Editing PiHKAL

{{Short description|1991 book by Alexander Shulgin and Ann Shulgin}}
{{More citations needed|date=December 2007}}
{{Use American English|date=July 2022}}
{{Use mdy dates|date=July 2022}}
{{Infobox book
| name          = PiHKAL: A Chemical Love Story
| image         = Pihkal.jpg
| caption       = Cover of ''PiHKAL'', 1st ed.
| author        = [[Alexander Shulgin|Alexander]] and [[Ann Shulgin]]
| cover_artist  =
| country       = United States
| subject       = [[Pharmacology]], [[Autobiography]], [[Psychoactive drug]]s
| publisher     = [[Transform Press]]
| release_date  = 1991
| media_type    = Paperback
| pages         =
| isbn          = 0-9630096-0-5
| oclc          = 269100404
| followed_by   = [[TiHKAL]]
}}

'''''PiHKAL: A Chemical Love Story''''' is a [[book]] by [[Alexander Shulgin]] and [[Ann Shulgin]] published in 1991.<ref name="Johnson2018">{{cite book | last=Johnson | first=C. | title=Magic Medicine: A Trip Through the Intoxicating History and Modern-Day Use of Psychedelic Plants and Substances | publisher=Fair Winds Press | year=2018 | isbn=978-1-63159-428-1 | url=https://books.google.com/books?id=N-NfDwAAQBAJ&pg=PA22 | access-date=30 January 2025 | pages=22–24}}</ref><ref name="PiHKAL1991">{{cite book | author1 = [[Alexander T. Shulgin]] | author2 = [[Ann Shulgin]] | title = PiHKAL: A Chemical Love Story | date = 1991 | publisher = [[Transform Press]] | edition = 1st | location = Berkeley, CA | isbn = 978-0-9630096-0-9 | oclc = 25627628 | url = https://books.google.com/books?id=O8AdHBGybpcC }}</ref> The subject of the work is [[Psychoactive drug|psychoactive]] [[phenethylamine]] [[Derivative (chemistry)|chemical derivatives]], notably those that act as [[psychedelic drug|psychedelics]] and/or [[empathogen-entactogen]]s. The main title, PiHKAL, is an [[acronym]] that stands for "Phenethylamines I Have Known and Loved".

The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179 different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, [[bioassay]]s, dosages, and other commentary.

The second part was made freely available by Shulgin on [[Erowid]] while the first part is available only in the printed text. While the reactions described are beyond the ability of people with a basic chemistry education, some tend to emphasize techniques that do not require difficult-to-obtain chemicals. Notable among these are the use of [[Aluminium amalgam|mercury-aluminium amalgam]] (an unusual but easy to obtain [[reagent]]) as a [[reducing agent]] and detailed suggestions on legal plant sources of important drug precursors such as [[safrole]].

==Impact and popularity==
Through ''PIHKAL'' (and later ''[[TIHKAL]]''), Shulgin sought to ensure that his discoveries would escape the limits of professional research labs and find their way to the public, a goal consistent with his stated beliefs that [[psychedelic drug]]s can be valuable tools for self-exploration. The [[MDMA]] ("ecstasy") synthesis published in ''PIHKAL'' remains one of the most common [[clandestine chemistry|clandestine]] methods of its manufacture to this day. Many countries have banned the major substances for which this book gives directions for synthesis, such as [[2C-B]], [[2C-T-2]], and [[2C-T-7]].

In 1994, two years after ''PIHKAL'' was published, the [[Drug Enforcement Administration]] (DEA) raided Shulgin's laboratory and requested that he surrender his DEA license. Richard Meyer, spokesman for DEA's San Francisco Field Division, has stated in reference to ''PIHKAL'' "It is our opinion that those books are pretty much cookbooks on how to make illegal drugs. Agents tell me that in clandestine labs that they have raided, they have found copies of those books", suggesting that the publication of ''PIHKAL'' and the termination of Shulgin's license may have been related.<ref name="Dr. Ecstasy">{{cite news | first = Drake |last=Bennett | url = https://www.nytimes.com/2005/01/30/magazine/30ECSTASY.html | title = Dr. Ecstasy | work = New York Times Magazine | date = January 30, 2005}}</ref>

==Notable compounds==
===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:

