PiHKAL

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Not to be confused with Pikal.

PiHKAL: A Chemical Love Story
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Cover of PiHKAL, 1st ed.
AuthorAlexander and Ann Shulgin
SubjectPharmacology, Autobiography, Psychoactive drugs
PublisherTransform Press
Publication date
1991
Publication placeUnited States
Media typePaperback
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OCLC269100404
Followed byTiHKAL (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.[1][2][3] The subject of the work is psychoactive phenethylamine chemical derivatives, notably those that act as psychedelics and/or entactogens.[2][3] The book has two halves, with the second part containing detailed entries on 179 phenethylamines.[2][3] PiHKAL was followed by TiHKAL: The Continuation (Tryptamines I Have Known and Loved) (1997).[4][5]

Content

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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.[2][3]

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.[3] 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.[3]

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.[6][7]

Response

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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.[8]

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.[9]

Notable compounds

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Some compounds in PiHKAL, like mescaline, DOM, 2C-B, MDA, and MDMA, are widely known and/or used psychedelics and/or entactogens.[3]

Essential amphetamines

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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).[3] The list consists of:[3]

  • PMA (para-methoxy-amphetamine)
  • 2,4-DMA (2,4-dimethoxy-amphetamine)
  • 3,4-DMA (3,4-dimethoxy-amphetamine)
  • MDA (3,4-methylenedioxy-amphetamine)
  • MMDA (3-methoxy-4,5-methylendioxy-amphetamine)
  • MMDA-3a (2-methoxy-3,4-methylendioxyamphetamine)
  • MMDA-2 (2-methoxy-4,5-methylendioxyamphetamine)
  • TMA (3,4,5-trimethoxyamphetamine)
  • TMA-2 (2,4,5-trimethoxyamphetamine)
  • DMMDA (2,5-dimethoxy-3,4-methylenedioxyamphetamine)
  • DMMDA-2 (2,3-dimethoxy-4,5-methylenedioxyamphetamine)
  • TeMA (2,3,4,5-tetramethoxyamphetamine)

Not all of these chemicals are bioassayed in PiHKAL; some are merely mentioned.[3]

Magical half-dozen

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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.[3] They are found within the first book of PiHKAL, and are as follows:[3]

  • 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.[10]

Ten classic ladies

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"Methyl-DOM" redirects here. For N-methyl-DOM, see Beatrice (drug).

Shulgin systematically replaced the 10 unique hydrogen atoms in DOM with methyl groups in order to explore its activity and named these compounds the 10 classic ladies.[11][3] The resulting compounds were as follows:[11][3]

As with the essential amphetamines, not all of these compounds have been bioassayed.[3]

Some additional "ladies" have also since been named, including Julia (DOTMA; 3,6-dimethyl-DOM), Jelena (2C-IP), and Selene (2C-P).[11][12]

