Chemistry:PiHKAL

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Short description: 1991 book by Alexander Shulgin and Ann Shulgin
PIHKAL: A Chemical Love Story
Pihkal.jpg
Cover of PIHKAL, 1st ed.
AuthorAlexander and Ann Shulgin
CountryUnited States
SubjectPharmacology, Autobiography, Psychoactive drugs
PublisherTransform Press
Publication date
1991
Media typePaperback
ISBNISBN:0-9630096-0-5
OCLC269100404
Followed byTiHKAL 

PiHKAL: A Chemical Love Story is a book by Dr. Alexander Shulgin and Ann Shulgin, 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, 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-aluminum 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 the United Kingdom, all but phenethylamine are illegal.[citation needed]

In 1994, two years after PIHKAL was published, the Drug Enforcement Administration (DEA) raided Shulgin's lab and requested that he turn over 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.[1]

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 (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:

  • Mescaline (3,4,5-trimethoxyphenethylamine)
  • 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.
  • 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)

All six are now Schedule I controlled substances in the United States.[2]

Phenethylamines listed

Substance Chemical name
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 (Dimoxamine) 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 (PMA) 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 (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 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 [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-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

See also

  • Olivetol
  • List of psychedelic literature
  • Substituted Amphetamine (AMPH)
  • Substituted Methylenedioxyphenethylamine (MDxx)
  • Substituted Phenethylamine (PEA)
  • TiHKAL, the 1997 book by the same authors on tryptamines

References

  1. ↑ Drake Bennett (January 30, 2005). "Dr. Ecstasy". New York Times Magazine. https://www.nytimes.com/2005/01/30/magazine/30ECSTASY.html. 
  2. ↑ "Controlled Substances". February 2016. http://www.deadiversion.usdoj.gov/schedules/orangebook/c_cs_alpha.pdf. 

External links



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