TiHKAL

Lysergic acid diethylamide, commonly known as LSD (from German ) and by the nicknames acid and lucy, is a semisynthetic hallucinogenic drug derived from ergot, known for its powerful psychological effects and serotonergic activity. It was historically used in psychiatry and 1960s counterculture; it is currently legally restricted but receiving renewed scientific interest and increasing use.

Melatonin, an indoleamine, is a natural compound produced by various organisms, including bacteria and eukaryotes. Its discovery in 1958 by Aaron B. Lerner and colleagues stemmed from the isolation of a substance from the pineal gland of cows that could induce skin lightening in common frogs. This compound was later identified as a hormone secreted in the brain during the night, playing a crucial role in regulating the sleep-wake cycle, also known as the circadian rhythm, in vertebrates.

Psilocybin, also known as '4-phosphoryloxy-N,N-dimethyltryptamine (4-PO-DMT'), is a naturally occurring tryptamine alkaloid and investigational drug found in more than 200 species of mushrooms, with hallucinogenic and serotonergic effects. Effects include euphoria, changes in perception, a distorted sense of time, and perceived spiritual experiences. It can also cause adverse reactions such as nausea and panic attacks.

Dimethyltryptamine (DMT), also known as '''N,N-dimethyltryptamine (N,N-DMT'''), is a serotonergic hallucinogen and investigational drug of the tryptamine family that occurs naturally in many plants and animals. DMT is used as a psychedelic drug and prepared by various cultures for ritual purposes as an entheogen.

Tryptamine, also known as 2-(3-indolyl)ethylamine, is an indolamine metabolite of the essential amino acid tryptophan. The chemical structure is defined by an indole—a fused benzene and pyrrole ring, and a 2-aminoethyl group at the second carbon (third aromatic atom, with the first one being the heterocyclic nitrogen). The structure of tryptamine is a shared feature of certain aminergic neuromodulators including melatonin, serotonin, bufotenin and psychedelic derivatives such as dimethyltryptamine (DMT), psilocybin, psilocin and others.

Psilocin, also known as '4-hydroxy-N,N-dimethyltryptamine (4-HO-DMT'), is a psychedelic drug and fungal alkaloid of the tryptamine and 4-hydroxytryptamine families. Along with its phosphate ester psilocybin, it is found in most species of psilocybin-containing mushrooms, such as Psilocybe cubensis and Psilocybe mexicana, and is the compound responsible for their hallucinogenic effects, although concentrations of psilocin are variably lower than those of psilocybin. The drug is taken orally and its effects include perceptual changes and visual effects, emotional changes, ego dissolution, time d

Ibogaine is a psychoactive indole alkaloid derived from plants such as Tabernanthe iboga, characterized by hallucinogenic and oneirogenic effects. Traditionally used by Central African foragers, it has undergone controversial research for the treatment of substance use disorders. Ibogaine exhibits complex pharmacology by interacting with multiple neurotransmitter systems, notably affecting opioid, serotonin, sigma, and NMDA receptors, while its metabolite noribogaine primarily acts as a serotonin reuptake inhibitor and κ-opioid receptor agonist.

Bufotenin, also known as dimethylserotonin or as '5-hydroxy-N,N-dimethyltryptamine (5-HO-DMT'), is a serotonergic psychedelic of the tryptamine family. It is a derivative of the psychedelic dimethyltryptamine (DMT) and of the neurotransmitter serotonin (5-hydroxytryptamine; 5-HT). The compound is an alkaloid found in some species of mushrooms, plants, and toads. It is also found naturally in the human body in small amounts. Bufotenin, for instance derived from the trees Anadenanthera colubrina and Anadenanthera peregrina, has a long history of entheogenic use as a snuff in South America.

