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 179 phenethylamines. 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 179 different 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"-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 10 unique 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 | [1] |
| 2 | AL (allylescaline) | 4-Allyloxy-3,5-dimethoxy-PEA | Scaline | 20–35 mg | 8–12 hours | [2] |
| 3 | ALEPH (DOT, para-DOT) | 4-Methylthio-2,5-dimethoxy-A | DOx | 5–10 mg | 6–8 hours | [3] |
| 4 | ALEPH-2 | 4-Ethylthio-2,5-dimethoxy-A | DOx | 4–8 mg | 8–16 hours | [4] |
| 5 | ALEPH-4 | 4-Isopropylthio-2,5-dimethoxy-A | DOx | 7–12 mg | 12–20 hours | [5] |
| 6 | ALEPH-6 | 4-Phenylthio-2,5-dimethoxy-A | DOx | >40 mg | "Probably long" | [6] |
| 7 | ALEPH-7 | 4-Propylthio-2,5-dimethoxy-A | DOx | 4–7 mg | 15–30 hours | [7] |
| 8 | ARIADNE (4C-D; Dimoxamine) | 2,5-Dimethoxy-α-ethyl-4-methyl-PEA | 4C | Unknownb | Short | [8] |
| 9 | ASB (asymbescaline) | 3,4-Diethoxy-5-methoxy-PEA | Scaline (mod.) | 200–280 mg | 10–15 hours | [9] |
| 10 | B (buscaline) | 4-Butoxy-3,5-dimethoxy-PEA | Scaline | >150 mg | "Several hours" | [10] |
| 11 | BEATRICE (N-methyl-DOM) | 2,5-Dimethoxy-4,N-dimethyl-A | DOx | >30 mg | 6–10 hours | [11] |
| 12 | Bis-TOM (2,5-dithio-DOM) | 2,5-Bismethylthio-4-methyl-A | Thio-DOx | >160 mg | Unknown | [12] |
| 13 | BOB (β-methoxy-2C-B) | 4-Bromo-2,5,β-trimethoxy-PEA | BOx, 2C | 10–20 mg | 10–20 hours | [13] |
| 14 | BOD (β-methoxy-2C-D) | 2,5,β-Trimethoxy-4-methyl-PEA | BOx, 2C | 15–25 mg | 8–16 hours | [14] |
| 15 | BOH (β-methoxy-MDPEA) | β-Methoxy-3,4-methylenedioxy-PEA | BOx, MDxx | 80–120 mg | 6–8 hours | [15] |
| 16 | BOHD (β-hydroxy-2C-D) | 2,5-Dimethoxy-β-hydroxy-4-methyl-PEA | BOx, 2C | >50 mg | Unknown | [16] |
| 17 | BOM (β-methoxymescaline) | 3,4,5,β-Tetramethoxy-PEA | BOx, scaline | >200 mg | Unknown | [17] |
| 18 | 4-Br-3,5-DMA | 4-Bromo-3,5-dimethoxy-A | 3C-desoxyscaline | 4–10 mg | 8–12 hours | [18] |
| 19 | 2-Br-4,5-MDA | 2-Bromo-4,5-methylenedioxy-A | MDxx | 350 mg | Unknown | [19] |
| 20 | 2C-B | 4-Bromo-2,5-dimethoxy-PEA | 2C | 12–24 mg | 4–8 hours | [20] |
| 21 | 3C-BZ (3C-benzscaline) | 4-Benzyloxy-3,5-dimethoxy-A | 3C-scaline | 25–200 mg | 18–24 hours | [21] |
| 22 | 2C-C | 4-Chloro-2,5-dimethoxy-PEA | 2C | 20–40 mg | 4–8 hours | [22] |
| 23 | 2C-D | 4-Methyl-2,5-dimethoxy-PEA | 2C | 20–60 mg | 4–6 hours | [23] |
| 24 | 2C-E | 4-Ethyl-2,5-dimethoxy-PEA | 2C | 10–25 mg | 8–12 hours | [24] |
| 25 | 3C-E (3C-escaline) | 4-Ethoxy-3,5-dimethoxy-A | 3C-scaline | 30–60 mg | 8–12 hours | [25] |
