be accessed in its original form via Erowid.org. There is also an updated, interactive edition made available by Isomer Design which has corrected publishing errors and cross-references the substances described with additional information available on the website. The first part of PiHKAL is available only to those who buy the entire book.

Listed phenethylamines

  1. AEM - alpha-Ethyl-3,4,5-trimethoxy-PEA
  2. AL - 4-Allyloxy-3,5-dimethoxy-PEA
  3. ALEPH - 4-Methylthio-2,5-dimethoxy-A
  4. ALEPH-2 - 4-Ethylthio-2,5-dimethoxy-A
  5. ALEPH-4 - 4-Isopropylthio-2,5-dimethoxy-A
  6. ALEPH-6 - 4-Phenylthio-2,5-dimethoxy-A
  7. ALEPH-7 - 4-Propylthio-2,5-dimethoxy-A
  8. ARIADNE - 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA
  9. ASB - 3,4-Diethoxy-5-methoxy-PEA
  10. B - 4-Butoxy-3,5-dimethoxy-PEA
  11. BEATRICE - 2,5-Dimethoxy-4,N-dimethyl-A
  12. BIS-TOM - 2,5-Bismethylthio-4-methyl-A
  13. BOB - 4-Bromo-2,5,beta-trimethoxy-PEA
  14. BOD - 2,5,beta-Trimethoxy-4-methyl-PEA
  15. BOH - beta-Methoxy-3,4-methylenedioxy-PEA
  16. BOHD - 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA
  17. BOM - 3,4,5,beta-Tetramethoxy-PEA
  18. 4-Br-3,5-DMA - 4-Bromo-3,5-dimethoxy-A
  19. 2-Br-4,5-MDA - 2-Bromo-4,5-methylenedioxy-A
  20. 2C-B - 4-Bromo-2,5-dimethoxy-PEA
  21. 3C-BZ - 4-Benzyloxy-3,5-dimethoxy-A
  22. 2C-C - 4-Chloro-2,5-dimethoxy-PEA
  23. 2C-D - 4-Methyl-2,5-dimethoxy-PEA
  24. 2C-E - 4-Ethyl-2,5-dimethoxy-PEA
  25. 3C-E - 4-Ethoxy-3,5-dimethoxy-A
  26. 2C-F - 4-Fluoro-2,5-dimethoxy-PEA
  27. 2C-G - 3,4-Dimethyl-2,5-dimethoxy-PEA
  28. 2C-G-3 - 3,4-Trimethylene-2,5-dimethoxy-PEA
  29. 2C-G-4 - 3,4-Tetramethylene-2,5-dimethoxy-PEA
  30. 2C-G-5 - 3,4-Norbornyl-2,5-dimethoxy-PEA
  31. 2C-G-N - 1,4-Dimethoxynaphthyl-2-ethylamine
  32. 2C-H - 2,5-Dimethoxy-PEA
  33. 2C-I - 4-Iodo-2,5-dimethoxy-PEA
  34. 2C-N - 4-Nitro-2,5-dimethoxy-PEA
  35. 2C-O-4 - 4-Isopropoxy-2,5-dimethoxy-PEA
  36. 2C-P - 4-Propyl-2,5-dimethoxy-PEA
  37. CPM - 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA
  38. 2C-SE - 4-Methylseleno-2,5-dimethoxy-PEA
  39. 2C-T - 4-Methylthio-2,5-dimethoxy-PEA
  40. 2C-T-2 - 4-Ethylthio-2,5-dimethoxy-PEA
  41. 2C-T-4 - 4-Isopropylthio-2,5-dimethoxy-PEA
  42. psi-2C-T-4 - 4-Isopropylthio-2,6-dimethoxy-PEA
  43. 2C-T-7 - 4-Propylthio-2,5-dimethoxy-PEA
  44. 2C-T-8 - 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA
  45. 2C-T-9 - 4-(t)-Butylthio-2,5-dimethoxy-PEA
  46. 2C-T-13 - 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA
  47. 2C-T-15 - 4-Cyclopropylthio-2,5-dimethoxy-PEA
  48. 2C-T-17 - 4-(s)-Butylthio-2,5-dimethoxy-PEA
  49. 2C-T-21 - 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA
  50. 4-D - 4-Trideuteromethyl-3,5-dimethoxy-PEA
  51. beta-D - beta,beta-Dideutero-3,4,5-trimethoxy-PEA
  52. DESOXY - 4-Methyl-3,5-Dimethoxy-PEA
  53. 2,4-DMA - 2,4-Dimethoxy-A