* [[Paramethoxyamphetamine|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)
* [[3,4-Methylenedioxyamphetamine|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)
* [[Trimethoxyamphetamine|TMA]] (3,4,5-'''t'''ri'''m'''ethoxy'''a'''mphetamine)
* [[Trimethoxyamphetamine|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|TeMA]] (2,3,4,5-'''te'''tra'''m'''ethoxy'''a'''mphetamine)

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

===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:

* [[2C-B]] (2,5-dimethoxy-4-'''b'''romophenethylamine)
* [[2C-E]] (2,5-dimethoxy-4-'''e'''thylphenethylamine)
* [[2C-T-2]] (2,5-dimethoxy-4-ethyl'''t'''hiophenethylamine)
* [[2C-T-7]] (2,5-dimethoxy-4-propyl'''t'''hiophenethylamine)
* [[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.
* [[Mescaline]] (3,4,5-trimethoxyphenethylamine)

All six are now Schedule I controlled substances in the United States.<ref>{{Cite web|url=http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf|title=Controlled Substances|date=February 2016|website=[[Drug Enforcement Administration]]|access-date=April 13, 2016|archive-date=April 17, 2016|archive-url=https://web.archive.org/web/20160417085659/http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf|url-status=dead}}</ref>

==Phenethylamines listed==
{{Sticky}}
{| class="wikitable sticky-header"
! #
! Substance
! Chemical name
|-
| 1
| [[AEM (psychedelic)|AEM]]
| α-Ethyl-3,4,5-trimethoxy-PEA
|-
| 2
| [[Allylescaline|AL]]
| 4-Allyloxy-3,5-dimethoxy-PEA
|-
| 3
| [[Aleph (psychedelic)|ALEPH]]
| 4-Methylthio-2,5-dimethoxy-A
|-
| 4
| [[Aleph (psychedelic)|ALEPH-2]]
| 4-Ethylthio-2,5-dimethoxy-A
|-
| 5
| [[Aleph (psychedelic)|ALEPH-4]]
| 4-Isopropylthio-2,5-dimethoxy-A
|-
| 6
| [[Aleph (psychedelic)|ALEPH-6]]
| 4-Phenylthio-2,5-dimethoxy-A
|-
| 7
| [[Aleph (psychedelic)|ALEPH-7]]
| 4-Propylthio-2,5-dimethoxy-A
|-
| 8
| [[Ariadne (psychedelic)|ARIADNE]] (Dimoxamine)
| 2,5-Dimethoxy-α-ethyl-4-methyl-PEA
|-
| 9
| [[Asymbescaline|ASB]]
| 3,4-Diethoxy-5-methoxy-PEA
|-
| 10
| [[Buscaline|B]]
| 4-Butoxy-3,5-dimethoxy-PEA
|-
| 11
| [[Beatrice (psychedelic)|BEATRICE]]
| 2,5-Dimethoxy-4,N-dimethyl-A
|-
| 12
| [[Bis-TOM]]
| 2,5-Bismethylthio-4-methyl-A
|-
| 13
| [[BOB (psychedelic)|BOB]]
| 4-Bromo-2,5,β-trimethoxy-PEA
|-
| 14
| [[BOD (psychedelic)|BOD]]
| 2,5,β-Trimethoxy-4-methyl-PEA
|-
| 15
| [[BOH (psychedelic)|BOH]]
| β-Methoxy-3,4-methylenedioxy-PEA
|-
| 16
| [[BOHD (psychedelic)|BOHD]]
| 2,5-Dimethoxy-β-hydroxy-4-methyl-PEA
|-
| 17
| [[BOM (psychedelic)|BOM]]
| 3,4,5,β-Tetramethoxy-PEA
|-
| 18
| [[4-Bromo-3,5-dimethoxyamphetamine|4-Br-3,5-DMA]]
| 4-Bromo-3,5-dimethoxy-A
|-
| 19
| [[2-Bromo-4,5-methylenedioxyamphetamine|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|2C-G-3]]
| 3,4-Trimethylene-2,5-dimethoxy-PEA
|-
| 29
| [[2C-G|2C-G-4]]
| 3,4-Tetramethylene-2,5-dimethoxy-PEA
|-
| 30
| [[2C-G|2C-G-5]]
| 3,4-Norbornyl-2,5-dimethoxy-PEA
|-
