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Tryptamine, also known as 2-(3-indolyl)ethylamine, is an indolamine metabolite of the essential amino acid tryptophan.[9][10] 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).[9] 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.[11][12][13]
Tryptamine has been shown to activate serotonin receptors[5][14] and trace amine-associated receptors expressed in the mammalian brain, and regulates the activity of dopaminergic, serotonergic and glutamatergic systems.[15][16] In the human gut, bacteria convert dietary tryptophan to tryptamine, which activates 5-HT4 receptors and regulates gastrointestinal motility.[10][17][18]
Multiple tryptamine-derived drugs have been developed to treat migraines, while trace amine-associated receptors are being explored as a potential treatment target for neuropsychiatric disorders.[19][20][21]
Natural occurrences
For a list of plants, fungi and animals containing tryptamines, see List of psychoactive plants and List of naturally occurring tryptamines.
Mammalian brain
Endogenous levels of tryptamine in the mammalian brain are less than 100 ng per gram of tissue.[12][16] However, elevated levels of trace amines have been observed in patients with certain neuropsychiatric disorders taking medications, such as bipolar depression and schizophrenia.[22]
Mammalian gut microbiome
Tryptamine is relatively abundant in the gut and feces of humans and rodents.[10][17] Commensal bacteria, including Ruminococcus gnavus and Clostridium sporogenes in the gastrointestinal tract, possess the enzyme tryptophan decarboxylase, which aids in the conversion of dietary tryptophan to tryptamine.[10] Tryptamine is a ligand for gut epithelial serotonin type 4 (5-HT4) receptors and regulates gastrointestinal electrolyte balance through colonic secretions.[17]
Metabolism
Biosynthesis
To yield tryptamine in vivo, tryptophan decarboxylase removes the carboxylic acid group on the α-carbon of tryptophan.[12] Synthetic modifications to tryptamine can produce serotonin and melatonin; however, these pathways do not occur naturally as the main pathway for endogenous neurotransmitter synthesis.[23]
Catabolism
Monoamine oxidases A and B are the primary enzymes involved in tryptamine metabolism to produce indole-3-acetaldehyde, however it is unclear which isoform is specific to tryptamine degradation.[24]
Figure
In addition to its pharmaceutical relevance, tryptamine is also used in the production of various dyes and pigments, showcasing its versatility across different industries. Its unique properties, such as its ability to cross the blood-brain barrier, enhance its appeal for researchers looking to develop new treatments for neurological disorders. With ongoing studies into its effects and applications, tryptamine holds significant potential for innovation in both therapeutic and industrial contexts. Buy Tryptamine 2-(3-indolyl)ethylamine online
Structure
IUPAC Name |
N-[2-(1H-indol-3-yl)ethyl]-N-propylpropan-1-amine;hydrochloride |
Source
 |
|---|---|---|
InChI |
InChI=1S/C16H24N2.ClH/c1-3-10-18(11-4-2)12-9-14-13-17-16-8-6-5-7-15(14)16;/h5-8,13,17H,3-4,9-12H2,1-2H3;1H |
Source
|
InChI Key |
AIAASKTUEVUIQM-UHFFFAOYSA-N |
Source
|
Canonical SMILES |
CCCN(CCC)CCC1=CNC2=CC=CC=C21.Cl |
Source
|
Molecular Formula |
C16H25ClN2 |
Source
|
DSSTOX Substance ID |
DTXSID5048897 |
Source
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Molecular Weight |
280.83 g/mol |
Source
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CAS No. |
7558-73-8 |
Source
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Biosynthetic and Metabolic Pathways of Tryptamine Derivatives Relevant to Dpt
Precursor Conversion to Tryptamine (B22526)
The foundational molecule for the synthesis of tryptamine and its derivatives is the essential amino acid L-tryptophan. The primary biosynthetic step involves the decarboxylation of L-tryptophan, a reaction that removes the carboxylic acid group from the amino acid to yield tryptamine. This conversion is a critical link between primary metabolism and the synthesis of a wide array of biologically active indole (B1671886) alkaloids.
