PiHKAL: The Chemical Story [Picture of PiHKAL Cover]

Phenethylamines i Have Known And Loved

Part 2: The Chemical Story

By Alexander Shulgin and Ann Shulgin


NOTICE: The trust fund for Alexander Shulgin has achieved it's goals.

Index to the Indicies

Copyright Notice

The Copyright for Part 1 of PiHKAL has been reserved in all forms and it may not be distributed. Part 2 of PiHKAL may be distributed for non-commerical reproduction provided that this notice, the cautionary notice and the ordering information are retained.

Introduction

This is the second half of the book PiHKAL: A Chemical Love Story by Alexander Shulgin and Ann Shulgin. It was originally transcribed into ASCII by Simson Garfinkle ([email protected]):
Please forgive any typos or misprints in this file; further, because of ASCII limitations, many of the typographical symbols in the original book could not be properly represented in these files. -- [email protected]

Cautionary Note: READ BEFORE PROCEEDING

This is excerpted from the book:
At the present time, restrictive laws are in force in the United States and it is very difficult for researchers to abide by the regulations which govern efforts to obtain legal approval to do work with these compounds in human beings.... No one who is lacking legal authorization should attempt the synthesis of any of the compounds described in these files, with the intent to give them to man. To do so is to risk legal action which might lead to the tragic ruination of a life. It should also be noted that any person anywhere who experiments on himself, or on another human being, with any of the drugs described herin, without being familiar with that drug's action and aware of the physical and/or mental disturbance or harm it might cause, is acting irresponsibly and immorally, whether or not he is doing so within the bounds of the law. -- Alexander T. Shulgin

Info on the HTML version of PiHKAL

The HTML version of PiHKAL has some notable improvements over the ASCII text version. The numerous cross-references in the text will eventually be setup with hypertext links. I've also been attmpting to convert the badly scanned non-ASCII characters into something a little more readable. At some point in the future there are vague ideas about having the chemical structures scanned in as .gif images.

Note: Intermediate chemicals which are used in other syntheses have been written in boldface. This is to make it easier to quickly follow links from one synthesis to another. Unfortunately, it also means that those intermediate chemicals which are used in other syntheses will stand out in boldface for no obviously discernable reason from the immediate context. If someone who is skilled at writing HTML documents knows of a better way to accomplish what i'm trying to do, please drop me a note about it.

PiHKAL was coverted into an HTML document by Lamont Granquist with the permission of the author Alexander Shulgin. Any comments on the HTML version should be sent to me. I can also forward appropriate comments to the author if they are e-mailed to me.

I'd also like to note that if you buy the book you get an extensive commentary on the Shulgin's personal experiences with phenethylamines, the appendicies, diagrams of all the 179 chemicals in book 2, the correct typesettings for the non-ASCII letters and you get a text which is less likely to have typographical errors. Plus if you don't buy it and just leach this copy, your conscience will haunt you till the day you die. BUY IT! BUY IT! BUY IT!!!! ( Dammit, where's my valium? )-- [email protected]

Ordering Information

If you are seriously interested in the chemistry contained in these files, you should order a copy of the book PiHKAL. The book may be purchased for $22.95 ($18.95 + $4.00 postage and handling) from Transform Press, Box 13675, Berkeley, CA 94701. (510)934-4930 (voice), (510)934-5999 (fax). California residents please add $1.38 State sales tax.

Other PiHKAL Sites and Files

(Tip: link to http://hyperreal.com/drugs/pihkal/index.html#INDEX to jump right to this spot)

INDEX TO THE PHENETHYLAMINES

This index to the phenethylamines lists the 179 entries that follow in alphebetical order. There is another index sorted by number of hits which is also available. The abbreviation PEA is for phenethylamine, and A is for amphetamine.

7453 total hits since May 27 1995 (updated daily -- not!)