  54. 2,5-DMA - 2,5-Dimethoxy-A
  55. 3,4-DMA - 3,4-Dimethoxy-A
  56. DMCPA - 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine
  57. DME - 3,4-Dimethoxy-beta-hydroxy-PEA
  58. DMMDA - 2,5-Dimethoxy-3,4-methylenedioxy-A
  59. DMMDA-2 - 2,3-Dimethoxy-4,5-methylenedioxy-A
  60. DMPEA - 3,4-Dimethoxy-PEA
  61. DOAM - 4-Amyl-2,5-dimethoxy-A
  62. DOB - 4-Bromo-2,5-dimethoxy-A
  63. DOBU - 4-Butyl-2,5-dimethoxy-A
  64. DOC - 4-Chloro-2,5-dimethoxy-A
  65. DOEF - 4-(2-Fluoroethyl)-2,5-dimethoxy-A
  66. DOET - 4-Ethyl-2,5-dimethoxy-A
  67. DOI - 4-Iodo-2,5-dimethoxy-A
  68. DOM (STP) - 4-Methyl-2,5-dimethoxy-A
  69. psi-DOM - 4-Methyl-2,6-dimethoxy-A
  70. DON - 4-Nitro-2,5-dimethoxy-A
  71. DOPR - 4-Propyl-2,5-dimethoxy-A
  72. E - 4-Ethoxy-3,5-dimethoxy-PEA
  73. EEE - 2,4,5-Triethoxy-A
  74. EEM - 2,4-Diethoxy-5-methoxy-A
  75. EME - 2,5-Diethoxy-4-methoxy-A
  76. EMM - 2-Ethoxy-4,5-dimethoxy-A
  77. ETHYL-J - N,alpha-diethyl-3,4-methylenedioxy-PEA
  78. ETHYL-K - N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA
  79. F-2 - Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)
  80. F-22 - Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)
  81. FLEA - N-Hydroxy-N-methyl-3,4-methylenedioxy-A
  82. G-3 - 3,4-Trimethylene-2,5-dimethoxy-A
  83. G-4 - 3,4-Tetramethylene-2,5-dimethoxy-A
  84. G-5 - 3,4-Norbornyl-2,5-dimethoxy-A
  85. GANESHA - 3,4-Dimethyl-2,5-dimethoxy-A
  86. G-N - 1,4-Dimethoxynaphthyl-2-isopropylamine
  87. HOT-2 - 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA
  88. HOT-7 - 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA
  89. HOT-17 - 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA
  90. IDNNA - 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A
  91. IM - 2,3,4-Trimethoxy-PEA
  92. IP - 3,5-Dimethoxy-4-isopropoxy-PEA
  93. IRIS - 5-Ethoxy-2-methoxy-4-methyl-A
  94. J - alpha-Ethyl-3,4-methylenedioxy-PEA
  95. LOPHOPHINE - 3-Methoxy-4,5-methylenedioxy-PEA
  96. M - 3,4,5-Trimethoxy-PEA
  97. 4-MA - 4-Methoxy-A
  98. MADAM-6 - 2,N-Dimethyl-4,5-methylenedioxy-A
  99. MAL - 3,5-Dimethoxy-4-methallyloxy-PEA
  100. MDA - 3,4-Methylenedioxy-A
  101. MDAL - N-Allyl-3,4-methylenedioxy-A
  102. MDBU - N-Butyl-3,4-methylenedioxy-A
  103. MDBZ - N-Benzyl-3,4-methylenedioxy-A
  104. MDCPM - N-Cyclopropylmethyl-3,4-methylenedioxy-A
  105. MDDM - N,N-Dimethyl-3,4-methylenedioxy-A
  106. MDE - N-Ethyl-3,4-methylenedioxy-A
  107. MDHOET - N-(2-Hydroxyethyl)-3,4-methylenedioxy-A
  108. MDIP - N-Isopropyl-3,4-methylenedioxy-A
  109. MDMA - N-Methyl-3,4-methylenedioxy-A
  110. MDMC - N-Methyl-3,4-ethylenedioxy-A
  111. MDMEO - N-Methoxy-3,4-methylenedioxy-A
  112. MDMEOET - N-(2-Methoxyethyl)-3,4-methylenedioxy-A
  113. MDMP - alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA
  114. MDOH - N-Hydroxy-3,4-methylenedioxy-A
  115. MDPEA - 3,4-Methylenedioxy-PEA
