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The Shulgin Index

The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds is a 2011 book written by Alexander Shulgin, Tania Manning, and Paul F. Daley and published by Transform Press.[1][2][3] It followed the earlier books PiHKAL: A Chemical Love Story (1991) and TiHKAL: The Continuation (1997) by Shulgin and his wife Ann Shulgin.[1][2][4][5] The book is about psychedelic substituted phenethylamines and related compounds and their chemistry and pharmacology.[1][2][3] It discusses 126 main compounds from this family as well as 1,300 compounds discussed in total.[1][3]

The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds
AuthorAlexander Shulgin, Tania Manning, and Paul F. Daley
LanguageEnglish
SubjectPharmacology; Chemistry; Psychoactive drugs; Phenethylamines; Psychedelics
PublisherTransform Press
Publication date
2011
Publication placeUnited States
Media typeHardcover
Pages811
ISBN978-0963009630
OCLC709667010
TextThe Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds at Internet Archive
Websitehttps://transformpress.com/publications/

A second volume on substituted tryptamines was being prepared but was never completed due to Shulgin's death in 2014.[1][6][7] According to the Multidisciplinary Association for Psychedelic Studies (MAPS) in 2014 however, the second volume would be finished at some point in the near future.[7]

Compounds listed

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# Compound IUPAC Name Link
1 AEM (α-ethylmescaline) α-Ethyl-1-(3,4,5-trimethoxyphenyl)ethylamine [1]
2 AL (allylescaline) 4-Allyloxy-3,5-dimethoxyphenethylamine [2]
3 ALEPH 2,5-Dimethoxy-4-methylthioamphetamine [3]
4 ALEPH-2 2,5-Dimethoxy-4-ethylthioamphetamine [4]
5 ALEPH-4 2,5-Dimethoxy-4-(i)-propylthioamphetamine [5]
6 ALEPH-7 2,5-Dimethoxy-4-propylthioamphetamine [6]
7 ARIADNE 2,5-Dimethoxy-4-methyl-α-ethylphenethylamine [7]
8 ASB (asymbescaline) 3,4-Diethoxy-5-methoxyphenethylamine [8]
9 BDB α-Ethyl-3,4-methylenedioxyphenethylamine [9]
10 B-DFLY (Bromo-DragonFLY) 1-(8-Bromobenzo [1,2-b;4,5-b']difuran-4-yl)-2-aminopropane [10]
11 BEATRICE 2,5-Dimethoxy-N,4-dimethylamphetamine [11]
12 B-FLY (DOB-FLY) 1-(8-Bromo-2,3,6,7-tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminopropane [12]
13 BOB 4-Bromo-β,2,5-trimethoxyphenethylamine [13]
14 BOD 4-Methyl-2,5,β-trimethoxyphenethylamine [14]
15 BOH β-Methoxy-3,4-methylenedioxyphenethylamine [15]
16 BOM β,3,4,5-Tetramethoxyphenethylamine [16]
17 B-SF 1-(7-Bromo-5-methoxy-2,3-dihydrobenzofuran-4-yl)-2-aminopropane [17]
18 2C-B 4-Bromo-2,5-dimethoxyphenethylamine [18]
19 2C-C 4-Chloro-2,5-dimethoxyphenethylamine [19]
20 2C-D 2,5-Dimethoxy-4-methylphenethylamine [20]