5-MeO-DMT, also known as '5-methoxy-N,N-dimethyltryptamine, as well as O-methylbufotenin or mebufotenin', is an atypical psychedelic drug, entheogen, and alkaloid of the tryptamine and 5-methoxytryptamine families. It is found naturally in a wide variety of plant species, and is also secreted by the glands of at least one toad species, the Colorado River toad (Incilius alvarius, formerly Bufo alvarius). It may occur naturally in humans as well. Like its close relatives dimethyltryptamine (DMT) and bufotenin (5-HO-DMT), it has been used as an entheogen in South America. Slang terms include five

α-Methyltryptamine (αMT, AMT) is a psychedelic, stimulant, and entactogen drug of the tryptamine and α-alkyltryptamine families. It was originally developed as an antidepressant at Upjohn in the 1960s, and was used briefly as an antidepressant in the Soviet Union under the brand name Indopan or Indopane before being discontinued.

Harmine, also known as banisterine or telepathine, as well as 7-methoxyharman or 7-methoxy-1-methyl-β-carboline, is a β-carboline and a harmala alkaloid which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It occurs in a number of different plants, most notably Peganum harmala and Banisteriopsis caapi. Harmine reversibly inhibits monoamine oxidase A (MAO-A), an enzyme which breaks down monoamines, making it a reversible inhibitor of monoamine oxidase A (RIMA). Harmine does not inhibit MAO-B.

Harmaline, also known as 7-methoxyharmalan or as 3,4-dihydro-7-methoxy-1-methyl-β-carboline, is a harmala alkaloid and β-carboline which has hallucinogenic effects and monoamine oxidase inhibitor (MAOI) activity. It is the partly hydrogenated form of harmine.

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

'''N-Methyltryptamine (NMT), also known as monomethyltryptamine''', is a chemical compound of the tryptamine family and a naturally occurring compound found in various plants and animals, including humans.

Dipropyltryptamine (DPT), also known as '''N,N-dipropyltryptamine or as "The Light'''", is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is taken orally or by other routes.

Diethyltryptamine (DET), also known as '''N,N-diethyltryptamine or T-9''', is a psychedelic drug of the tryptamine family closely related to dimethyltryptamine (DMT). It is taken orally, but can also be used by parenteral routes.

α-Ethyltryptamine (αET, AET), also known as etryptamine, is an entactogen and stimulant drug of the tryptamine family. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s before being withdrawn due to toxicity.

5-MeO-DiPT, also known as '5-methoxy-N,N-diisopropyltryptamine and sometimes as foxy methoxy or simply foxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and distinct effects from other serotonergic tryptamines, including some stimulant- and entactogen-like effects, robust tactile and sexual enhancement, and only light hallucinogenic effects. The drug is usually taken orally, but may also be used by other routes.

Diisopropyltryptamine (DiPT), also known as '''N,N-diisopropyltryptamine''', is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT). It is unusual among psychedelics in that at usual doses it primarily or exclusively produces strong auditory changes, including decreased pitch, harmonic distortion, and sound unfamiliarity, but produces no other hallucinogenic effects such as visuals. However, the drug may produce more classically psychedelic effects at very high doses. It is taken orally, but can also be smoked.

4-HO-DiPT, also known as '4-hydroxy-N,N-diisopropyltryptamine or as iprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally. The drug has an unusually fast onset, short duration, and narrow dose range. Among orally administered psychedelics, it is one of the shortest-acting compounds known.

'''N-Ethyltryptamine (NET), also abbreviated as NETP', is a tryptamine that is structurally related to N-methyltryptamine (NMT) and the psychedelic drugs N,N-dimethyltryptamine (DMT) and N,N''-diethyltryptamine (DET).

4-HO-MET, also known as '4-hydroxy-N-methyl-N-ethyltryptamine, as well as metocin or methylcybin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

AL-LAD, or ALLAD, also known as ALLY-LAD or as 6-allyl-6-nor-LSD, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is taken orally.

