PiHKAL

PiHKAL: A Chemical Love Story
Autor(es)	Alexander e Ann Shulgin
Idioma	inglês
Editora	Transform Press
Lançamento	1991
ISBN	0-9630096-0-5
Cronologia
TiHKAL

PiHKAL: A Chemical Love Story é um livro de não ficção de Alexander Shulgin e Ann Shulgin, publicado em 1991. O tema da obra são os derivados químicos psicoativos da fenetilamina, notadamente aqueles que atuam como psicodélicos e/ou empatógenos-entactogênicos. O título principal, PiHKAL, é uma sigla que significa "Fenetilaminas que conheci e amei".

O livro está organizado em duas partes, sendo a primeira parte uma autobiografia ficcional do casal e a segunda parte descrevendo 179 compostos psicodélicos diferentes (a maioria dos quais o próprio Shulgin descobriu), incluindo instruções detalhadas de síntese, bioensaios, dosagens e outros comentários.

A segunda parte foi disponibilizada gratuitamente por Shulgin no Erowid, enquanto a primeira parte está disponível apenas no texto impresso. Embora as reações descritas estejam além da capacidade de pessoas com formação básica em química, alguns tendem a enfatizar técnicas que não requerem produtos químicos difíceis de obter. Destacam-se entre eles o uso de amálgama de mercúrio-alumínio (um reagente incomum, mas fácil de obter) como agente redutor e sugestões detalhadas sobre fontes vegetais legais de importantes precursores de drogas, como o safrol.

Através do PIHKAL (e mais tarde do TiHKAL), Shulgin procurou garantir que suas descobertas escapassem dos limites dos laboratórios de pesquisa profissionais e chegassem ao público, um objetivo consistente com suas crenças declaradas de que as drogas psicodélicas podem ser ferramentas valiosas para a autoexploração. A síntese de MDMA ("ecstasy") publicada no PIHKAL continua a ser um dos métodos clandestinos mais comuns de sua fabricação até hoje. Muitos países proibiram as principais substâncias para as quais este livro fornece instruções de síntese, como 2C-B, 2C-T-2 e 2C-T-7. No Reino Unido, todos, exceto a fenetilamina, são ilegais.

Em 1994, dois anos após a publicação de PIHKAL, a Drug Enforcement Administration (DEA) invadiu o laboratório de Shulgin e solicitou que ele entregasse sua licença da DEA. Richard Meyer, porta-voz da Divisão de Campo da DEA em São Francisco, declarou em referência a PIHKAL: "É nossa opinião que esses livros são basicamente livros de receitas sobre como fazer drogas ilegais. Os agentes me disseram que em laboratórios clandestinos que invadiram, eles encontrei cópias desses livros", sugerindo que a publicação de PIHKAL e o término da licença de Shulgin podem estar relacionados.^[1]

As "anfetaminas essenciais" são o que Shulgin descreve como dez anfetaminas que diferem de produtos naturais como o safrol ou a miristicina por um grupo amina (PIHKAL Entry #157 TMA). A lista consiste em:

• 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)

A chamada "meia dúzia mágica" refere-se aos compostos de fenetilamina autodenominados mais importantes de Shulgin, todos os quais, exceto a mescalina, ele mesmo desenvolveu e sintetizou. Eles são encontrados no primeiro livro de PIHKAL e são os seguintes:

• Mescaline (3,4,5-trimethoxyphenethylamine)
• DOM (2,5-dimethoxy-4-methylamphetamine)
• 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)

Todas as seis são agora substâncias controladas de Classe I nos Estados Unidos.^[2]

	Substância	Nome químico
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

• Erowid Online Books: PIHKAL: A Chemical Love Story by Alexander & Ann Shulgin

• Portal da literatura
• Portal dos Estados Unidos