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Merck
CN

93650

Sigma-Aldrich

Tryptamine hydrochloride

≥98.0% (AT)

Synonym(s):

2-(3-Indolyl)ethylamine hydrochloride, 3-(2-Aminoethyl)indole hydrochloride

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About This Item

Empirical Formula (Hill Notation):
C10H12N2 · HCl
CAS Number:
343-94-2
Molecular Weight:
196.68
Beilstein:
3568419
EC Number:
206-446-4
MDL number:
MFCD00012682
UNSPSC Code:
12352100
PubChem Substance ID:
24889915

Key Documents

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Assay

≥98.0% (AT)

mp

253-255 °C (lit.)
253-255 °C

SMILES string

Cl[H].NCCc1c[nH]c2ccccc12

InChI

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

InChI key

KDFBGNBTTMPNIG-UHFFFAOYSA-N

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Application

Reactant for preparation of:
  • Tryptamine derivatives as inhibitors against hepatitis B virus
  • Carbamoyl epipodophyllotoxins as potential antitumor agents
  • Anthranilic acid derivatives as CCK receptor antagonists
  • Brassinin derivatives as indoleamine 2,3-dioxygenase inhibitors
  • Antispasmodic agents
  • β-carbolinium cations as new antimalarial agents

Biochem/physiol Actions

Vasoactive; may have a neuromodulator function.

Other Notes

Biogenic amine formed from the decarboxylation of tryptophan by L-aromatic amino acid decarboxylase.
Substrate for the assay of arylamine N-methyltransferase; and for the determination of monoamine oxidase activity in tissue homogenates

Regulatory Information

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Arylamine N-methyltransferase.
E S Lyon et al.
Methods in enzymology, 77, 263-266 (1981-01-01)
S.H. Snyder et al.
Methods in Enzymology, 17B, 741-741 (1971)
Parawee Kanjanaphachoat et al.
Plant molecular biology, 78(6), 525-543 (2012-02-03)
A mutant M47286 with a stunted growth, low fertility and dark-brown phenotype was identified from a T-DNA-tagged rice mutant library. This mutant contained a copy of the T-DNA tag inserted at the location where the expression of two putative tryptophan
Desirée Cigaran Schuck et al.
Cytometry. Part A : the journal of the International Society for Analytical Cytology, 79(11), 959-964 (2011-10-22)
Melatonin and its derivatives modulate the Plasmodium falciparum and Plasmodium chabaudi cell cycle. Flow cytometry was employed together with the nucleic acid dye YOYO-1 allowing precise discrimination between mono- and multinucleated forms of P. falciparum-infected red blood cell. The use
Weslee S Glenn et al.
Journal of the American Chemical Society, 133(48), 19346-19349 (2011-11-05)
Installing halogens onto natural products can generate compounds with novel or improved properties. Notably, enzymatic halogenation is now possible as a result of the discovery of several classes of halogenases; however, applications are limited because of the narrow substrate specificity
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