TiHKAL

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Not to be confused with Tikal.

TiHKAL: The Continuation
Cover of TiHKAL, 1st ed.
AuthorAlexander and Ann Shulgin
SubjectPharmacology, Autobiography, Psychedelic drugs
PublisherTransform Press
Publication date
1997
Publication placeUnited States
Media typePaperback
Pagesxxviii, 804 p.
ISBN0-9630096-9-9
OCLC38503252
Preceded byPiHKAL (1991) 

TiHKAL: The Continuation, also known as Tryptamines I Have Known and Loved, is a 1997 book written by Alexander Shulgin and Ann Shulgin.[1][2] It is about a family of psychoactive drugs known as tryptamines, which includes psychedelics, other hallucinogens, and entactogens.[1][2] The book has two halves, and the second part of the book contains detailed entries on 55 tryptamines.[2] TiHKAL is a sequel to PiHKAL: A Chemical Love Story (Phenethylamines I Have Known and Loved) (1991).[1][2]

Content

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TiHKAL, much like its predecessor PiHKAL, is divided into two parts.[2] The first part, for which all rights are reserved, begins with a fictionalized autobiography, picking up where the similar section of PiHKAL left off; it then continues with a collection of essays on topics ranging from psychotherapy and the Jungian mind to the prevalence of DMT in nature, ayahuasca and the war on drugs.[2]

The second part of TiHKAL, which may be conditionally distributed for non-commercial reproduction (see § External links, below), is a detailed synthesis manual for 55 tryptamines (many discovered by Alexander Shulgin himself), including their chemical structures, doses, durations, and commentary.[2] It includes entries on compounds including simple tryptamines like dimethyltryptamine (DMT), psilocin, and 5-MeO-DMT, α-alkyltryptamines like α-methyltryptamine (AMT), β-carbolines or harmala alkaloids like harmaline, the iboga alkaloid ibogaine, and lysergamides like LSD.[2] Whereas PiHKAL had 179 entries on phenethylamines, TiHKAL has only 55 entries.[3][2] Shulgin has made the second part freely available on Erowid while the first part is available only in the printed text.

Members of Shulgin's research who contributed to the experience reports included Shulgin himself, Ann Shulgin, Myron Stolaroff, and Jean Stolaroff, among others.[4][5]

Response

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As with PiHKAL, the Shulgins were motivated to release the synthesis information as a way to protect the public's access to information about psychedelic compounds, a goal Alexander Shulgin has noted many times.[6] Following a raid of his laboratory in 1994 by the United States DEA,[7] Richard Meyer, spokesman for DEA's San Francisco Field Division, stated that "It is our opinion that those books [referring to the previous work, PiHKAL 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."

Notable compounds

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Some compounds in TiHKAL, including dimethyltryptamine (DMT), psilocybin (4-PO-DMT), psilocin (4-HO-DMT), bufotenin (5-HO-DMT), 5-MeO-DMT, α-methyltryptamine (AMT), lysergic acid diethylamide (LSD), harmaline, and ibogaine, are widely known and/or used hallucinogens.[2]

