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TiHKAL

From Wikipedia, the free encyclopedia
1997 book by Alexander Shulgin and Ann Shulgin
Not to be confused withTikal.

TiHKAL: The Continuation
Cover ofTiHKAL, 1st ed.
AuthorAlexander andAnn 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 asTryptamines I Have Known and Loved, is a 1997 book written byAlexander Shulgin andAnn Shulgin.[1][2] It is about a family ofpsychoactive drugs known astryptamines, which includespsychedelics, otherhallucinogens, andentactogens.[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 toPiHKAL: A Chemical Love Story (Phenethylamines I Have Known and Loved) (1991).[1][2]

Content

[edit]

TiHKAL, much like its predecessorPiHKAL, 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 ofPiHKAL left off; it then continues with a collection of essays on topics ranging frompsychotherapy and theJungian mind to the prevalence ofDMT in nature,ayahuasca and thewar on drugs.[2]

The second part ofTiHKAL, which may be conditionally distributed for non-commercial reproduction(see§ External links, below), is a detailedsynthesis manual for 55 tryptamines (many discovered by Alexander Shulgin himself), including theirchemical structures,doses,durations, and commentary.[2] It includes entries on compounds including simple tryptamines likedimethyltryptamine (DMT),psilocin, and5-MeO-DMT,α-alkyltryptamines likeα-methyltryptamine (AMT),β-carbolines orharmala alkaloids likeharmaline, theiboga alkaloidibogaine, andlysergamides likeLSD.[2] WhereasPiHKAL had 179 entries onphenethylamines,TiHKAL has only 55 entries.[3][2] Shulgin has made the second part freely available onErowid 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

[edit]

As withPiHKAL, 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 theUnited 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 inTiHKAL, includingdimethyltryptamine (DMT),psilocybin (4-PO-DMT),psilocin (4-HO-DMT),bufotenin (5-HO-DMT),5-MeO-DMT,α-methyltryptamine (AMT),lysergic acid diethylamide (LSD),harmaline, andibogaine, are widely known and/or usedhallucinogens.[2]

