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PiHKAL

1991 book by Alexander Shulgin and Ann Shulgin

Field	Value
name	PiHKAL: A Chemical Love Story
image	Pihkal.jpg
image_size	200px
caption	Cover of PiHKAL, 1st ed.
author	Alexander and Ann Shulgin
country	United States
subject	Pharmacology, Autobiography, Psychoactive drugs
publisher	Transform Press
release_date	1991
media_type	Paperback
isbn	0-9630096-0-5
oclc	269100404
followed_by	TiHKAL (1997)

PiHKAL: A Chemical Love Story, also known as Phenethylamines I Have Known and Loved, 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 entactogens. The book has two halves, with the second part containing detailed entries on 179phenethylamines. PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).

Content

The book is arranged into two parts, the first part being a fictionalized autobiography of the couple and the second part describing 179different psychedelic compounds (most of which Shulgin discovered himself), including detailed synthesis instructions, bioassays, doses, durations, 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-aluminium 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.

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.

Response

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 laboratory and requested that he surrender 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.

Notable compounds

Some compounds in PiHKAL, like mescaline, DOM, 2C-B, MDA, and MDMA, are widely known and/or used psychedelics and/or entactogens.

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-methoxyamphetamine)
2,4-DMA (2,4-dimethoxyamphetamine)
3,4-DMA (3,4-dimethoxyamphetamine)
MDA (3,4-methylenedioxyamphetamine)
MMDA (3-methoxy-4,5-methylendioxyamphetamine)
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 des-oxy-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.

Ten classic ladies

Shulgin systematically replaced the 10unique hydrogen atoms in DOM with methyl groups in order to explore its activity and named these compounds the "ten classic ladies". The resulting compounds were as follows:

Ariadne (α-desmethyl-α-ethyl-DOM)
Beatrice (N-methyl-DOM)
Charmian (α-methyl-DOM)
Daphne (threo-β-methyl-DOM)
Elvira (erythro-β-methyl-DOM)
Florence (2-desmethoxy-2-ethoxy-DOM; DOM-2-EtO)
Ganesha (3-methyl-DOM)
Hecate (DOET; 4-desmethyl-4-ethyl-DOM)
Iris (5-desmethoxy-5-ethoxy-DOM; DOM-5-EtO)
Juno (6-methyl-DOM)

As with the essential amphetamines, not all of these compounds have been bioassayed.

Some additional "ladies" have also since been named, including Julia (DOTMA; 3,6-dimethyl-DOM), Jelena (2C-IP), and Selene (2C-P).