Tryptamines listed

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# Substance Chemical name Group Dosea Duration Link
1 AL-LAD (6-allyl-6-nor-LSD) 6-Allyl-N,N-diethyl-NL Lysergamide 80–160 μg 6–8 hours [1]
2 DBT (dibutyltryptamine) N,N-Dibutyl-T Tryptamine Unknown Unknown [2]
3 DET (diethyltryptamine) N,N-Diethyl-T Tryptamine 50–100 mg 2–4 hours [3]
4 DiPT (diisopropyltryptamine) N,N-Diisopropyl-T Tryptamine 25–100 mg 6–8 hours [4]
5 α,O-DMS (5-MeO-AMT) 5-Methoxy-α-methyl-T α-Alkyltryptamine 2.5–4.5 mg 12–18 hours [5]
6 DMT (dimethyltryptamine) N,N-Dimethyl-T Tryptamine Variousb Up to 1 hour [6]
7 2,α-DMT (2-methyl-AMT) 2,α-Dimethyl-T α-Alkyltryptamine 300–500 mg 7–10 hours [7]
8 α,N-DMT (N-methyl-AMT) α,N-Dimethyl-T α-Alkyltryptamine 50–100 mg 6–8 hours [8]
9 DPT (dipropyltryptamine) N,N-Dipropyl-T Tryptamine 100–250 mg 2–4 hours [9]
10 EiPT (ethylisopropyltryptamine) N-Ethyl-N-isopropyl-T Tryptamine 24–40 mg 4–6 hours [10]
11 α-ET (AET; α-ethyltryptamine) α-Ethyl-T α-Alkyltryptamine 100–150 mg 6–8 hours [11]
12 ETH-LAD (6-ethyl-6-nor-LSD) 6,N,N-Triethyl-NL Lysergamide 40–150 μg 8–12 hours [12]
13 Harmaline (dihydroharmine) 3,4-Dihydro-7-methoxy-1-methyl-BC β-Carboline 150–300 mg 5–8 hours [13]
14 Harmine 7-Methoxy-1-methyl-BC β-Carboline >300 mg Unknown [14]
15 4-HO-DBT N,N-Dibutyl-4-hydroxy-T 4-Hydroxytryptamine >20 mg Unknown [15]
16 4-HO-DET N,N-Diethyl-4-hydroxy-T 4-Hydroxytryptamine 10–25 mg 4–6 hours [16]
17 4-HO-DiPT N,N-Diisopropyl-4-hydroxy-T 4-Hydroxytryptamine 15–20 mg 2–3 hours [17]
18 4-HO-DMT (psilocin) N,N-Dimethyl-4-hydroxy-T 4-Hydroxytryptamine 10–20 mg 3–6 hours [18]
19 5-HO-DMT (bufotenin) N,N-Dimethyl-5-hydroxy-T 5-Hydroxytryptamine 8–16 mg i.v. 1–2 hours [19]
20 4-HO-DPT N,N-Dipropyl-4-hydroxy-T 4-Hydroxytryptamine Unknown Unknown [20]
21 4-HO-MET N-Ethyl-4-hydroxy-N-methyl-T 4-Hydroxytryptamine 10–20 mg 4–6 hours [21]
22 4-HO-MiPT 4-Hydroxy-N-isopropyl-N-methyl-T 4-Hydroxytryptamine 12–25 mg 4–6 hours [22]
23 4-HO-MPT 4-Hydroxy-N-methyl-N-propyl-T 4-Hydroxytryptamine Unknown Unknown [23]
24 4-HO-pyr-T 4-Hydroxy-N,N-tetramethylene-T Pyrrolidinylethylindole >20 mg Unknown [24]
25 Ibogaine A complexly substituted-T Azepinoindole Variousc "Quite long" [25]
26 LSD (METH-LAD) N,N-Diethyl-L Lysergamide 60–200 μg 8–12 hours [26]
27 MBT (methylbutyltryptamine) N-Butyl-N-methyl-T Tryptamine 250–400 mg 4–6 hours [27]
28 4,5-MDO-DiPT N,N-Diisopropyl-4,5-methylenedioxy-T Other >25 mg Unknown [28]
29 5,6-MDO-DiPT N,N-Diisopropyl-5,6-methylenedioxy-T Other Unknown Unknown [29]
30 4,5-MDO-DMT N,N-Dimethyl-4,5-methylenedioxy-T Other Unknown Unknown [30]
31 5,6-MDO-DMT N,N-Dimethyl-5,6-methylenedioxy-T Other >5 mg Unknown [31]
32 5,6-MDO-MiPT N-Isopropyl-N-methyl-5,6-methylenedioxy-T Other >50 mg Unknown [32]