(I need to reconfigure the script that is supposed to update this to deal with the 'new' logfile format that we've been using at hypereal for about the past 2 years -- lamont)

#   Substance     Hits   Chemical Name
1   AEM           [ 131] alpha-Ethyl-3,4,5-trimethoxy-PEA
2   AL            [  39] 4-Allyloxy-3,5-dimethoxy-PEA
3   ALEPH         [  49] 4-Methylthio-2,5-dimethoxy-A
4   ALEPH-2       [  38] 4-Ethylthio-2,5-dimethoxy-A
5   ALEPH-4       [  27] 4-Isopropylthio-2,5-dimethoxy-A
6   ALEPH-6       [  28] 4-Phenylthio-2,5-dimethoxy-A
7   ALEPH-7       [  23] 4-Propylthio-2,5-dimethoxy-A
8   ARIADNE       [  80] 2,5-Dimethoxy-alpha-ethyl-4-methyl-PEA
9   ASB           [  28] 3,4-Diethoxy-5-methoxy-PEA
10  B             [  24] 4-Butoxy-3,5-dimethoxy-PEA
11  BEATRICE      [  58] 2,5-Dimethoxy-4,N-dimethyl-A
12  BIS-TOM       [  29] 2,5-Bismethylthio-4-methyl-A
13  BOB           [  86] 4-Bromo-2,5,beta-trimethoxy-PEA
14  BOD           [  30] 2,5,beta-Trimethoxy-4-methyl-PEA
15  BOH           [  23] beta-Methoxy-3,4-methylenedioxy-PEA
16  BOHD          [  26] 2,5-Dimethoxy-beta-hydroxy-4-methyl-PEA
17  BOM           [  24] 3,4,5,beta-Tetramethoxy-PEA
18  4-Br-3,5-DMA  [  27] 4-Bromo-3,5-dimethoxy-A
19  2-Br-4,5-MDA  [  34] 2-Bromo-4,5-methylenedioxy-A
20  2C-B          [ 323] 4-Bromo-2,5-dimethoxy-PEA
21  3C-BZ         [  33] 4-Benzyloxy-3,5-dimethoxy-A
22  2C-C          [  31] 4-Chloro-2,5-dimethoxy-PEA
23  2C-D          [  64] 4-Methyl-2,5-dimethoxy-PEA
24  2C-E          [  38] 4-Ethyl-2,5-dimethoxy-PEA
25  3C-E          [  27] 4-Ethoxy-3,5-dimethoxy-A
26  2C-F          [  29] 4-Fluoro-2,5-dimethoxy-PEA
27  2C-G          [  31] 3,4-Dimethyl-2,5-dimethoxy-PEA
28  2C-G-3        [  28] 3,4-Trimethylene-2,5-dimethoxy-PEA
29  2C-G-4        [  22] 3,4-Tetramethylene-2,5-dimethoxy-PEA
30  2C-G-5        [  21] 3,4-Norbornyl-2,5-dimethoxy-PEA
31  2C-G-N        [  25] 1,4-Dimethoxynaphthyl-2-ethylamine
32  2C-H          [  31] 2,5-Dimethoxy-PEA
33  2C-I          [  20] 4-Iodo-2,5-dimethoxy-PEA
34  2C-N          [  30] 4-Nitro-2,5-dimethoxy-PEA
35  2C-O-4        [  18] 4-Isopropoxy-2,5-dimethoxy-PEA
36  2C-P          [  22] 4-Propyl-2,5-dimethoxy-PEA
37  CPM           [  29] 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA
38  2C-SE         [  22] 4-Methylseleno-2,5-dimethoxy-PEA
39  2C-T          [  28] 4-Methylthio-2,5-dimethoxy-PEA
40  2C-T-2        [  36] 4-Ethylthio-2,5-dimethoxy-PEA
41  2C-T-4        [  24] 4-Isopropylthio-2,5-dimethoxy-PEA
42  gamma-2C-T-4  [  42] 4-Isopropylthio-2,6-dimethoxy-PEA