Phenethylamines listed

#	Substance	Chemical name	Group	Dosea	Duration	Link
1	AEM (α-ethylmescaline)	α-Ethyl-3,4,5-trimethoxy-PEA	4C-scaline	220 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal001.shtml
2	AL (allylescaline)	4-Allyloxy-3,5-dimethoxy-PEA	Scaline	20–35 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal002.shtml
3	ALEPH (DOT, para-DOT)	4-Methylthio-2,5-dimethoxy-A	DOx	5–10 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal003.shtml
4	ALEPH-2	4-Ethylthio-2,5-dimethoxy-A	DOx	4–8 mg	8–16 hours	https://erowid.org/library/books_online/pihkal/pihkal004.shtml
5	ALEPH-4	4-Isopropylthio-2,5-dimethoxy-A	DOx	7–12 mg	12–20 hours	https://erowid.org/library/books_online/pihkal/pihkal005.shtml
6	ALEPH-6	4-Phenylthio-2,5-dimethoxy-A	DOx	40 mg	"Probably long"	https://erowid.org/library/books_online/pihkal/pihkal006.shtml
7	ALEPH-7	4-Propylthio-2,5-dimethoxy-A	DOx	4–7 mg	15–30 hours	https://erowid.org/library/books_online/pihkal/pihkal007.shtml
8	ARIADNE (4C-D; Dimoxamine)	2,5-Dimethoxy-α-ethyl-4-methyl-PEA	4C	Unknownb	Short	https://erowid.org/library/books_online/pihkal/pihkal008.shtml
9	ASB (asymbescaline)	3,4-Diethoxy-5-methoxy-PEA	Scaline (mod.)	200–280 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal009.shtml
10	B (buscaline)	4-Butoxy-3,5-dimethoxy-PEA	Scaline	150 mg	"Several hours"	https://erowid.org/library/books_online/pihkal/pihkal010.shtml
11	BEATRICE (N-methyl-DOM)	2,5-Dimethoxy-4,N-dimethyl-A	DOx	30 mg	6–10 hours	https://erowid.org/library/books_online/pihkal/pihkal011.shtml
12	Bis-TOM (2,5-dithio-DOM)	2,5-Bismethylthio-4-methyl-A	DOx (mod.)	160 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal012.shtml
13	BOB (β-methoxy-2C-B)	4-Bromo-2,5,β-trimethoxy-PEA	BOx, 2C	10–20 mg	10–20 hours	https://erowid.org/library/books_online/pihkal/pihkal013.shtml
14	BOD (β-methoxy-2C-D)	2,5,β-Trimethoxy-4-methyl-PEA	BOx, 2C	15–25 mg	8–16 hours	https://erowid.org/library/books_online/pihkal/pihkal014.shtml
15	BOH (β-methoxy-MDPEA)	β-Methoxy-3,4-methylenedioxy-PEA	BOx, MDxx	80–120 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal015.shtml
16	BOHD (β-hydroxy-2C-D)	2,5-Dimethoxy-β-hydroxy-4-methyl-PEA	BOx, 2C	50 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal016.shtml
17	BOM (β-methoxymescaline)	3,4,5,β-Tetramethoxy-PEA	BOx, scaline	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal017.shtml
18	4-Br-3,5-DMA	4-Bromo-3,5-dimethoxy-A	3C-scaline	4–10 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal018.shtml
19	2-Br-4,5-MDA	2-Bromo-4,5-methylenedioxy-A	MDxx	350 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal019.shtml
20	2C-B	4-Bromo-2,5-dimethoxy-PEA	2C	12–24 mg	4–8 hours	https://erowid.org/library/books_online/pihkal/pihkal020.shtml
21	3C-BZ (3C-benzscaline)	4-Benzyloxy-3,5-dimethoxy-A	3C-scaline	25–200 mg	18–24 hours	https://erowid.org/library/books_online/pihkal/pihkal021.shtml
22	2C-C	4-Chloro-2,5-dimethoxy-PEA	2C	20–40 mg	4–8 hours	https://erowid.org/library/books_online/pihkal/pihkal022.shtml
23	2C-D	4-Methyl-2,5-dimethoxy-PEA	2C	20–60 mg	4–6 hours	https://erowid.org/library/books_online/pihkal/pihkal023.shtml
24	2C-E	4-Ethyl-2,5-dimethoxy-PEA	2C	10–25 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal024.shtml
25	3C-E (3C-escaline)	4-Ethoxy-3,5-dimethoxy-A	3C-scaline	30–60 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal025.shtml
26	2C-F	4-Fluoro-2,5-dimethoxy-PEA	2C	250 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal026.shtml
27	2C-G	3,4-Dimethyl-2,5-dimethoxy-PEA	2C	20–35 mg	18–30 hours	https://erowid.org/library/books_online/pihkal/pihkal027.shtml
28	2C-G-3	3,4-Trimethylene-2,5-dimethoxy-PEA	2C (mod.)	16–25 mg	12–24 hours	https://erowid.org/library/books_online/pihkal/pihkal028.shtml
29	2C-G-4	3,4-Tetramethylene-2,5-dimethoxy-PEA	2C (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal029.shtml
30	2C-G-5	3,4-Norbornyl-2,5-dimethoxy-PEA	2C (mod.)	10–16 mg	32–48 hours	https://erowid.org/library/books_online/pihkal/pihkal030.shtml
