TiHKAL

TiHKAL: The Continuation
	Cover of TiHKAL, 1st ed.
Author	Alexander and Ann Shulgin
Subject	Pharmacology, Autobiography, Psychedelic drugs
Publisher	Transform Press
Publication date	1997
Publication place	United States
Media type	Paperback
Pages	xxviii, 804 p.
ISBN	0-9630096-9-9
OCLC	38503252
Preceded by	PiHKAL (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

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

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 ‘controlled drugs’. Agents tell me that in clandestine labs that they have raided, they have found copies of those books."

Notable compounds

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

#	Substance	Chemical name	Group	Dose^a	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	Various^b	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	Various^c	"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	Various^d	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 mg^e	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 mg^f	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-DALT^g	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]

References

^ ^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.
^ ^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.
^ Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.
^ 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.
^ 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).
^ Bennett, Drake (January 30, 2005). "Dr. Ecstasy". New York Times Magazine. Retrieved July 8, 2006.
^ "DEA Raid of Shulgin's Laboratory". Erowid. January 8, 2004. Retrieved July 8, 2006.
^ Morris H, Smith A (May 2, 2010). "The Last Interview With Alexander Shulgin". VICE.
^ 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.
^ 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.
^ 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.
^ 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.
^ 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

[Sessa2015-1] 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.

[TiHKAL1997-2] ^ ^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.

[PiHKAL-3] Shulgin, Alexander; Shulgin, Ann (September 1991). PiHKAL: A Chemical Love Story. Berkeley, California: Transform Press. ISBN 0-9630096-0-5. OCLC 25627628.

[BLTC2021-4] 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.

[PassieBrandt2018-5] 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).

[nyt-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.

[MorrisSmith2010-8] Morris H, Smith A (May 2, 2010). "The Last Interview With Alexander Shulgin". VICE.

[JacobShulgin1994-9] 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.

[Shulgin2003-10] 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.

[Shulgin1978-11] 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.

[Shulgin1980-12] 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.