33 2-Me-DET (2-methyl-DET) N,N-Diethyl-2-methyl-T Other 80–120 mg 6–8 hours [33]
34 2-Me-DMT (2-methyl-DMT) 2,N,N-Trimethyl-T Other 50–100 mg 4–6 hours [34]
35 Melatonin (5-MeO-NAcT) N-Acetyl-5-methoxy-T N-Acetyltryptamine 1–10 mg "A few hours" [35]
36 5-MeO-DET N,N-Diethyl-5-methoxy-T 5-Methoxytryptamine 1–3 mg 3–4 hours [36]
37 5-MeO-DiPT N,N-Diisopropyl-5-methoxy-T 5-Methoxytryptamine 6–12 mg 4–8 hours [37]
38 5-MeO-DMT 5-Methoxy-N,N-dimethyl-T 5-Methoxytryptamine Variousd 1–2 hours [38]
39 4-MeO-MiPT N-Isopropyl-4-methoxy-N-methyl-T Other 20–30 mg 4–6 hours [39]
40 5-MeO-MiPT N-Isopropyl-5-methoxy-N-methyl-T 5-Methoxytryptamine 4–6 mge 4–6 hours [40]
41 5,6-MeO-MiPT 5,6-Dimethoxy-N-isopropyl-N-methyl-T Other >75 mg Unknown [41]
42 5-MeO-NMT 5-Methoxy-N-methyl-T 5-Methoxytryptamine Unknown Unknown [42]
43 5-MeO-pyr-T 5-Methoxy-N,N-tetramethylene-T Pyrrolidinylethylindole 0.5–2 mg "Several hours" [43]
44 6-MeO-THH 6-Methoxy-1-methyl-1,2,3,4-tetrahydro-BC β-Carboline Unknown Unknown [44]
45 5-MeO-TMT 5-Methoxy-2,N,N-trimethyl-T Other 75–150 mg 5–10 hours [45]
46 5-MeS-DMT N,N-Dimethyl-5-methylthio-T Other 15–30 mg sm. <1 hour [46]
47 MiPT (methylisopropyltryptamine) N-Isopropyl-N-methyl-T Tryptamine 10–25 mg 3–4 hours [47]
48 α-MT (AMT; α-methyltryptamine) α-Methyl-T α-Alkyltryptamine 15–30 mgf 12–16 hours [48]
49 NET (N-ethyltryptamine) N-Ethyl-T Tryptamine Unknown Unknown [49]
50 NMT (N-methyltryptamine) N-Methyl-T Tryptamine Unknown Unknown [50]
51 PRO-LAD (6-propyl-6-nor-LSD) 6-Propyl-NL Lysergamide 100–200 μg 6–8 hours [51]
52 pyr-T (pyrrolidinyltryptamine) N,N-Tetramethylene-T Pyrrolidinylethylindole Unknown Unknown [52]
53 T (tryptamine) Tryptamine Tryptamine 250 mg i.v. "Very short" [53]
54 Tetrahydroharmine (THH) 7-Methoxy-1-methyl-1,2,3,4-tetrahydro-BC β-Carboline 300 mg Unknown [54]
55 α,N,O-TMS (5-MeO-α,N-DMT) α,N-Dimethyl-5-methoxy-T α-Alkyltryptamine 10–20 mg 6–8 hours [55]
56 5-MeO-DALTg 5-Methoxy-N,N-diallyl-T 5-Methoxytryptamine 12–20 mg 2–4 hours [56] [57]
57 DALT (diallyltryptamine)g N,N-Diallyl-T Tryptamine >40 mg Unknown [58]
Acronyms (in chemical names): T = tryptamine; BC = β-carboline; L = lysergamide; NL = 6-norlysergamide. Footnotes: a = Dose and duration for compounds are orally unless otherwise specified. b = DMT doses are >350 mg orally, 60–100 mg intramuscularly, subcutaneously, or smoked, and 4–30 mg intravenously. c = Ibogaine dose is "from hundreds of [mg] up to [1 g] or more". d = 5-MeO-DMT doses are 6–20 mg smoked and 2–3 mg intravenously. e = 5-MeO-MiPT doses are 4–6 mg orally and 12–20 mg smoked. f = AMT doses are 15–30 mg orally and 5–20 mg smoked. g = The 5-MeO-DALT (#56) and DALT (#57) entries were not included in the published version of TiHKAL and were subsequently released in 2004.[8]