| 26 | 2C-F | 4-Fluoro-2,5-dimethoxy-PEA | 2C | >250 mg | Unknown | [26] |
| 27 | 2C-G | 3,4-Dimethyl-2,5-dimethoxy-PEA | 2C | 20–35 mg | 18–30 hours | [27] |
| 28 | 2C-G-3 | 3,4-Trimethylene-2,5-dimethoxy-PEA | 2C (mod.) | 16–25 mg | 12–24 hours | [28] |
| 29 | 2C-G-4 | 3,4-Tetramethylene-2,5-dimethoxy-PEA | 2C (mod.) | Unknown | Unknown | [29] |
| 30 | 2C-G-5 | 3,4-Norbornyl-2,5-dimethoxy-PEA | 2C (mod.) | 10–16 mg | 32–48 hours | [30] |
| 31 | 2C-G-N | 1,4-Dimethoxynaphthyl-2-ethylamine | 2C (mod.) | 20–40 mg | 20–30 hours | [31] |
| 32 | 2C-H (2,5-DMPEA) | 2,5-Dimethoxy-PEA | 2C | Unknown | Unknown | [32] |
| 33 | 2C-I | 4-Iodo-2,5-dimethoxy-PEA | 2C | 14–22 mg | 6–10 hours | [33] |
| 34 | 2C-N | 4-Nitro-2,5-dimethoxy-PEA | 2C | 100–150 mg | 4–6 hours | [34] |
| 35 | 2C-O-4 | 4-Isopropoxy-2,5-dimethoxy-PEA | 2C | >60 mg | Unknown | [35] |
| 36 | 2C-P | 4-Propyl-2,5-dimethoxy-PEA | 2C | 6–10 mg | 10–16 hours | [36] |
| 37 | CPM (cyclopropylmescaline) | 4-Cyclopropylmethoxy-3,5-dimethoxy-PEA | Scaline | 60–80 mg | 12–18 hours | [37] |
| 38 | 2C-Se | 4-Methylseleno-2,5-dimethoxy-PEA | 2C | ~100 mg | 6–8 hours | [38] |
| 39 | 2C-T | 4-Methylthio-2,5-dimethoxy-PEA | 2C | 60–100 mg | 3–5 hours | [39] |
| 40 | 2C-T-2 | 4-Ethylthio-2,5-dimethoxy-PEA | 2C | 12–25 mg | 6–8 hours | [40] |
| 41 | 2C-T-4 | 4-Isopropylthio-2,5-dimethoxy-PEA | 2C | 8–20 mg | 12–18 hours | [41] |
| 42 | Psi-2C-T-4 (ψ-2C-T-4) | 4-Isopropylthio-2,6-dimethoxy-PEA | ψ-PEA | >12 mg | "Probably short" | [42] |
| 43 | 2C-T-7 | 4-Propylthio-2,5-dimethoxy-PEA | 2C | 10–30 mg | 8–15 hours | [43] |
| 44 | 2C-T-8 | 4-Cyclopropylmethylthio-2,5-dimethoxy-PEA | 2C | 30–50 mg | 10–15 hours | [44] |
| 45 | 2C-T-9 | 4-(t)-Butylthio-2,5-dimethoxy-PEA | 2C | 60–100 mg | 12–18 hours | [45] |
| 46 | 2C-T-13 | 4-(2-Methoxyethylthio)-2,5-dimethoxy-PEA | 2C | 25–40 mg | 6–8 hours | [46] |
| 47 | 2C-T-15 | 4-Cyclopropylthio-2,5-dimethoxy-PEA | 2C | >30 mg | "Several hours" | [47] |
| 48 | 2C-T-17 | 4-(s)-Butylthio-2,5-dimethoxy-PEA | 2C | 60–100 mg | 10–15 hours | [48] |
| 49 | 2C-T-21 | 4-(2-Fluoroethylthio)-2,5-dimethoxy-PEA | 2C | 8–12 mg | 7–10 hours | [49] |
| 50 | 4-D (4-trideuteromescaline) | 4-Trideuteromethyl-3,5-dimethoxy-PEA | Scaline | ~200–400 mgc | 12 hours | [50] |
| 51 | Beta-D (β,β-dideuteromescaline) | β,β-Dideutero-3,4,5-trimethoxy-PEA | Scaline | ~200–400 mgc | 12 hours | [51] |
| 52 | DESOXY (4-desoxymescaline) | 4-Methyl-3,5-dimethoxy-PEA | Desoxyscaline | 40–120 mg | 6–8 hours | [52] |
