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Merck
CN

93640

Tryptamine

≥98.0% (NT)

Synonym(s):

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

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About This Item

Empirical Formula (Hill Notation):
C10H12N2
CAS Number:
61-54-1
Molecular Weight:
160.22
EC Number:
200-510-5
UNSPSC Code:
12352100
MDL number:
MFCD00005661
Beilstein/REAXYS Number:
125513

Key Documents

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assay

≥98.0% (NT)

ign. residue

≤0.05%

bp

137 °C/0.15 mmHg (lit.)

mp

113-116 °C (lit.), 115-118 °C

storage temp.

2-8°C

SMILES string

NCCc1c[nH]c2ccccc12

InChI

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

InChI key

APJYDQYYACXCRM-UHFFFAOYSA-N

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Biochem/physiol Actions

Vasoactive; may have a neuromodulator function.
Vasoactive; may have a neuromodulator function; biogenic amine formed from the decarboxylation of tryptophan by L-aromatic amino acid decarboxylase.

pictograms

CorrosionExclamation mark
GHS05,GHS07

signalword

Danger

Hazard Classifications

Acute Tox. 4 Oral - Eye Dam. 1 - Skin Sens. 1A

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

365.0 °F - closed cup

flash_point_c

185 °C - closed cup

ppe

Eyeshields, Gloves, type N95 (US)

Regulatory Information

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Marika Righi et al.
The Journal of organic chemistry, 77(14), 6351-6357 (2012-06-26)
An efficient, one-pot reductive alkylation of indoles with N-protected aminoethyl acetals in the presence of TES/TFA is reported. It represents the first general method for the direct synthesis of tryptamine derivatives from indoles and nitrogen-functionalized acetals. This convergent and versatile
Xianrong Xing et al.
Biosensors & bioelectronics, 31(1), 277-283 (2011-11-15)
An imprinted electrochemical sensor based on polypyrrole-sulfonated graphene (PPy-SG)/hyaluronic acid-multiwalled carbon nanotubes (HA-MWCNTs) for sensitive detection of tryptamine was presented. Molecularly imprinted polymers (MIPs) were synthesized by electropolymerization using tryptamine as the template, and para-aminobenzoic acid (pABA) as the monomer.
Taketo Tsugehara et al.
Comparative biochemistry and physiology. Toxicology & pharmacology : CBP, 157(1), 93-102 (2012-10-16)
Arylalkylamine N-acetyltransferase (AANAT; EC 2.3.1.87) catalyzes the N-acetylation of arylalkylamines. A cDNA encoding AANAT (ApAANAT) was cloned from Antheraea pernyi by PCR. The cDNA of 1966 bp encodes a 261 amino acid protein. The amino acid sequence was found to
Xiangbing Qi et al.
Journal of the American Chemical Society, 133(26), 10050-10053 (2011-06-16)
We report the first total synthesis of (±)-trigonoliimine C, a member of a family of structurally complex alkaloids, in 10 steps from tryptamine and 6-methoxytryptamine. Our convergent synthetic strategy relies on a selective oxidative rearrangement of an unsymmetrical 2,2'-bis-tryptamine.
6-halogenochromones bearing tryptamine: one-step access to potent and highly selective inhibitors of breast cancer resistance protein.
Glaucio Valdameri et al.
ChemMedChem, 7(7), 1177-1180 (2012-05-23)
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