31	2C-G-N	1,4-Dimethoxynaphthyl-2-ethylamine	2C (mod.)	20–40 mg	20–30 hours	https://erowid.org/library/books_online/pihkal/pihkal031.shtml
32	2C-H (2,5-DMPEA)	2,5-Dimethoxy-PEA	2C	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal032.shtml
33	2C-I	4-Iodo-2,5-dimethoxy-PEA	2C	14–22 mg	6–10 hours	https://erowid.org/library/books_online/pihkal/pihkal033.shtml
34	2C-N	4-Nitro-2,5-dimethoxy-PEA	2C	100–150 mg	4–6 hours	https://erowid.org/library/books_online/pihkal/pihkal034.shtml
35	2C-O-4	4-Isopropoxy-2,5-dimethoxy-PEA	2C	60 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal035.shtml
36	2C-P	4-Propyl-2,5-dimethoxy-PEA	2C	6–10 mg	10–16 hours	https://erowid.org/library/books_online/pihkal/pihkal036.shtml
37	CPM (cyclopropylmescaline)	4-Cyclopropylmethoxy-3,5-dimethoxy-PEA	Scaline	60–80 mg	12–18 hours	https://erowid.org/library/books_online/pihkal/pihkal037.shtml
38	2C-Se	4-Methylseleno-2,5-dimethoxy-PEA	2C	~100 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal038.shtml
39	2C-T	4-Methylthio-2,5-dimethoxy-PEA	2C	60–100 mg	3–5 hours	https://erowid.org/library/books_online/pihkal/pihkal039.shtml
40	2C-T-2	4-Ethylthio-2,5-dimethoxy-PEA	2C	12–25 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal040.shtml
41	2C-T-4	4-Isopropylthio-2,5-dimethoxy-PEA	2C	8–20 mg	12–18 hours	https://erowid.org/library/books_online/pihkal/pihkal041.shtml
42	Psi-2C-T-4 (ψ-2C-T-4)	4-Isopropylthio-2,6-dimethoxy-PEA	ψ-PEA	12 mg	"Probably short"	https://erowid.org/library/books_online/pihkal/pihkal042.shtml
43	2C-T-7	4-Propylthio-2,5-dimethoxy-PEA	2C	10–30 mg	8–15 hours	https://erowid.org/library/books_online/pihkal/pihkal043.shtml
44	2C-T-8	4-Cyclopropylmethylthio-2,5-dimethoxy-PEA	2C	30–50 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal044.shtml
45	2C-T-9	4-(t)-Butylthio-2,5-dimethoxy-PEA	2C	60–100 mg	12–18 hours	https://erowid.org/library/books_online/pihkal/pihkal045.shtml
46	2C-T-13	4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA	2C	25–40 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal046.shtml
47	2C-T-15	4-Cyclopropylthio-2,5-dimethoxy-PEA	2C	30 mg	"Several hours"	https://erowid.org/library/books_online/pihkal/pihkal047.shtml
48	2C-T-17	4-(s)-Butylthio-2,5-dimethoxy-PEA	2C	60–100 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal048.shtml
49	2C-T-21	4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA	2C	8–12 mg	7–10 hours	https://erowid.org/library/books_online/pihkal/pihkal049.shtml
50	4-D (4-trideuteromescaline)	4-Trideuteromethyl-3,5-dimethoxy-PEA	Scaline	~200–400 mgc	12 hours	https://erowid.org/library/books_online/pihkal/pihkal050.shtml
51	Beta-D (β,β-dideuteromescaline)	β,β-Dideutero-3,4,5-trimethoxy-PEA	Scaline	~200–400 mgc	12 hours	https://erowid.org/library/books_online/pihkal/pihkal051.shtml
52	DESOXY (4-desoxymescaline)	4-Methyl-3,5-dimethoxy-PEA	Scaline (mod.)	40–120 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal052.shtml
53	2,4-DMA	2,4-Dimethoxy-A	Other	60 mg	"Short"	https://erowid.org/library/books_online/pihkal/pihkal053.shtml
54	2,5-DMA (DOH)	2,5-Dimethoxy-A	DOx	80–160 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal054.shtml
55	3,4-DMA (DMA)	3,4-Dimethoxy-A	Other	"A few [100 mg]"	Unknown	https://erowid.org/library/books_online/pihkal/pihkal055.shtml
56	DMCPA	2,5-Dimethoxy-4-methyl-PCPA	DOx (mod.)	15–20 mg	4–8 hours	https://erowid.org/library/books_online/pihkal/pihkal056.shtml
57	DME (β-hydroxy-3,4-DMPEA)	3,4-Dimethoxy-β-hydroxy-PEA	BOx, other	115 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal057.shtml
58	DMMDA (2,5-dimethoxy-MDA)	2,5-Dimethoxy-3,4-methylenedioxy-A	MDxx	30–75 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal058.shtml
59	DMMDA-2 (5,6-dimethoxy-MDA)	2,3-Dimethoxy-4,5-methylenedioxy-A	MDxx	~50 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal059.shtml
60	DMPEA (3,4-DMPEA)	3,4-Dimethoxy-PEA	Other	1,000 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal060.shtml
61	DOAM	4-Amyl-2,5-dimethoxy-A	DOx	10 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal061.shtml
62	DOB	4-Bromo-2,5-dimethoxy-A	DOx	1–3 mg	18–30 hours	https://erowid.org/library/books_online/pihkal/pihkal062.shtml