| 53 | 2,4-DMA | 2,4-Dimethoxy-A | Other | >60 mg | "Short" | [53] |
| 54 | 2,5-DMA (DOH) | 2,5-Dimethoxy-A | DOx | 80–160 mg | 6–8 hours | [54] |
| 55 | 3,4-DMA (DMA) | 3,4-Dimethoxy-A | Other | "A few [100 mg]" | Unknown | [55] |
| 56 | DMCPA | 2,5-Dimethoxy-4-methyl-PCPA | DOx (mod.) | 15–20 mg | 4–8 hours | [56] |
| 57 | DME (β-hydroxy-3,4-DMPEA) | 3,4-Dimethoxy-β-hydroxy-PEA | BOx, other | >115 mg | Unknown | [57] |
| 58 | DMMDA (2,5-dimethoxy-MDA) | 2,5-Dimethoxy-3,4-methylenedioxy-A | MDxx | 30–75 mg | 6–8 hours | [58] |
| 59 | DMMDA-2 (5,6-dimethoxy-MDA) | 2,3-Dimethoxy-4,5-methylenedioxy-A | MDxx | ~50 mg | Unknown | [59] |
| 60 | DMPEA (3,4-DMPEA) | 3,4-Dimethoxy-PEA | Other | >1,000 mg | Unknown | [60] |
| 61 | DOAM | 4-Amyl-2,5-dimethoxy-A | DOx | >10 mg | Unknown | [61] |
| 62 | DOB | 4-Bromo-2,5-dimethoxy-A | DOx | 1–3 mg | 18–30 hours | [62] |
| 63 | DOBU | 4-Butyl-2,5-dimethoxy-A | DOx | Uncertain | "Very long" | [63] |
| 64 | DOC | 4-Chloro-2,5-dimethoxy-A | DOx | 1.5–3 mg | 12–24 hours | [64] |
| 65 | DOEF | 4-(2-Fluoroethyl)-2,5-dimethoxy-A | DOx | 2–3.5 mg | 12–16 hours | [65] |
| 66 | DOET | 4-Ethyl-2,5-dimethoxy-A | DOx | 2–6 mg | 14–20 hours | [66] |
| 67 | DOI | 4-Iodo-2,5-dimethoxy-A | DOx | 1.5–3 mg | 16–30 hours | [67] |
| 68 | DOM (STP) | 4-Methyl-2,5-dimethoxy-A | DOx | 3–10 mg | 14–20 hours | [68] |
| 69 | Psi-DOM (ψ-DOM) | 4-Methyl-2,6-dimethoxy-A | ψ-PEA | 15–25 mg | 6–8 hours | [69] |
| 70 | DON | 4-Nitro-2,5-dimethoxy-A | DOx | 3–4.5 mg | 8–15 hours | [70] |
| 71 | DOPR | 4-Propyl-2,5-dimethoxy-A | DOx | 2.5–5 mg | 20–30 hours | [71] |
| 72 | E (escaline) | 4-Ethoxy-3,5-dimethoxy-PEA | Scaline | 40–60 mg | 8–12 hours | [72] |
| 73 | EEE (TMA2-2,4,5-TriEtO) | 2,4,5-Triethoxy-A | DOx-TWEETIO | Unknown | Unknown | [73] |
| 74 | EEM (TMA2-2,4-DiEtO) | 2,4-Diethoxy-5-methoxy-A | DOx-TWEETIO | Unknown | Unknown | [74] |
| 75 | EME (TMA2-2,5-DiEtO) | 2,5-Diethoxy-4-methoxy-A | DOx-TWEETIO | Unknown | Unknown | [75] |
| 76 | EMM (TMA2-2-EtO) | 2-Ethoxy-4,5-dimethoxy-A | DOx-TWEETIO | >50 mg | Unknown | [76] |
| 77 | ETHYL-J (EBDB) | N,α-Diethyl-3,4-methylenedioxy-PEA | MDxx | >90 mg | "Probably short" | [77] |
| 78 | ETHYL-K (EBDP) | N-Ethyl-α-propyl-3,4-methylenedioxy-PEA | MDxx | >40 mg | Unknown | [78] |
| 79 | F-2 (2-Me-5-MeO-6-APDB) | 2-Methyl-5-methoxy-2,3-dihydro-6-APBF | Benzofuran | >15 mg | Unknown | [79] |
| 80 | F-22 (2,2-DiMe-5-MeO-6-APDB) | 2,2-Dimethyl-5-methoxy-2,3-dihydro-6-APBF | Benzofuran | >15 mg | Unknown | [80] |
| 81 | FLEA (MDMOH) | N-Hydroxy-N-methyl-3,4-methylenedioxy-A | MDxx | 100–160 mg | 4–8 hours | [81] |