Tryptamines listed

[edit]
#SubstanceChemical nameGroupDoseaDurationLink
1AL-LAD (6-allyl-6-nor-LSD)6-Allyl-N,N-diethyl-NLLysergamide80–160 μg6–8 hours[1]
2DBT (dibutyltryptamine)N,N-Dibutyl-TTryptamineUnknownUnknown[2]
3DET (diethyltryptamine)N,N-Diethyl-TTryptamine50–100 mg2–4 hours[3]
4DiPT (diisopropyltryptamine)N,N-Diisopropyl-TTryptamine25–100 mg6–8 hours[4]
5α,O-DMS (5-MeO-AMT)5-Methoxy-α-methyl-Tα-Alkyltryptamine2.5–4.5 mg12–18 hours[5]
6DMT (dimethyltryptamine)N,N-Dimethyl-TTryptamineVariousbUp to 1 hour[6]
72,α-DMT (2-methyl-AMT)2,α-Dimethyl-Tα-Alkyltryptamine300–500 mg7–10 hours[7]
8α,N-DMT (N-methyl-AMT)α,N-Dimethyl-Tα-Alkyltryptamine50–100 mg6–8 hours[8]
9DPT (dipropyltryptamine)N,N-Dipropyl-TTryptamine100–250 mg2–4 hours[9]
10EiPT (ethylisopropyltryptamine)N-Ethyl-N-isopropyl-TTryptamine24–40 mg4–6 hours[10]
11α-ET (AET; α-ethyltryptamine)α-Ethyl-Tα-Alkyltryptamine100–150 mg6–8 hours[11]
12ETH-LAD (6-ethyl-6-nor-LSD)6,N,N-Triethyl-NLLysergamide40–150 μg8–12 hours[12]
13Harmaline (dihydroharmine)3,4-Dihydro-7-methoxy-1-methyl-BCβ-Carboline150–300 mg5–8 hours[13]
14Harmine7-Methoxy-1-methyl-BCβ-Carboline>300 mgUnknown[14]
154-HO-DBTN,N-Dibutyl-4-hydroxy-T4-Hydroxytryptamine>20 mgUnknown[15]
164-HO-DETN,N-Diethyl-4-hydroxy-T4-Hydroxytryptamine10–25 mg4–6 hours[16]
174-HO-DiPTN,N-Diisopropyl-4-hydroxy-T4-Hydroxytryptamine15–20 mg2–3 hours[17]
184-HO-DMT (psilocin)N,N-Dimethyl-4-hydroxy-T4-Hydroxytryptamine10–20 mg3–6 hours[18]
195-HO-DMT (bufotenin)N,N-Dimethyl-5-hydroxy-T5-Hydroxytryptamine8–16 mgi.v.1–2 hours[19]
204-HO-DPTN,N-Dipropyl-4-hydroxy-T4-HydroxytryptamineUnknownUnknown[20]
214-HO-METN-Ethyl-4-hydroxy-N-methyl-T4-Hydroxytryptamine10–20 mg4–6 hours[21]
224-HO-MiPT4-Hydroxy-N-isopropyl-N-methyl-T4-Hydroxytryptamine12–25 mg4–6 hours[22]
234-HO-MPT4-Hydroxy-N-methyl-N-propyl-T4-HydroxytryptamineUnknownUnknown[23]
244-HO-pyr-T4-Hydroxy-N,N-tetramethylene-TPyrrolidinylethylindole>20 mgUnknown[24]
25IbogaineA complexly substituted-TAzepinoindoleVariousc"Quite long"[25]
26LSD (METH-LAD)N,N-Diethyl-LLysergamide60–200 μg8–12 hours[26]
27MBT (methylbutyltryptamine)N-Butyl-N-methyl-TTryptamine250–400 mg4–6 hours[27]
284,5-MDO-DiPTN,N-Diisopropyl-4,5-methylenedioxy-TOther>25 mgUnknown[28]
295,6-MDO-DiPTN,N-Diisopropyl-5,6-methylenedioxy-TOtherUnknownUnknown[29]
304,5-MDO-DMTN,N-Dimethyl-4,5-methylenedioxy-TOtherUnknownUnknown[30]
315,6-MDO-DMTN,N-Dimethyl-5,6-methylenedioxy-TOther>5 mgUnknown[31]
325,6-MDO-MiPTN-Isopropyl-N-methyl-5,6-methylenedioxy-TOther>50 mgUnknown[32]
332-Me-DET (2-methyl-DET)N,N-Diethyl-2-methyl-TOther80–120 mg6–8 hours[33]
342-Me-DMT (2-methyl-DMT)2,N,N-Trimethyl-TOther50–100 mg4–6 hours[34]
35Melatonin (5-MeO-NAcT)N-Acetyl-5-methoxy-TN-Acetyltryptamine1–10 mg"A few hours"[35]
365-MeO-DETN,N-Diethyl-5-methoxy-T5-Methoxytryptamine1–3 mg3–4 hours[36]
375-MeO-DiPTN,N-Diisopropyl-5-methoxy-T5-Methoxytryptamine6–12 mg4–8 hours[37]
385-MeO-DMT5-Methoxy-N,N-dimethyl-T5-MethoxytryptamineVariousd1–2 hours[38]
394-MeO-MiPTN-Isopropyl-4-methoxy-N-methyl-TOther20–30 mg4–6 hours[39]
405-MeO-MiPTN-Isopropyl-5-methoxy-N-methyl-T5-Methoxytryptamine4–6 mge4–6 hours[40]
415,6-MeO-MiPT5,6-Dimethoxy-N-isopropyl-N-methyl-TOther>75 mgUnknown[41]
425-MeO-NMT5-Methoxy-N-methyl-T5-MethoxytryptamineUnknownUnknown[42]
435-MeO-pyr-T5-Methoxy-N,N-tetramethylene-TPyrrolidinylethylindole0.5–2 mg"Several hours"[43]
446-MeO-THH6-Methoxy-1-methyl-1,2,3,4-tetrahydro-BCβ-CarbolineUnknownUnknown[44]
455-MeO-TMT5-Methoxy-2,N,N-trimethyl-TOther75–150 mg5–10 hours[45]
465-MeS-DMTN,N-Dimethyl-5-methylthio-TOther15–30 mgsm.<1 hour[46]
47MiPT (methylisopropyltryptamine)N-Isopropyl-N-methyl-TTryptamine10–25 mg3–4 hours[47]
48α-MT (AMT; α-methyltryptamine)α-Methyl-Tα-Alkyltryptamine15–30 mgf12–16 hours[48]
49NET (N-ethyltryptamine)N-Ethyl-TTryptamineUnknownUnknown[49]
50NMT (N-methyltryptamine)N-Methyl-TTryptamineUnknownUnknown[50]
51PRO-LAD (6-propyl-6-nor-LSD)6-Propyl-NLLysergamide100–200 μg6–8 hours[51]
52pyr-T (pyrrolidinyltryptamine)N,N-Tetramethylene-TPyrrolidinylethylindoleUnknownUnknown[52]
53T (tryptamine)TryptamineTryptamine250 mgi.v."Very short"[53]
54Tetrahydroharmine (THH)7-Methoxy-1-methyl-1,2,3,4-tetrahydro-BCβ-Carboline300 mgUnknown[54]
55α,N,O-TMS (5-MeO-α,N-DMT)α,N-Dimethyl-5-methoxy-Tα-Alkyltryptamine10–20 mg6–8 hours[55]
565-MeO-DALTg5-Methoxy-N,N-diallyl-T5-Methoxytryptamine12–20 mg2–4 hours[56][57]
57DALT (diallyltryptamine)gN,N-Diallyl-TTryptamine>40 mgUnknown[58]
Acronyms (in chemical names): T =tryptamine; BC =β-carboline; L =lysergamide; NL =6-norlysergamide.Footnotes:a =Dose andduration for compounds areorally unless otherwise specified.b =DMT doses are >350 mg orally, 60–100 mgintramuscularly,subcutaneously, orsmoked, and 4–30 mgintravenously.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 = The5-MeO-DALT (#56) andDALT (#57) entries were not included in the published version ofTiHKAL and were subsequently released in 2004.[8]

