PiHKAL

PIHKAL: A Chemical Love Story
	Cover of PIHKAL, 1st ed.
Author	Alexander and Ann Shulgin
Subject	Pharmacology, Autobiography, Psychoactive drugs
Publisher	Transform Press
Publication date	1991
Publication place	United States
Media type	Paperback
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. 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 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:

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.^[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

References

^ Bennett, Drake (January 30, 2005). "Dr. Ecstasy". New York Times Magazine.
^ "Controlled Substances" (PDF). Drug Enforcement Administration. February 2016. Archived from the original (PDF) on April 17, 2016. Retrieved April 13, 2016.