63	DOBU	4-Butyl-2,5-dimethoxy-A	DOx	Uncertain	"Very long"	https://erowid.org/library/books_online/pihkal/pihkal063.shtml
64	DOC	4-Chloro-2,5-dimethoxy-A	DOx	1.5–3 mg	12–24 hours	https://erowid.org/library/books_online/pihkal/pihkal064.shtml
65	DOEF	4-(2-Fluoroethyl)-2,5-dimethoxy-A	DOx	2–3.5 mg	12–16 hours	https://erowid.org/library/books_online/pihkal/pihkal065.shtml
66	DOET	4-Ethyl-2,5-dimethoxy-A	DOx	2–6 mg	14–20 hours	https://erowid.org/library/books_online/pihkal/pihkal066.shtml
67	DOI	4-Iodo-2,5-dimethoxy-A	DOx	1.5–3 mg	16–30 hours	https://erowid.org/library/books_online/pihkal/pihkal067.shtml
68	DOM (STP)	4-Methyl-2,5-dimethoxy-A	DOx	3–10 mg	14–20 hours	https://erowid.org/library/books_online/pihkal/pihkal068.shtml
69	Psi-DOM (ψ-DOM)	4-Methyl-2,6-dimethoxy-A	ψ-PEA	15–25 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal069.shtml
70	DON	4-Nitro-2,5-dimethoxy-A	DOx	3–4.5 mg	8–15 hours	https://erowid.org/library/books_online/pihkal/pihkal070.shtml
71	DOPR	4-Propyl-2,5-dimethoxy-A	DOx	2.5–5 mg	20–30 hours	https://erowid.org/library/books_online/pihkal/pihkal071.shtml
72	E (escaline)	4-Ethoxy-3,5-dimethoxy-PEA	Scaline	40–60 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal072.shtml
73	EEE	2,4,5-Triethoxy-A	DOx (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal073.shtml
74	EEM	2,4-Diethoxy-5-methoxy-A	DOx (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal074.shtml
75	EME	2,5-Diethoxy-4-methoxy-A	DOx (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal075.shtml
76	EMM	2-Ethoxy-4,5-dimethoxy-A	DOx (mod.)	50 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal076.shtml
77	ETHYL-J (EBDB)	N,α-Diethyl-3,4-methylenedioxy-PEA	MDxx	90 mg	"Probably short"	https://erowid.org/library/books_online/pihkal/pihkal077.shtml
78	ETHYL-K (EBDP)	N-Ethyl-α-propyl-3,4-methylenedioxy-PEA	MDxx	40 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal078.shtml
79	F-2	2-Methyl-5-methoxy-2,3-dihydro-6-APBF	Benzofuran	15 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal079.shtml
80	F-22	2,2-Dimethyl-5-methoxy-2,3-dihydro-6-APBF	Benzofuran	15 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal080.shtml
81	FLEA (MDMOH)	N-Hydroxy-N-methyl-3,4-methylenedioxy-A	MDxx	100–160 mg	4–8 hours	https://erowid.org/library/books_online/pihkal/pihkal081.shtml
82	G-3	3,4-Trimethylene-2,5-dimethoxy-A	DOx (mod.)	12–18 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal082.shtml
83	G-4	3,4-Tetramethylene-2,5-dimethoxy-A	DOx (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal083.shtml
84	G-5	3,4-Norbornyl-2,5-dimethoxy-A	DOx (mod.)	14–20 mg	16–30 hours	https://erowid.org/library/books_online/pihkal/pihkal084.shtml
85	GANESHA (G; 3-methyl-DOM)	3,4-Dimethyl-2,5-dimethoxy-A	DOx	20–32 mg	18–24 hours	https://erowid.org/library/books_online/pihkal/pihkal085.shtml
86	G-N	1,4-Dimethoxynaphthyl-2-isopropylamine	DOx (mod.)	Unknown	Unknown	https://erowid.org/library/books_online/pihkal/pihkal086.shtml
87	HOT-2 (N-hydroxy-2C-T-2)	2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEA	HOT-x, 2C	10–18 mg	6–10 hours	https://erowid.org/library/books_online/pihkal/pihkal087.shtml
88	HOT-7 (N-hydroxy-2C-T-7)	2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEA	HOT-x, 2C	15–25 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal088.shtml
89	HOT-17 (N-hydroxy-2C-T-17)	2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEA	HOT-x, 2C	70–120 mg	12–18 hours	https://erowid.org/library/books_online/pihkal/pihkal089.shtml
90	IDNNA (N,N-dimethyl-DOI)	2,5-Dimethoxy-N,N-dimethyl-4-iodo-A	DOx	2.6 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal090.shtml
91	IM (isomescaline)	2,3,4-Trimethoxy-PEA	Scaline (mod.)	400 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal091.shtml
92	IP (isoproscaline)	3,5-Dimethoxy-4-isopropoxy-PEA	Scaline (mod.)	40–80 mg	10–16 hours	https://erowid.org/library/books_online/pihkal/pihkal092.shtml
93	IRIS (DOM-5-EtO)	5-Ethoxy-2-methoxy-4-methyl-A	DOx (mod.)	9 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal093.shtml