43  2C-T-7        [  32] 4-Propylthio-2,5-dimethoxy-PEA
44  2C-T-8        [  21] 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA
45  2C-T-9        [  26] 4-(t)-Butylthio-2,5-dimethoxy-PEA
46  2C-T-13       [  15] 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA
47  2C-T-15       [  26] 4-Cyclopropylthio-2,5-dimethoxy-PEA
48  2C-T-17       [  17] 4-(s)-Butylthio-2,5-dimethoxy-PEA
49  2C-T-21       [  20] 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA
50  4-D           [  25] 4-Trideuteromethyl-3,5-dimethoxy-PEA
51  beta-D        [  26] beta,beta-Dideutero-3,4,5-trimethoxy-PEA
52  DESOXY        [  32] 4-Methyl-3,5-Dimethoxy-PEA
53  2,4-DMA       [  31] 2,4-Dimethoxy-A
54  2,5-DMA       [  26] 2,5-Dimethoxy-A
55  3,4-DMA       [  22] 3,4-Dimethoxy-A
56  DMCPA         [  23] 2-(2,5-Dimethoxy-4-methylphenyl)-cyclopropylamine
57  DME           [  29] 3,4-Dimethoxy-beta-hydroxy-PEA
58  DMMDA         [  39] 2,5-Dimethoxy-3,4-methylenedioxy-A
59  DMMDA-2       [  20] 2,3-Dimethoxy-4,5-methylenedioxy-A
60  DMPEA         [  38] 3,4-Dimethoxy-PEA
61  DOAM          [  30] 4-Amyl-2,5-dimethoxy-A
62  DOB           [  76] 4-Bromo-2,5-dimethoxy-A
63  DOBU          [  20] 4-Butyl-2,5-dimethoxy-A
64  DOC           [  28] 4-Chloro-2,5-dimethoxy-A
65  DOEF          [  18] 4-(2-Fluoroethyl)-2,5-dimethoxy-A
66  DOET          [  24] 4-Ethyl-2,5-dimethoxy-A
67  DOI           [  24] 4-Iodo-2,5-dimethoxy-A
68  DOM           [ 133] 4-Methyl-2,5-dimethoxy-A
69  gamma-DOM     [  27] 4-Methyl-2,6-dimethoxy-A
70  DON           [  28] 4-Nitro-2,5-dimethoxy-A
71  DOPR          [  20] 4-Propyl-2,5-dimethoxy-A
72  E             [  51] 4-Ethoxy-3,5-dimethoxy-PEA
73  EEE           [  25] 2,4,5-Triethoxy-A
74  EEM           [  21] 2,4-Diethoxy-5-methoxy-A
75  EME           [  18] 2,5-Diethoxy-4-methoxy-A
76  EMM           [  17] 2-Ethoxy-4,5-dimethoxy-A
77  ETHYL-J       [  24] N,alpha-diethyl-3,4-methylenedioxy-PEA
78  ETHYL-K       [  26] N-Ethyl-alpha-propyl-3,4-methylenedioxy-PEA
79  F-2           [  16] Benzofuran-2-methyl-5-methoxy-6-(2-aminopropane)
80  F-22          [  26] Benzofuran-2,2-dimethyl-5-methoxy-6-(2-aminopropane)
81  FLEA          [  40] N-Hydroxy-N-methyl-3,4-methylenedioxy-A
82  G-3           [  22] 3,4-Trimethylene-2,5-dimethoxy-A
83  G-4           [  24] 3,4-Tetramethylene-2,5-dimethoxy-A
84  G-5           [  21] 3,4-Norbornyl-2,5-dimethoxy-A
85  GANESHA       [  58] 3,4-Dimethyl-2,5-dimethoxy-A
86  G-N           [  19] 1,4-Dimethoxynaphthyl-2-isopropylamine
87  HOT-2         [  28] 2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA
