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'''''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 drug|psychoactive]] [[phenethylamine]] chemical derivatives, notably those that act as [[psychedelic]]s and/~~or [[empathogen]-[entactogen]]s. The main title is an [[acronym]] that stands for "Phenethylamines I Have Known and Loved".~~

The book ~~is arranged into~~ two parts~~. Part one~~ is a ~~fictionalized~~ autobiography of the couple ~~while~~ part ~~two is~~ detailed ~~synthesis~~ instructions for 179 ~~different psychedelic compounds (most of~~ which Shulgin ~~discovered~~ himself), ~~including bioassays~~, ~~dosages~~, and ~~other~~ commentary. The second part is made ~~freely~~ available ~~by Shulgin on~~ [https://www.erowid.org/library/books_online/pihkal/pihkal.shtml Erowid.org] ~~while~~ the first part is available only in the ~~printed text~~.

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|Published=September 1991

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'''''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 [[substituted phenethylamines]] chemical derivatives, notably those that act as [[psychedelic]]s and/or [[empathogen]]-[[entactogen]]s. 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 substituted 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 [https://www.erowid.org/library/books_online/pihkal/pihkal.shtml Erowid.org]. There is also an updated, interactive edition made available by [http://isomerdesign.com/PiHKAL/ 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 ==

{{List|

# [[AEM]] - alpha-Ethyl-3,4,5-trimethoxy-PEA

# [[Allylescaline|AL]] - 4-Allyloxy-3,5-dimethoxy-PEA

# [[Aleph|ALEPH]] - 4-Methylthio-2,5-dimethoxy-A

# [[Aleph-2|ALEPH-2]] - 4-Ethylthio-2,5-dimethoxy-A

# [[Aleph-4|ALEPH-4]] - 4-Isopropylthio-2,5-dimethoxy-A

# [[Aleph-6|ALEPH-6]] - 4-Phenylthio-2,5-dimethoxy-A

# [[Aleph-7|ALEPH-7]] - 4-Propylthio-2,5-dimethoxy-A

# [[Ariadne|ARIADNE]] - 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA

# [[Asymbescaline|ASB]] - 3,4-Diethoxy-5-methoxy-PEA

# [[Buscaline|B]] - 4-Butoxy-3,5-dimethoxy-PEA

# [[Beatrice|BEATRICE]] - 2,5-Dimethoxy-4,N-dimethyl-A

# [[Bis-TOM|BIS-TOM]] - 2,5-Bismethylthio-4-methyl-A

# [[BOB]] - 4-Bromo-2,5,beta-trimethoxy-PEA

# [[BOD]] - 2,5,beta-Trimethoxy-4-methyl-PEA

# [[BOH]] - beta-Methoxy-3,4-methylenedioxy-PEA

# [[BOHD]] - 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA

# [[BOM]] - 3,4,5,beta-Tetramethoxy-PEA

# [[4-Br-3,5-DMA]] - 4-Bromo-3,5-dimethoxy-A

# [[2-Br-4,5-MDA]] - 2-Bromo-4,5-methylenedioxy-A

# [[2C-B]] - 4-Bromo-2,5-dimethoxy-PEA

# [[3C-BZ]] - 4-Benzyloxy-3,5-dimethoxy-A

# [[2C-C]] - 4-Chloro-2,5-dimethoxy-PEA

# [[2C-D]] - 4-Methyl-2,5-dimethoxy-PEA

# [[2C-E]] - 4-Ethyl-2,5-dimethoxy-PEA

# [[3C-E]] - 4-Ethoxy-3,5-dimethoxy-A

# [[2C-F]] - 4-Fluoro-2,5-dimethoxy-PEA

# [[2C-G]] - 3,4-Dimethyl-2,5-dimethoxy-PEA

# [[2C-G-3]] - 3,4-Trimethylene-2,5-dimethoxy-PEA

# [[2C-G-4]] - 3,4-Tetramethylene-2,5-dimethoxy-PEA

# [[2C-G-5]] - 3,4-Norbornyl-2,5-dimethoxy-PEA

# [[2C-G-N]] - 1,4-Dimethoxynaphthyl-2-ethylamine

# [[2C-H]] - 2,5-Dimethoxy-PEA

# [[2C-I]] - 4-Iodo-2,5-dimethoxy-PEA

# [[2C-N]] - 4-Nitro-2,5-dimethoxy-PEA

# [[2C-O-4]] - 4-Isopropoxy-2,5-dimethoxy-PEA

# [[2C-P]] - 4-Propyl-2,5-dimethoxy-PEA

# [[CPM]] - 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA

# [[2C-SE]] - 4-Methylseleno-2,5-dimethoxy-PEA

# [[2C-T]] - 4-Methylthio-2,5-dimethoxy-PEA

# [[2C-T-2]] - 