Home Discussion Topics Dictionary Almanac

Signup Login

Tryptamine

Overview

Tryptamine is a monoamine alkaloid

Alkaloid

Alkaloids are a group of naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids...

found in plant

Plant

Plants are living organisms belonging to the kingdom Plantae. Precise definitions of the kingdom vary, but as the term is used here, plants include familiar organisms such as trees, flowers, herbs, bushes, grasses, vines, ferns, mosses, and green algae. The group is also called green plants or...

s, fungi, and animal

Animal

Animals are a major group of multicellular, eukaryotic organisms of the kingdom Animalia or Metazoa. Their body plan eventually becomes fixed as they develop, although some undergo a process of metamorphosis later on in their life. Most animals are motile, meaning they can move spontaneously and...

s. It is based around the indole

Indole

Indole is an aromatic heterocyclic organic compound. It has a bicyclic structure, consisting of a six-membered benzene ring fused to a five-membered nitrogen-containing pyrrole ring. Indole is a popular component of fragrances and the precursor to many pharmaceuticals. Compounds that contain an...

ring structure, and is chemically related to the amino acid

Amino acid

Amino acids are molecules containing an amine group, a carboxylic acid group and a side-chain that varies between different amino acids. The key elements of an amino acid are carbon, hydrogen, oxygen, and nitrogen...

tryptophan

Tryptophan

Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...

, from which its name is derived. Tryptamine is found in trace

Trace amine

Trace amines are endogenous compounds structurally related to classical biogenic amines, such as catecholamines, serotonin and histamine. Trace amines include p-tyramine, β-phenylethylamine, tryptamine, octopamine, and 3-iodothyronamine, and are found in the nervous systems of animals from insects...

amounts in the brain

Brain

The brain is the center of the nervous system in all vertebrate and most invertebrate animals—only a few primitive invertebrates such as sponges, jellyfish, sea squirts and starfishes do not have one. It is located in the head, usually close to primary sensory apparatus such as vision, hearing,...

s of mammal

Mammal

Mammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...

s and is believed to play a role as a neuromodulator or neurotransmitter

Neurotransmitter

Neurotransmitters are endogenous chemicals that transmit signals from a neuron to a target cell across a synapse. Neurotransmitters are packaged into synaptic vesicles clustered beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they bind to...

Discussion

Ask a question about 'Tryptamine'

Start a new discussion about 'Tryptamine'

Answer questions from other users

Full Discussion Forum

Recent Discussions

What was tryptamine first used for

Encyclopedia

Tryptamine is a monoamine alkaloid

Alkaloid

found in plant

Plant

s, fungi, and animal

Animal

s. It is based around the indole

Indole

ring structure, and is chemically related to the amino acid

Amino acid

tryptophan

Tryptophan

Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...

, from which its name is derived. Tryptamine is found in trace

Trace amine

amounts in the brain

Brain

s of mammal

Mammal

Mammals are members of a class of air-breathing vertebrate animals characterised by the possession of endothermy, hair, three middle ear bones, and mammary glands functional in mothers with young...

s and is believed to play a role as a neuromodulator or neurotransmitter

Neurotransmitter

.

Tryptamine is also the backbone for a group of compounds known collectively as tryptamines. This group includes many biologically active

Biological activity

In pharmacology, biological activity or pharmacological activity describes the beneficial or adverse effects of a drug on living matter. When a drug is a complex chemical mixture, this activity is exerted by the substance's active ingredient or pharmacophore but can be modified by the other...

compound

Chemical compound

A chemical compound is a pure chemical substance consisting of two or more different chemical elements that can be separated into simpler substances by chemical reactions. Chemical compounds have a unique and defined chemical structure; they consist of a fixed ratio of atoms that are held together...

s, including neurotransmitter

Neurotransmitter

s and psychedelic drug

Psychedelic drug

A psychedelic substance is a psychoactive drug whose primary action is to alter cognition and perception. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, a class that also includes related substances such as dissociatives and deliriants...

s.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.

