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 (). 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"-position of its parent compound TMA-2
  • 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:

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

#SubstanceChemical nameGroupDoseaDurationLink
1AEM (α-ethylmescaline)α-Ethyl-3,4,5-trimethoxy-PEA4C-scaline>220mgUnknown
2AL (allylescaline)4-Allyloxy-3,5-dimethoxy-PEAScaline20–35mg8–12 hours
3ALEPH (DOT, para-DOT)4-Methylthio-2,5-dimethoxy-ADOx5–10mg6–8 hours
4ALEPH-24-Ethylthio-2,5-dimethoxy-ADOx4–8mg8–16 hours
5ALEPH-44-Isopropylthio-2,5-dimethoxy-ADOx7–12mg12–20 hours
6ALEPH-64-Phenylthio-2,5-dimethoxy-ADOx>40mg"Probably long"
7ALEPH-74-Propylthio-2,5-dimethoxy-ADOx4–7mg15–30 hours
8ARIADNE (4C-D; Dimoxamine)2,5-Dimethoxy-α-ethyl-4-methyl-PEA4CUnknownbShort
9ASB (asymbescaline)3,4-Diethoxy-5-methoxy-PEAScaline (mod.)200–280mg10–15 hours
10B (buscaline)4-Butoxy-3,5-dimethoxy-PEAScaline>150mg"Several hours"
11BEATRICE (N-methyl-DOM)2,5-Dimethoxy-4,N-dimethyl-ADOx>30mg6–10 hours
12Bis-TOM (2,5-dithio-DOM)2,5-Bismethylthio-4-methyl-AThio-DOx>160mgUnknown
13BOB (β-methoxy-2C-B)4-Bromo-2,5,β-trimethoxy-PEABOx, 2C10–20mg10–20 hours
14BOD (β-methoxy-2C-D)2,5,β-Trimethoxy-4-methyl-PEABOx, 2C15–25mg8–16 hours
15BOH (β-methoxy-MDPEA)β-Methoxy-3,4-methylenedioxy-PEABOx, MDxx80–120mg6–8 hours
16BOHD (β-hydroxy-2C-D)2,5-Dimethoxy-β-hydroxy-4-methyl-PEABOx, 2C>50mgUnknown
17BOM (β-methoxymescaline)3,4,5,β-Tetramethoxy-PEABOx, scaline>200mgUnknown
184-Br-3,5-DMA4-Bromo-3,5-dimethoxy-A3C-desoxyscaline4–10mg8–12 hours
192-Br-4,5-MDA2-Bromo-4,5-methylenedioxy-AMDxx350mgUnknown
202C-B4-Bromo-2,5-dimethoxy-PEA2C12–24mg4–8 hours
213C-BZ (3C-benzscaline)4-Benzyloxy-3,5-dimethoxy-A3C-scaline25–200mg18–24 hours
222C-C4-Chloro-2,5-dimethoxy-PEA2C20–40mg4–8 hours
232C-D4-Methyl-2,5-dimethoxy-PEA2C20–60mg4–6 hours
242C-E4-Ethyl-2,5-dimethoxy-PEA2C10–25mg8–12 hours
253C-E (3C-escaline)4-Ethoxy-3,5-dimethoxy-A3C-scaline30–60mg8–12 hours
262C-F4-Fluoro-2,5-dimethoxy-PEA2C>250mgUnknown
272C-G3,4-Dimethyl-2,5-dimethoxy-PEA2C20–35mg18–30 hours
282C-G-33,4-Trimethylene-2,5-dimethoxy-PEA2C (mod.)16–25mg12–24 hours
292C-G-43,4-Tetramethylene-2,5-dimethoxy-PEA2C (mod.)UnknownUnknown
302C-G-53,4-Norbornyl-2,5-dimethoxy-PEA2C (mod.)10–16mg32–48 hours
312C-G-N1,4-Dimethoxynaphthyl-2-ethylamine2C (mod.)20–40mg20–30 hours
322C-H (2,5-DMPEA)2,5-Dimethoxy-PEA2CUnknownUnknown
332C-I4-Iodo-2,5-dimethoxy-PEA2C14–22mg6–10 hours
342C-N4-Nitro-2,5-dimethoxy-PEA2C100–150mg4–6 hours
352C-O-44-Isopropoxy-2,5-dimethoxy-PEA2C>60mgUnknown
362C-P4-Propyl-2,5-dimethoxy-PEA2C6–10mg10–16 hours