88  HOT-7         [  17] 2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA
89  HOT-17        [  26] 2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA
90  IDNNA         [  27] 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A
91  IM            [  25] 2,3,4-Trimethoxy-PEA
92  IP            [  21] 3,5-Dimethoxy-4-isopropoxy-PEA
93  IRIS          [  37] 5-Ethoxy-2-methoxy-4-methyl-A
94  J             [  34] alpha-Ethyl-3,4-methylenedioxy-PEA
95  LOPHOPHINE    [  48] 3-Methoxy-4,5-methylenedioxy-PEA
96  M             [ 135] 3,4,5-Trimethoxy-PEA
97  4-MA          [  44] 4-Methoxy-A
98  MADAM-6       [  39] 2,N-Dimethyl-4,5-methylenedioxy-A
99  MAL           [  32] 3,5-Dimethoxy-4-methallyloxy-PEA
100 MDA           [ 296] 3,4-Methylenedioxy-A
101 MDAL          [  35] N-Allyl-3,4-methylenedioxy-A
102 MDBU          [  27] N-Butyl-3,4-methylenedioxy-A
103 MDBZ          [  27] N-Benzyl-3,4-methylenedioxy-A
104 MDCPM         [  30] N-Cyclopropylmethyl-3,4-methylenedioxy-A
105 MDDM          [  45] N,N-Dimethyl-3,4-methylenedioxy-A
106 MDE           [ 105] N-Ethyl-3,4-methylenedioxy-A
107 MDHOET        [  48] N-(2-Hydroxyethyl)-3,4-methylenedioxy-A
108 MDIP          [  59] N-Isopropyl-3,4-methylenedioxy-A
109 MDMA          [ 733] N-Methyl-3,4-methylenedioxy-A
110 MDMC          [  59] N-Methyl-3,4-ethylenedioxy-A
111 MDMEO         [  43] N-Methoxy-3,4-methylenedioxy-A
112 MDMEOET       [  38] N-(2-Methoxyethyl)-3,4-methylenedioxy-A
113 MDMP          [  60] alpha,alpha,N-Trimethyl-3,4-methylenedioxy-PEA
114 MDOH          [  55] N-Hydroxy-3,4-methylenedioxy-A
115 MDPEA         [  28] 3,4-Methylenedioxy-PEA
116 MDPH          [  36] alpha,alpha-Dimethyl-3,4-methylenedioxy-PEA
117 MDPL          [  18] N-Propargyl-3,4-methylenedioxy-A
118 MDPR          [  27] N-Propyl-3,4-methylenedioxy-A
119 ME            [  27] 3,4-Dimethoxy-5-ethoxy-PEA
120 MEDA          [  27] 3,4-Ethylenedioxy-5-methoxy-A
121 MEE           [  20] 2-Methoxy-4,5-diethoxy-A
122 MEM           [  36] 2,5-Dimethoxy-4-ethoxy-A
123 MEPEA         [  27] 3-Methoxy-4-ethoxy-PEA
124 META-DOB      [  26] 5-Bromo-2,4-dimethoxy-A
125 META-DOT      [  23] 5-Methylthio-2,4-dimethoxy-A
126 METHYL-DMA    [  31] N-Methyl-2,5-dimethoxy-A
127 METHYL-DOB    [  31] 4-Bromo-2,5-dimethoxy-N-methyl-A
128 METHYL-J      [  58] N-Methyl-alpha-ethyl-3,4-methylenedioxy-PEA
129 METHYL-K      [  29] N-Methyl-alpha-propyl-3,4-methylenedioxy-PEA
130 METHYL-MA     [  23] N-Methyl-4-methoxy-A
131 METHYL-MMDA-2 [  28] N-Methyl-2-methoxy-4,5-methylenedioxy-A