4-Ethylthio-2,5-dimethoxy-PEA

# [[2C-T-4]] - 4-Isopropylthio-2,5-dimethoxy-PEA

# [[psi-2C-T-4]] - 4-Isopropylthio-2,6-dimethoxy-PEA

# [[2C-T-7]] - 4-Propylthio-2,5-dimethoxy-PEA

# [[2C-T-8]] - 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA

# [[2C-T-9]] - 4-(t)-Butylthio-2,5-dimethoxy-PEA

# [[2C-T-13]] - 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA

# [[2C-T-15]] - 4-Cyclopropylthio-2,5-dimethoxy-PEA

# [[2C-T-17]] - 4-(s)-Butylthio-2,5-dimethoxy-PEA

# [[2C-T-21]] - 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA

# [[4-D]] - 4-Trideuteromethyl-3,5-dimethoxy-PEA

# [[beta-D]] - beta,beta-Dideutero-3,4,5-trimethoxy-PEA

# [[DESOXY]] - 4-Methyl-3,5-Dimethoxy-PEA

# [[2,4-DMA]] - 2,4-Dimethoxy-A

# [[2,5-DMA]] - 2,5-Dimethoxy-A

# [[3,4-DMA]] - 3,4-Dimethoxy-A

# [[DMCPA]] - 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine

# [[DME]] - 3,4-Dimethoxy-beta-hydroxy-PEA

# [[DMMDA]] - 2,5-Dimethoxy-3,4-methylenedioxy-A

# [[DMMDA-2]] - 2,3-Dimethoxy-4,5-methylenedioxy-A

# [[DMPEA]] - 3,4-Dimethoxy-PEA

# [[DOAM]] - 4-Amyl-2,5-dimethoxy-A

# [[DOB]] - 4-Bromo-2,5-dimethoxy-A

# [[DOBU]] - 4-Butyl-2,5-dimethoxy-A

# [[DOC]] - 4-Chloro-2,5-dimethoxy-A

# [[DOEF]] - 4-(2-Fluoroethyl)-2,5-dimethoxy-A

# [[DOET]] - 4-Ethyl-2,5-dimethoxy-A

# [[DOI]] - 4-Iodo-2,5-dimethoxy-A

# [[DOM|DOM (STP)]] - 4-Methyl-2,5-dimethoxy-A

# [[psi-DOM]] - 4-Methyl-2,6-dimethoxy-A

# [[DON]] - 4-Nitro-2,5-dimethoxy-A

# [[DOPR]] - 4-Propyl-2,5-dimethoxy-A

# [[Escaline|E]] - 4-Ethoxy-3,5-dimethoxy-PEA

# [[EEE]] - 2,4,5-Triethoxy-A

# [[EEM]] - 2,4-Diethoxy-5-methoxy-A

# [[EME]] - 2,5-Diethoxy-4-methoxy-A

# [[EMM]] - 2-Ethoxy-4,5-dimethoxy-A

# [[Ethyl-J|ETHYL-J]] - N,alpha-diethyl-3,4-methylenedioxy-PEA

# [[Ethyl-K|ETHYL-K]] - N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA

# [[F-2]] - Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)

# [[F-22]] - Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)

# [[FLEA]] - N-Hydroxy-N-methyl-3,4-methylenedioxy-A

# [[G-3]] - 3,4-Trimethylene-2,5-dimethoxy-A

# [[G-4]] - 3,4-Tetramethylene-2,5-dimethoxy-A

# [[G-5]] - 3,4-Norbornyl-2,5-dimethoxy-A

# [[Ganesha|GANESHA]] - 3,4-Dimethyl-2,5-dimethoxy-A

# [[G-N]] - 1,4-Dimethoxynaphthyl-2-isopropylamine

# [[HOT-2]] - 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA

# [[HOT-7]] - 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA

# [[HOT-17]] - 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA

# [[IDNNA]] - 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A

# [[Isomescaline|IM]] - 2,3,4-Trimethoxy-PEA

# [[Isoproscaline|IP]] - 3,5-Dimethoxy-4-isopropoxy-PEA

# [[IRIS]] - 5-Ethoxy-2-methoxy-4-methyl-A

# [[MDB|J]] - alpha-Ethyl-3,4-methylenedioxy-PEA

# [[Lophophine|LOPHOPHINE]] - 3-Methoxy-4,5-methylenedioxy-PEA

# [[Mescaline|M]] - 3,4,5-Trimethoxy-PEA

# [[4-MA]] - 4-Methoxy-A

# [[MADAM-6]] - 2,N-Dimethyl-4,5-methylenedioxy-A

# [[MAL]] - 3,5-Dimethoxy-4-methallyloxy-PEA

# [[MDA]] - 3,4-Methylenedioxy-A

# [[MDAL]] - N-Allyl-3,4-methylenedioxy-A

# [[MDBU]] - N-Butyl-3,4-methylenedioxy-A

# [[MDBZ]] - N-Benzyl-3,4-methylenedioxy-A

# [[MDCPM]] - N-Cyclopropylmethyl-3,4-methylenedioxy-A

# [[MDDM]] - N,N-Dimethyl-3,4-methylenedioxy-A

# [[MDE]] - N-Ethyl-3,4-methylenedioxy-A

# [[MDHOET]] - N-(2-Hydroxyethyl)-3,4-methylenedioxy-A

# [[MDIP]] - N-Isopropyl-3,4-methylenedioxy-A

# [[MDMA]] - N-Methyl-3,4-methylenedioxy-A

# [[MDMC]] - N-Methyl-3,4-ethylenedioxy-A