'4-Acetoxy-N,N-dimethyltryptamine (4-AcO-DMT or 4-acetoxy-DMT), also known as O-acetylpsilocin or psilacetin', is a psychedelic drug of the tryptamine family related to psilocybin and psilocin. It is a synthetic derivative of psilocin (4-HO-DMT) in which the hydroxyl group has been acetylated, and is the analogue of psilocybin (4-PO-DMT) in which the phosphate ester has been replaced with an acetate ester. The drug is a prodrug of psilocin and is used orally similarly to psilocybin.

5-MeS-DMT, also known as '5-methylthio-N,N-dimethyltryptamine or as 5-methylthio-DMT', is a lesser-known psychedelic drug of the tryptamine family. It is the 5-methylthio derivative of dimethyltryptamine (DMT) and is an analogue of 5-MeO-DMT.

Methylisopropyltryptamine (MiPT), also known as '''N-methyl-N-isopropyltryptamine''', is a psychedelic drug of the tryptamine family related to other psychedelics like dimethyltryptamine (DMT) and diisopropyltryptamine (DiPT). It is taken orally.

4-AcO-DET, also known as '4-acetoxy-N,N-diethyltryptamine as well as ethacetin or ethylacybin', is a psychedelic tryptamine. It was first synthesized in 1958 by Albert Hofmann in the Sandoz lab.

PRO-LAD, or PROLAD, also known as 6-propyl-6-nor-LSD, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD). It is taken orally.

ETH-LAD, or ETHLAD, also known as 6-ethyl-6-nor-LSD, is a psychedelic drug of the lysergamide family related to lysergic acid diethylamide (LSD; also known as METH-LAD). It is slightly more potent than LSD and is among the most potent psychedelics known. The drug is taken orally.

Pyr-T, also known as '''N,N-tetramethylenetryptamine or as 3-(2-pyrrolidinoethyl)indole', is a lesser-known serotonin receptor modulator of the tryptamine and pyrrolidinylethylindole families. It is the cyclized derivative of diethyltryptamine (DET) in which the N,N''-diethyl groups have been fused into a pyrrolidine ring.

Tetrahydroharmine (THH), also known as 7-methoxy-1,2,3,4-tetrahydroharman (7-MeO-THH), is a fluorescent indole alkaloid and β-carboline that occurs in the tropical liana species Banisteriopsis caapi.

4-MeO-MiPT, also known as '4-methoxy-N-methyl-N-isopropyltryptamine', is a lesser-known psychedelic drug of the tryptamine and 4-methoxytryptamine families. It is the 4-methoxy analogue of MiPT and the O-methyl ether of 4-HO-MiPT. The drug is taken orally.

4-HO-MiPT, also known as '4-hydroxy-N-methyl-N-isopropyltryptamine or as miprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It appears to be similar to psilocin in terms of onset, duration, and effects. The drug is taken orally.

5-MeO-αMT, also known as 5-methoxy-α-methyltryptamine or as 'α,O-dimethylserotonin (α,O-DMS or Alpha-O'), is a psychedelic drug of the tryptamine, α-alkyltryptamine, and 5-methoxytryptamine families. It is a derivative of α-methyltryptamine (αMT) and an analogue of 5-MeO-DMT. The drug is said to be the most potent psychedelic of the simple indolealkylamines (i.e., tryptamines). It is taken orally and is used at doses of 2 to 4mg.

2-Me-DET, or 2-methyl-DET, also known as '2-methyl-N,N-diethyltryptamine', is a psychedelic drug of the tryptamine family. It is the 2-methyl derivative of diethyltryptamine (DET). The drug is taken orally.

5-MeO-DALT, also known as '''N,N-diallyl-5-methoxytryptamine or as foxtrot''', is a psychedelic drug of the tryptamine and 5-methoxytryptamine families. It is taken orally.

6-MeO-THH, also known as 6-methoxy-1,2,3,4-tetrahydroharman, is a β-carboline (or more specifically a pinoline) derivative and a structural isomer of tetrahydroharmine (7-MeO-THH). It is mentioned in Alexander Shulgin's book TiHKAL (Tryptamines I Have Known and Loved), stating that 6-MeO-THH is very similar to the other carbolines. The compound has been isolated from certain plants of the Virola family.

