PiHKAL

{{Short description|1991 book by Alexander Shulgin and Ann Shulgin}}

{{Infobox book

| name = PiHKAL: A Chemical Love Story

| image = Pihkal.jpg

| caption = Cover of PiHKAL, 1st ed.

| author = Alexander and Ann Shulgin

| cover_artist =

| country = United States

| subject = Pharmacology, Autobiography, Psychoactive drugs

| 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.{{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}}{{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 }} The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or empathogen-entactogens. 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, bioassays, 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 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 drugs can be valuable tools for self-exploration. The MDMA ("ecstasy") synthesis published in PIHKAL remains one of the most common 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.{{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}}

Notable compounds

===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-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)
TeMA (2,3,4,5-tetramethoxyamphetamine)

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-bromophenethylamine)
2C-E (2,5-dimethoxy-4-ethylphenethylamine)
2C-T-2 (2,5-dimethoxy-4-ethylthiophenethylamine)
2C-T-7 (2,5-dimethoxy-4-propylthiophenethylamine)
DOM (2,5-dimethoxy-4-methylamphetamine), DOM being short for desoxy methyl, 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.{{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}}

Phenethylamines listed

class="wikitable sticky-header"

! #

! Substance

! Chemical name

| AEM

| α-Ethyl-3,4,5-trimethoxy-PEA

| AL

| 4-Allyloxy-3,5-dimethoxy-PEA

| ALEPH

| 4-Methylthio-2,5-dimethoxy-A

| ALEPH-2

| 4-Ethylthio-2,5-dimethoxy-A

| ALEPH-4

| 4-Isopropylthio-2,5-dimethoxy-A

| ALEPH-6

| 4-Phenylthio-2,5-dimethoxy-A

| ALEPH-7

| 4-Propylthio-2,5-dimethoxy-A

| ARIADNE (Dimoxamine)

| 2,5-Dimethoxy-α-ethyl-4-methyl-PEA

| ASB

| 3,4-Diethoxy-5-methoxy-PEA

| B

| 4-Butoxy-3,5-dimethoxy-PEA

| BEATRICE

| 2,5-Dimethoxy-4,N-dimethyl-A

| Bis-TOM

| 2,5-Bismethylthio-4-methyl-A

| BOB

| 4-Bromo-2,5,β-trimethoxy-PEA

| BOD

| 2,5,β-Trimethoxy-4-methyl-PEA

| BOH

| β-Methoxy-3,4-methylenedioxy-PEA

| BOHD

| 2,5-Dimethoxy-β-hydroxy-4-methyl-PEA

| BOM

| 3,4,5,β-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

| β,β-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-β-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 (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

| 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

| N,α-Diethyl-3,4-methylenedioxy-PEA

| ETHYL-K

| N-Ethyl-α-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

| 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

| IM

| 2,3,4-Trimethoxy-PEA

| IP

| 3,5-Dimethoxy-4-isopropoxy-PEA

| IRIS

| 5-Ethoxy-2-methoxy-4-methyl-A

| J

| α-Ethyl-3,4-methylenedioxy-PEA

| LOPHOPHINE

| 3-Methoxy-4,5-methylenedioxy-PEA

| M

| 3,4,5-Trimethoxy-PEA

| 4-MA (PMA)

| 4-Methoxy-A

| MADAM-6

| 2,N-Dimethyl-4,5-methylenedioxy-A

| 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 (EDMA)

| 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

| α,α,N-Trimethyl-3,4-methylenedioxy-PEA

114

| MDOH

| N-Hydroxy-3,4-methylenedioxy-A

115

| MDPEA

| 3,4-Methylenedioxy-PEA

116

| MDPH

| α,α-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 [Erowid corrected]

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-α-ethyl-3,4-methylenedioxy-PEA

129

| Methyl-K

| N-Methyl-α-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

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

References

External links

[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]

Category:1991 non-fiction books

Category:Psychedelic drug research

Category:Psychedelic literature

Category:Psychedelic phenethylamines

Category:Science books