Plants containing tryptamine

Many if not all plants contain small amounts of tryptamine which is an intermediate in one biosynthetic pathway

Metabolism

Metabolism is the set of chemical reactions that happen in the cells of living organisms to sustain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories...

to the plant hormone indole-3-acetic acid

Indole-3-acetic acid

Indole-3-acetic acid, also known as IAA, is a heterocyclic compound that is a phytohormone called auxin. This colourless solid is native plant compound, potent and the most important auxin...

(heteroauxin). Higher concentrations can be found in many Acacia

Acacia

Acacia is a genus of shrubs and trees belonging to the subfamily Mimosoideae of the family Fabaceae, first described in Africa by the Swedish botanist Carl Linnaeus in 1773. Many non-Australian species tend to be thorny, whereas the majority of Australian acacias are not...

species.

Tryptamine acts as a natural pesticide in plants.

Tryptamine derivatives

The best-known tryptamines are serotonin

Serotonin

Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...

, an important neurotransmitter

Neurotransmitter

, and melatonin

Melatonin

Melatonin , also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes...

, a hormone

Hormone

A hormone is a chemical released by a cell or a gland in one part of the body that sends out messages that affect cells in other parts of the organism. Only a small amount of hormone is required to alter cell metabolism. In essence, it is a chemical messenger that transports a signal from one...

involved in regulating the sleep-wake cycle. Tryptamine alkaloids found in fungi, plants and animal

Animal

s are commonly used by humans for their psychotropic effects. Prominent examples include psilocybin

Psilocybin

Psilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...

(from "magic mushroom

Psychedelic mushroom

Psilocybin mushrooms are fungi that contain the psychoactive compounds psilocybin and psilocin. There are multiple colloquial terms for psilocybin mushrooms, the most common being shrooms or magic mushrooms....

s") and DMT

Dimethyltryptamine

N,N-Dimethyltryptamine is a naturally occurring psychedelic compound of the tryptamine family. DMT is found in several plants, and also in trace amounts in humans and other mammals, where it is originally derived from the essential amino acid tryptophan, and ultimately produced by the enzyme INMT...

(from numerous plant sources, e.g. chacruna, often used in ayahuasca

Ayahuasca

Ayahuasca is any of various psychoactive infusions or decoctions prepared from the Banisteriopsis spp. vine, usually mixed with the leaves of dimethyltryptamine-containing species of shrubs from the Psychotria genus...

brews). Many synthetic

Chemical synthesis

In chemistry, chemical synthesis is purposeful execution of chemical reactions to get a product, or several products. This happens by physical and chemical manipulations usually involving one or more reactions...

tryptamines have also been made, including the migraine

Migraine

Migraine is a chronic neurological disorder characterized by moderate to severe headaches, and nausea...

drug

Medication

A pharmaceutical drug, also referred to as medicine, medication or medicament, can be loosely defined as any chemical substance intended for use in the medical diagnosis, cure, treatment, or prevention of disease.- Classification :...

sumatriptan

Sumatriptan

Sumatriptan is a triptan sulfa drug containing a sulfonamide group. It is used for the treatment of migraine headaches. Sumatriptan is produced and marketed by various drug manufacturers with many different trade names such as Sumatriptan, Imitrex, Imigran, Imigran recovery.-Approval and...

and its relatives. The tables below list some commonly encountered substituted tryptamines.

The tryptamine backbone can also be identified as part of the structure of some
more complex compounds, for example: LSD

LSD

Lysergic acid diethylamide, abbreviated LSD or LSD-25, also known as lysergide and colloquially as acid, is a semisynthetic psychedelic drug of the ergoline family, well known for its psychological effects which can include altered thinking processes, closed and open eye visuals, synaesthesia, an...