  116. MDPH - alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA
  117. MDPL - N-Propargyl-3,4-methylenedioxy-A
  118. MDPR - N-Propyl-3,4-methylenedioxy-A
  119. ME - 3,4-Dimethoxy-5-ethoxy-PEA
  120. MEDA - 3-methoxy-4,5-Ethylenedioxy-A
  121. MEE - 2-Methoxy-4,5-diethoxy-A
  122. MEM - 2,5-Dimethoxy-4-ethoxy-A
  123. MEPEA - 3-Methoxy-4-ethoxy-PEA
  124. META-DOB - 5-Bromo-2,4-dimethoxy-A
  125. META-DOT - 5-Methylthio-2,4-dimethoxy-A
  126. METHYL-DMA - N-Methyl-2,5-dimethoxy-A
  127. METHYL-DOB - 4-Bromo-2,5-dimethoxy-N-methyl-A
  128. METHYL-J - N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA
  129. METHYL-K - N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA
  130. METHYL-MA - N-Methyl-4-methoxy-A
  131. METHYL-MMDA-2 - N-Methyl-2-methoxy-4,5-methylenedioxy-A
  132. MMDA - 3-Methoxy-4,5-methylenedioxy-A
  133. MMDA-2 - 2-Methoxy-4,5-methylenedioxy-A
  134. MMDA-3a - 2-Methoxy-3,4-methylenedioxy-A
  135. MMDA-3b - 4-Methoxy-2,3-methylenedioxy-A
  136. MME - 2,4-Dimethoxy-5-ethoxy-A
  137. MP - 3,4-Dimethoxy-5-propoxy-PEA
  138. MPM - 2,5-Dimethoxy-4-propoxy-A
  139. ORTHO-DOT - 2-Methylthio-4,5-dimethoxy-A
  140. P - 3,5-Dimethoxy-4-propoxy-PEA
  141. PE - 3,5-Dimethoxy-4-phenethyloxy-PEA
  142. PEA - PEA
  143. PROPYNYL - 4-Propynyloxy-3,5-dimethoxy-PEA
  144. SB - 3,5-Diethoxy-4-methoxy-PEA
  145. TA - 2,3,4,5-Tetramethoxy-A
  146. 3-TASB - 4-Ethoxy-3-ethylthio-5-methoxy-PEA
  147. 4-TASB - 3-Ethoxy-4-ethylthio-5-methoxy-PEA
  148. 5-TASB - 3,4-Diethoxy-5-methylthio-PEA
  149. TB - 4-Thiobutoxy-3,5-dimethoxy-PEA
  150. 3-TE - 4-Ethoxy-5-methoxy-3-methylthio-PEA
  151. 4-TE - 3,5-Dimethoxy-4-ethylthio-PEA
  152. 2-TIM - 2-Methylthio-3,4-dimethoxy-PEA
  153. 3-TIM - 3-Methylthio-2,4-dimethoxy-PEA
  154. 4-TIM - 4-Methylthio-2,3-dimethoxy-PEA
  155. 3-TM - 3-Methylthio-4,5-dimethoxy-PEA
  156. 4-TM - 4-Methylthio-3,5-dimethoxy-PEA
  157. TMA - 3,4,5-Trimethoxy-A
  158. TMA-2 - 2,4,5-Trimethoxy-A
  159. TMA-3 - 2,3,4-Trimethoxy-A
  160. TMA-4 - 2,3,5-Trimethoxy-A
  161. TMA-5 - 2,3,6-Trimethoxy-A
  162. TMA-6 - 2,4,6-Trimethoxy-A
  163. 3-TME - 4,5-Dimethoxy-3-ethylthio-PEA
  164. 4-TME - 3-Ethoxy-5-methoxy-4-methylthio-PEA
  165. 5-TME - 3-Ethoxy-4-methoxy-5-methylthio-PEA
  166. 2T-MMDA-3a - 2-Methylthio-3,4-methylenedioxy-A
  167. 4T-MMDA-2 - 4,5-Thiomethyleneoxy-2-methoxy-A
  168. TMPEA - 2,4,5-Trimethoxy-PEA
  169. 2-TOET - 4-Ethyl-5-methoxy-2-methylthio-A
  170. 5-TOET - 4-Ethyl-2-methoxy-5-methylthio-A
  171. 2-TOM - 5-Methoxy-4-methyl-2-methylthio-A
  172. 5-TOM - 2-Methoxy-4-methyl-5-methylthio-A
  173. TOMSO - 2-Methoxy-4-methyl-5-methylsulfinyl-A
  174. TP - 4-Propylthio-3,5-dimethoxy-PEA
  175. TRIS - 3,4,5-Triethoxy-PEA
  176. 3-TSB - 3-Ethoxy-5-ethylthio-4-methoxy-PEA
  177. 4-TSB - 3,5-Diethoxy-4-methylthio-PEA
  178. 3-T-TRIS - 4,5-Diethoxy-3-ethylthio-PEA
  179. 4-T-TRIS - 3,5-Diethoxy-4-ethylthio-PEA