21 2C-E 2,5-Dimethoxy-4-ethylphenethylamine [21]
22 2C-H 2,5-Dimethoxyphenethylamine [22]
23 2C-I 2,5-Dimethoxy-4-iodophenethylamine [23]
24 mCPP 1-(3-Chlorophenyl)piperazine [24]
25 2C-T 2,5-Dimethoxy-4-methylthiophenethylamine [25]
26 2C-T-2 2,5-Dimethoxy-4-ethy lthiophenethylamine [26]
27 2C-T-7 2,5-Dimethoxy-4-(n)-propylthiophenethylamine [27]
28 2C-TFM 2,5-Dimethoxy-4-trifluoromethylphenethylamine [28]
29 DESMETHYL (4-desmethylmescaline) 3,5-Dimethoxy-4-hydroxyphenethylamine [29]
30 3-DESMETHYL (3-desmethylmescaline) 3,4-Dimethoxy-5-hydroxyphenethylamine [30]
31 DESOXY (4-desoxymescaline) 3,5-Dimethoxy-4-methylphenethylamine [31]
32 DFLY (DragonFLY) 1-(Benzo[1,2-b:4,5-b']difuran-4-yl)-2-aminopropane [32]
33 DHA (α-methyldopamine) 3,4-Dihydroxyamphetamine [33]
34 2,3-DMA 2,3-Dimethoxyamphetamine [34]
35 2,4-DMA 2,4-Dimethoxyamphetamine [35]
36 2,5-DMA 2,5-Dimethoxyamphetamine [36]
37 2,6-DMA 2,6-Dimethoxyamphetamine [37]
38 DMA 3,4-Dimethoxyamphetamine [38]
39 3,5-DMA 3,5-Dimethoxyamphetamine [39]
40 DMAP (metamfepramone) 2-Dimethylaminopropiophenone [40]
41 DMCPA 4-Methyl-2,5-methoxycyclopropylamine [41]
42 DMeA (xylopropamine) 3,4-Dimethylamphetamine [42]
43 DMePEA 3,4-Dimethylphenethylamine [43]
44 DMMDA 2,5-Dimethoxy-3,4-methylenedioxyamphetamine [44]
45 α,N-DMMDBA (MDM1EA) α,N-Dimethyl-3,4-methylenedioxybenzylamine [45]
46 2,3-DMPEA 2,3-Dimethoxyphenethylamine [46]
47 2,4-DMPEA 2,4-Dimethoxyphenethylamine [47]
48 2,6-DMPEA 2,6-Dimethoxyphenethylamine [48]
49 DMPEA 3,4-Dimethoxyphenethylamine [49]
50 3,5-DMPEA 3,5-Dimethoxyphenethylamine [50]
51 DOAM 4-Amyl-2,5-dimethoxyamphetamine [51]
52 DOB 4-Bromo-2,5-dimethoxyamphetamine [52]
53 DOBU 4-Butyl-2,5-dimethoxyamphetamine [53]
54 DOC 4-Chloro-2,5-dimethoxyamphetamine [54]
55 DOCN 4-Cyano-2,5-dimethoxyamphetamine [55]
56 DOET 2,5-Dimethoxy-4-ethylamphetamine [56]
57 DOF 2,5-Dimethoxy-4-fluoroamphetamine [57]
58 DOI 2,5-Dimethoxy-4-iodoamphetamine [58]
59 DOIP 2,5-Dimethoxy-4-isopropylamphetamine [59]
60 DOM 2,5-Dimethoxy-4-methylamphetamine [60]
61 DON 2,5-Dimethoxy-4-nitroamphetamine [61]
62 DOPR 2,5-Dimethoxy-4-propylamphetamine [62]
63 DOTFM 2,5-Dimethoxy-4-trifluoromethylamphetamine [63]
64 Escaline 3 ,5-Dimethoxy-4-ethoxyphenethylamine [64]
65 EDA 3,4-Ethylenedioxyamphetamine [65]
66 F (semi-fly) 1-(5-Methoxy-2,3-dihydrobenzofuran-6-yl)-2-aminopropane [66]
67 FEA 2-Furylethylamine [67]
68 FLY 1-(2,3,6,7-Tetrahydrobenzo[1,2-b:4,5-b']difuran-4-yl)-2-aminopropane [68]
69 GEA (3-methoxytyramine) 4-Hydroxy-3-methoxyphenethylamine [69]
70 HMePEA (N-methyltyramine) 4-Hydroxy-N-methylphenethylamine [70]
71 Hordenine N,N-Dimethyl-4-hydroxyphenethylamine [71]
72 IM (isomescaline) 2,3,4-Trimethoxyphenethylamine [72]
