Erowid Online Books : "PIHKAL" - The Chemical Story

pihkal

Modern humans must learn how to relate to psychoactives
responsibly, treating them with respect and awareness,
working to minimize harms and maximize benefits, and
integrating use into a healthy, enjoyable, and productive life.

Phenethylamines I Have Known And Loved:

A Chemical Love Story

By Alexander and Ann Shulgin

phen-ethyl-amine \fen-'eth-al-a-,men\ n. [phenyl fr. F. phène, fr. Gk. phainein, to show (from its occurrence in illuminating gas)+ ethyl ( + yl) + amine fr. NL ammonia] 1: A naturally occurring compound found in both the animal and plant kingdoms. It is an endogenous component of the human brain. 2: Any of a series of compounds containing the phenethylamine skeleton, and modified by chemical constituents at appropriate positions in the molecule.

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 the introductory information, copyright notice, cautionary notice and ordering information remain attached.

CAUTIONARY NOTE: READ BEFORE PROCEEDING

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

ABOUT THIS HTML VERSION OF PiHKAL

This is the online version of the second half of the book "PiHKAL: A Chemical Love Story" by Alexander and Ann Shulgin. It is presented with the express permission of the authors in order to spread the factual information as widely as possible and make it permanently available in the public domain. It was originally transcribed into ASCII by Simson Garfinkle and was coverted into HTML by Lamont Granquist. Any comments or corrections about the HTML version should be sent to Erowid. We can also forward serious and appropriate comments to the author if they are e-mailed to us. Bolded entries indicate those substances that have been more popular or more available than others since 1991.

ORDERING INFORMATION

The first half of PiHKAL is an excellent commentary on the Shulgin's personal experiences with phenethylamines. It is highly recommended and well worth purchasing the book. Purchasing the book also gets you a far more complete cross-index into the chemicals described in the second half. If you are seriously interested in the chemistry contained in these files, you should order a copy. The book may be ordered through Transform Press, for $22.95 ($18.95 + $4 p&h U.S., $8 p&h overseas). Box 13675, Berkeley, CA 94701. (510)934-4930 (voice), (510)934-5999 (fax). California residents please add $1.56 State sales tax.

INDEX TO THE PHENETHYLAMINES

#	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	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	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	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
Appendix B: Glossary

OTHER PiHKAL RELATED FILES

Shulgin Rating Scale
PiHKAL Chemical Legal Status
Quick Index to 17 of the more important chemicals, by Lamont Granquist
A Chemical Glossary, by Lamont Granquist
Printable version (1 page - 1.4 meg ASCII file)
Printable version (1 page - .5 meg zip of a 1.7 meg MSWord file)
An 'Interview' with Shulgin, by Clifton
A Bibliography of Shulgin's work
Review of PiHKAL, by Tyrone Slothrop Includes notes on PiHKAL and
his list of the 300+ chemicals in Book II -- hella impressive (postscript version)