4-HO-pyr-T, also known as '4-hydroxy-N,N-tetramethylenetryptamine', is a serotonin receptor modulator of the tryptamine, 4-hydroxytryptamine, and pyrrolidinylethylindole families. It is the 4-hydroxyl analogue of pyr-T and the analogue of psilocin (4-HO-DMT) and 4-HO-DET in which the N,N-dialkyl moiety has been cyclized into a pyrrolidine ring.

5-MeO-DET, also known as '5-methoxy-N,N-diethyltryptamine' is a psychedelic drug of the tryptamine family related to 5-MeO-DMT. It is taken orally but can also be used parenterally.

Dibutyltryptamine (DBT), also known as '''N,N-dibutyltryptamine (N,N-DBT'''), is a psychedelic drug of the tryptamine family related to dimethyltryptamine (DMT).

4-HO-DET, also known as '4-hydroxy-N,N-diethyltryptamine as well as ethocin or CZ-74', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

Ethocybin also known as '4-phosphoryloxy-N,N-diethyltryptamine (4-PO-DET) or as CEY-19', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to the psilocybin-containing mushroom alkaloid psilocybin. It is assumed to act as a prodrug of 4-HO-DET (CZ-74) analogously to how psilocybin (4-PO-DMT) acts as a prodrug of psilocin (4-HO-DMT). The drug was first described in the literature by Albert Hofmann and colleagues at Sandoz by 1963.

5-MeO-pyr-T, also known as '5-methoxy-N,N-tetramethylenetryptamine or as 5-methoxy-3-(2-pyrrolidinoethyl)indole', is a serotonin receptor modulator and psychedelic drug of the tryptamine, 5-methoxytryptamine, and pyrrolidinylethylindole families. It is the 5-methoxy analogue of pyr-T and the derivative of 5-MeO-DMT and 5-MeO-DET in which their N,N-dialkyl groups have been cyclized into a pyrrolidine ring.

5-MeO-MiPT, also known as '5-methoxy-N-methyl-N-isopropyltryptamine or by its nickname Moxy', is an atypical psychedelic drug of the tryptamine and 5-methoxytryptamine families. It has unique and unusual effects compared to other psychedelic tryptamines. At low doses, its effects include stimulation, tactile and sexual enhancement, some MDMA-like entactogenic effects, and introspective and mild perceptual changes with few or no psychedelic visuals or time dilation, whereas at higher doses, it produces 5-MeO-DMT-like classical psychedelic effects. It is usually taken orally or smoked.

Diallyltryptamine (DALT), also known as '''N,N-diallyltryptamine''', is a tryptamine derivative which has been identified as a designer drug.

4-HO-DPT, also known as '4-hydroxy-N,N-dipropyltryptamine or as deprocin', is a psychedelic drug of the tryptamine and 4-hydroxytryptamine families related to psilocin (4-HO-DMT). It is taken orally.

4-HO-DBT, also known as '4-hydroxy-N,N-dibutyltryptamine', is a psychedelic drug of the tryptamine family related to psilocin (4-HO-DMT). It is taken orally.

5,6-MeO-MiPT, also known as '5,6-dimethoxy-N-methyl-N-isopropyltryptamine', is a chemical compound of the tryptamine family. It is the 5,6-dimethoxy derivative of methylisopropyltryptamine (MiPT) and is an analogue of 5-MeO-MiPT. In his 1991 book TiHKAL (Tryptamines I Have Known and Loved), Alexander Shulgin listed the dose as greater than 75mg orally and the duration as unknown. The drug produced few to no effects at doses of up to 75mg orally. Very little data exists about the pharmacological properties, metabolism, and toxicity of 5,6-MeO-MiPT. However, the drug has been found to have aboli