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Tryptamine

Overview

Tryptamine is a monoamine alkaloid

Alkaloid

Alkaloids are naturally occurring chemical compounds containing basic nitrogen atoms. The name derives from the word alkaline and was used to describe any nitrogen-containing base. Alkaloids are produced by a large variety of organisms, including bacteria, fungi, plants, and animals and are part of...

found in plants, fungi, and animals. 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 one of the twenty R-groups. These molecules are particularly important in biochemistry, where this term refers to alpha-amino acids with the general formula H₂NCHRCOOH, where R is an organic substituent...

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. Some primitive animals such as jellyfish and starfish have a decentralized nervous system without a brain, while sponges lack any nervous system at all...

s of mammal

Mammal

Mammals are a class of vertebrate animals whose females are characterized by the possession of mammary glands while both males and females are characterized by sweat glands, hair, three middle ear bones used in hearing, and a neocortex region in the brain.Mammals are divided into three main...

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

Neurotransmitter

Neurotransmitters are endogenous chemicals which relay, amplify, and modulate signals between a neuron and another cell. Neurotransmitters are packaged into synaptic vesicles that cluster beneath the membrane on the presynaptic side of a synapse, and are released into the synaptic cleft, where they...

.

Tryptamine is also the backbone for a group of compounds known collectively as tryptamines.

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Encyclopedia

Tryptamine is a monoamine alkaloid

Alkaloid

found in plants, fungi, and animals. 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

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

Pharmacological or biological activity is an expression describing the beneficial or adverse effects of a drug on living matter. When the 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 constituents....

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 the cognition and perception of the mind. Psychedelics are part of a wider class of psychoactive drugs known as hallucinogens, which 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 most plants contain small amounts of tryptamine which is an intermediate in one biosynthetic pathway

Metabolism

Metabolism is the set of chemical reactions that occur in living organisms to maintain life. These processes allow organisms to grow and reproduce, maintain their structures, and respond to their environments. Metabolism is usually divided into two categories. Catabolism breaks down organic matter,...

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 an phytohormone called auxins. This colourless solid is probably the most important plant auxin. The molecule is derived from indole, containing a carboxymethyl group ....

(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 Carolus Linnaeus in 1773. The plants tend to be thorny and pod-bearing, with sap and leaves typically bearing large amounts of tannins...

species.

Tryptamine acts as a natural pesticide in plants.

Tryptamine derivatives

The most well-known tryptamines are serotonin

Serotonin

Serotonin is a monoamine neurotransmitter. It is found extensively in the gastrointestinal tract of animals, and about 80 to 90 percent of the human body's total serotonin is located in the enterochromaffin cells in the gut, where it is used to regulate intestinal movements...

, an important neurotransmitter

Neurotransmitter

, and melatonin

Melatonin

Melatonin , also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring hormone found in animals and in some other living organisms, including algae. Circulating levels vary in a daily cycle, and melatonin is important in the regulation of the circadian rhythms of several...

, a hormone

Hormone

A hormone is a chemical released by one or more cells that affects cells in other parts of the organism. Only a small amount of hormone is required to alter cell metabolism. It is essentially a chemical messenger that transports a signal from one cell to another. All multicellular organisms...

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

Animal

Animals are a major group of mostly 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...

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

Psilocybin

Psilocybin is a hallucinogenic indole of the tryptamine family, found in psilocybin mushrooms. It is present in hundreds of species of fungi, including those of the genus Psilocybe, such as Psilocybe cubensis and Psilocybe semilanceata, but also reportedly isolated from a dozen or so other genera...

(from "magic mushroom

Psychedelic mushroom

Psilocybin mushrooms are fungi mainly of the psilocybe genus that contain the psychedelic substances psilocybin and psilocin, and occasionally other psychoactive tryptamines...

s") and DMT

Dimethyltryptamine

Dimethyltryptamine is a naturally-occurring tryptamine and potent psychedelic drug, found not only in many plants, but also in trace amounts in the human body where its natural function is undetermined. Structurally, it is analogous to the neurotransmitter serotonin and other psychedelic...

(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 neurological syndrome characterized by altered bodily perceptions, severe headaches, and nausea. Physiologically, the migraine headache is a neurological condition more common to women than to men. The word migraine was borrowed from Old French migraigne...

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 drug including a sulfonamide group for the treatment of migraine headaches...

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, LSD-25, LSD, formerly lysergide, commonly known as acid, is a semisynthetic psychedelic drug of the ergoline family...

, ibogaine

Ibogaine

Ibogaine is a naturally occurring psychoactive compound found in a number of plants, principally in a member of the dogbane family known as iboga . Ibogaine-containing preparations are used in medicinal and ritual purposes within African spiritual traditions of the Bwiti, who claim to have learned...

and yohimbine

Yohimbine

Yohimbine is a psychoactive drug of the tryptamine chemical class with stimulant and aphrodisiac effects. It is an alkaloid and is found naturally in Pausinystalia yohimbe , formerly known as Corynanthe yohimbe, as the herb's primary active constituent...