Notable excerpts

Magical half-dozen

The so-called "magical half-dozen" refers to Shulgin's self-rated most important phenethylamine compounds, all of which except mescaline he developed and synthesized himself. They are found within the first book of PIHKAL, and are as follows:

  • Mescaline (3,4,5-trimethoxyphenethylamine)
  • DOM (2,5-dimethoxy-4-methylamphetamine)
  • 2C-B (2,5-dimethoxy-4-bromophenethylamine)
  • 2C-E (2,5-dimethoxy-4-ethylphenethylamine)
  • 2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine)
  • 2C-T-7 (2,5-dimethoxy-4-propylthiophenethylamine)

Essential amphetamines

The Essential Amphetamines are what Shulgin describes as ten amphetamines that differ from natural products such as safrole or myristicin by an amine group (PIHKAL Entry #157 TMA). The list consists of:

  • PMA (para-methoxy-amphetamine)
  • 2,4-DMA (2,4-dimethoxy-amphetamine)
  • 3,4-DMA (3,4-dimethoxy-amphetamine)
  • MDA (3,4-methylenedioxy-amphetamine)
  • MMDA (3-methoxy-4,5-methylendioxy-amphetamine)
  • MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine)
  • MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine)
  • TMA (3,4,5-trimethoxyamphetamine)
  • TMA-2 (2,4,5-trimethoxyamphetamine)
  • DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine)
  • DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine)
  • TA (2,3,4,5-tetramethoxyamphetamine)

Not all of these chemicals are bioassayed in PIHKAL; some are merely mentioned.

See also

External links