| 31
| [[2C-G|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
| [[Cyclopropylmescaline|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 (psychedelic)|4-D]]
| 4-Trideuteromethyl-3,5-dimethoxy-PEA
|-
| 51
| [[Beta-D]]
| β,β-Dideutero-3,4,5-trimethoxy-PEA
|-
| 52
| [[DESOXY]]
| 4-Methyl-3,5-Dimethoxy-PEA
|-
| 53
| [[Dimethoxyamphetamine|2,4-DMA]]
| 2,4-Dimethoxy-A
|-
| 54
| [[Dimethoxyamphetamine|2,5-DMA]]
| 2,5-Dimethoxy-A
|-
| 55
| [[Dimethoxyamphetamine|3,4-DMA]]
| 3,4-Dimethoxy-A
|-
| 56
| [[2,5-Dimethoxy-4-methylphenylcyclopropylamine|DMCPA]]
| 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine
|-
| 57
| [[DME (psychedelic)|DME]]
| 3,4-Dimethoxy-β-hydroxy-PEA
|-
| 58
| [[DMMDA]]
| 2,5-Dimethoxy-3,4-methylenedioxy-A
|-
| 59
| [[DMMDA-2]]
| 2,3-Dimethoxy-4,5-methylenedioxy-A
|-
| 60
| [[3,4-Dimethoxyphenethylamine|DMPEA]]
| 3,4-Dimethoxy-PEA
|-
| 61
| [[2,5-Dimethoxy-4-amylamphetamine|DOAM]]
| 4-Amyl-2,5-dimethoxy-A
|-
| 62
| [[2,5-Dimethoxy-4-bromoamphetamine|DOB]]
| 4-Bromo-2,5-dimethoxy-A
|-
| 63
| [[2,5-Dimethoxy-4-butylamphetamine|DOBU]]
| 4-Butyl-2,5-dimethoxy-A
|-
| 64
| [[2,5-Dimethoxy-4-chloroamphetamine|DOC]]
| 4-Chloro-2,5-dimethoxy-A
|-
| 65
| [[2,5-Dimethoxy-4-(2-fluoroethyl)amphetamine|DOEF]]
| 4-(2-Fluoroethyl)-2,5-dimethoxy-A
|-
| 66
| [[2,5-Dimethoxy-4-ethylamphetamine|DOET]]
| 4-Ethyl-2,5-dimethoxy-A
|-
| 67
| [[2,5-Dimethoxy-4-iodoamphetamine|DOI]]
| 4-Iodo-2,5-dimethoxy-A
|-
| 68
| [[2,5-Dimethoxy-4-methylamphetamine|DOM]] (STP)
| 4-Methyl-2,5-dimethoxy-A
|-
| 69
| [[Psi-DOM]]
| 4-Methyl-2,6-dimethoxy-A
|-
| 70
| [[2,5-Dimethoxy-4-nitroamphetamine|DON]]
| 4-Nitro-2,5-dimethoxy-A
|-
| 71
| [[2,5-Dimethoxy-4-propylamphetamine|DOPR]]
| 4-Propyl-2,5-dimethoxy-A
|-
| 72
| [[Escaline|E]]
| 4-Ethoxy-3,5-dimethoxy-PEA
|-
| 73
| [[EEE (psychedelic)|EEE]]
| 2,4,5-Triethoxy-A
|-
| 74
| [[EEM (psychedelic)|EEM]]
| 2,4-Diethoxy-5-methoxy-A
|-
| 75
| [[EME (psychedelic)|EME]]
| 2,5-Diethoxy-4-methoxy-A
|-
| 76
| [[EMM (psychedelic)|EMM]]
| 2-Ethoxy-4,5-dimethoxy-A
|-
| 77
| [[1,3-Benzodioxolyl-N-ethylbutanamine|ETHYL-J]]
| N,α-Diethyl-3,4-methylenedioxy-PEA
|-
| 78
| [[1,3-Benzodioxolyl-N-ethylpentanamine|ETHYL-K]]
| N-Ethyl-α-propyl-3,4-methylenedioxy-PEA
|-
| 79
| [[F-2 (drug)|F-2]]
| Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)
|-
| 80
| [[F-22 (psychedelic)|F-22]]
| Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)
|-
| 81
| [[3,4-Methylenedioxy-N-hydroxy-N-methylamphetamine|FLEA]]
| N-Hydroxy-N-methyl-3,4-methylenedioxy-A
|-
| 82
| [[Ganesha (psychedelic)|G-3]]
| 3,4-Trimethylene-2,5-dimethoxy-A
|-
| 83
| [[Ganesha (psychedelic)|G-4]]
| 3,4-Tetramethylene-2,5-dimethoxy-A
|-
| 84
| [[Ganesha (psychedelic)|G-5]]
| 3,4-Norbornyl-2,5-dimethoxy-A
|-
| 85
| [[Ganesha (psychedelic)|GANESHA]]
| 3,4-Dimethyl-2,5-dimethoxy-A
|-
| 86
| [[Ganesha (psychedelic)|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
| [[Isomescaline|IM]]