, ibogaine

Ibogaine

Ibogaine is a naturally occurring psychoactive substance found in a number of plants, principally in a member of the Apocynaceae family known as Iboga . A hallucinogen with both psychedelic and dissociative properties, the substance is banned in some countries; in other countries it is being used...

and yohimbine

Yohimbine

Yohimbine is an alkaloid with stimulant and aphrodisiac effects found naturally in Pausinystalia yohimbe . It is also found naturally in Rauwolfia serpentina , Alchornea floribunda , along with several other active alkaloids...

. A thorough investigation of dozens of tryptamine compounds was published by Ann

Ann Shulgin

Ann Shulgin is an American author and the wife of chemist Alexander Shulgin.Ann Shulgin grew up in the village Opicina outside the Italian city Trieste where her father was American Consul for six years before World War II. She has worked as a lay therapist with psychedelic substances such as MDMA...

and Alexander Shulgin

Alexander Shulgin

Alexander "Sasha" Theodore Shulgin is an American pharmacologist, chemist, artist, and drug developer.Shulgin is credited with the popularization of MDMA, commonly known as ecstasy, in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and...

under the title TiHKAL

TiHKAL

TiHKAL: The Continuation is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PiHKAL: A Chemical Love Story, TiHKAL is an acronym that stands for Tryptamines I Have Known and Loved.-Content:TiHKAL, much like its...