73 Lophophine 3-Methoxy-4,5-methylenedioxyphenethylamine [73]
74 2-MA 2-Methoxyamphetamine [74]
75 3-MA 3-Methoxyamphetamine [75]
76 MBDB α-Ethyl-N-methyl-1,3-benzodioxole-5-ethanamine [76]
77 MDA 3,4-Methylenedioxyamphetamine [77]
78 homo-MDA 1-(3,4-Methylenedioxylphenyl)-3-isobutylamine [78]
79 MDBP (MDBZP) 1-(3,4-Methylenedioxybenzyl)piperazine [79]
80 MDDMA 3,4-Methylenedioxy-N,N-dimethylamphetamine [80]
81 MDE (MDEA) N-Ethyl-3,4-methylenedioxyamphetamine [81]
82 MDMA 3,4-Methylenedioxymethamphetamine [82]
83 homo-MDMA N-Methyl-1-(3,4-methylenedioxyphenyl)-3-isobutylamine [83]
84 MDOH N-Hydroxy-3,4-methylenedioxyamphetamine [84]
85 MDPEA 3,4-Methylenedioxyphenethylamine [85]
86 MDPR 3,4-Methylenedioxy-N-propylamphetamine [86]
87 MEM 2,5-Dimethoxy-4-ethoxyamphetamine [87]
88 MeOPP (pMeOPP) 1-(4-Methoxyphenyl)piperazine [88]
89 N-MePEA N-Methylphenethylamine [89]
90 MEPEA 3-Methoxy-4-ethoxyphenethylamine [90]
91 Mescaline 3,4,5-Trimethoxyphenethylamine [91]
92 METHCATH (methcathinone) β-Keto-N-methylamphetamine [92]
93 Methylone 3,4-Methylenedioxymethcathinone [93]
94 MHA (HMA) 3-Methoxy-4-hydroxyamphetamine [94]
95 M-M (N-methylmescaline) N-Methyl-3,4,5-trimethoxyphenethylamine [95]
96 3,4-MMA (MMA) 3-Methoxy-4-methylamphetamine [96]
97 MMDA 3-Methoxy-4,5-methylenedioxyamphetamine [97]
98 MMDA-2 2-Methoxy-4,5-methylenedioxyamphetamine [98]
99 MMDA-3a 2-Methoxy-3,4-methylenedioxyamphetamine [99]
100 2-MPEA 2-Methoxyphenethylamine [100]
101 3-MPEA 3-Methoxyphenethylamine [101]
102 4-MPEA 4-Methoxyphenethylamine [102]
103 MTA (4-MTA) 4-Methylthioamphetamine [103]
104 Proscaline 3,5-Dimethoxy-4-propoxyphenethylamine [104]
105 PAT (8-OH-DPAT) 8-Hydroxy-2-(dipropylamino)tetralin [105]
106 PCA (4-CA) 4-Chloroamphetamine [106]
107 PEA (phenethylamine) 2-Phenylethylamine [107]
108 PeMPEA 2,3,4,5,6-Pentamethoxyphenethylamine [108]
109 PHA (norpholedrine) 4-Hydroxyamphetamine [109]
110 PMA 4-Methoxyamphetamine [110]
111 PMeA (4-MA) 4-Methylamphetamine [111]
112 PMMA 4-Methoxy-N-methylamphetamine [112]
113 TeMA 2,3,4,5-Tetramethoxyamphetamine [113]
114 TeMPEA 2,3,4,5-Tetramethoxyphenethylamine [114]
115 TeMPEA-3 2,3,5,6-Tetramethoxyphenethylamine [115]
116 mTFMPP (TFMPP) 1-(3-(Trifluoromethyl)phenyl)piperazine [116]
117 TMA 3,4,5-Trimethoxyamphetamine [117]
118 TMA-2 2,4,5-Trimethoxyamphetamine [118]
119 TMA-3 2,3,4-Trimethoxyamphetamine [119]
120 TMA-4 2,3,5-Trimethoxyamphetamine [120]
121 TMA-5 2,3,6-Trimethoxyamphetamine [121]
122 TMA-6 2,4,6-Trimethoxyamphetamine [122]
123 TMePEA 3,4,5-Trimethylphenethylamine [123]
124 TMPEA-2 2,4,5-Trimethoxyphenethylamine [124]
125 Trichocereine N,N-Dimethyl-3,4,5-trimethoxyphenethylamine [125]
126 Tyramine 4-Hydroxyphenethylamine [126]