| 82 | G-3 | 3,4-Trimethylene-2,5-dimethoxy-A | DOx (mod.) | 12–18 mg | 8–12 hours | [82] |
| 83 | G-4 | 3,4-Tetramethylene-2,5-dimethoxy-A | DOx (mod.) | Unknown | Unknown | [83] |
| 84 | G-5 | 3,4-Norbornyl-2,5-dimethoxy-A | DOx (mod.) | 14–20 mg | 16–30 hours | [84] |
| 85 | GANESHA (G; 3-methyl-DOM) | 3,4-Dimethyl-2,5-dimethoxy-A | DOx | 20–32 mg | 18–24 hours | [85] |
| 86 | G-N | 1,4-Dimethoxynaphthyl-2-isopropylamine | DOx (mod.) | Unknown | Unknown | [86] |
| 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 | [87] |
| 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 | [88] |
| 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 | [89] |
| 90 | IDNNA (N,N-dimethyl-DOI) | 2,5-Dimethoxy-N,N-dimethyl-4-iodo-A | DOx | >2.6 mg | Unknown | [90] |
| 91 | IM (isomescaline) | 2,3,4-Trimethoxy-PEA | Scaline (mod.) | >400 mg | Unknown | [91] |
| 92 | IP (isoproscaline) | 3,5-Dimethoxy-4-isopropoxy-PEA | Scaline (mod.) | 40–80 mg | 10–16 hours | [92] |
| 93 | IRIS (DOM-5-EtO) | 5-Ethoxy-2-methoxy-4-methyl-A | DOx-TWEETIO | >9 mg | Unknown | [93] |
| 94 | J (BDB) | α-Ethyl-3,4-methylenedioxy-PEA | MDxx | 150–230 mg | 4–8 hours | [94] |
| 95 | LOPHOPHINE (MMDPEA) | 3-Methoxy-4,5-methylenedioxy-PEA | MDxx | >200 mg | Unknown | [95] |
| 96 | M (mescaline; 3,4,5-TMPEA) | 3,4,5-Trimethoxy-PEA | Scaline | ~200–400 mgc | 10–12 hours | [96] |
| 97 | 4-MA (PMA) | 4-Methoxy-A | Other | 50–80 mg | "Short" | [97] |
| 98 | MADAM-6 (6-methyl-MDMA) | 2,N-Dimethyl-4,5-methylenedioxy-A | MDxx | >280 mg | Unknown | [98] |
| 99 | MAL (methallylescaline) | 3,5-Dimethoxy-4-methallyloxy-PEA | Scaline | 40–65 mg | 12–16 hours | [99] |
| 100 | MDA | 3,4-Methylenedioxy-A | MDxx | 80–160 mg | 4–6 hoursd | [100] |
| 101 | MDAL | N-Allyl-3,4-methylenedioxy-A | MDxx | >180 mg | Unknown | [101] |
| 102 | MDBU | N-Butyl-3,4-methylenedioxy-A | MDxx | >40 mg | Unknown | [102] |
| 103 | MDBZ | N-Benzyl-3,4-methylenedioxy-A | MDxx | >150 mg | Unknown | [103] |
| 104 | MDCPM | N-Cyclopropylmethyl-3,4-methylenedioxy-A | MDxx | >10 mg | Unknown | [104] |
| 105 | MDDM | N,N-Dimethyl-3,4-methylenedioxy-A | MDxx | >150 mg | Unknown | [105] |
| 106 | MDE (MDEA) | N-Ethyl-3,4-methylenedioxy-A | MDxx | 100–200 mg | 3–5 hours | [106] |
| 107 | MDHOET | N-(2-Hydroxyethyl)-3,4-methylenedioxy-A | MDxx | >50 mg | Unknown | [107] |
| 108 | MDIP | N-Isopropyl-3,4-methylenedioxy-A | MDxx | >250 mg | Unknown | [108] |
| 109 | MDMA | N-Methyl-3,4-methylenedioxy-A | MDxx | 80–150 mg | 4–6 hours | [109] |