**Selected Tryptamines**
Short Name	Origin	R^α	R⁴	R⁵	R^N1	R^N2	Full Name
Bufotenin Bufotenin Bufotenin , or 5-hydroxy-dimethyltryptamine , is a tryptamine related to the neurotransmitter serotonin...	Natural	H	H	OH	CH₃	CH₃	5-hydroxy-N,N-dimethyltryptamine
DMT Dimethyltryptamine N,N-Dimethyltryptamine is a naturally occurring psychedelic compound of the tryptamine family. DMT is found in several plants, and also in trace amounts in humans and other mammals, where it is originally derived from the essential amino acid tryptophan, and ultimately produced by the enzyme INMT...	Natural	H	H	H	CH₃	CH₃	N,N-dimethyltryptamine
Melatonin Melatonin Melatonin , also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring compound found in animals, plants, and microbes...	Natural	H	H	OCH₃ Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...	O=C-CH₃ Acetyl In organic chemistry, acetyl is a functional group, the acyl with chemical formula COCH3. It is sometimes represented by the symbol Ac . The acetyl group contains a methyl group single-bonded to a carbonyl...	H	5-methoxy-N-acetyltryptamine
5-MeO-DMT 5-MeO-DMT 5-MeO-DMT is a powerful psychedelic tryptamine. It is found in a wide variety of plant and psychoactive toad species and, like its close relatives DMT and bufotenin , it has been used as an entheogen by South American shamans for thousands of years.-Chemistry:5-MeO-DMT was first synthesized in...	Natural	H	H	OCH₃	CH₃	CH₃	5-methoxy-N,N-dimethyltryptamine
NMT N-Methyltryptamine N-Methyltryptamine , or methyltryptamine, is a member of the tryptamine chemical class. It is an alkaloid, probably derived from L-tryptophan, that has been found in the bark, shoots and leaves of several plant species, including Virola, Acacia, Mimosa and Desmanthus often together with the...	Natural	H	H	H	H	CH₃	N-methyltryptamine
Psilocybin Psilocybin Psilocybin is a naturally occurring psychedelic prodrug, with mind-altering effects similar to those of LSD and mescaline, after it is converted to psilocin. The effects can include altered thinking processes, perceptual distortions, an altered sense of time, and spiritual experiences, as well as...	Natural	H	PO₄ Phosphate A phosphate, an inorganic chemical, is a salt of phosphoric acid. In organic chemistry, a phosphate, or organophosphate, is an ester of phosphoric acid. Organic phosphates are important in biochemistry and biogeochemistry or ecology. Inorganic phosphates are mined to obtain phosphorus for use in...	H	CH₃	CH₃	4-phosphoryloxy-N,N-dimethyltryptamine
Psilocin Psilocin Psilocin , an aromatic compound, sometimes also spelled psilocine, psilocyn, or psilotsin, is a psychedelic mushroom alkaloid. It is found in most psychedelic mushrooms together with its phosphorylated counterpart psilocybin...	Natural	H	OH Hydroxyl A hydroxyl is a chemical group containing an oxygen atom covalently bonded with a hydrogen atom. In inorganic chemistry, the hydroxyl group is known as the hydroxide ion, and scientists and reference works generally use these different terms though they refer to the same chemical structure in...	H	CH₃	CH₃	4-hydroxy-N,N-dimethyltryptamine
Serotonin Serotonin Serotonin or 5-hydroxytryptamine is a monoamine neurotransmitter. Biochemically derived from tryptophan, serotonin is primarily found in the gastrointestinal tract, platelets, and in the central nervous system of animals including humans...	Natural	H	H	OH	H	H	5-hydroxytryptamine
N-methylserotonin	Natural	H	H	OH	CH₃	H	5-hydroxy-N-methyltryptamine
Tryptophan Tryptophan Tryptophan is one of the 20 standard amino acids, as well as an essential amino acid in the human diet. It is encoded in the standard genetic code as the codon UGG...	Natural	COOH	H	H	H	H	α-carboxyltryptamine
AET Alpha-Ethyltryptamine α-ethyltryptamine , also known as etryptamine, is a psychedelic, stimulant and entactogen of the tryptamine chemical class.- History :...	artificial	CH₂CH₃ Ethyl group In chemistry, an ethyl group is an alkyl substituent derived from ethane . It has the formula -C2H5 and is very often abbreviated -Et.Ethylation is the formation of a compound by introduction of the ethyl functional group, C2H5....	H	H	H	H	α-ethyltryptamine
AMT Alphamethyltryptamine α-Methyltryptamine , is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s.- History :...	artificial	CH₃	H	H	H	H	α-methyltryptamine
DALT	artificial	H	H	H	H₂C=CH-CH₂ Allyl An allyl group is a substituent with the structural formula H2C=CH-CH2R, where R is the connection to the rest of the molecule. It is made up of a methylene , attached to a vinyl group . The name is derived from the Latin word for garlic, Allium sativum. Theodor Wertheim isolated an allyl...	H₂C=CH-CH₂	N,N-diallyltryptamine
DET Diethyltryptamine DET, also known under its chemical name N,N-diethyltryptamine and as T-9, is a psychedelic drug closely related to DMT and 4-HO-DET...	artificial	H	H	H	CH₂CH₃	CH₂CH₃	N,N-diethyltryptamine
