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T2891

Sigma-Aldrich

Tryptamine

≥99%, crystalline

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
Beilstein:
125513
EC Number:
200-510-5
MDL number:
MFCD00005661
UNSPSC Code:
12352100

Assay

≥99%

form

crystalline

color

white

bp

137 °C/0.15 mmHg (lit.)

mp

113-116 °C (lit.)

storage temp.

−20°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; biogenic amine formed from the decarboxylation of tryptophan by L-aromatic amino acid decarboxylase.

Pictograms

CorrosionExclamation mark
GHS05,GHS07

Signal Word

Danger

Hazard Statements

H302,H317,H318

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

365.0 °F - closed cup

Flash Point(C)

185 °C - closed cup

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Tryptamine may couple dopaminergic and serotonergic transmission in the brain.
A V Juorio et al.
General pharmacology, 21(5), 613-616 (1990-01-01)
A J Greenshaw
Progress in neuro-psychopharmacology & biological psychiatry, 13(3-4), 431-443 (1989-01-01)
1. The relevance of trace amine research is outlined for PEA and T in the context of psychotherapeutic drug action, particularly in relation to the actions of MAO-inhibitor antidepressant drugs. 2. Evidence for the neuronal localization of these amines and
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)
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.
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.
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