Phenethylamines listed

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# 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-Bismethylthio-4-methyl-A DOx (mod.) >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-scaline 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 Scaline (mod.) 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 2,4,5-Triethoxy-A DOx (mod.) Unknown Unknown [73]
74 EEM 2,4-Diethoxy-5-methoxy-A DOx (mod.) Unknown Unknown [74]
75 EME 2,5-Diethoxy-4-methoxy-A DOx (mod.) Unknown Unknown [75]
76 EMM 2-Ethoxy-4,5-dimethoxy-A DOx (mod.) >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-Methyl-5-methoxy-2,3-dihydro-6-APBF Benzofuran >15 mg Unknown [79]
80 F-22 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 (mod.) >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 2-Methoxy-4,5-diethoxy-A DOx (mod.) >4.6 mg Unknown [121]
122 MEM 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-Methylthio-2,4-dimethoxy-A DOx (mod.) >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 2,4-Dimethoxy-5-ethoxy-A DOx (mod.) ≥40 mg ~6–10 hours [136]
137 MP (metaproscaline) 3,4-Dimethoxy-5-propoxy-PEA Scaline (mod.) >240 mg Unknown [137]
138 MPM 2,5-Dimethoxy-4-propoxy-A DOx ≥30 mg "Probably short" [138]
139 Ortho-DOT 2-Methylthio-4,5-dimethoxy-A DOx (mod.) >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 Scaline (mod.) ~160 mg 10–18 hours [146]
147 4-TASB (4-thioasymbescaline) 3-Ethoxy-4-ethylthio-5-methoxy-PEA Scaline (mod.) 60–100 mg 10–15 hours [147]
148 5-TASB (5-thioasymbescaline) 3,4-Diethoxy-5-methylthio-PEA Scaline (mod.) ~160 mg ~8 hours [148]
149 TB (thiobuscaline) 4-Thiobutoxy-3,5-dimethoxy-PEA Scaline (mod.) 60–120 mg ~8 hours [149]
150 3-TE (3-thioescaline) 4-Ethoxy-5-methoxy-3-methylthio-PEA Scaline (mod.) 60–80 mg 8–12 hours [150]
151 4-TE (4-thioescaline) 3,5-Dimethoxy-4-ethylthio-PEA Scaline (mod.) 20–30 mg 9–12 hours [151]
152 2-TIM (2-thioisomescaline) 2-Methylthio-3,4-dimethoxy-PEA Scaline (mod.) >240 mg Unknown [152]
153 3-TIM (3-thioisomescaline) 3-Methylthio-2,4-dimethoxy-PEA Scaline (mod.) >240 mg Unknown [153]
154 4-TIM (4-thioisomescaline) 4-Methylthio-2,3-dimethoxy-PEA Scaline (mod.) >160 mg Unknown [154]
155 3-TM (3-thiomescaline) 3-Methylthio-4,5-dimethoxy-PEA Scaline (mod.) 60–100 mg 8–12 hours [155]
156 4-TM (4-thiomescaline) 4-Methylthio-3,5-dimethoxy-PEA Scaline (mod.) 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 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 Scaline (mod.) 60–100 mg 10–15 hours [163]
164 4-TME (4-thiometaescaline) 3-Ethoxy-5-methoxy-4-methylthio-PEA Scaline (mod.) 60–100 mg 10–15 hours [164]
165 5-TME (5-thiometaescaline) 3-Ethoxy-4-methoxy-5-methylthio-PEA Scaline (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 4-Ethyl-5-methoxy-2-methylthio-A DOx (mod.) >65 mg Unknown [169]
170 5-TOET 4-Ethyl-2-methoxy-5-methylthio-A DOx (mod.) 12–25 mg 8–24 hours [170]
171 2-TOM 5-Methoxy-4-methyl-2-methylthio-A DOx (mod.) 60–100 mg 8–10 hours [171]
172 5-TOM 2-Methoxy-4-methyl-5-methylthio-A DOx (mod.) 30–50 mg 6–10 hours [172]
173 TOMSO 2-Methoxy-4-methyl-5-methylsulfinyl-A DOx (mod.) ≥100–150 mge 10–16 hours [173]
174 TP (thioproscaline) 4-Propylthio-3,5-dimethoxy-PEA Scaline (mod.) 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 Scaline (mod.) >200 mg Unknown [176]
177 4-TSB (4-thiosymbescaline) 3,5-Diethoxy-4-methylthio-PEA Scaline (mod.) >240 mg Unknown [177]
178 3-T-TRIS (3-thiotrisescaline) 4,5-Diethoxy-3-ethylthio-PEA Scaline (mod.) >160 mg Unknown [178]
179 4-T-TRIS (4-thiotrisescaline) 3,5-Diethoxy-4-ethylthio-PEA Scaline (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.

In addition to PiHKAL, Shulgin has also described the properties of psychedelic phenethylamines in humans in literature reviews.[13][14][15][16][17][18]

See also

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References

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