37CPM (cyclopropylmescaline)4-Cyclopropylmethoxy-3,5-dimethoxy-PEAScaline60–80mg12–18 hours
382C-Se4-Methylseleno-2,5-dimethoxy-PEA2C~100mg6–8 hours
392C-T4-Methylthio-2,5-dimethoxy-PEA2C60–100mg3–5 hours
402C-T-24-Ethylthio-2,5-dimethoxy-PEA2C12–25mg6–8 hours
412C-T-44-Isopropylthio-2,5-dimethoxy-PEA2C8–20mg12–18 hours
42Psi-2C-T-4 (ψ-2C-T-4)4-Isopropylthio-2,6-dimethoxy-PEAψ-PEA>12mg"Probably short"
432C-T-74-Propylthio-2,5-dimethoxy-PEA2C10–30mg8–15 hours
442C-T-84-Cyclopropylmethylthio-2,5-dimethoxy-PEA2C30–50mg10–15 hours
452C-T-94-(t)-Butylthio-2,5-dimethoxy-PEA2C60–100mg12–18 hours
462C-T-134-(2-Methoxyethylthio)-2,5-dimethoxy-PEA2C25–40mg6–8 hours
472C-T-154-Cyclopropylthio-2,5-dimethoxy-PEA2C>30mg"Several hours"
482C-T-174-(s)-Butylthio-2,5-dimethoxy-PEA2C60–100mg10–15 hours
492C-T-214-(2-Fluoroethylthio)-2,5-dimethoxy-PEA2C8–12mg7–10 hours
504-D (4-trideuteromescaline)4-Trideuteromethyl-3,5-dimethoxy-PEAScaline~200–400mgc12 hours
51Beta-D (β,β-dideuteromescaline)β,β-Dideutero-3,4,5-trimethoxy-PEAScaline~200–400mgc12 hours
52DESOXY (4-desoxymescaline)4-Methyl-3,5-dimethoxy-PEADesoxyscaline40–120mg6–8 hours
532,4-DMA2,4-Dimethoxy-AOther>60mg"Short"
542,5-DMA (DOH)2,5-Dimethoxy-ADOx80–160mg6–8 hours
553,4-DMA (DMA)3,4-Dimethoxy-AOther"A few [100 mg]"Unknown
56DMCPA2,5-Dimethoxy-4-methyl-PCPADOx (mod.)15–20mg4–8 hours
57DME (β-hydroxy-3,4-DMPEA)3,4-Dimethoxy-β-hydroxy-PEABOx, other>115mgUnknown
58DMMDA (2,5-dimethoxy-MDA)2,5-Dimethoxy-3,4-methylenedioxy-AMDxx30–75mg6–8 hours
59DMMDA-2 (5,6-dimethoxy-MDA)2,3-Dimethoxy-4,5-methylenedioxy-AMDxx~50mgUnknown
60DMPEA (3,4-DMPEA)3,4-Dimethoxy-PEAOther>1,000mgUnknown
61DOAM4-Amyl-2,5-dimethoxy-ADOx>10mgUnknown
62DOB4-Bromo-2,5-dimethoxy-ADOx1–3mg18–30 hours
63DOBU4-Butyl-2,5-dimethoxy-ADOxUncertain"Very long"
64DOC4-Chloro-2,5-dimethoxy-ADOx1.5–3mg12–24 hours
65DOEF4-(2-Fluoroethyl)-2,5-dimethoxy-ADOx2–3.5mg12–16 hours
66DOET4-Ethyl-2,5-dimethoxy-ADOx2–6mg14–20 hours
67DOI4-Iodo-2,5-dimethoxy-ADOx1.5–3mg16–30 hours
68DOM (STP)4-Methyl-2,5-dimethoxy-ADOx3–10mg14–20 hours
69Psi-DOM (ψ-DOM)4-Methyl-2,6-dimethoxy-Aψ-PEA15–25mg6–8 hours
70DON4-Nitro-2,5-dimethoxy-ADOx3–4.5mg8–15 hours
71DOPR4-Propyl-2,5-dimethoxy-ADOx2.5–5mg20–30 hours
72E (escaline)4-Ethoxy-3,5-dimethoxy-PEAScaline40–60mg8–12 hours
73EEE (TMA2-2,4,5-TriEtO)2,4,5-Triethoxy-ADOx-TWEETIOUnknownUnknown
74EEM (TMA2-2,4-DiEtO)2,4-Diethoxy-5-methoxy-ADOx-TWEETIOUnknownUnknown
75EME (TMA2-2,5-DiEtO)2,5-Diethoxy-4-methoxy-ADOx-TWEETIOUnknownUnknown
76EMM (TMA2-2-EtO)2-Ethoxy-4,5-dimethoxy-ADOx-TWEETIO>50mgUnknown
77ETHYL-J (EBDB)N,α-Diethyl-3,4-methylenedioxy-PEAMDxx>90mg"Probably short"