[Shulgin1982-13] 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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v t e Tryptamines
Tryptamines	1-Methyl-DMT (1,N,N-TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N,N-TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-MeS-DMT 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-Nitro-T (Nitro-I) 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T 7-Hydroxytryptophan Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) CPI-CG-8 DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 HBL20016 (5-MeS-6-F-DMT) HBL20017 (4-F-5-MeS-DMT) Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T) N-DEAOP-NET N-DEAOP-NMT NAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan
4-Hydroxytryptamines and esters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin; O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Luvesilocin (4-GO-DiPT; RE-104; FT-104) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N,N,O-TMS; O-methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MBT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O-methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N,N,N-TMS) Bufotenin (5-HO-DMT; N,N-DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) NB-5-MeO-DALT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT)
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin; N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αET 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) N-Hydroxy-AMT Soclenicant (BNC-210; Ile–Trp) 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O-DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 β-Keto-α-alkyltryptamines: BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATA N-(4-carboxybutyl) CH-PIATA N-(4-hydroxypentyl) CHM-FUBIATA
Cyclized tryptamines	5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Harmala alkaloids and β-carbolines (e.g., 5-methoxyharmalan, norharmine 6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine, tabernanthine) Ibogalogs (e.g., catharanthalog, fluorogainalog, ibogainalog, ibogaminalog (DM-506), LS-22925, noribogainalog, noribogaminalog, PHA-57378, Pharm-136, PNU-22394, tabernanthalog) Imidazolylindoles (e.g., AGH-107, AGH-192, AH-494) Metralindole Morpholinylethylindoles (e.g., mor-T, 5-MeO-mor-T) Partial ergolines and lysergamides (e.g., NDTDI, RU-27849, RU-28251, RU-28306, FHATHBIN, LY-178210, Bay R 1531 (LY-197206), LY-293284, 10,11-seco-LSD, 10,11-secoergoline (α,N-Pip-T), CT-5252) Pertines (e.g., alpertine, milipertine, oxypertine, solypertine) Piperidinylethylindoles (e.g., pip-T, 5-MeO-pip-T, indoramin, indolylethylfentanyl) Pyrrolidinylethylindoles (e.g., pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, L-760790) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-122288, CP-135807, eletriptan, MSP-2020) Tetrahydrocarbazolamines (e.g., ciclindole, flucindole, frovatriptan, LY-344864, ramatroban) Tetrahydropyridinylindoles (e.g., RS134-49, RU-28253, NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g., bufothionine, O-methylnordehydrobufotenine, dehydrobufotenine) Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine)
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines: DLX-0002700 JRT PNU-181731
Related compounds	1-Methylmedmain 2-Azapsilocin 2,3-Dihydro-L-tryptophan 2,3-Dihydrotryptamine 2,3-Dihydro-DMT 2,3-Dihydro-NMT 2,3-Dihydro-DET 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline, 2MePI, 8MeO-2MePI, alosetron, gevotroline, latrepirdine, lurosetron, mebhydrolin, tiflucarbine) Amedalin Benzindopyrine Benzydamine Benzofurans (e.g., 3-APB (1-oxa-AMT), 5-MeO-DiBF (1-oxa-5-MeO-DiPT), BPAP, 3-F-BPAP, dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT), MiPBF (1-oxa-MiPT), oxa-noribogaine) Benzothiophenes (e.g., S-DMT (1-thia-DMT), 3-APBT (1-thia-AMT)) Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT, DMHT) I-32 IAL IN-399 Indalpine Indazolethylamines (e.g., AL-34662, AL-38022A, O-methyl-AL-34662, VU6067416, YM-348) Indenylethylamines (e.g., C-DMT (1-carba-DMT)) Indolizinylethylamines (e.g., TACT908 (2ZEDMA), 1ZP2MA, 1Z2MAP1O) Indolylaminopropanes (e.g., 1-API, 2-API, 4-API, 5-API (5-IT; PAL-571), 6-API (6-IT), 7-API) Iprindole Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134) Phenethylamines (e.g., phenethylamine, amphetamine) Piperidinylbenzimidazolines (e.g., benperidol, timiperone) Piperazinylbenzisothiazoles (e.g., lurasidone, perospirone, tiospirone, ziprasidone) Piperidinylbenzisoxazoles (e.g., iloperidone, milsaperidone, ocaperidone, paliperidone, risperidone) Piperidinylindoles (e.g., BRL-54443, LY-334370, naratriptan, sertindole, SN-22) Pirlindole Pyridinylbenzimidazoles (e.g., droperidol) Pyridinylindoles (e.g., tepirindole) Pyridopyrroloquinoxalines (e.g., IHCH-7113, IHCH-7079, IHCH-7086, lumateperone, deulumateperone, ITI-1549) Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA), 3-pyrrolylethylamine (3-NEA), 3-pyrrolylpropylamine) Pyrrolopyridinylethylamines (e.g., WAY-208466) Quinolinylethylamines (e.g., mefloquine) Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088, LY-367265, RU-24,969) Tetrahydropyridinylpyrrolopyridines (e.g., (R)-69 (3IQ), (R)-70, CP-93129, CP-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also: Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