132 MMDA          [ 106] 3-Methoxy-4,5-methylenedioxy-A
133 MMDA-2        [  37] 2-Methoxy-4,5-methylenedioxy-A
134 MMDA-3a       [  52] 2-Methoxy-3,4-methylenedioxy-A
135 MMDA-3b       [  40] 4-Methoxy-2,3-methylenedioxy-A
136 MME           [  21] 2,4-Dimethoxy-5-ethoxy-A
137 MP            [  18] 3,4-Dimethoxy-5-propoxy-PEA
138 MPM           [  18] 2,5-Dimethoxy-4-propoxy-A
139 ORTHO-DOT     [  25] 2-Methylthio-4,5-dimethoxy-A
140 P             [  23] 3,5-Dimethoxy-4-propoxy-PEA
141 PE            [  26] 3,5-Dimethoxy-4-phenethyloxy-PEA
142 PEA           [ 157] PEA
143 PROPYNYL      [  32] 4-Propynyloxy-3,5-dimethoxy-PEA
144 SB            [  21] 3,5-Diethoxy-4-methoxy-PEA
145 TA            [  24] 2,3,4,5-Tetramethoxy-A
146 3-TASB        [  23] 4-Ethoxy-3-ethylthio-5-methoxy-PEA
147 4-TASB        [  21] 3-Ethoxy-4-ethylthio-5-methoxy-PEA
148 5-TASB        [  22] 3,4-Diethoxy-5-methylthio-PEA
149 TB            [  15] 4-Thiobutoxy-3,5-dimethoxy-PEA
150 3-TE          [  21] 4-Ethoxy-5-methoxy-3-methylthio-PEA
151 4-TE          [  18] 3,5-Dimethoxy-4-ethylthio-PEA
152 2-TIM         [  16] 2-Methylthio-3,4-dimethoxy-PEA
153 3-TIM         [  17] 3-Methylthio-2,4-dimethoxy-PEA
154 4-TIM         [  24] 4-Methylthio-2,3-dimethoxy-PEA
155 3-TM          [  25] 3-Methylthio-4,5-dimethoxy-PEA
156 4-TM          [  42] 4-Methylthio-3,5-dimethoxy-PEA
157 TMA           [ 234] 3,4,5-Trimethoxy-A
158 TMA-2         [  67] 2,4,5-Trimethoxy-A
159 TMA-3         [  29] 2,3,4-Trimethoxy-A
160 TMA-4         [  20] 2,3,5-Trimethoxy-A
161 TMA-5         [  31] 2,3,6-Trimethoxy-A
162 TMA-6         [  42] 2,4,6-Trimethoxy-A
163 3-TME         [  24] 4,5-Dimethoxy-3-ethylthio-PEA
164 4-TME         [  16] 3-Ethoxy-5-methoxy-4-methylthio-PEA
165 5-TME         [  17] 3-Ethoxy-4-methoxy-5-methylthio-PEA
166 2T-MMDA-3a    [  21] 2-Methylthio-3,4-methylenedioxy-A
167 4T-MMDA-2     [  29] 4,5-Thiomethyleneoxy-2-methoxy-A
168 TMPEA         [  29] 2,4,5-Trimethoxy-PEA
169 2-TOET        [  15] 4-Ethyl-5-methoxy-2-methylthio-A
170 5-TOET        [  22] 4-Ethyl-2-methoxy-5-methylthio-A
171 2-TOM         [  27] 5-Methoxy-4-methyl-2-methylthio-A
172 5-TOM         [  20] 2-Methoxy-4-methyl-5-methylthio-A
173 TOMSO         [  35] 2-Methoxy-4-methyl-5-methylsulfinyl-A
174 TP            [  23] 4-Propylthio-3,5-dimethoxy-PEA
175 TRIS          [  42] 3,4,5-Triethoxy-PEA
176 3-TSB         [  18] 3-Ethoxy-5-ethylthio-4-methoxy-PEA
177 4-TSB         [  29] 3,5-Diethoxy-4-methylthio-PEA
178 3-T-TRIS      [  25] 4,5-Diethoxy-3-ethylthio-PEA
179 4-T-TRIS      [  44] 3,5-Diethoxy-4-ethylthio-PEA