DiPT Diisopropyltryptamine DiPT or diisopropyltryptamine is a psychedelic hallucinogenic drug of the tryptamine family that has a unique effect. While the majority of hallucinogens affect the visual sense, DiPT is primarily aural...	artificial	H	H	H	CH(CH₃)₂ Isopropyl In organic chemistry, isopropyl is a propyl with a group attached to the secondary carbon. If viewed as a functional group an isopropyl is an organic compound with a propyl group attached at its secondary carbon.The bond is therefore on the middle carbon....	CH(CH₃)₂	N,N-diisopropyltryptamine
DPT Dipropyltryptamine Dipropyltryptamine is a psychedelic drug belonging to the tryptamine family, first reported in 1973. It is found either as its crystalline hydrochloride salt or as an oily or crystalline base...	artificial	H	H	H	CH₂CH₂CH₃ Propyl In organic chemistry, propyl is a three-carbon alkyl substituent with chemical formula -C3H7. It is the substituent form of the alkane propane...	CH₂CH₂CH₃	N,N-dipropyltryptamine
5-MeO-AMT 5-MeO-AMT 5-MeO-AMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin is a potent psychedelic tryptamine. It is soluble in alcohol.-Pharmacology:...	artificial	CH₃	H	OCH₃ Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...	H	H	5-methoxy-α-methyltryptamine
5-MeO-DALT 5-MeO-DALT 5-MeO-DALT or N,N-diallyl-5-methoxytryptamine is a psychedelic tryptamine first synthesized by Alexander Shulgin.-Chemistry:The full name of the chemical is N-allyl-N-[2-ethyl]prop-2-en-1-amine...	artificial	H	H	OCH₃ Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. This alkoxy group has the formula O–CH3.The word is used in organic nomenclature usually to describe an ether...	H₂C=CH-CH₂ Allyl An allyl group is a substituent with the structural formula H2C=CH-CH2R, where R is the connection to the rest of the molecule. It is made up of a methylene , attached to a vinyl group . The name is derived from the Latin word for garlic, Allium sativum. Theodor Wertheim isolated an allyl...	H₂C=CH-CH₂	5-methoxy-N,N-diallyltryptamine
4-HO-DET 4-HO-DET 4-HO-DET, also known as 4-hydroxy-diethyl-tryptamine, CZ-74, or ethocin, is a hallucinogenic drug and psychedelic compound of moderate duration. 4-HO-DET is a substituted tryptamine, structurally related to psilocin and 4-HO-DIPT.-Analogs:...	artificial	H	OH	H	CH₂CH₃	CH₂CH₃	4-hydroxy-N,N-diethyltryptamine
O-Acetylpsilocin	artificial						4-acetoxy-N,N-diethyltryptamine
4-HO-DIPT 4-HO-DIPT 4-Hydroxy-di-isopropyl-tryptamine is a synthetic hallucinogen. It is a close structural analogue of psilocin and classified as a tryptamine derivative.-Effects:...	artificial	H	OH	H	CH(CH₃)₂	CH(CH₃)₂	4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT 5-MeO-DIPT 5-methoxy-diisopropyltryptamine is a tryptamine psychedelic used as a recreational drug under the street names "foxy" and "foxy methoxy". 5-MeO-DiPT is orally active, and dosages between 6–20 mg are commonly reported. Many users note an unpleasant body load accompanies higher dosages...	artificial	H	H	OCH₃	CH(CH₃)₂	CH(CH₃)₂	5-methoxy-N,N-diisopropyltryptamine
4-HO-MiPT	artificial	H	OH	H	CH(CH₃)₂	CH₃	4-hydroxy-N-isopropyl-N-methyltryptamine
Sumatriptan Sumatriptan Sumatriptan is a triptan sulfa drug containing a sulfonamide group. It is used for the treatment of migraine headaches. Sumatriptan is produced and marketed by various drug manufacturers with many different trade names such as Sumatriptan, Imitrex, Imigran, Imigran recovery.-Approval and...	artificial	H	H	SO₂NHCH₃	CH₃	CH₃	5-methylaminosulfonyl-N,N-dimethyltryptamine
Zolmitriptan Zolmitriptan Zolmitriptan is a selective serotonin receptor agonist of the 1B and 1D subtypes. It is a triptan, used in the acute treatment of migraine attacks with or without aura and cluster headaches....	artificial
Short Name	Origin	R^α	R⁴	R⁵	R^N1	R^N2	Full Name

Synthesis

The Abramovitch–Shapiro tryptamine synthesis is an organic reaction

Organic reaction

Organic reactions are chemical reactions involving organic compounds. The basic organic chemistry reaction types are addition reactions, elimination reactions, substitution reactions, pericyclic reactions, rearrangement reactions, photochemical reactions and redox reactions. In organic synthesis,...

for the synthesis of tryptamines starting from a beta-Carboline

Beta-carboline

β-Carboline is an organic amine that is the prototype of a class of compounds known as β-carbolines.-Pharmacology:...

External links

Tryptamine FAQ
Tryptamine Hallucinogens and Consciousness
Tryptamind Psychoactives, reference site on tryptamine and other psychoactives.
Tryptamine (T) entry in TiHKAL • info

Tryptamine

Plants containing tryptamine

Tryptamine derivatives

Synthesis

See also

External links