94	J (BDB)	α-Ethyl-3,4-methylenedioxy-PEA	MDxx	150–230 mg	4–8 hours	https://erowid.org/library/books_online/pihkal/pihkal094.shtml
95	LOPHOPHINE (MMDPEA)	3-Methoxy-4,5-methylenedioxy-PEA	MDxx	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal095.shtml
96	M (mescaline; 3,4,5-TMPEA)	3,4,5-Trimethoxy-PEA	Scaline	~200–400 mgc	10–12 hours	https://erowid.org/library/books_online/pihkal/pihkal096.shtml
97	4-MA (PMA)	4-Methoxy-A	Other	50–80 mg	"Short"	https://erowid.org/library/books_online/pihkal/pihkal097.shtml
98	MADAM-6 (6-methyl-MDMA)	2,N-Dimethyl-4,5-methylenedioxy-A	MDxx	280 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal098.shtml
99	MAL (methallylescaline)	3,5-Dimethoxy-4-methallyloxy-PEA	Scaline	40–65 mg	12–16 hours	https://erowid.org/library/books_online/pihkal/pihkal099.shtml
100	MDA	3,4-Methylenedioxy-A	MDxx	80–160 mg	4–6 hoursd	https://erowid.org/library/books_online/pihkal/pihkal100.shtml
101	MDAL	N-Allyl-3,4-methylenedioxy-A	MDxx	180 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal101.shtml
102	MDBU	N-Butyl-3,4-methylenedioxy-A	MDxx	40 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal102.shtml
103	MDBZ	N-Benzyl-3,4-methylenedioxy-A	MDxx	150 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal103.shtml
104	MDCPM	N-Cyclopropylmethyl-3,4-methylenedioxy-A	MDxx	10 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal104.shtml
105	MDDM	N,N-Dimethyl-3,4-methylenedioxy-A	MDxx	150 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal105.shtml
106	MDE (MDEA)	N-Ethyl-3,4-methylenedioxy-A	MDxx	100–200 mg	3–5 hours	https://erowid.org/library/books_online/pihkal/pihkal106.shtml
107	MDHOET	N-(2-Hydroxyethyl)-3,4-methylenedioxy-A	MDxx	50 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal107.shtml
108	MDIP	N-Isopropyl-3,4-methylenedioxy-A	MDxx	250 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal108.shtml
109	MDMA	N-Methyl-3,4-methylenedioxy-A	MDxx	80–150 mg	4–6 hours	https://erowid.org/library/books_online/pihkal/pihkal109.shtml
110	MDMC (EDMA)	N-Methyl-3,4-ethylenedioxy-A	EDxx	≥200 mg	3–5 hours	https://erowid.org/library/books_online/pihkal/pihkal110.shtml
111	MDMEO	N-Methoxy-3,4-methylenedioxy-A	MDxx	180 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal111.shtml
112	MDMEOET	N-(2-Methoxyethyl)-3,4-methylenedioxy-A	MDxx	180 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal112.shtml
113	MDMP	α,α,N-Trimethyl-3,4-methylenedioxy-PEA	MDxx	~110 mg	~6 hours	https://erowid.org/library/books_online/pihkal/pihkal113.shtml
114	MDOH	N-Hydroxy-3,4-methylenedioxy-A	MDxx	100–160 mg	3–6 hours	https://erowid.org/library/books_online/pihkal/pihkal114.shtml
115	MDPEA	3,4-Methylenedioxy-PEA	MDxx	300 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal115.shtml
116	MDPH	α,α-Dimethyl-3,4-methylenedioxy-PEA	MDxx	160–240 mg	3–5 hours	https://erowid.org/library/books_online/pihkal/pihkal116.shtml
117	MDPL	N-Propargyl-3,4-methylenedioxy-A	MDxx	150 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal117.shtml
118	MDPR	N-Propyl-3,4-methylenedioxy-A	MDxx	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal118.shtml
119	ME (metaescaline)	3,4-Dimethoxy-5-ethoxy-PEA	Scaline (mod.)	200–350 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal119.shtml
120	MEDA (5-methoxy-EDA)	3-Methoxy-4,5-ethylenedioxy-A	EDxx	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal120.shtml
121	MEE	2-Methoxy-4,5-diethoxy-A	DOx (mod.)	4.6 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal121.shtml
122	MEM	2,5-Dimethoxy-4-ethoxy-A	DOx	20–50 mg	10–14 hours	https://erowid.org/library/books_online/pihkal/pihkal122.shtml
123	MEPEA	3-Methoxy-4-ethoxy-PEA	Other	≥300 mg	"Short"	https://erowid.org/library/books_online/pihkal/pihkal123.shtml
124	Meta-DOB	5-Bromo-2,4-dimethoxy-A	DOx (mod.)	50–100 mg	5–6 hours	https://erowid.org/library/books_online/pihkal/pihkal124.shtml
125	Meta-DOT (5-thio-TMA-2)	5-Methylthio-2,4-dimethoxy-A	DOx (mod.)	35 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal125.shtml