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

Ann Shulgin

Ann Shulgin is an author and the wife of famous chemist Alexander Shulgin.She has worked as a lay therapist with psychedelic substances such as MDMA and 2C-B in therapeutic settings while these drugs were still legal...

and Alexander Shulgin

Alexander Shulgin

Alexander "Sasha" Shulgin is a Russian-American pharmacologist, chemist and drug developer.Shulgin is credited with the popularization of MDMA in the late 1970s and early 1980s, especially for psychopharmaceutical use and the treatment of depression and post-traumatic stress disorder...

under the title TiHKAL

TiHKAL

TiHKAL is a 1997 book written by Alexander Shulgin and Ann Shulgin about a family of psychoactive drugs known as tryptamines. A sequel to PiHKAL , the full title of the book is Tryptamines i Have Known And Loved: The Continuation.TiHKAL, much like its predecessor PiHKAL, is divided into two parts...

**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 Dimethyltryptamine is a naturally-occurring tryptamine and potent psychedelic drug, found not only in many plants, but also in trace amounts in the human body where its natural function is undetermined. Structurally, it is analogous to the neurotransmitter serotonin and other psychedelic...	Natural	H	H	H	CH₃	CH₃	N,N-dimethyltryptamine
Melatonin Melatonin Melatonin , also known chemically as N-acetyl-5-methoxytryptamine, is a naturally occurring hormone found in animals and in some other living organisms, including algae. Circulating levels vary in a daily cycle, and melatonin is important in the regulation of the circadian rhythms of several...	Natural	H	H	OCH₃ Methoxy In chemistry , methoxy refers to the functional group consisting of a methyl group bound to oxygen. It has the formula:...	O=C-CH₃ Acetyl In organic chemistry, acetyl is a functional group, the acyl with chemical formula COCH₃. It is sometimes abbreviated as 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 merely methyltryptamine, is a putative psychoactive drug of the tryptamine chemical class which may purportedly have psychedelic properties...	Natural	H	H	H	H	CH₃	N-methyltryptamine
Psilocybin Psilocybin Psilocybin is a hallucinogenic indole of the tryptamine family, found in psilocybin mushrooms. It is present in hundreds of species of fungi, including those of the genus Psilocybe, such as Psilocybe cubensis and Psilocybe semilanceata, but also reportedly isolated from a dozen or so other genera...	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 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. Psilocin is a Schedule I drug under the Convention on Psychotropic Substances...	Natural	H	OH Hydroxy Hydroxy can refer to:* In chemical nomenclature, the prefix "hydroxy-" shows the presence of a hydroxyl functional group '* An abbreviation for the medication hydroxyzine, which is commonly sold under the brand names Atarax, Ucerax, Serecid, and Vistaril* Hydroxy gas: A nickname for oxyhydrogen, a...	H	CH₃	CH₃	4-hydroxy-N,N-dimethyltryptamine
Serotonin Serotonin Serotonin is a monoamine neurotransmitter. It is found extensively in the gastrointestinal tract of animals, and about 80 to 90 percent of the human body's total serotonin is located in the enterochromaffin cells in the gut, where it is used to regulate intestinal movements...	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 is a psychoactive drug and member of the tryptamine chemical class. It was investigated as an antidepressant by Upjohn Chemical Company under the name Monase, but was withdrawn from commercial use after a year due to the unacceptable occurrence of agranulocytosis...	artificial	CH₂CH₃ Ethyl group In chemistry, an ethyl group is an alkyl functional group derived from ethane . It has the formula -C₂H₅ and is very often abbreviated -Et....	H	H	H	H	α-ethyltryptamine
AMT Alphamethyltryptamine α-Methyltryptamine is a synthetic drug of the tryptamine family. First developed as an antidepressant in the 1960s, it was produced commercially for this purpose in the Soviet Union under the trade name "Indopan" in 5–10 mg pills. Like many other tryptamines, at sufficient dosages α-MT acts...	artificial	CH₃	H	H	H	H	α-methyltryptamine
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 substituent form of propane, the three-carbon alkyl functional group. As an isomer of propyl, bonding to an R group occurs at the secondary 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.For example:This is propyl ethanoate, an ester...	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. It has the formula:...	H	H	5-methoxy-α-methyltryptamine
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
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...	artificial	H	OH	H	CH(CH₃)₂	CH(CH₃)₂	4-hydroxy-N,N-diisopropyltryptamine
5-MeO-DIPT 5-MeO-DIPT 5-methoxy-diisopropyltryptamine, also known as 5-methoxy-N,N-diisopropyltryptamine, 5-MeO-DiPT, foxy methoxy, or just foxy, is a tryptamine that is used recreationally as a psychedelic. 5-MeO-DiPT is orally active, and dosages between 6–20 mg are commonly reported. Many users note an unpleasant...	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 drug including a sulfonamide group for the treatment of migraine headaches...	artificial	H	H	SO₂NHCH₃	CH₃	CH₃	5-methylaminosulfonyl-N,N-dimethyltryptamine
Short Name	Origin	R^α	R⁴	R⁵	R^N1	R^N2	Full Name

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 and redox reactions. In organic synthesis, organic reactions are used...

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

Plants containing tryptamine

Tryptamine derivatives

See also

External links