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.
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.
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.
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".
Phenethylamines listed
{| class="wikitable sticky-header sortable" style="font-size:small;"
! #
! Substance
! Chemical name
! Group
! Dose<sup>a</sup>
! 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
| Unknown<sup>b</sup>
| 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
| Thio-DOx
| >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-desoxyscaline
| 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 mg<sup>c</sup>
| 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 mg<sup>c</sup>
| 12 hours
| [https://erowid.org/library/books_online/pihkal/pihkal051.shtml]
|-
| 52
| DESOXY (4-desoxymescaline)
| 4-Methyl-3,5-dimethoxy-PEA
| Desoxyscaline
| 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 (TMA2-2,4,5-TriEtO)
| 2,4,5-Triethoxy-A
| DOx-TWEETIO
| Unknown
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal073.shtml]
|-
| 74
| EEM (TMA2-2,4-DiEtO)
| 2,4-Diethoxy-5-methoxy-A
| DOx-TWEETIO
| Unknown
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal074.shtml]
|-
| 75
| EME (TMA2-2,5-DiEtO)
| 2,5-Diethoxy-4-methoxy-A
| DOx-TWEETIO
| Unknown
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal075.shtml]
|-
| 76
| EMM (TMA2-2-EtO)
| 2-Ethoxy-4,5-dimethoxy-A
| DOx-TWEETIO
| >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-Me-5-MeO-6-APDB)
| 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-DiMe-5-MeO-6-APDB)
| 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-TWEETIO
| >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 mg<sup>c</sup>
| 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 hours<sup>d</sup>
| [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 (TMA2-4,5-DiEtO)
| 2-Methoxy-4,5-diethoxy-A
| DOx-TWEETIO
| >4.6 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal121.shtml]
|-
| 122
| MEM (TMA2-4-EtO)
| 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
| Thio-DOx
| >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 (TMA2-5-EtO)
| 2,4-Dimethoxy-5-ethoxy-A
| DOx-TWEETIO
| ≥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 (TMA2-4-PrO)
| 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
| Thio-DOx
| >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
| Thioscaline (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
| Thioscaline (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
| Thioscaline (mod.)
| ~160 mg
| ~8 hours
| [https://erowid.org/library/books_online/pihkal/pihkal148.shtml]
|-
| 149
| TB (thiobuscaline)
| 4-Thiobutoxy-3,5-dimethoxy-PEA
| Thioscaline
| 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
| Thioscaline
| 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
| Thioscaline
| 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
| Thioscaline (mod.)
| >240 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal152.shtml]
|-
| 153
| 3-TIM (3-thioisomescaline)
| 3-Methylthio-2,4-dimethoxy-PEA
| Thioscaline (mod.)
| >240 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal153.shtml]
|-
| 154
| 4-TIM (4-thioisomescaline)
| 4-Methylthio-2,3-dimethoxy-PEA
| Thioscaline (mod.)
| >160 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal154.shtml]
|-
| 155
| 3-TM (3-thiomescaline)
| 3-Methylthio-4,5-dimethoxy-PEA
| Thioscaline
| 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
| Thioscaline
| 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
| Thioscaline (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
| Thioscaline (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
| Thioscaline (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
| Thio-DOx
| >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
| Thio-DOx
| 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
| Thio-DOx
| 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
| Thio-DOx
| 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
| Thio-DOx (mod.)
| ≥100–150 mg<sup>e</sup>
| 10–16 hours
| [https://erowid.org/library/books_online/pihkal/pihkal173.shtml]
|-
| 174
| TP (thioproscaline)
| 4-Propylthio-3,5-dimethoxy-PEA
| Thioscaline
| 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
| Thioscaline (mod.)
| >200 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal176.shtml]
|-
| 177
| 4-TSB (4-thiosymbescaline)
| 3,5-Diethoxy-4-methylthio-PEA
| Thioscaline (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
| Thioscaline (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
| Thioscaline (mod.)
| >200 mg
| Unknown
| [https://erowid.org/library/books_online/pihkal/pihkal179.shtml]
|- class="sortbottom"
| colspan="7" style="width: 1px; background-color:var(--background-color-notice-subtle,#eaecf0); color:inherit; text-align: center;" | Acronyms (in chemical names): PEA = phenethylamine; A = amphetamine; PCPA = 2-phenylcyclopropylamine; 6-APBF = 6-(2-aminopropyl)benzofuran. Footnotes: <sup>a</sup> = Dose and duration for compounds are orally unless otherwise specified. <sup>b</sup> = Ariadne dose is as a psychedelic. Otherwise doses of 12–32mg as the racemate and 25mg as (R)-Ariadne were active. <sup>c</sup> = 4-D, beta-D, and mescaline doses are 200–400 mg as the sulfate salt and 178–356mg as the hydrochloride salt. <sup>d</sup> = MDA duration was originally 8–12hours but was later revised by Shulgin to 4–6hours in September 2001 following the publication of PiHKAL. <sup>e</sup> = TOMSO dose is >150mg 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.
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
- Bibliography of Alexander Shulgin
- TiHKAL (Tryptamines I Have Known and Loved) (1997)
- The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds (2011)
- List of psychedelic literature
- Substituted phenethylamine (PEA)
- Substituted methoxyphenethylamine
- Substituted amphetamine (AMPH)
- Substituted methylenedioxyphenethylamine (MDxx)
- 2C, DOx, 4C, scaline, 3C, Ψ-PEA, 25-NB, FLY
References
External links
<!-- Note: These links are not a copyright violation: Shulgin allows reproduction of the second half of PiHKAL for non-commercial uses -->
- Erowid Online Books: PiHKAL: A Chemical Love Story by Alexander & Ann Shulgin
- PiHKAL • Info: A Visual Index and Map of PiHKAL: A Chemical Love Story by Alexander & Ann Shulgin
- "Shulgin in Spanish" Project – Information on the first complete translation of PiHKAL and TiHKAL into Spanish
- Transform Press – Publisher of PiHKAL
- PiHKAL - Wikipedia Massviews Analysis (Wikipedia Page Views of Individual PiHKAL Entries)