v t e Chemical classes of psychoactive drugs
Stimulants	Amphetamine-type/dopamine releasing agents: Alkylamines Cycloalkylaminopropanes Arylpiperazines Benzylpiperazines Phenylpiperazines Phenethylamines Aminorexes/phenyloxazolamines Amphetamines/α-methylphenethylamines Cathinones/β-ketoamphetamines β-Hydroxyamphetamines/cathinols Naphthylaminopropanes Phentermines Phenylisobutylamines/α-ethylphenethylamines α-Propylphenethylamines Phenylmorpholines/phenmetrazines Thiopropamines/thienylaminopropanes Cocaine-type/typical dopamine reuptake inhibitors: Phenethylamines Phenidates/benzylpiperidines Phenylethylpyrrolidines Pyrrolidinophenones Phenyltropanes/cocaine analogues Modafinil-type/atypical dopamine reuptake inhibitors: Modafinil analogues Phenylpiracetams Caffeine-type/adenosine receptor antagonists: Xanthines/methylxanthines Nicotine-type/nicotinic acetylcholine receptor agonists: Nicotine analogues
Depressants	GABA_A receptor positive allosteric modulators: Alcohols/ethanol analogues Barbiturates Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Carbamates Ethers Neuroactive steroids Nonbenzodiazepines β-Carbolines Cyclopyrrolones Imidazopyridines Pyrazolopyrimidines Phenols Piperidinediones Quinazolinones GABA_A receptor agonists: Isoxazoles GHB receptor agonists: 1,4-Butanediols α₂δ subunit-containing voltage-gated calcium channel blockers: Gabapentinoids Opioids/μ-opioid receptor agonists: Benzimidazoles Nitazenes Fentanyl analogues/phenylpiperidines Mitragyna alkaloids Morphinans/phenanthrenes Opiates/opium alkaloids Utopioids Antihistamines/H₁ receptor antagonists: Benzimidazoles Diarylmethanes Ethylenediamines Tricyclics Dibenzocycloheptenes
Hallucinogens	Serotonergic psychedelics/serotonin 5-HT_2A receptor agonists: Arylpiperazines Phenylpiperazines Quinolinylpiperazines Cyclized phenethylamines 3-Benzazepines Cyclized tryptamines Azepinoindoles Ibogalogs Iboga alkaloids β-Carbolines Harmala alkaloids Ergolines Lysergamides Simplified/partial lysergamides Phenethylamines (methoxyphenethylamines) 2Cs 25-NB/NBOMes 2C-Os 2C-Ts HOT-x TWEETIOs Amphetamines/α-methylphenethylamines 3Cs Dimethoxyamphetamines/DMAs DOx Alephs Ethylenedioxyamphetamines/EDxx Methylenedioxyamphetamines/MDxx Trimethoxyamphetamines/TMAs BOx FLYs/benzofurans Phenylisobutylamines/α-ethylphenethylamines 4Cs Scalines Ψ-PEAs Tryptamines α-Alkyltryptamines α-Alkyl-β-ketotryptamines 4-Hydroxytryptamines 5-Hydroxytryptamines 5-Methoxytryptamines Miscellaneous Dissociatives/NMDA receptor antagonists: Adamantanes Arylcyclohexylamines Diarylethylamines Morphinans κ-Opioid receptor agonists: Benzomorphans Salvinorins GABA_A receptor agonists: Isoxazoles Deliriants/anticholinergics/muscarinic acetylcholine receptor antagonists: Diarylmethanes Tropanes Others: Cyclized tryptamines Azepinoindoles Iboga alkaloids (Phyto)cannabinoids
Entactogens	Serotonin releasing agents: Phenethylamines 2-Aminoindanes 2-Aminotetralins Amphetamines Benzofuranylaminopropanes Benzothiophenylaminopropanes Ethylenedioxyamphetamines/EDxx Indanylaminopropanes Indolylaminopropanes Methylenedioxyamphetamines/MDxx Tetralinylaminopropanes Tryptamines α-Alkyltryptamines Miscellaneous
Psychiatric drugs	Anxiolytics: Azapirones Benzodiazepines Pyrrolobenzodiazepines Thienobenzodiazepines Thienodiazepines Thienotriazolodiazepines Triazolobenzodiazepines Antidepressants: Tricyclic antidepressants Dibenzazepines Dibenzocycloheptenes Dibenzothiepins Dibenzoxazepines Dibenzoxepins Tetracyclic antidepressants Antipsychotics/dopamine D₂ receptor antagonists or partial agonists: Benzamides Benzimidazoles Benzisothiazoles Benzisoxazoles Butyrophenones Diphenylbutylpiperidines Phenylpiperazines Tricyclics Dibenzazepines Dibenzodiazepines Dibenzothiazepines Dibenzothiepins Dibenzoxazepines Phenothiazines Thienobenzodiazepines Mood stabilizers/anticonvulsants: Gabapentinoids Tricyclics Dibenzazepines Valproates
Others	Nootropics: Racetams Phenylpiracetams Miscellaneous: 3-Benzazepines Adamantanes Catecholamines Tetrahydroisoquinolines Yohimbans

Cover of TiHKAL, 1st ed.
Author	Alexander and Ann Shulgin
Subject	Pharmacology, Autobiography, Psychedelic drugs
Publisher	Transform Press
Publication date	1997
Publication place	United States
Media type	Paperback
Pages	xxviii, 804 p.
ISBN	0-9630096-9-9
OCLC	38503252
Preceded by	PiHKAL (1991)