# [[MDMEO]] - N-Methoxy-3,4-methylenedioxy-A

# [[MDMEOET]] - N-(2-Methoxyethyl)-3,4-methylenedioxy-A

# [[MDMP]] - alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA

# [[MDOH]] - N-Hydroxy-3,4-methylenedioxy-A

# [[MDPEA]] - 3,4-Methylenedioxy-PEA

# [[MDPH]] - alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA

# [[MDPL]] - N-Propargyl-3,4-methylenedioxy-A

# [[MDPR]] - N-Propyl-3,4-methylenedioxy-A

# [[Metaescaline|ME]] - 3,4-Dimethoxy-5-ethoxy-PEA

# [[MEDA]] - 3-methoxy-4,5-Ethylenedioxy-A

# [[MEE]] - 2-Methoxy-4,5-diethoxy-A

# [[MEM]] - 2,5-Dimethoxy-4-ethoxy-A

# [[MEPEA]] - 3-Methoxy-4-ethoxy-PEA

# [[Meta-DOB|META-DOB]] - 5-Bromo-2,4-dimethoxy-A

# [[Meta-DOT|META-DOT]] - 5-Methylthio-2,4-dimethoxy-A

# [[Methyl-DMA|METHYL-DMA]] - N-Methyl-2,5-dimethoxy-A

# [[Methyl-DOB|METHYL-DOB]] - 4-Bromo-2,5-dimethoxy-N-methyl-A

# [[Methyl-J|METHYL-J]] - N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA

# [[Methyl-K|METHYL-K]] - N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA

# [[Methyl-MA|METHYL-MA]] - N-Methyl-4-methoxy-A

# [[Methyl-MMDA-2|METHYL-MMDA-2]] - N-Methyl-2-methoxy-4,5-methylenedioxy-A

# [[MMDA]] - 3-Methoxy-4,5-methylenedioxy-A

# [[MMDA-2]] - 2-Methoxy-4,5-methylenedioxy-A

# [[MMDA-3a]] - 2-Methoxy-3,4-methylenedioxy-A

# [[MMDA-3b]] - 4-Methoxy-2,3-methylenedioxy-A

# [[MME]] - 2,4-Dimethoxy-5-ethoxy-A

# [[Metaproscaline|MP]] - 3,4-Dimethoxy-5-propoxy-PEA

# [[MPM]] - 2,5-Dimethoxy-4-propoxy-A

# [[Ortho-DOT|ORTHO-DOT]] - 2-Methylthio-4,5-dimethoxy-A

# [[Proscaline|P]] - 3,5-Dimethoxy-4-propoxy-PEA

# [[Phenescaline|PE]] - 3,5-Dimethoxy-4-phenethyloxy-PEA

# [[PEA]] - PEA

# [[Propynyl|PROPYNYL]] - 4-Propynyloxy-3,5-dimethoxy-PEA

# [[Symbescaline|SB]] - 3,5-Diethoxy-4-methoxy-PEA

# [[2,3,4,5-Tetramethoxyamphetamine|TA]] - 2,3,4,5-Tetramethoxy-A

# [[3-TASB]] - 4-Ethoxy-3-ethylthio-5-methoxy-PEA

# [[4-TASB]] - 3-Ethoxy-4-ethylthio-5-methoxy-PEA

# [[5-TASB]] - 3,4-Diethoxy-5-methylthio-PEA

# [[Thiobuscaline|TB]] - 4-Thiobutoxy-3,5-dimethoxy-PEA

# [[3-TE]] - 4-Ethoxy-5-methoxy-3-methylthio-PEA

# [[4-TE]] - 3,5-Dimethoxy-4-ethylthio-PEA

# [[2-TIM]] - 2-Methylthio-3,4-dimethoxy-PEA

# [[3-TIM]] - 3-Methylthio-2,4-dimethoxy-PEA

# [[4-TIM]] - 4-Methylthio-2,3-dimethoxy-PEA

# [[3-TM]] - 3-Methylthio-4,5-dimethoxy-PEA

# [[4-TM]] - 4-Methylthio-3,5-dimethoxy-PEA

# [[TMA]] - 3,4,5-Trimethoxy-A

# [[TMA-2]] - 2,4,5-Trimethoxy-A

# [[TMA-3]] - 2,3,4-Trimethoxy-A

# [[TMA-4]] - 2,3,5-Trimethoxy-A

# [[TMA-5]] - 2,3,6-Trimethoxy-A

# [[TMA-6]] - 2,4,6-Trimethoxy-A

# [[3-TME]] - 4,5-Dimethoxy-3-ethylthio-PEA

# [[4-TME]] - 3-Ethoxy-5-methoxy-4-methylthio-PEA

# [[5-TME]] - 3-Ethoxy-4-methoxy-5-methylthio-PEA

# [[2T-MMDA-3a]] - 2-Methylthio-3,4-methylenedioxy-A

# [[4T-MMDA-2]] - 4,5-Thiomethyleneoxy-2-methoxy-A

# [[TMPEA]] - 2,4,5-Trimethoxy-PEA

# [[2-TOET]] - 4-Ethyl-5-methoxy-2-methylthio-A

# [[5-TOET]] - 4-Ethyl-2-methoxy-5-methylthio-A

# [[2-TOM]] - 5-Methoxy-4-methyl-2-methylthio-A

# [[5-TOM]] - 2-Methoxy-4-methyl-5-methylthio-A

# [[TOMSO]] - 2-Methoxy-4-methyl-5-methylsulfinyl-A

# [[Thioproscaline|TP]] - 4-Propylthio-3,5-dimethoxy-PEA

# [[TRIS]] - 3,4,5-Triethoxy-PEA

# [[3-TSB]] - 3-Ethoxy-5-ethylthio-4-methoxy-PEA

# [[4-TSB]] - 3,5-Diethoxy-4-methylthio-PEA

# [[3-T-TRIS]] - 4,5-Diethoxy-3-ethylthio-PEA

# [[4-T-TRIS]] - 3,5-Diethoxy-4-ethylthio-PEA

}}

== Notable excerpts ==

=== Magical ~~Half~~-~~Dozen~~ ===

=== 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)