126	Methyl-DMA (N-methyl-2,5-DMA)	N-Methyl-2,5-dimethoxy-A	DOx	250 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal126.shtml
127	Methyl-DOB (N-methyl-DOB)	4-Bromo-2,5-dimethoxy-N-methyl-A	DOx	8 mg	"Probably long"	https://erowid.org/library/books_online/pihkal/pihkal127.shtml
128	Methyl-J (MBDB)	N-Methyl-α-ethyl-3,4-methylenedioxy-PEA	MDxx	180–210 mg	4–6 hours	https://erowid.org/library/books_online/pihkal/pihkal128.shtml
129	Methyl-K (MBDP)	N-Methyl-α-propyl-3,4-methylenedioxy-PEA	MDxx	100 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal129.shtml
130	Methyl-MA (PMMA)	N-Methyl-4-methoxy-A	Other	100 mg	"Short"	https://erowid.org/library/books_online/pihkal/pihkal130.shtml
131	Methyl-MMDA-2 (6-methoxy-MDMA)	N-Methyl-2-methoxy-4,5-methylenedioxy-A	MDxx	70 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal131.shtml
132	MMDA (5-methoxy-MDA)	3-Methoxy-4,5-methylenedioxy-A	MDxx	100–250 mg	"Moderate"	https://erowid.org/library/books_online/pihkal/pihkal132.shtml
133	MMDA-2 (6-methoxy-MDA)	2-Methoxy-4,5-methylenedioxy-A	MDxx	25–50 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal133.shtml
134	MMDA-3a (2-methoxy-MDA)	2-Methoxy-3,4-methylenedioxy-A	MDxx	20–80 mg	10–16 hours	https://erowid.org/library/books_online/pihkal/pihkal134.shtml
135	MMDA-3b (4-methoxy-2,3-MDA)	4-Methoxy-2,3-methylenedioxy-A	MDxx	80 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal135.shtml
136	MME	2,4-Dimethoxy-5-ethoxy-A	DOx (mod.)	≥40 mg	~6–10 hours	https://erowid.org/library/books_online/pihkal/pihkal136.shtml
137	MP (metaproscaline)	3,4-Dimethoxy-5-propoxy-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal137.shtml
138	MPM	2,5-Dimethoxy-4-propoxy-A	DOx	≥30 mg	"Probably short"	https://erowid.org/library/books_online/pihkal/pihkal138.shtml
139	Ortho-DOT (2-thio-TMA-2)	2-Methylthio-4,5-dimethoxy-A	DOx (mod.)	25 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal139.shtml
140	P (proscaline)	3,5-Dimethoxy-4-propoxy-PEA	Scaline	30–60 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal140.shtml
141	PE (phenescaline)	3,5-Dimethoxy-4-phenethyloxy-PEA	Scaline	150 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal141.shtml
142	PEA (phenethylamine)	PEA	Other	1,600 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal142.shtml
143	PROPYNYL (propynylscaline)	4-Propynyloxy-3,5-dimethoxy-PEA	Scaline	≥80 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal143.shtml
144	SB (symbescaline)	3,5-Diethoxy-4-methoxy-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal144.shtml
145	TA (TeMA)	2,3,4,5-Tetramethoxy-A	Other	~50 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal145.shtml
146	3-TASB (3-thioasymbescaline)	4-Ethoxy-3-ethylthio-5-methoxy-PEA	Scaline (mod.)	~160 mg	10–18 hours	https://erowid.org/library/books_online/pihkal/pihkal146.shtml
147	4-TASB (4-thioasymbescaline)	3-Ethoxy-4-ethylthio-5-methoxy-PEA	Scaline (mod.)	60–100 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal147.shtml
148	5-TASB (5-thioasymbescaline)	3,4-Diethoxy-5-methylthio-PEA	Scaline (mod.)	~160 mg	~8 hours	https://erowid.org/library/books_online/pihkal/pihkal148.shtml
149	TB (thiobuscaline)	4-Thiobutoxy-3,5-dimethoxy-PEA	Scaline (mod.)	60–120 mg	~8 hours	https://erowid.org/library/books_online/pihkal/pihkal149.shtml
150	3-TE (3-thioescaline)	4-Ethoxy-5-methoxy-3-methylthio-PEA	Scaline (mod.)	60–80 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal150.shtml
151	4-TE (4-thioescaline)	3,5-Dimethoxy-4-ethylthio-PEA	Scaline (mod.)	20–30 mg	9–12 hours	https://erowid.org/library/books_online/pihkal/pihkal151.shtml
152	2-TIM (2-thioisomescaline)	2-Methylthio-3,4-dimethoxy-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal152.shtml
153	3-TIM (3-thioisomescaline)	3-Methylthio-2,4-dimethoxy-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal153.shtml
154	4-TIM (4-thioisomescaline)	4-Methylthio-2,3-dimethoxy-PEA	Scaline (mod.)	160 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal154.shtml
155	3-TM (3-thiomescaline)	3-Methylthio-4,5-dimethoxy-PEA	Scaline (mod.)	60–100 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal155.shtml