In addition to TiHKAL, Shulgin has also described the properties of psychedelic tryptamines in humans in literature reviews.[9][10][11][12][13]

See also

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References

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  1. ^ a b c Ben Sessa (2015). "Continuing History of Psychedelics in Medical Practices: The Renaissance of Ps chedelic Medical Research". In Ellens, J.H.; D, T.B.R.P. (eds.). The Psychedelic Policy Quagmire: Health, Law, Freedom, and Society. Psychology, Religion, and Spirituality. Bloomsbury Publishing. p. 50. ISBN 979-8-216-13356-8. Retrieved January 30, 2025.
  2. ^ a b c d e f g h i j Alexander T. Shulgin; Ann Shulgin (1997). TiHKAL: The Continuation (1st ed.). Berkeley, CA: Transform Press. ISBN 978-0-9630096-9-2. OCLC 38503252. Retrieved January 30, 2025.
  3. ^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
  4. ^ Connie Littlefield (director, writer), Siobhan Flanagan, Alexander Shulgin (subject), Ann Shulgin (subject), Paul F. Daley (subject), Myron Stolaroff (subject), Jean Stolaroff (subject), Wendy Perry Tucker (subject), Tania Manning (subject), Greg Manning (subject), Keeper Trout (subject), Earth and Fire Erowid, others (2021). Better Living Through Chemistry (Motion picture). Better Living Through Film, Incorporated. Archived from the original on September 21, 2021.
  5. ^ Passie T, Brandt SD (2018). "Self-Experiments with Psychoactive Substances: A Historical Perspective". Handb Exp Pharmacol. 252: 69–110. doi:10.1007/164_2018_177. PMID 30478735. More ambitious explorations of subjective effects elicited by a series of new psychoactive substances developed by Shulgin were conducted by his close associate and psychologist, Myron Stolaroff. Following SEs with LSD in the mid-1950s, Stolaroff became involved in scientific research on psychedelics. After the control of most psychedelic drugs in the 1970s, Stolaroff conducted SEs with newly synthesized psychedelics 2C-B, 2C-E, 2C-T-2, 2C-T-7, 2C-T4, 2C-T-21, and MEM but also MDMA. Besides Shulgin, Stolaroff was the first who systematically explored the psychological states and their possible uses but under noncontrolled conditions (Stolaroff 1994). He understood his research as an attempt "to make the unconscious conscious" and to give some "guidelines for the proper and safe use of psychedelic drugs in therapy and for spiritual growth" (Stolaroff 1994, pp. 13–14).
  6. ^ Bennett, Drake (January 30, 2005). "Dr. Ecstasy". New York Times Magazine. Retrieved July 8, 2006.
  7. ^ "DEA Raid of Shulgin's Laboratory". Erowid. January 8, 2004. Retrieved July 8, 2006.
  8. ^ Morris H, Smith A (May 2, 2010). "The Last Interview With Alexander Shulgin". VICE.
  9. ^ Jacob P, Shulgin AT (1994). "Structure-Activity Relationships of the Classic Hallucinogens and Their Analogs". In Lin GC, Glennon RA (eds.). Hallucinogens: An Update (PDF). National Institute on Drug Abuse Research Monograph Series. Vol. 146. National Institute on Drug Abuse. pp. 74–91. PMID 8742795. Archived from the original on July 13, 2025.
  10. ^ Shulgin AT (2003). "Basic Pharmacology and Effects". In Laing RR (ed.). Hallucinogens: A Forensic Drug Handbook. Forensic Drug Handbook Series. Elsevier Science. pp. 67–137. ISBN 978-0-12-433951-4. Archived from the original on July 13, 2025.
  11. ^ Shulgin AT (1978). "Psychotomimetic Drugs: Structure-Activity Relationships". In Iversen LL, Iversen SD, Snyder SH (eds.). Stimulants. Boston, MA: Springer US. pp. 243–333. doi:10.1007/978-1-4757-0510-2_6. ISBN 978-1-4757-0512-6.
  12. ^ Shulgin AT (1980). "Hallucinogens". In Burger A, Wolf ME (eds.). Burger's Medicinal Chemistry. Vol. 3 (4 ed.). New York: Wiley. pp. 1109–1137. ISBN 978-0-471-01572-7. OCLC 219960627.
  13. ^ Shulgin AT (1982). "Chemistry of Psychotomimetics". In Hoffmeister F, Stille G (eds.). Psychotropic Agents, Part III: Alcohol and Psychotomimetics, Psychotropic Effects of Central Acting Drugs. Handbook of Experimental Pharmacology. Vol. 55. Berlin: Springer Berlin Heidelberg. pp. 3–29. doi:10.1007/978-3-642-67770-0_1. ISBN 978-3-642-67772-4. OCLC 8130916.
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