| 110 | MDMC (EDMA) | N-Methyl-3,4-ethylenedioxy-A | EDxx | ≥200 mg | 3–5 hours | [110] |
| 111 | MDMEO | N-Methoxy-3,4-methylenedioxy-A | MDxx | >180 mg | Unknown | [111] |
| 112 | MDMEOET | N-(2-Methoxyethyl)-3,4-methylenedioxy-A | MDxx | >180 mg | Unknown | [112] |
| 113 | MDMP | α,α,N-Trimethyl-3,4-methylenedioxy-PEA | MDxx | ~110 mg | ~6 hours | [113] |
| 114 | MDOH | N-Hydroxy-3,4-methylenedioxy-A | MDxx | 100–160 mg | 3–6 hours | [114] |
| 115 | MDPEA | 3,4-Methylenedioxy-PEA | MDxx | >300 mg | Unknown | [115] |
| 116 | MDPH | α,α-Dimethyl-3,4-methylenedioxy-PEA | MDxx | 160–240 mg | 3–5 hours | [116] |
| 117 | MDPL | N-Propargyl-3,4-methylenedioxy-A | MDxx | >150 mg | Unknown | [117] |
| 118 | MDPR | N-Propyl-3,4-methylenedioxy-A | MDxx | >200 mg | Unknown | [118] |
| 119 | ME (metaescaline) | 3,4-Dimethoxy-5-ethoxy-PEA | Scaline (mod.) | 200–350 mg | 8–12 hours | [119] |
| 120 | MEDA (5-methoxy-EDA) | 3-Methoxy-4,5-ethylenedioxy-A | EDxx | >200 mg | Unknown | [120] |
| 121 | MEE (TMA2-4,5-DiEtO) | 2-Methoxy-4,5-diethoxy-A | DOx-TWEETIO | >4.6 mg | Unknown | [121] |
| 122 | MEM (TMA2-4-EtO) | 2,5-Dimethoxy-4-ethoxy-A | DOx | 20–50 mg | 10–14 hours | [122] |
| 123 | MEPEA | 3-Methoxy-4-ethoxy-PEA | Other | ≥300 mg | "Short" | [123] |
| 124 | Meta-DOB | 5-Bromo-2,4-dimethoxy-A | DOx (mod.) | 50–100 mg | 5–6 hours | [124] |
| 125 | Meta-DOT (5-thio-TMA-2) | 5-Methylthio-2,4-dimethoxy-A | Thio-DOx | >35 mg | Unknown | [125] |
| 126 | Methyl-DMA (N-methyl-2,5-DMA) | N-Methyl-2,5-dimethoxy-A | DOx | >250 mg | Unknown | [126] |
| 127 | Methyl-DOB (N-methyl-DOB) | 4-Bromo-2,5-dimethoxy-N-methyl-A | DOx | >8 mg | "Probably long" | [127] |
| 128 | Methyl-J (MBDB) | N-Methyl-α-ethyl-3,4-methylenedioxy-PEA | MDxx | 180–210 mg | 4–6 hours | [128] |
| 129 | Methyl-K (MBDP) | N-Methyl-α-propyl-3,4-methylenedioxy-PEA | MDxx | >100 mg | Unknown | [129] |
| 130 | Methyl-MA (PMMA) | N-Methyl-4-methoxy-A | Other | >100 mg | "Short" | [130] |
| 131 | Methyl-MMDA-2 (6-methoxy-MDMA) | N-Methyl-2-methoxy-4,5-methylenedioxy-A | MDxx | >70 mg | Unknown | [131] |
| 132 | MMDA (5-methoxy-MDA) | 3-Methoxy-4,5-methylenedioxy-A | MDxx | 100–250 mg | "Moderate" | [132] |
| 133 | MMDA-2 (6-methoxy-MDA) | 2-Methoxy-4,5-methylenedioxy-A | MDxx | 25–50 mg | 8–12 hours | [133] |
| 134 | MMDA-3a (2-methoxy-MDA) | 2-Methoxy-3,4-methylenedioxy-A | MDxx | 20–80 mg | 10–16 hours | [134] |
| 135 | MMDA-3b (4-methoxy-2,3-MDA) | 4-Methoxy-2,3-methylenedioxy-A | MDxx | >80 mg | Unknown | [135] |
| 136 | MME (TMA2-5-EtO) | 2,4-Dimethoxy-5-ethoxy-A | DOx-TWEETIO | ≥40 mg | ~6–10 hours | [136] |