156	4-TM (4-thiomescaline)	4-Methylthio-3,5-dimethoxy-PEA	Scaline (mod.)	20–40 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal156.shtml
157	TMA (α-methylmescaline; 3C-M)	3,4,5-Trimethoxy-A	3C-scaline	100–250 mg	6–8 hours	https://erowid.org/library/books_online/pihkal/pihkal157.shtml
158	TMA-2 (DOMeO)	2,4,5-Trimethoxy-A	DOx	20–40 mg	8–12 hours	https://erowid.org/library/books_online/pihkal/pihkal158.shtml
159	TMA-3 (α-methylisomescaline)	2,3,4-Trimethoxy-A	Other	100 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal159.shtml
160	TMA-4	2,3,5-Trimethoxy-A	Other	80 mg	~6 hours	https://erowid.org/library/books_online/pihkal/pihkal160.shtml
161	TMA-5	2,3,6-Trimethoxy-A	Other	≥30 mg	8–10 hours	https://erowid.org/library/books_online/pihkal/pihkal161.shtml
162	TMA-6 (ψ-TMA-2)	2,4,6-Trimethoxy-A	ψ-PEA	25–50 mg	12–16 hours	https://erowid.org/library/books_online/pihkal/pihkal162.shtml
163	3-TME (3-thiometaescaline)	4,5-Dimethoxy-3-ethylthio-PEA	Scaline (mod.)	60–100 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal163.shtml
164	4-TME (4-thiometaescaline)	3-Ethoxy-5-methoxy-4-methylthio-PEA	Scaline (mod.)	60–100 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal164.shtml
165	5-TME (5-thiometaescaline)	3-Ethoxy-4-methoxy-5-methylthio-PEA	Scaline (mod.)	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal165.shtml
166	2T-MMDA-3a (2-methylthio-MDA)	2-Methylthio-3,4-methylenedioxy-A	MDxx	12 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal166.shtml
167	4T-MMDA-2 (4-thio-MMDA-2)	4,5-Thiomethyleneoxy-2-methoxy-A	MDxx (mod.)	25 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal167.shtml
168	TMPEA (2,4,5-TMPEA; 2C-O)	2,4,5-Trimethoxy-PEA	2C	300 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal168.shtml
169	2-TOET (2-thio-DOET)	4-Ethyl-5-methoxy-2-methylthio-A	DOx (mod.)	65 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal169.shtml
170	5-TOET (5-thio-DOET)	4-Ethyl-2-methoxy-5-methylthio-A	DOx (mod.)	12–25 mg	8–24 hours	https://erowid.org/library/books_online/pihkal/pihkal170.shtml
171	2-TOM (2-thio-DOM)	5-Methoxy-4-methyl-2-methylthio-A	DOx (mod.)	60–100 mg	8–10 hours	https://erowid.org/library/books_online/pihkal/pihkal171.shtml
172	5-TOM (5-thio-DOM)	2-Methoxy-4-methyl-5-methylthio-A	DOx (mod.)	30–50 mg	6–10 hours	https://erowid.org/library/books_online/pihkal/pihkal172.shtml
173	TOMSO (5-TOM-sulfoxide)	2-Methoxy-4-methyl-5-methylsulfinyl-A	DOx (mod.)	≥100–150 mge	10–16 hours	https://erowid.org/library/books_online/pihkal/pihkal173.shtml
174	TP (thioproscaline)	4-Propylthio-3,5-dimethoxy-PEA	Scaline (mod.)	20–25 mg	10–15 hours	https://erowid.org/library/books_online/pihkal/pihkal174.shtml
175	TRIS (trisescaline)	3,4,5-Triethoxy-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal175.shtml
176	3-TSB (3-thiosymbescaline)	3-Ethoxy-5-ethylthio-4-methoxy-PEA	Scaline (mod.)	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal176.shtml
177	4-TSB (4-thiosymbescaline)	3,5-Diethoxy-4-methylthio-PEA	Scaline (mod.)	240 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal177.shtml
178	3-T-TRIS (3-thiotrisescaline)	4,5-Diethoxy-3-ethylthio-PEA	Scaline (mod.)	160 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal178.shtml
179	4-T-TRIS (4-thiotrisescaline)	3,5-Diethoxy-4-ethylthio-PEA	Scaline (mod.)	200 mg	Unknown	https://erowid.org/library/books_online/pihkal/pihkal179.shtml
Acronyms (in chemical names): PEA = phenethylamine; A = amphetamine; PCPA = 2-phenylcyclopropylamine; 6-APBF = 6-(2-aminopropyl)benzofuran. Footnotes: a = Dose and duration for compounds are orally unless otherwise specified. b = Ariadne dose is as a psychedelic. Otherwise doses of 12–32mg as the racemate and 25mg as (R)-Ariadne were active. c = 4-D, beta-D, and mescaline doses are 200–400 mg as the sulfate salt and 178–356mg as the hydrochloride salt. d = MDA duration was originally 8–12hours but was later revised by Shulgin to 4–6hours in September 2001 following the publication of PiHKAL. e = TOMSO dose is 150mg alone or 100–150 mg with alcohol.

