TRYPTAMINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C10H12N2
Molecular Weight	160.2157
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NCCC1=CNC2=C1C=CC=C2

InChI

InChIKey=APJYDQYYACXCRM-UHFFFAOYSA-N

InChI=1S/C10H12N2/c11-6-5-8-7-12-10-4-2-1-3-9(8)10/h1-4,7,12H,5-6,11H2

HIDE SMILES / InChI

Molecular Formula	C10H12N2
Molecular Weight	160.2157
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Approval Year

Targets

Primary Target	Pharmacology	Potency
Monoamine oxidase A 52 Target ID: CHEMBL1951 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3094536	Substrate 661
Monoamine oxidase B 75 Target ID: CHEMBL2039 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3094536	Substrate 661
Trace amine-associated receptor 1 48 Target ID: CHEMBL5857 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27424325	Agonist 2752	46.9 µM [EC50]

PubMed

Title	Date	PubMed
Agonist high and low affinity state ratios predict drug intrinsic activity and a revised ternary complex mechanism at serotonin 5-HT(2A) and 5-HT(2C) receptors.	2000 Feb	10611640
[Metabolism and transport of auxin in plants].	2001	11757319
Heterocyclic derivatives of 2-(3,5-dimethylphenyl)tryptamine as GnRH receptor antagonists.	2001 Apr 23	11327594
2-(3,5-Dimethylphenyl)tryptamine derivatives that bind to the GnRH receptor.	2001 Apr 23	11327593
Exciplex-type behavior and partition of 3-substituted indole derivatives in reverse micelles made with benzylhexadecyldimethylammonium chloride, water and benzene.	2001 Feb	11272737
Characterization of 5-HT receptors in the parasitic nematode, Ascaris suum.	2001 Feb	11272652
Biological evaluation of hepatitis C virus helicase inhibitors.	2001 Jul 9	11425528
A tryptamine analog with high affinity to the heart tissues is a potential antiarrhythmic agent.	2001 Jun	11428666
Evaluation of methoxsalen, tranylcypromine, and tryptamine as specific and selective CYP2A6 inhibitors in vitro.	2001 Jun	11353760
The role of water bridges in directing the conformational preferences of 3-indole-propionic acid and tryptamine.	2001 Jun 13	11389651
Amino acid-decarboxylase activity of bacteria isolated from fermented pork sausages.	2001 Jun 15	11428577
Structure-activity studies leading to (-)1-(benzofuran-2-yl)-2-propylaminopentane, ((-)BPAP), a highly potent, selective enhancer of the impulse propagation mediated release of catecholamines and serotonin in the brain.	2001 May	11377178
Genotoxicity of naturally occurring indole compounds: correlation between covalent DNA binding and other genotoxicity tests.	2002	12211071
Poly(dimethylsiloxane) microchip for precolumn reaction and micellar electrokinetic chromatography of biogenic amines.	2002 Apr	11981862
Haploscleridamine, a novel tryptamine-derived alkaloid from a sponge of the order haplosclerida: an inhibitor of cathepsin K.	2002 Apr	11975521
1,2-bis(1H-indol-3-yl)ethane-1,2-dione, an indole alkaloid from the marine sponge Smenospongia sp.	2002 Apr	11975511
High-performance liquid chromatographic determination of biogenic amines in poultry carcasses.	2002 Aug 28	12188600
Screening for biologically active metabolites with endosymbiotic bacilli isolated from arthropods.	2002 Dec 17	12480104
Redox intermediates of plant and mammalian peroxidases: a comparative transient-kinetic study of their reactivity toward indole derivatives.	2002 Feb 1	11811944
Endogenous alkaloids in man. XXXVIII. "Chiral" and "achiral" determination of the neurotoxin TaClo (1-trichloromethyl-1,2,3,4-tetrahydro-beta-carboline) from blood and urine samples by high-performance liquid chromatography--electrospray ionization tandem mass spectrometry.	2002 Feb 15	11885861
Evaluation of isotryptamine derivatives at 5-HT(2) serotonin receptors.	2002 Jan 21	11755343
Role of 5-HT(2) receptors in the tryptamine-induced 5-HT syndrome in rats.	2002 Jul	12218512
Characterization of selected Spanish table wine samples according to their biogenic amine content from liquid chromatographic determination.	2002 Jul 31	12137502
In vitro and in vivo assessment of the antioxidant activity of melatonin and related indole derivatives.	2002 Jun	12236544