References

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  1. ^ a b c d e Sumnall HR, Evans-Brown M, McVeigh J (2011). "Social, policy, and public health perspectives on new psychoactive substances". Drug Test Anal. 3 (7–8): 515–523. doi:10.1002/dta.310. PMID 21744515. Shulgin's PIHKAL[25] and TIHKAL[26] describe synthesis routes and basic human psychopharmacology of many potential hallucinogenic and entactogenic compounds [...] The Shulgin Index Volume 1, Psychedelic Phenethylamines and Related Compounds (to be followed by a similar volume on tryptamines) was published in 2011,[119] providing a focused, fully referenced examination of the chemistry and pharmacology of 126 compounds, many of them new.
  2. ^ a b c Francis, Arie P.; Smith, Silas W. (2022). "Availability and supply of novel psychoactive substances". Novel Psychoactive Substances. Elsevier. pp. 57–84. doi:10.1016/b978-0-12-818788-3.00001-2. ISBN 978-0-12-818788-3. [Novel psychoactive substance (NPS)] development and manufacturing efforts are aided by those with scientific training who develop or scan research literature for novel structures or derivatives [59]. Substituted phenethylamines and tryptamines were explicitly described in the 1990s by synthetic chemist Alexander Shulgin in the books PiHKAL and TiHKAL, which maintain an online presence [101,102]. The Shulgin Index, cataloguing psychedelic phenethylamines, amphetamines, phenylpiperazines, and others, including synthesis and pharmacological properties, was released in 2011 [103].
  3. ^ a b c Shulgin, A.; Manning, T.; Daley, P.F. (2011). The Shulgin Index, Volume One: Psychedelic Phenethylamines and Related Compounds. Vol. 1. Berkeley: Transform Press. ISBN 978-0-9630096-3-0. Retrieved 2 November 2024. The Shulgin Index is a comprehensive collection of the known psychedelic phenethylamines and related compounds. There are 126 main compounds with detailed physical properties, synthesis and analytical chemistry, biochemistry, pharmacological properties, and legal status. Fully referenced with over 2,000 citations. There are sub-tables of lesser-studied structural homologues and analogues, over 1300 total compounds covered. GCMS scans are included for 229 compounds. This book is an invaluable resource for researchers, physicians, chemists, and law enforcement.
  4. ^ Shulgin, A.T.; Shulgin, A. (1991). PiHKAL: A Chemical Love Story. Transform Press. ISBN 978-0-9630096-0-9. Retrieved 2 November 2024.
  5. ^ Shulgin, A.; Shulgin, A. (1997). TiHKAL: The Continuation. Transform Press. ISBN 978-0-9630096-9-2. Retrieved 2 November 2024.
  6. ^ Weber, Bruce (7 June 2014). "Alexander Shulgin, Psychedelia Researcher, Dies at 88". The New York Times. Retrieved 3 November 2024.
  7. ^ a b Multidisciplinary Association for Psychedelic Studies (Summer 2014). "In Memoriam: Alexander "Sasha" Shulgin, Ph.D. (June 17, 1925–June 2, 2014)" (PDF). MAPS Newsletter. 24 (2): 9–12 (11). ON JUNE 2, 2014, AT THE age of 88, pioneering psychedelic researcher Alexander "Sasha" Shulgin died surrounded by friends and family at his home in Lafayette, California. [...] In 2011, his life's work was published in The Shulgin Index, Volume 1: Psychedelic Phenethylamines and Related Compounds. While the first volume contains over 1,300 compounds, there is more to come. The Shulgin Index, Volume 2 will be published in the near future. Sasha understood that the exploration of novel psychoactive compounds—and ways to use them—would not be completed in his lifetime, so he preserved his research in these volumes for future generations.
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