This enzymatic conversion is catalyzed by a class of enzymes known as aromatic L-amino acid decarboxylases (AADC, EC 4.1.1.28). In some organisms, a more substrate-specific enzyme, L-tryptophan decarboxylase (TDC, EC 4.1.1.105), performs this function. These enzymes are found across various life forms, including mammals, plants, and microbes. In the mammalian brain, AADC is responsible for the synthesis of tryptamine, which acts as a trace amine neuromodulator. Additionally, certain commensal bacteria within the human gastrointestinal tract, such as Ruminococcus gnavus, possess tryptophan decarboxylase and contribute to the body’s tryptamine pool by converting dietary tryptophan.
The reaction can be summarized as follows: L-Tryptophan → Tryptamine + CO₂ (Catalyzed by AADC/TDC)
N-Methylation Processes in Tryptamine Biosynthesis
Following the formation of the primary tryptamine structure, further modification can occur at the amino group of the ethylamine (B1201723) side chain. The process of N-methylation is a key pathway for the biosynthesis of various naturally occurring tryptamine derivatives, such as N,N-dimethyltryptamine (DMT). This process serves as a relevant biological model for understanding the synthesis of N,N-dialkylated tryptamines like DPT.
N-methylation is a two-step process for dimethylated compounds, catalyzed by a specific enzyme that transfers methyl groups to the primary amine. The first methylation results in the formation of N-methyltryptamine (NMT), and a subsequent second methylation of NMT yields N,N-dimethyltryptamine (DMT).
Role of Indolethylamine-N-methyltransferase (INMT)
The primary enzyme responsible for the N-methylation of tryptamine and related indolethylamines is Indolethylamine-N-methyltransferase (INMT, EC 2.1.1.49). INMT is a member of the methyltransferase family of enzymes, which facilitate the transfer of a methyl group from a donor molecule to an acceptor.
The universal methyl donor for this reaction is S-adenosyl-L-methionine (SAM). INMT catalyzes the transfer of a methyl group from SAM to the nitrogen atom of the tryptamine’s amino group. In this process, SAM is converted to S-adenosyl-L-homocysteine (SAH). The enzymatic activity of INMT has been identified in various mammalian tissues, including the lungs.
The reactions are as follows:
Tryptamine + SAM → N-Methyltryptamine (NMT) + SAH (Catalyzed by INMT)
NMT + SAM → N,N-Dimethyltryptamine (DMT) + SAH (Catalyzed by INMT)
While INMT specifically catalyzes methylation, this enzymatic mechanism of N-alkylation provides a framework for understanding how N,N-dipropyltryptamine could be biosynthetically formed, should an analogous enzyme capable of transferring propyl groups exist.
Enzymatic Metabolism of Tryptamine Compounds
Tryptamine and its derivatives are subject to enzymatic breakdown, which is a critical process for their clearance from the body. The primary metabolic pathway involves oxidative deamination, a reaction catalyzed by a family of enzymes known as monoamine oxidases. This process is fundamental to the metabolism of many monoamine neurotransmitters and dietary amines.
Monoamine Oxidase (MAO) Involvement
Monoamine oxidase (MAO, EC 1.4.3.4) is the principal enzyme involved in the catabolism of tryptamines. MAO exists in two main isoforms, MAO-A and MAO-B, which are located on the outer membrane of mitochondria. Both isoforms are capable of metabolizing tryptamine.
The preference for each isoform can vary depending on the specific tryptamine derivative and the tissue type. For unsubstituted tryptamine, both MAO-A and MAO-B contribute significantly to its metabolism in various human tissues, including the liver, kidneys, and brain. MAO-A preferentially metabolizes serotonin (B10506), while MAO-B shows a preference for phenylethylamine, but both act on dopamine (B1211576) and tryptamine. The metabolism of N,N-dialkylated tryptamines like DMT is also primarily carried out by MAO, which protects the body from their effects when ingested orally without an MAO inhibitor. It is understood that DPT is also metabolized by monoamine oxidase.