* [[2,5-~~Dimethoxy~~-4-methylamphetamine~~|DOM~~]] (2,5-dimethoxy-4-~~methylamphetamine~~, ~~DOM being short for~~ '''d'''es'''o'''xy '''m'''~~ethyl~~, ~~referring to the removal of the Oxygen atom from the~~ Methoxy ~~group on the "~~4~~" carbon.~~

* [[DOM]] (2,5-dimethoxy-4-methylamphetamine)

* [[2C-B]] (2,5-~~dimethoxy~~-4-'''b'''~~romophenethylamine~~)

* [[2C-B]] (2,5-dimethoxy-4-bromophenethylamine)

* [[2C-E]] (2,5-~~dimethoxy-~~4-'''e'''~~thylphenethylamine~~)

* [[2C-E]] (2,5-dimethoxy-4-ethylphenethylamine)

* [[2C-T-2]] (2,5-~~dimethoxy~~-4-~~ethyl~~'''t'''~~hiophenethylamine~~)

* [[2C-T-2]] (2,5-dimethoxy-4-ethylthiophenethylamine)

* [[2C-~~T-7~~]] (2,5-~~dimethoxy-~~4-~~propyl~~'''t'''~~hiophenethylamine~~)

* [[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 ([http://www.erowid.org/library/books_online/pihkal/pihkal157.shtml ''PIHKAL'' Entry #157 TMA]). The list consists of:

* [[PMA]] (''para''-'''m'''ethoxy-'''a'''mphetamine)

* [[2,4-DMA]] (2,4-'''d'''i'''m'''ethoxy-'''a'''mphetamine)

* [[3,4-DMA]] (3,4-'''d'''i'''m'''ethoxy-'''a'''mphetamine)

* [[MDA]] (3,4-'''m'''ethylene'''d'''ioxy-'''a'''mphetamine)

* [[3-Methoxy-4,5-methylendioxyamphetamine|MMDA]] (3-'''m'''ethoxy-4,5-'''m'''ethylen'''d'''ioxy-'''a'''mphetamine)

* [[MMDA-3a]] (2-'''m'''ethoxy-3,4-'''m'''ethylen'''d'''ioxy'''a'''mphetamine)

* [[MMDA-2]] (2-'''m'''ethoxy-4,5-'''m'''ethylen'''d'''ioxy'''a'''mphetamine)

* [[TMA]] (3,4,5-'''t'''ri'''m'''ethoxy'''a'''mphetamine)

* [[TMA-2]] (2,4,5-'''t'''ri'''m'''ethoxy'''a'''mphetamine)

* [[DMMDA]] (2,5-'''d'''i'''m'''ethoxy-3,4-'''m'''ethylene'''d'''ioxy'''a'''mphetamine)

* [[DMMDA-2]] (2,3-'''d'''i'''m'''ethoxy-4,5-'''m'''ethylene'''d'''ioxy'''a'''mphetamine)

* [[Tetramethoxyamphetamine|TA]] (2,3,4,5-'''t'''etramethoxy'''a'''mphetamine)

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

== See also ==

* [[Phenethylamine]]

*[[Responsible use]]

* [[Amphetamine]] (~~AMPH~~)

*[[Phenethylamine]]

* [[~~MDMA]~~] (~~MDxx~~)

*[[Amphetamine]]

* [[Alexander Shulgin]]

*[[Alexander Shulgin]]

*[[TiHKAL]]

==External links==

*[https://en.wikipedia.org/wiki/PiHKAL PiHKAL (Wikipedia)]

*[https://en.wikipedia.org/wiki/Substituted_amphetamine Substituted amphetamine (Wikipedia)]

*[https://en.wikipedia.org/wiki/Substituted_phenethylamine Substituted phenethylamine (Wikipedia)]

*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_phenethylamines List of naturally occurring phenethylamines (Wikipedia)]

*[http://isomerdesign.com/PiHKAL/ ''PIHKAL'' • Info: A Visual Index and Map of ''PIHKAL: A Chemical Love Story'' by Alexander & Ann Shulgin]

[[Category:Book]]

[[Category:Substance-related lists]]