| 2,3,4-Trimethoxy-PEA
|-
| 92
| [[Isoproscaline|IP]]
| 3,5-Dimethoxy-4-isopropoxy-PEA
|-
| 93
| [[IRIS (psychedelic)|IRIS]]
| 5-Ethoxy-2-methoxy-4-methyl-A
|-
| 94
| [[1,3-Benzodioxolylbutanamine|J]]
| α-Ethyl-3,4-methylenedioxy-PEA
|-
| 95
| [[Lophophine|LOPHOPHINE]]
| 3-Methoxy-4,5-methylenedioxy-PEA
|-
| 96
| [[Mescaline|M]]
| 3,4,5-Trimethoxy-PEA
|-
| 97
| [[para-Methoxyamphetamine|4-MA]] (PMA)
| 4-Methoxy-A
|-
| 98
| [[MADAM-6]]
| 2,N-Dimethyl-4,5-methylenedioxy-A
|-
| 99
| [[Methallylescaline|MAL]]
| 3,5-Dimethoxy-4-methallyloxy-PEA
|-
| 100
| [[3,4-Methylenedioxyamphetamine|MDA]]
| 3,4-Methylenedioxy-A
|-
| 101
| [[Methylenedioxyallylamphetamine|MDAL]]
| N-Allyl-3,4-methylenedioxy-A
|-
| 102
| [[Methylenedioxybutylamphetamine|MDBU]]
| N-Butyl-3,4-methylenedioxy-A
|-
| 103
| [[Methylenedioxybenzylamphetamine|MDBZ]]
| N-Benzyl-3,4-methylenedioxy-A
|-
| 104
| [[Methylenedioxycyclopropylmethylamphetamine|MDCPM]]
| N-Cyclopropylmethyl-3,4-methylenedioxy-A
|-
| 105
| [[Methylenedioxydimethylamphetamine|MDDM]]
| N,N-Dimethyl-3,4-methylenedioxy-A
|-
| 106
| [[3,4-Methylenedioxy-N-ethylamphetamine|MDE]]
| N-Ethyl-3,4-methylenedioxy-A
|-
| 107
| [[Methylenedioxyhydroxyethylamphetamine|MDHOET]]
| N-(2-Hydroxyethyl)-3,4-methylenedioxy-A
|-
| 108
| [[3,4-Methylenedioxy-N-isopropylamphetamine|MDIP]]
| N-Isopropyl-3,4-methylenedioxy-A
|-
| 109
| [[MDMA]]
| N-Methyl-3,4-methylenedioxy-A
|-
| 110
| [[EDMA|MDMC]] (EDMA)
| N-Methyl-3,4-ethylenedioxy-A
|-
| 111
| [[3,4-Methylenedioxy-N-methoxyamphetamine|MDMEO]]
| N-Methoxy-3,4-methylenedioxy-A
|-
| 112
| [[Methylenedioxymethoxyethylamphetamine|MDMEOET]]
| N-(2-Methoxyethyl)-3,4-methylenedioxy-A
|-
| 113
| [[3,4-Methylenedioxy-N-methylphentermine|MDMP]]
| α,α,N-Trimethyl-3,4-methylenedioxy-PEA
|-
| 114
| [[3,4-Methylenedioxy-N-hydroxyamphetamine|MDOH]]
| N-Hydroxy-3,4-methylenedioxy-A
|-
| 115
| [[3,4-Methylenedioxyphenethylamine|MDPEA]]
| 3,4-Methylenedioxy-PEA
|-
| 116
| [[3,4-Methylenedioxyphentermine|MDPH]]
| α,α-Dimethyl-3,4-methylenedioxy-PEA
|-
| 117
| [[3,4-Methylenedioxy-N-propargylamphetamine|MDPL]]
| N-Propargyl-3,4-methylenedioxy-A
|-
| 118
| [[3,4-Methylenedioxy-N-propylamphetamine|MDPR]]
| N-Propyl-3,4-methylenedioxy-A
|-
| 119
| [[Metaescaline|ME]]
| 3,4-Dimethoxy-5-ethoxy-PEA
|-
| 120
| [[MEDA]]
| 3-methoxy-4,5-Ethylenedioxy-A [Erowid corrected]
|-
| 121
| [[MEE (psychedelic)|MEE]]
| 2-Methoxy-4,5-diethoxy-A
|-
| 122
| [[2,5-Dimethoxy-4-ethoxyamphetamine|MEM]]
| 2,5-Dimethoxy-4-ethoxy-A
|-
| 123
| [[3-Methoxy-4-ethoxyphenethylamine|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
| [[MBDB|Methyl-J]]
| N-Methyl-α-ethyl-3,4-methylenedioxy-PEA
|-
| 129
| [[1,3-Benzodioxolyl-N-methylpentanamine|Methyl-K]]
| N-Methyl-α-propyl-3,4-methylenedioxy-PEA
|-
| 130
| [[para-Methoxy-N-methylamphetamine|Methyl-MA]]
| N-Methyl-4-methoxy-A
|-
| 131
| [[Methyl-MMDA-2]]
| N-Methyl-2-methoxy-4,5-methylenedioxy-A
|-
| 132