| 137 | MP (metaproscaline) | 3,4-Dimethoxy-5-propoxy-PEA | Scaline (mod.) | >240 mg | Unknown | [137] |
| 138 | MPM (TMA2-4-PrO) | 2,5-Dimethoxy-4-propoxy-A | DOx | ≥30 mg | "Probably short" | [138] |
| 139 | Ortho-DOT (2-thio-TMA-2) | 2-Methylthio-4,5-dimethoxy-A | Thio-DOx | >25 mg | Unknown | [139] |
| 140 | P (proscaline) | 3,5-Dimethoxy-4-propoxy-PEA | Scaline | 30–60 mg | 8–12 hours | [140] |
| 141 | PE (phenescaline) | 3,5-Dimethoxy-4-phenethyloxy-PEA | Scaline | >150 mg | Unknown | [141] |
| 142 | PEA (phenethylamine) | PEA | Other | >1,600 mg | Unknown | [142] |
| 143 | PROPYNYL (propynylscaline) | 4-Propynyloxy-3,5-dimethoxy-PEA | Scaline | ≥80 mg | 8–12 hours | [143] |
| 144 | SB (symbescaline) | 3,5-Diethoxy-4-methoxy-PEA | Scaline (mod.) | >240 mg | Unknown | [144] |
| 145 | TA (TeMA) | 2,3,4,5-Tetramethoxy-A | Other | >~50 mg | Unknown | [145] |
| 146 | 3-TASB (3-thioasymbescaline) | 4-Ethoxy-3-ethylthio-5-methoxy-PEA | Thioscaline (mod.) | ~160 mg | 10–18 hours | [146] |
| 147 | 4-TASB (4-thioasymbescaline) | 3-Ethoxy-4-ethylthio-5-methoxy-PEA | Thioscaline (mod.) | 60–100 mg | 10–15 hours | [147] |
| 148 | 5-TASB (5-thioasymbescaline) | 3,4-Diethoxy-5-methylthio-PEA | Thioscaline (mod.) | ~160 mg | ~8 hours | [148] |
| 149 | TB (thiobuscaline) | 4-Thiobutoxy-3,5-dimethoxy-PEA | Thioscaline | 60–120 mg | ~8 hours | [149] |
| 150 | 3-TE (3-thioescaline) | 4-Ethoxy-5-methoxy-3-methylthio-PEA | Thioscaline | 60–80 mg | 8–12 hours | [150] |
| 151 | 4-TE (4-thioescaline) | 3,5-Dimethoxy-4-ethylthio-PEA | Thioscaline | 20–30 mg | 9–12 hours | [151] |
| 152 | 2-TIM (2-thioisomescaline) | 2-Methylthio-3,4-dimethoxy-PEA | Thioscaline (mod.) | >240 mg | Unknown | [152] |
| 153 | 3-TIM (3-thioisomescaline) | 3-Methylthio-2,4-dimethoxy-PEA | Thioscaline (mod.) | >240 mg | Unknown | [153] |
| 154 | 4-TIM (4-thioisomescaline) | 4-Methylthio-2,3-dimethoxy-PEA | Thioscaline (mod.) | >160 mg | Unknown | [154] |
| 155 | 3-TM (3-thiomescaline) | 3-Methylthio-4,5-dimethoxy-PEA | Thioscaline | 60–100 mg | 8–12 hours | [155] |
| 156 | 4-TM (4-thiomescaline) | 4-Methylthio-3,5-dimethoxy-PEA | Thioscaline | 20–40 mg | 10–15 hours | [156] |
| 157 | TMA (α-methylmescaline; 3C-M) | 3,4,5-Trimethoxy-A | 3C-scaline | 100–250 mg | 6–8 hours | [157] |
| 158 | TMA-2 (DOMeO) | 2,4,5-Trimethoxy-A | DOx | 20–40 mg | 8–12 hours | [158] |
| 159 | TMA-3 (α-methylisomescaline) | 2,3,4-Trimethoxy-A | Other | >100 mg | Unknown | [159] |
| 160 | TMA-4 | 2,3,5-Trimethoxy-A | Other | >80 mg | ~6 hours | [160] |