@@ Line 1: / Line 1: @@
-'''''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 drug|psychoactive]] [[phenethylamine]] chemical derivatives, notably those that act as [[psychedelic]]s and/or [[empathogen]-[entactogen]]s. The main title is an [[acronym]] that stands for "Phenethylamines I Have Known and Loved".
+{{Information/Substituted phenethylamines}}
-The book is arranged into two parts. Part one is a fictionalized autobiography of the couple while part two is detailed synthesis instructions for 179 different psychedelic compounds (most of which Shulgin discovered himself), including bioassays, dosages, and other commentary. The second part is made freely available by Shulgin on [https://www.erowid.org/library/books_online/pihkal/pihkal.shtml Erowid.org] while the first part is available only in the printed text.
+{{BookBox
+    <!-- Table Properties -->
+    |BookTable_MaxWidth=250px
+    |BookTable_Title=PiHKAL
+    <!-- Modules -->
+    |ModuleSource=true
+    |ModuleBookInformation=true
+    <!-- Source -->
+    |PhotoImageFile=File:Pihkal.jpg
+    |PhotoImageWidth=250px
+    <!-- Book Information -->
+    |BookName=Pihkal: A Chemical Love Story
+    |ISBN13=9780963009609
+    |ISBN10=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 [[substituted phenethylamines]] chemical derivatives, notably those that act as [[psychedelic]]s and/or [[empathogen]]-[[entactogen]]s. The main title is an acronym that stands for ''&ldquo;Phenethylamines I Have Known and Loved&rdquo;''.
+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 substituted 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 [https://www.erowid.org/library/books_online/pihkal/pihkal.shtml Erowid.org]. There is also an updated, interactive edition made available by [http://isomerdesign.com/PiHKAL/ 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 ==
+{{List|
+# [[AEM]] - alpha-Ethyl-3,4,5-trimethoxy-PEA
+# [[Allylescaline|AL]] - 4-Allyloxy-3,5-dimethoxy-PEA
+# [[Aleph|ALEPH]] - 4-Methylthio-2,5-dimethoxy-A
+# [[Aleph-2|ALEPH-2]] - 4-Ethylthio-2,5-dimethoxy-A
+# [[Aleph-4|ALEPH-4]] - 4-Isopropylthio-2,5-dimethoxy-A
+# [[Aleph-6|ALEPH-6]] - 4-Phenylthio-2,5-dimethoxy-A
+# [[Aleph-7|ALEPH-7]] - 4-Propylthio-2,5-dimethoxy-A
+# [[Ariadne|ARIADNE]] - 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA
+# [[Asymbescaline|ASB]] - 3,4-Diethoxy-5-methoxy-PEA
+# [[Buscaline|B]] - 4-Butoxy-3,5-dimethoxy-PEA
+# [[Beatrice|BEATRICE]] - 2,5-Dimethoxy-4,N-dimethyl-A
+# [[Bis-TOM|BIS-TOM]] - 2,5-Bismethylthio-4-methyl-A
+# [[BOB]] - 4-Bromo-2,5,beta-trimethoxy-PEA
+# [[BOD]] - 2,5,beta-Trimethoxy-4-methyl-PEA
+# [[BOH]] - beta-Methoxy-3,4-methylenedioxy-PEA
+# [[BOHD]] - 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA
+# [[BOM]] - 3,4,5,beta-Tetramethoxy-PEA
+# [[4-Br-3,5-DMA]] - 4-Bromo-3,5-dimethoxy-A
+# [[2-Br-4,5-MDA]] - 2-Bromo-4,5-methylenedioxy-A
+# [[2C-B]] - 4-Bromo-2,5-dimethoxy-PEA
+# [[3C-BZ]] - 4-Benzyloxy-3,5-dimethoxy-A
+# [[2C-C]] - 4-Chloro-2,5-dimethoxy-PEA
+# [[2C-D]] - 4-Methyl-2,5-dimethoxy-PEA
+# [[2C-E]] - 4-Ethyl-2,5-dimethoxy-PEA
+# [[3C-E]] - 4-Ethoxy-3,5-dimethoxy-A
+# [[2C-F]] - 4-Fluoro-2,5-dimethoxy-PEA
+# [[2C-G]] - 3,4-Dimethyl-2,5-dimethoxy-PEA
+# [[2C-G-3]] - 3,4-Trimethylene-2,5-dimethoxy-PEA
+# [[2C-G-4]] - 3,4-Tetramethylene-2,5-dimethoxy-PEA
+# [[2C-G-5]] - 3,4-Norbornyl-2,5-dimethoxy-PEA
+# [[2C-G-N]] - 1,4-Dimethoxynaphthyl-2-ethylamine