Effect of precursor feeding on alkaloid accumulation by a tryptophan decarboxylase over-expressing transgenic cell line T22 of Catharanthus roseus.	2002 Jun 26	12039535
Pharacine, a natural p-cyclophane and other indole derivatives from Cytophaga sp. strain AM13.1.	2002 Nov	12444694
Transient expression of strictosidine synthase in tobacco leaves by vacuum infiltration.	2002 Nov	12417910
A versatile linkage strategy for solid-phase synthesis of N,N-dimethyltryptamines and beta-carbolines.	2002 Nov 14	12423079
The use of restraints in Rietveld refinement of molecular compounds; a case study using the crystal structure determination of tryptamine free base.	2002 Oct	12324696
Phylogenetic analysis of 277 human G-protein-coupled receptors as a tool for the prediction of orphan receptor ligands.	2002 Oct 17	12429062
Formation of biogenic amines in a typical semihard Italian cheese.	2002 Sep	12233866
Stimulation of the catecholaminergic and serotoninergic neurons in the rat brain by R-(-)-1-(benzofuran-2-yl)-2-propylaminopentane, (-)-BPAP.	2002 Sep 20	12204771
Multiple forms of arylalkylamine N-acetyltransferase (NAT) from cockroach female colleterial glands and activity changes during oocyte maturation.	2003 Apr	12814788
Tryptamine-induced resistance in tryptophan decarboxylase transgenic poplar and tobacco plants against their specific herbivores.	2003 Apr	12775143
Determination of the amino acid tryptophan and the biogenic amine tryptamine in foods by the heavy atom induced-room temperature phosphorescence methodology.	2003 Apr	12741649
Highly efficient Lewis acid-catalysed Pictet-Spengler reactions discovered by parallel screening.	2003 Apr 7	12739676
Relative reactivities of histamine and indoleamines with acetaldehyde.	2003 Aug	12913282
Characterization of the serotoninergic system in the C57BL/6 mouse skin.	2003 Aug	12899690
Two chromone-secoiridoid glycosides and three indole alkaloid glycosides from Neonauclea sessilifolia.	2003 Feb	12620349
Monitoring volatile and nonvolatile amines in dried and salted roes of tuna (Thunnus thynnus L.) during manufacture and storage.	2003 Feb	12597499
Serotonin 5-hydroxytryptamine 2A receptor-coupled phospholipase C and phospholipase A2 signaling pathways have different receptor reserves.	2003 Jan	12490596
Foxy, a designer tryptamine hallucinogen.	2003 Jul-Aug	12908946
Functional study of rat 5-HT2A receptors using antisense oligonucleotides.	2003 Jun	12753068
Diurnal regulation of arylalkylamine N-acetyltransferase activity in chicken retinal cells in vitro: analysis of culture conditions.	2003 Mar 5	12629487
The influence of the brewing process on the formation of biogenic amines in beers.	2003 May	12677337
Total synthesis of debromoflustramine B via biomimetic alkylative cyclization.	2003 May 15	12735781
[Neurological syndromes associated with the ingestion of plants and fungi with a toxic component (II). Hallucinogenic fungi and plants, mycotoxins and medicinal herbs].	2003 May 16-31	12766871
Determination of biogenic amines by 3-(2-furoyl)quinoline-2-carboxaldehyde and capillary electrophoresis with laser-induced fluorescence detection.	2003 May 23	12862385
Qualitative determination of false-positive effects in the acetylcholinesterase assay using thin layer chromatography.	2003 May-Jun	12793457

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 20:02:59 GMT 2025` Edited by `admin` on `Mon Mar 31 20:02:59 GMT 2025`
Record UNII	422ZU9N5TV
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NSC-165212

Preferred Name

English

TRYPTAMINE

Systematic Name

English

2-(3-INDOLYL)ETHYLAMINE

Systematic Name

English

2-(1H-INDOL-3-YL)ETHANAMINE

Systematic Name

English

3-(2-AMINOETHYL)INDOLE

Systematic Name

English

2-(1H-INDOL-3-YL)ETHAN-1-AMINE

Systematic Name

English

3-INDOLEETHYLAMINE

Systematic Name

English

3-(2-AMINOETHYL)-1H-INDOLE

Systematic Name

English

INDOLE, 3-(2-AMINOETHYL)-

Systematic Name

English

TRYPTAMINE [MI]

Common Name

English

.BETA.-(3-INDOLYL)ETHYLAMINE

Systematic Name

English

2-(1H-INDOL-3-YL)ETHYLAMINE

Systematic Name

English

1H-INDOLE-3-ETHANAMINE

Systematic Name

English

3-INDOLEETHANAMINE

Systematic Name

English

Classification Tree Code System Code

WIKIPEDIA

TiHKAL