| 161 | TMA-5 | 2,3,6-Trimethoxy-A | Other | ≥30 mg | 8–10 hours | [161] |
| 162 | TMA-6 (ψ-TMA-2) | 2,4,6-Trimethoxy-A | ψ-PEA | 25–50 mg | 12–16 hours | [162] |
| 163 | 3-TME (3-thiometaescaline) | 4,5-Dimethoxy-3-ethylthio-PEA | Thioscaline (mod.) | 60–100 mg | 10–15 hours | [163] |
| 164 | 4-TME (4-thiometaescaline) | 3-Ethoxy-5-methoxy-4-methylthio-PEA | Thioscaline (mod.) | 60–100 mg | 10–15 hours | [164] |
| 165 | 5-TME (5-thiometaescaline) | 3-Ethoxy-4-methoxy-5-methylthio-PEA | Thioscaline (mod.) | >200 mg | Unknown | [165] |
| 166 | 2T-MMDA-3a (2-methylthio-MDA) | 2-Methylthio-3,4-methylenedioxy-A | MDxx | >12 mg | Unknown | [166] |
| 167 | 4T-MMDA-2 (4-thio-MMDA-2) | 4,5-Thiomethyleneoxy-2-methoxy-A | MDxx (mod.) | >25 mg | Unknown | [167] |
| 168 | TMPEA (2,4,5-TMPEA; 2C-O) | 2,4,5-Trimethoxy-PEA | 2C | >300 mg | Unknown | [168] |
| 169 | 2-TOET (2-thio-DOET) | 4-Ethyl-5-methoxy-2-methylthio-A | Thio-DOx | >65 mg | Unknown | [169] |
| 170 | 5-TOET (5-thio-DOET) | 4-Ethyl-2-methoxy-5-methylthio-A | Thio-DOx | 12–25 mg | 8–24 hours | [170] |
| 171 | 2-TOM (2-thio-DOM) | 5-Methoxy-4-methyl-2-methylthio-A | Thio-DOx | 60–100 mg | 8–10 hours | [171] |
| 172 | 5-TOM (5-thio-DOM) | 2-Methoxy-4-methyl-5-methylthio-A | Thio-DOx | 30–50 mg | 6–10 hours | [172] |
| 173 | TOMSO (5-TOM-sulfoxide) | 2-Methoxy-4-methyl-5-methylsulfinyl-A | Thio-DOx (mod.) | ≥100–150 mge | 10–16 hours | [173] |
| 174 | TP (thioproscaline) | 4-Propylthio-3,5-dimethoxy-PEA | Thioscaline | 20–25 mg | 10–15 hours | [174] |
| 175 | TRIS (trisescaline) | 3,4,5-Triethoxy-PEA | Scaline (mod.) | >240 mg | Unknown | [175] |
| 176 | 3-TSB (3-thiosymbescaline) | 3-Ethoxy-5-ethylthio-4-methoxy-PEA | Thioscaline (mod.) | >200 mg | Unknown | [176] |
| 177 | 4-TSB (4-thiosymbescaline) | 3,5-Diethoxy-4-methylthio-PEA | Thioscaline (mod.) | >240 mg | Unknown | [177] |
| 178 | 3-T-TRIS (3-thiotrisescaline) | 4,5-Diethoxy-3-ethylthio-PEA | Thioscaline (mod.) | >160 mg | Unknown | [178] |
| 179 | 4-T-TRIS (4-thiotrisescaline) | 3,5-Diethoxy-4-ethylthio-PEA | Thioscaline (mod.) | >200 mg | Unknown | [179] |
| 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 12–32 mg as the racemate and 25 mg as (R)-Ariadne were active. c = 4-D, beta-D, and mescaline doses are 200–400 mg as the sulfate salt and 178–356 mg as the hydrochloride salt. d = MDA duration was originally 8–12 hours but was later revised by Shulgin to 4–6 hours in September 2001 following the publication of PiHKAL. e = TOMSO dose is >150 mg alone or 100–150 mg 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.