78ETHYL-K (EBDP)N-Ethyl-α-propyl-3,4-methylenedioxy-PEAMDxx>40mgUnknown
79F-2 (2-Me-5-MeO-6-APDB)2-Methyl-5-methoxy-2,3-dihydro-6-APBFBenzofuran>15mgUnknown
80F-22 (2,2-DiMe-5-MeO-6-APDB)2,2-Dimethyl-5-methoxy-2,3-dihydro-6-APBFBenzofuran>15mgUnknown
81FLEA (MDMOH)N-Hydroxy-N-methyl-3,4-methylenedioxy-AMDxx100–160mg4–8 hours
82G-33,4-Trimethylene-2,5-dimethoxy-ADOx (mod.)12–18mg8–12 hours
83G-43,4-Tetramethylene-2,5-dimethoxy-ADOx (mod.)UnknownUnknown
84G-53,4-Norbornyl-2,5-dimethoxy-ADOx (mod.)14–20mg16–30 hours
85GANESHA (G; 3-methyl-DOM)3,4-Dimethyl-2,5-dimethoxy-ADOx20–32mg18–24 hours
86G-N1,4-Dimethoxynaphthyl-2-isopropylamineDOx (mod.)UnknownUnknown
87HOT-2 (N-hydroxy-2C-T-2)2,5-Dimethoxy-N-hydroxy-4-ethylthio-PEAHOT-x, 2C10–18mg6–10 hours
88HOT-7 (N-hydroxy-2C-T-7)2,5-Dimethoxy-N-hydroxy-4-(n)-propylthio-PEAHOT-x, 2C15–25mg6–8 hours
89HOT-17 (N-hydroxy-2C-T-17)2,5-Dimethoxy-N-hydroxy-4-(s)-butylthio-PEAHOT-x, 2C70–120mg12–18 hours
90IDNNA (N,N-dimethyl-DOI)2,5-Dimethoxy-N,N-dimethyl-4-iodo-ADOx>2.6mgUnknown
91IM (isomescaline)2,3,4-Trimethoxy-PEAScaline (mod.)>400mgUnknown
92IP (isoproscaline)3,5-Dimethoxy-4-isopropoxy-PEAScaline (mod.)40–80mg10–16 hours
93IRIS (DOM-5-EtO)5-Ethoxy-2-methoxy-4-methyl-ADOx-TWEETIO>9mgUnknown
94J (BDB)α-Ethyl-3,4-methylenedioxy-PEAMDxx150–230mg4–8 hours
95LOPHOPHINE (MMDPEA)3-Methoxy-4,5-methylenedioxy-PEAMDxx>200mgUnknown
96M (mescaline; 3,4,5-TMPEA)3,4,5-Trimethoxy-PEAScaline~200–400mgc10–12 hours
974-MA (PMA)4-Methoxy-AOther50–80mg"Short"
98MADAM-6 (6-methyl-MDMA)2,N-Dimethyl-4,5-methylenedioxy-AMDxx>280mgUnknown
99MAL (methallylescaline)3,5-Dimethoxy-4-methallyloxy-PEAScaline40–65mg12–16 hours
100MDA3,4-Methylenedioxy-AMDxx80–160mg4–6 hoursd
101MDALN-Allyl-3,4-methylenedioxy-AMDxx>180mgUnknown
102MDBUN-Butyl-3,4-methylenedioxy-AMDxx>40mgUnknown
103MDBZN-Benzyl-3,4-methylenedioxy-AMDxx>150mgUnknown
104MDCPMN-Cyclopropylmethyl-3,4-methylenedioxy-AMDxx>10mgUnknown
105MDDMN,N-Dimethyl-3,4-methylenedioxy-AMDxx>150mgUnknown
106MDE (MDEA)N-Ethyl-3,4-methylenedioxy-AMDxx100–200mg3–5 hours
107MDHOETN-(2-Hydroxyethyl)-3,4-methylenedioxy-AMDxx>50mgUnknown
108MDIPN-Isopropyl-3,4-methylenedioxy-AMDxx>250mgUnknown
109MDMAN-Methyl-3,4-methylenedioxy-AMDxx80–150mg4–6 hours
110MDMC (EDMA)N-Methyl-3,4-ethylenedioxy-AEDxx≥200mg3–5 hours
111MDMEON-Methoxy-3,4-methylenedioxy-AMDxx>180mgUnknown
112MDMEOETN-(2-Methoxyethyl)-3,4-methylenedioxy-AMDxx>180mgUnknown
113MDMPα,α,N-Trimethyl-3,4-methylenedioxy-PEAMDxx~110mg~6 hours
114MDOHN-Hydroxy-3,4-methylenedioxy-AMDxx100–160mg3–6 hours
115MDPEA3,4-Methylenedioxy-PEAMDxx>300mgUnknown