In addition to PiHKAL, Shulgin has also described the properties of psychedelic phenethylamines in humans in literature reviews.

Censorship

In December 2025, the Lukashenko regime added the book to the List of printed publications containing information materials, the distribution of which could harm the national interests of Belarus.

References

Johnson, C.. (2018). "Magic Medicine: A Trip Through the Intoxicating History and Modern-Day Use of Psychedelic Plants and Substances". Fair Winds Press.
(17 July 2023). "Introduction to the chemistry and pharmacology of psychedelic drugs". Australian Journal of Chemistry.
(1991). "PiHKAL: A Chemical Love Story". [[Transform Press]].
Ben Sessa. (2015). "The Psychedelic Policy Quagmire: Health, Law, Freedom, and Society". Bloomsbury Publishing.
(1997). "TiHKAL: The Continuation". [[Transform Press]].
(2021). "Better Living Through Chemistry". Better Living Through Film, Incorporated.
(2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective". Handb Exp Pharmacol.
(June 2013). "2C or not 2C: phenethylamine designer drug review". J Med Toxicol.
Bennett, Drake. (January 30, 2005). "Dr. Ecstasy". New York Times Magazine.
(February 2016). "Controlled Substances".
"Triple Goddess of the Night". British Neuroscience Association Bulletin.
(2013). "Phenethylamine: von der Struktur zur Funktion". Nachtschatten-Verlag.
(1994). "Hallucinogens: An Update". National Institute on Drug Abuse.
(2003). "Hallucinogens: A Forensic Drug Handbook". Elsevier Science.
Shulgin, Alexander T.. (1978). "Stimulants". Springer US.
(1978). "Mescaline analogs: substitutions at the 4-position". NIDA Res Monogr.
(1980). "Burger's Medicinal Chemistry". Wiley.
(1982). "Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs". Springer Berlin Heidelberg.
(2025-12-29). "У Беларусі забаранілі навуковую кнігу па гісторыі БНР".

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