The reaction catalyzed by MAO is an oxidative deamination, which converts the amine group into an aldehyde and produces ammonia (B1221849) and hydrogen peroxide as byproducts.
Identification of Specific Metabolites
The action of monoamine oxidase on tryptamine results in the formation of an unstable intermediate, which is then converted to a primary metabolite. The principal product of tryptamine’s oxidative deamination is indole-3-acetaldehyde (IAL).
This aldehyde is a key intermediate that can be further metabolized by other enzymes. Indole-3-acetaldehyde can be oxidized by aldehyde dehydrogenase (ALDH) to form indole-3-acetic acid (IAA), a major urinary metabolite. Alternatively, it can be reduced by aldehyde reductase to form tryptophol.
For N,N-dialkylated tryptamines such as DMT, the metabolic pathways are similar and include:
N-Oxidation: Formation of N,N-dimethyltryptamine-N-oxide (DMT-NO).
N-Dealkylation: Removal of one of the alkyl groups to form the corresponding secondary amine (e.g., N-methyltryptamine from DMT).
Aromatic and Aliphatic Hydroxylation: The addition of hydroxyl groups to the indole ring or the alkyl side chains, often mediated by cytochrome P450 (CYP) enzymes like CYP2D6.
Glucuronidation and Sulfation: Phase II metabolic reactions where glucuronic acid or sulfate (B86663) groups are attached to hydroxylated metabolites to increase water solubility and facilitate excretion.
These pathways, particularly N-dealkylation, hydroxylation, and N-oxidation, are considered the main routes for the biotransformation of various synthetic tryptamines.
Data Tables
Table 1: Key Enzymes in Tryptamine Biosynthesis and Metabolism
| Enzyme Name | Abbreviation | EC Number | Function |
| Aromatic L-amino acid decarboxylase | AADC | 4.1.1.28 | Catalyzes the decarboxylation of L-tryptophan to tryptamine. |
| L-tryptophan decarboxylase | TDC | 4.1.1.105 | A more specific enzyme that catalyzes the decarboxylation of L-tryptophan to tryptamine. |
| Indolethylamine-N-methyltransferase | INMT | 2.1.1.49 | Catalyzes the N-methylation of tryptamine and N-methyltryptamine using SAM as a methyl donor. |
| Monoamine Oxidase A/B | MAO-A / MAO-B | 1.4.3.4 | Catalyzes the oxidative deamination of tryptamines to their corresponding aldehydes. |
| Aldehyde Dehydrogenase | ALDH | 1.2.1.3 | Oxidizes indole-3-acetaldehyde to indole-3-acetic acid. |
| Cytochrome P450 2D6 | CYP2D6 | 1.14.14.1 | Can mediate hydroxylation of the indole ring of N,N-dialkylated tryptamines. |
Table 2: Precursors and Metabolites in Tryptamine Pathways
| Compound Name | Role | Description |
| L-Tryptophan | Precursor | The essential amino acid that serves as the starting material for tryptamine biosynthesis. |
| Tryptamine | Intermediate | The core molecule formed by the decarboxylation of L-tryptophan. |
| S-Adenosyl-L-methionine | Co-substrate | The universal methyl group donor for N-methylation reactions catalyzed by INMT. |
| N-Methyltryptamine | Intermediate | The product of the first methylation of tryptamine. |
| N,N-Dimethyltryptamine | Product Example | The final product of the double methylation of tryptamine, used as a model for DPT. |
| Indole-3-acetaldehyde | Primary Metabolite | The aldehyde formed from the oxidative deamination of tryptamine by MAO. |
| Indole-3-acetic acid | Secondary Metabolite | Formed by the oxidation of indole-3-acetaldehyde. |
| Tryptophol | Secondary Metabolite | Formed by the reduction of indole-3-acetaldehyde. |
| N,N-Dialkyltryptamine-N-oxide | Metabolite | A potential metabolite for compounds like DPT, formed by N-oxidation. |
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