116MDPHα,α-Dimethyl-3,4-methylenedioxy-PEAMDxx160–240mg3–5 hours
117MDPLN-Propargyl-3,4-methylenedioxy-AMDxx>150mgUnknown
118MDPRN-Propyl-3,4-methylenedioxy-AMDxx>200mgUnknown
119ME (metaescaline)3,4-Dimethoxy-5-ethoxy-PEAScaline (mod.)200–350mg8–12 hours
120MEDA (5-methoxy-EDA)3-Methoxy-4,5-ethylenedioxy-AEDxx>200mgUnknown
121MEE (TMA2-4,5-DiEtO)2-Methoxy-4,5-diethoxy-ADOx-TWEETIO>4.6mgUnknown
122MEM (TMA2-4-EtO)2,5-Dimethoxy-4-ethoxy-ADOx20–50mg10–14 hours
123MEPEA3-Methoxy-4-ethoxy-PEAOther≥300mg"Short"
124Meta-DOB5-Bromo-2,4-dimethoxy-ADOx (mod.)50–100mg5–6 hours
125Meta-DOT (5-thio-TMA-2)5-Methylthio-2,4-dimethoxy-AThio-DOx>35mgUnknown
126Methyl-DMA (N-methyl-2,5-DMA)N-Methyl-2,5-dimethoxy-ADOx>250mgUnknown
127Methyl-DOB (N-methyl-DOB)4-Bromo-2,5-dimethoxy-N-methyl-ADOx>8mg"Probably long"
128Methyl-J (MBDB)N-Methyl-α-ethyl-3,4-methylenedioxy-PEAMDxx180–210mg4–6 hours
129Methyl-K (MBDP)N-Methyl-α-propyl-3,4-methylenedioxy-PEAMDxx>100mgUnknown
130Methyl-MA (PMMA)N-Methyl-4-methoxy-AOther>100mg"Short"
131Methyl-MMDA-2 (6-methoxy-MDMA)N-Methyl-2-methoxy-4,5-methylenedioxy-AMDxx>70mgUnknown
132MMDA (5-methoxy-MDA)3-Methoxy-4,5-methylenedioxy-AMDxx100–250mg"Moderate"
133MMDA-2 (6-methoxy-MDA)2-Methoxy-4,5-methylenedioxy-AMDxx25–50mg8–12 hours
134MMDA-3a (2-methoxy-MDA)2-Methoxy-3,4-methylenedioxy-AMDxx20–80mg10–16 hours
135MMDA-3b (4-methoxy-2,3-MDA)4-Methoxy-2,3-methylenedioxy-AMDxx>80mgUnknown
136MME (TMA2-5-EtO)2,4-Dimethoxy-5-ethoxy-ADOx-TWEETIO≥40mg~6–10 hours
137MP (metaproscaline)3,4-Dimethoxy-5-propoxy-PEAScaline (mod.)>240mgUnknown
138MPM (TMA2-4-PrO)2,5-Dimethoxy-4-propoxy-ADOx≥30mg"Probably short"
139Ortho-DOT (2-thio-TMA-2)2-Methylthio-4,5-dimethoxy-AThio-DOx>25mgUnknown
140P (proscaline)3,5-Dimethoxy-4-propoxy-PEAScaline30–60mg8–12 hours
141PE (phenescaline)3,5-Dimethoxy-4-phenethyloxy-PEAScaline>150mgUnknown
142PEA (phenethylamine)PEAOther>1,600mgUnknown
143PROPYNYL (propynylscaline)4-Propynyloxy-3,5-dimethoxy-PEAScaline≥80mg8–12 hours
144SB (symbescaline)3,5-Diethoxy-4-methoxy-PEAScaline (mod.)>240mgUnknown
145TA (TeMA)2,3,4,5-Tetramethoxy-AOther>~50mgUnknown
1463-TASB (3-thioasymbescaline)4-Ethoxy-3-ethylthio-5-methoxy-PEAThioscaline (mod.)~160mg10–18 hours
1474-TASB (4-thioasymbescaline)3-Ethoxy-4-ethylthio-5-methoxy-PEAThioscaline (mod.)60–100mg10–15 hours
1485-TASB (5-thioasymbescaline)3,4-Diethoxy-5-methylthio-PEAThioscaline (mod.)~160mg~8 hours
149TB (thiobuscaline)4-Thiobutoxy-3,5-dimethoxy-PEAThioscaline60–120mg~8 hours
1503-TE (3-thioescaline)4-Ethoxy-5-methoxy-3-methylthio-PEAThioscaline60–80mg8–12 hours
1514-TE (4-thioescaline)3,5-Dimethoxy-4-ethylthio-PEAThioscaline20–30mg9–12 hours