+# [[2C-H]] - 2,5-Dimethoxy-PEA
+# [[2C-I]] - 4-Iodo-2,5-dimethoxy-PEA
+# [[2C-N]] - 4-Nitro-2,5-dimethoxy-PEA
+# [[2C-O-4]] - 4-Isopropoxy-2,5-dimethoxy-PEA
+# [[2C-P]] - 4-Propyl-2,5-dimethoxy-PEA
+# [[CPM]] - 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA
+# [[2C-SE]] - 4-Methylseleno-2,5-dimethoxy-PEA
+# [[2C-T]] - 4-Methylthio-2,5-dimethoxy-PEA
+# [[2C-T-2]] - 4-Ethylthio-2,5-dimethoxy-PEA
+# [[2C-T-4]] - 4-Isopropylthio-2,5-dimethoxy-PEA
+# [[psi-2C-T-4]] - 4-Isopropylthio-2,6-dimethoxy-PEA
+# [[2C-T-7]] - 4-Propylthio-2,5-dimethoxy-PEA
+# [[2C-T-8]] - 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA
+# [[2C-T-9]] - 4-(t)-Butylthio-2,5-dimethoxy-PEA
+# [[2C-T-13]] - 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA
+# [[2C-T-15]] - 4-Cyclopropylthio-2,5-dimethoxy-PEA
+# [[2C-T-17]] - 4-(s)-Butylthio-2,5-dimethoxy-PEA
+# [[2C-T-21]] - 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA
+# [[4-D]] - 4-Trideuteromethyl-3,5-dimethoxy-PEA
+# [[beta-D]] - beta,beta-Dideutero-3,4,5-trimethoxy-PEA
+# [[DESOXY]] - 4-Methyl-3,5-Dimethoxy-PEA
+# [[2,4-DMA]] - 2,4-Dimethoxy-A
+# [[2,5-DMA]] - 2,5-Dimethoxy-A
+# [[3,4-DMA]] - 3,4-Dimethoxy-A
+# [[DMCPA]] - 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine
+# [[DME]] - 3,4-Dimethoxy-beta-hydroxy-PEA
+# [[DMMDA]] - 2,5-Dimethoxy-3,4-methylenedioxy-A
+# [[DMMDA-2]] - 2,3-Dimethoxy-4,5-methylenedioxy-A
+# [[DMPEA]] - 3,4-Dimethoxy-PEA
+# [[DOAM]] - 4-Amyl-2,5-dimethoxy-A
+# [[DOB]] - 4-Bromo-2,5-dimethoxy-A
+# [[DOBU]] - 4-Butyl-2,5-dimethoxy-A
+# [[DOC]] - 4-Chloro-2,5-dimethoxy-A
+# [[DOEF]] - 4-(2-Fluoroethyl)-2,5-dimethoxy-A
+# [[DOET]] - 4-Ethyl-2,5-dimethoxy-A
+# [[DOI]] - 4-Iodo-2,5-dimethoxy-A
+# [[DOM|DOM (STP)]] - 4-Methyl-2,5-dimethoxy-A
+# [[psi-DOM]] - 4-Methyl-2,6-dimethoxy-A
+# [[DON]] - 4-Nitro-2,5-dimethoxy-A
+# [[DOPR]] - 4-Propyl-2,5-dimethoxy-A
+# [[Escaline|E]] - 4-Ethoxy-3,5-dimethoxy-PEA
+# [[EEE]] - 2,4,5-Triethoxy-A
+# [[EEM]] - 2,4-Diethoxy-5-methoxy-A
+# [[EME]] - 2,5-Diethoxy-4-methoxy-A
+# [[EMM]] - 2-Ethoxy-4,5-dimethoxy-A
+# [[Ethyl-J|ETHYL-J]] - N,alpha-diethyl-3,4-methylenedioxy-PEA
+# [[Ethyl-K|ETHYL-K]] - N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA
+# [[F-2]] - Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)
+# [[F-22]] - Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)
+# [[FLEA]] - N-Hydroxy-N-methyl-3,4-methylenedioxy-A
+# [[G-3]] - 3,4-Trimethylene-2,5-dimethoxy-A
+# [[G-4]] - 3,4-Tetramethylene-2,5-dimethoxy-A
+# [[G-5]] - 3,4-Norbornyl-2,5-dimethoxy-A
+# [[Ganesha|GANESHA]] - 3,4-Dimethyl-2,5-dimethoxy-A
+# [[G-N]] - 1,4-Dimethoxynaphthyl-2-isopropylamine
+# [[HOT-2]] - 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA
+# [[HOT-7]] - 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA
+# [[HOT-17]] - 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA
+# [[IDNNA]] - 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A
+# [[Isomescaline|IM]] - 2,3,4-Trimethoxy-PEA
+# [[Isoproscaline|IP]] - 3,5-Dimethoxy-4-isopropoxy-PEA
+# [[IRIS]] - 5-Ethoxy-2-methoxy-4-methyl-A
+# [[MDB|J]] - alpha-Ethyl-3,4-methylenedioxy-PEA
+# [[Lophophine|LOPHOPHINE]] - 3-Methoxy-4,5-methylenedioxy-PEA
+# [[Mescaline|M]] - 3,4,5-Trimethoxy-PEA
+# [[4-MA]] - 4-Methoxy-A
+# [[MADAM-6]] - 2,N-Dimethyl-4,5-methylenedioxy-A
+# [[MAL]] - 3,5-Dimethoxy-4-methallyloxy-PEA
+# [[MDA]] - 3,4-Methylenedioxy-A
+# [[MDAL]] - N-Allyl-3,4-methylenedioxy-A