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

See also

[edit]

References

[edit]
  1. ^abcBen 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. RetrievedJanuary 30, 2025.
  2. ^abcdefghijAlexander T. Shulgin;Ann Shulgin (1997).TiHKAL: The Continuation (1st ed.). Berkeley, CA:Transform Press.ISBN 978-0-9630096-9-2.OCLC 38503252. RetrievedJanuary 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 fromthe 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. RetrievedJuly 8, 2006.
  7. ^"DEA Raid of Shulgin's Laboratory". Erowid. January 8, 2004. RetrievedJuly 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 fromthe 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 fromthe 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.

External links

[edit]
Tryptamines
4-Hydroxytryptamines
andesters/ethers
5-Hydroxy- and
5-methoxytryptamines
N-Acetyltryptamines
α-Alkyltryptamines
Cyclized tryptamines
Isotryptamines
Related compounds
Tryptamines
No ring subs.
4-Hydroxytryptamines
5-Hydroxytryptamines
5-Methoxytryptamines
Other ring subs.
α-Alkyltryptamines
Others
Cyclized
Bioisosteres
Phenethylamines
Scalines
2C-x
3C-x
DOx
4C-x
Ψ-PEA
MDxx
FLY
25x-NB (NBOMes)
Others
Cyclized
Lysergamides
  • Bioisosteres:JRT
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Natural sources
Stimulants
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Hallucinogens
Entactogens
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