1522-TIM (2-thioisomescaline)2-Methylthio-3,4-dimethoxy-PEAThioscaline (mod.)>240mgUnknown
1533-TIM (3-thioisomescaline)3-Methylthio-2,4-dimethoxy-PEAThioscaline (mod.)>240mgUnknown
1544-TIM (4-thioisomescaline)4-Methylthio-2,3-dimethoxy-PEAThioscaline (mod.)>160mgUnknown
1553-TM (3-thiomescaline)3-Methylthio-4,5-dimethoxy-PEAThioscaline60–100mg8–12 hours
1564-TM (4-thiomescaline)4-Methylthio-3,5-dimethoxy-PEAThioscaline20–40mg10–15 hours
157TMA (α-methylmescaline; 3C-M)3,4,5-Trimethoxy-A3C-scaline100–250mg6–8 hours
158TMA-2 (DOMeO)2,4,5-Trimethoxy-ADOx20–40mg8–12 hours
159TMA-3 (α-methylisomescaline)2,3,4-Trimethoxy-AOther>100mgUnknown
160TMA-42,3,5-Trimethoxy-AOther>80mg~6 hours
161TMA-52,3,6-Trimethoxy-AOther≥30mg8–10 hours
162TMA-6 (ψ-TMA-2)2,4,6-Trimethoxy-Aψ-PEA25–50mg12–16 hours
1633-TME (3-thiometaescaline)4,5-Dimethoxy-3-ethylthio-PEAThioscaline (mod.)60–100mg10–15 hours
1644-TME (4-thiometaescaline)3-Ethoxy-5-methoxy-4-methylthio-PEAThioscaline (mod.)60–100mg10–15 hours
1655-TME (5-thiometaescaline)3-Ethoxy-4-methoxy-5-methylthio-PEAThioscaline (mod.)>200mgUnknown
1662T-MMDA-3a (2-methylthio-MDA)2-Methylthio-3,4-methylenedioxy-AMDxx>12mgUnknown
1674T-MMDA-2 (4-thio-MMDA-2)4,5-Thiomethyleneoxy-2-methoxy-AMDxx (mod.)>25mgUnknown
168TMPEA (2,4,5-TMPEA; 2C-O)2,4,5-Trimethoxy-PEA2C>300mgUnknown
1692-TOET (2-thio-DOET)4-Ethyl-5-methoxy-2-methylthio-AThio-DOx>65mgUnknown
1705-TOET (5-thio-DOET)4-Ethyl-2-methoxy-5-methylthio-AThio-DOx12–25mg8–24 hours
1712-TOM (2-thio-DOM)5-Methoxy-4-methyl-2-methylthio-AThio-DOx60–100mg8–10 hours
1725-TOM (5-thio-DOM)2-Methoxy-4-methyl-5-methylthio-AThio-DOx30–50mg6–10 hours
173TOMSO (5-TOM-sulfoxide)2-Methoxy-4-methyl-5-methylsulfinyl-AThio-DOx (mod.)≥100–150mge10–16 hours
174TP (thioproscaline)4-Propylthio-3,5-dimethoxy-PEAThioscaline20–25mg10–15 hours
175TRIS (trisescaline)3,4,5-Triethoxy-PEAScaline (mod.)>240mgUnknown
1763-TSB (3-thiosymbescaline)3-Ethoxy-5-ethylthio-4-methoxy-PEAThioscaline (mod.)>200mgUnknown
1774-TSB (4-thiosymbescaline)3,5-Diethoxy-4-methylthio-PEAThioscaline (mod.)>240mgUnknown
1783-T-TRIS (3-thiotrisescaline)4,5-Diethoxy-3-ethylthio-PEAThioscaline (mod.)>160mgUnknown
1794-T-TRIS (4-thiotrisescaline)3,5-Diethoxy-4-ethylthio-PEAThioscaline (mod.)>200mgUnknown
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 200–400mg 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 100–150mg with alcohol.

Many additional compounds are also discussed within the individual compound entries of PiHKAL, for instance the 2C TWEETIOs.

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.

See also

External links