+# [[MDBU]] - N-Butyl-3,4-methylenedioxy-A
+# [[MDBZ]] - N-Benzyl-3,4-methylenedioxy-A
+# [[MDCPM]] - N-Cyclopropylmethyl-3,4-methylenedioxy-A
+# [[MDDM]] - N,N-Dimethyl-3,4-methylenedioxy-A
+# [[MDE]] - N-Ethyl-3,4-methylenedioxy-A
+# [[MDHOET]] - N-(2-Hydroxyethyl)-3,4-methylenedioxy-A
+# [[MDIP]] - N-Isopropyl-3,4-methylenedioxy-A
+# [[MDMA]] - N-Methyl-3,4-methylenedioxy-A
+# [[MDMC]] - N-Methyl-3,4-ethylenedioxy-A
+# [[MDMEO]] - N-Methoxy-3,4-methylenedioxy-A
+# [[MDMEOET]] - N-(2-Methoxyethyl)-3,4-methylenedioxy-A
+# [[MDMP]] - alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA
+# [[MDOH]] - N-Hydroxy-3,4-methylenedioxy-A
+# [[MDPEA]] - 3,4-Methylenedioxy-PEA
+# [[MDPH]] - alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA
+# [[MDPL]] - N-Propargyl-3,4-methylenedioxy-A
+# [[MDPR]] - N-Propyl-3,4-methylenedioxy-A
+# [[Metaescaline|ME]] - 3,4-Dimethoxy-5-ethoxy-PEA
+# [[MEDA]] - 3-methoxy-4,5-Ethylenedioxy-A
+# [[MEE]] - 2-Methoxy-4,5-diethoxy-A
+# [[MEM]] - 2,5-Dimethoxy-4-ethoxy-A
+# [[MEPEA]] - 3-Methoxy-4-ethoxy-PEA
+# [[Meta-DOB|META-DOB]] - 5-Bromo-2,4-dimethoxy-A
+# [[Meta-DOT|META-DOT]] - 5-Methylthio-2,4-dimethoxy-A
+# [[Methyl-DMA|METHYL-DMA]] - N-Methyl-2,5-dimethoxy-A
+# [[Methyl-DOB|METHYL-DOB]] - 4-Bromo-2,5-dimethoxy-N-methyl-A
+# [[Methyl-J|METHYL-J]] - N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA
+# [[Methyl-K|METHYL-K]] - N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA
+# [[Methyl-MA|METHYL-MA]] - N-Methyl-4-methoxy-A
+# [[Methyl-MMDA-2|METHYL-MMDA-2]] - N-Methyl-2-methoxy-4,5-methylenedioxy-A
+# [[MMDA]] - 3-Methoxy-4,5-methylenedioxy-A
+# [[MMDA-2]] - 2-Methoxy-4,5-methylenedioxy-A
+# [[MMDA-3a]] - 2-Methoxy-3,4-methylenedioxy-A
+# [[MMDA-3b]] - 4-Methoxy-2,3-methylenedioxy-A
+# [[MME]] - 2,4-Dimethoxy-5-ethoxy-A
+# [[Metaproscaline|MP]] - 3,4-Dimethoxy-5-propoxy-PEA
+# [[MPM]] - 2,5-Dimethoxy-4-propoxy-A
+# [[Ortho-DOT|ORTHO-DOT]] - 2-Methylthio-4,5-dimethoxy-A
+# [[Proscaline|P]] - 3,5-Dimethoxy-4-propoxy-PEA
+# [[Phenescaline|PE]] - 3,5-Dimethoxy-4-phenethyloxy-PEA
+# [[PEA]] - PEA
+# [[Propynyl|PROPYNYL]] - 4-Propynyloxy-3,5-dimethoxy-PEA
+# [[Symbescaline|SB]] - 3,5-Diethoxy-4-methoxy-PEA
+# [[2,3,4,5-Tetramethoxyamphetamine|TA]] - 2,3,4,5-Tetramethoxy-A
+# [[3-TASB]] - 4-Ethoxy-3-ethylthio-5-methoxy-PEA
+# [[4-TASB]] - 3-Ethoxy-4-ethylthio-5-methoxy-PEA
+# [[5-TASB]] - 3,4-Diethoxy-5-methylthio-PEA
+# [[Thiobuscaline|TB]] - 4-Thiobutoxy-3,5-dimethoxy-PEA
+# [[3-TE]] - 4-Ethoxy-5-methoxy-3-methylthio-PEA
+# [[4-TE]] - 3,5-Dimethoxy-4-ethylthio-PEA
+# [[2-TIM]] - 2-Methylthio-3,4-dimethoxy-PEA
+# [[3-TIM]] - 3-Methylthio-2,4-dimethoxy-PEA
+# [[4-TIM]] - 4-Methylthio-2,3-dimethoxy-PEA
+# [[3-TM]] - 3-Methylthio-4,5-dimethoxy-PEA
+# [[4-TM]] - 4-Methylthio-3,5-dimethoxy-PEA
+# [[TMA]] - 3,4,5-Trimethoxy-A
+# [[TMA-2]] - 2,4,5-Trimethoxy-A
+# [[TMA-3]] - 2,3,4-Trimethoxy-A
+# [[TMA-4]] - 2,3,5-Trimethoxy-A
+# [[TMA-5]] - 2,3,6-Trimethoxy-A
+# [[TMA-6]] - 2,4,6-Trimethoxy-A
+# [[3-TME]] - 4,5-Dimethoxy-3-ethylthio-PEA
+# [[4-TME]] - 3-Ethoxy-5-methoxy-4-methylthio-PEA
+# [[5-TME]] - 3-Ethoxy-4-methoxy-5-methylthio-PEA
+# [[2T-MMDA-3a]] - 2-Methylthio-3,4-methylenedioxy-A
+# [[4T-MMDA-2]] - 4,5-Thiomethyleneoxy-2-methoxy-A
+# [[TMPEA]] - 2,4,5-Trimethoxy-PEA
+# [[2-TOET]] - 4-Ethyl-5-methoxy-2-methylthio-A
+# [[5-TOET]] - 4-Ethyl-2-methoxy-5-methylthio-A
+# [[2-TOM]] - 5-Methoxy-4-methyl-2-methylthio-A