| [[MMDA (drug)|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 (psychedelic)|MME]]
| 2,4-Dimethoxy-5-ethoxy-A
|-
| 137
| [[Metaproscaline|MP]]
| 3,4-Dimethoxy-5-propoxy-PEA
|-
| 138
| [[MPM (psychedelic)|MPM]]
| 2,5-Dimethoxy-4-propoxy-A
|-
| 139
| [[Ortho-DOT]]
| 2-Methylthio-4,5-dimethoxy-A
|-
| 140
| [[Proscaline|P]]
| 3,5-Dimethoxy-4-propoxy-PEA
|-
| 141
| [[Phenescaline|PE]]
| 3,5-Dimethoxy-4-phenethyloxy-PEA
|-
| 142
| [[Phenethylamine|PEA]]
| PEA
|-
| 143
| [[Propynyl (psychedelic)|PROPYNYL]]
| 4-Propynyloxy-3,5-dimethoxy-PEA
|-
| 144
| [[Symbescaline|SB]]
| 3,5-Diethoxy-4-methoxy-PEA
|-
| 145
| [[2,3,4,5-Tetramethoxyamphetamine|TA]]
| 2,3,4,5-Tetramethoxy-A
|-
| 146
| [[TASB (psychedelics)|3-TASB]]
| 4-Ethoxy-3-ethylthio-5-methoxy-PEA
|-
| 147
| [[TASB (psychedelics)|4-TASB]]
| 3-Ethoxy-4-ethylthio-5-methoxy-PEA
|-
| 148
| [[TASB (psychedelics)|5-TASB]]
| 3,4-Diethoxy-5-methylthio-PEA
|-
| 149
| [[Thiobuscaline|TB]]
| 4-Thiobutoxy-3,5-dimethoxy-PEA
|-
| 150
| [[Thioescaline|3-TE]]
| 4-Ethoxy-5-methoxy-3-methylthio-PEA
|-
| 151
| [[Thioescaline|4-TE]]
| 3,5-Dimethoxy-4-ethylthio-PEA
|-
| 152
| [[TIM (psychedelics)|2-TIM]]
| 2-Methylthio-3,4-dimethoxy-PEA
|-
| 153
| [[TIM (psychedelics)|3-TIM]]
| 3-Methylthio-2,4-dimethoxy-PEA
|-
| 154
| [[TIM (psychedelics)|4-TIM]]
| 4-Methylthio-2,3-dimethoxy-PEA
|-
| 155
| [[Thiomescaline|3-TM]]
| 3-Methylthio-4,5-dimethoxy-PEA
|-
| 156
| [[Thiomescaline|4-TM]]
| 4-Methylthio-3,5-dimethoxy-PEA
|-
| 157
| [[Trimethoxyamphetamine|TMA]]
| 3,4,5-Trimethoxy-A
|-
| 158
| [[Trimethoxyamphetamine|TMA-2]]
| 2,4,5-Trimethoxy-A
|-
| 159
| [[Trimethoxyamphetamine|TMA-3]]
| 2,3,4-Trimethoxy-A
|-
| 160
| [[Trimethoxyamphetamine|TMA-4]]
| 2,3,5-Trimethoxy-A
|-
| 161
| [[Trimethoxyamphetamine|TMA-5]]
| 2,3,6-Trimethoxy-A
|-
| 162
| [[Trimethoxyamphetamine|TMA-6]]
| 2,4,6-Trimethoxy-A
|-
| 163
| [[TME (psychedelics)|3-TME]]
| 4,5-Dimethoxy-3-ethylthio-PEA
|-
| 164
| [[TME (psychedelics)|4-TME]]
| 3-Ethoxy-5-methoxy-4-methylthio-PEA
|-
| 165
| [[TME (psychedelics)|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
| [[2,4,5-Trimethoxyphenethylamine|TMPEA]]
| 2,4,5-Trimethoxy-PEA
|-
| 169
| [[TOET (psychedelic)|2-TOET]]
| 4-Ethyl-5-methoxy-2-methylthio-A
|-
| 170
| [[TOET (psychedelic)|5-TOET]]
| 4-Ethyl-2-methoxy-5-methylthio-A
|-
| 171
| [[TOM (psychedelic)|2-TOM]]
| 5-Methoxy-4-methyl-2-methylthio-A
|-
| 172
| [[TOM (psychedelic)|5-TOM]]
| 2-Methoxy-4-methyl-5-methylthio-A
|-
| 173
| [[TOMSO]]
| 2-Methoxy-4-methyl-5-methylsulfinyl-A
|-
| 174
| [[Thioproscaline|TP]]
| 4-Propylthio-3,5-dimethoxy-PEA
|-
| 175
| [[Trisescaline|TRIS]]
| 3,4,5-Triethoxy-PEA
|-
| 176
| [[Thiosymbescaline|3-TSB]]
| 3-Ethoxy-5-ethylthio-4-methoxy-PEA
|-
| 177
| [[Thiosymbescaline|4-TSB]]
| 3,5-Diethoxy-4-methylthio-PEA
|-
| 178
| [[Thiotrisescaline |3-T-TRIS]]
| 4,5-Diethoxy-3-ethylthio-PEA
|-
| 179
| [[Thiotrisescaline |4-T-TRIS]]
| 3,5-Diethoxy-4-ethylthio-PEA
|-
|}

==See also==
* [[List of psychedelic literature]]
* [[Substituted phenethylamine]] (PEA)
* [[Substituted amphetamine]] (AMPH)
* [[Substituted methylenedioxyphenethylamine]] (MDxx)
* [[Substituted methoxyphenethylamine]]
* [[2C (psychedelics)|2Cs]], [[DOx]], [[4C (psychedelics)|4Cs]], [[25-NB]], [[substituted mescaline analogue|scaline]]s, [[3C (psychedelics)|3Cs]], [[FLY (psychedelics)|FLY]]
* [[TiHKAL]], the 1997 book by the same authors on [[Substituted tryptamine|tryptamines]]
* ''[[The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds]]'' (2011)

==References==
{{Reflist}}

==External links==
<!-- Note: These links are not a copyright violation: Shulgin allows reproduction of the second half of ''PIHKAL'' for non-commercial uses -->
* [https://www.erowid.org/library/books_online/pihkal/pihkal.shtml Erowid Online Books: ''PIHKAL: A Chemical Love Story'' by Alexander & Ann Shulgin]
* [https://isomerdesign.com/pihkal/ ''PIHKAL'' • Info: A Visual Index and Map of ''PIHKAL: A Chemical Love Story'' by Alexander & Ann Shulgin]
* [http://www.shulgin.es "Shulgin in Spanish" Project – Information on the first complete translation of PIHKAL and TIHKAL into Spanish]
* [https://www.transformpress.com Transform Press – Publisher of PiHKAL]

{{Phenethylamines}}
{{Psychedelics}}
{{Entactogens}}
{{Chemical classes of psychoactive drugs}}

[[Category:1991 non-fiction books]]
[[Category:Alexander Shulgin]]
[[Category:Psychedelic drug research]]
[[Category:Psychedelic literature]]
[[Category:Psychedelic phenethylamines]]
[[Category:Science books]]