+# [[5-TOM]] - 2-Methoxy-4-methyl-5-methylthio-A
+# [[TOMSO]] - 2-Methoxy-4-methyl-5-methylsulfinyl-A
+# [[Thioproscaline|TP]] - 4-Propylthio-3,5-dimethoxy-PEA
+# [[TRIS]] - 3,4,5-Triethoxy-PEA
+# [[3-TSB]] - 3-Ethoxy-5-ethylthio-4-methoxy-PEA
+# [[4-TSB]] - 3,5-Diethoxy-4-methylthio-PEA
+# [[3-T-TRIS]] - 4,5-Diethoxy-3-ethylthio-PEA
+# [[4-T-TRIS]] - 3,5-Diethoxy-4-ethylthio-PEA
+}}
 == Notable excerpts ==
-=== Magical Half-Dozen ===
+=== 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)
-* [[2,5-Dimethoxy-4-methylamphetamine|DOM]] (2,5-dimethoxy-4-methylamphetamine, DOM being short for '''d'''es'''o'''xy '''m'''ethyl, referring to the removal of the Oxygen atom from the Methoxy group on the "4" carbon.
+* [[DOM]] (2,5-dimethoxy-4-methylamphetamine)
-* [[2C-B]] (2,5-dimethoxy-4-'''b'''romophenethylamine)
+* [[2C-B]] (2,5-dimethoxy-4-bromophenethylamine)
-* [[2C-E]] (2,5-dimethoxy-4-'''e'''thylphenethylamine)
+* [[2C-E]] (2,5-dimethoxy-4-ethylphenethylamine)
-* [[2C-T-2]] (2,5-dimethoxy-4-ethyl'''t'''hiophenethylamine)
+* [[2C-T-2]] (2,5-dimethoxy-4-ethylthiophenethylamine)
-* [[2C-T-7]] (2,5-dimethoxy-4-propyl'''t'''hiophenethylamine)
+* [[2C-T-7]] (2,5-dimethoxy-4-propylthiophenethylamine)
+=== Essential amphetamines === <!-- Note: a redirect, [[Essential amphetamines]], links to this subsection -->
+The Essential Amphetamines are what Shulgin describes as ten amphetamines that differ from natural products such as [[safrole]] or [[myristicin]] by an amine group ([http://www.erowid.org/library/books_online/pihkal/pihkal157.shtml ''PIHKAL'' Entry #157 TMA]). The list consists of:
+* [[PMA]] (''para''-'''m'''ethoxy-'''a'''mphetamine)
+* [[2,4-DMA]] (2,4-'''d'''i'''m'''ethoxy-'''a'''mphetamine)
+* [[3,4-DMA]] (3,4-'''d'''i'''m'''ethoxy-'''a'''mphetamine)
+* [[MDA]] (3,4-'''m'''ethylene'''d'''ioxy-'''a'''mphetamine)
+* [[3-Methoxy-4,5-methylendioxyamphetamine|MMDA]] (3-'''m'''ethoxy-4,5-'''m'''ethylen'''d'''ioxy-'''a'''mphetamine)
+* [[MMDA-3a]] (2-'''m'''ethoxy-3,4-'''m'''ethylen'''d'''ioxy'''a'''mphetamine)
+* [[MMDA-2]] (2-'''m'''ethoxy-4,5-'''m'''ethylen'''d'''ioxy'''a'''mphetamine)
+* [[TMA]] (3,4,5-'''t'''ri'''m'''ethoxy'''a'''mphetamine)
+* [[TMA-2]] (2,4,5-'''t'''ri'''m'''ethoxy'''a'''mphetamine)
+* [[DMMDA]] (2,5-'''d'''i'''m'''ethoxy-3,4-'''m'''ethylene'''d'''ioxy'''a'''mphetamine)
+* [[DMMDA-2]] (2,3-'''d'''i'''m'''ethoxy-4,5-'''m'''ethylene'''d'''ioxy'''a'''mphetamine)
+* [[Tetramethoxyamphetamine|TA]] (2,3,4,5-'''t'''etramethoxy'''a'''mphetamine)
+Not all of these chemicals are bioassayed in ''PIHKAL''; some are merely mentioned.
 == See also ==
-* [[Phenethylamine]]
+*[[Responsible use]]
-* [[Amphetamine]] (AMPH)
+*[[Phenethylamine]]
-* [[MDMA]] (MDxx)
+*[[Amphetamine]]
-* [[Alexander Shulgin]]
+*[[Alexander Shulgin]]
+*[[TiHKAL]]
+==External links==
+*[https://en.wikipedia.org/wiki/PiHKAL PiHKAL (Wikipedia)]
+*[https://en.wikipedia.org/wiki/Substituted_amphetamine Substituted amphetamine (Wikipedia)]
+*[https://en.wikipedia.org/wiki/Substituted_phenethylamine Substituted phenethylamine (Wikipedia)]
+*[https://en.wikipedia.org/wiki/List_of_naturally_occurring_phenethylamines List of naturally occurring phenethylamines (Wikipedia)]
+*[http://isomerdesign.com/PiHKAL/ ''PIHKAL'' • Info: A Visual Index and Map of ''PIHKAL: A Chemical Love Story'' by Alexander & Ann Shulgin]
+[[Category:Book]]
+[[Category:Substance-related lists]]
+{{#set:Featured=true}}