T2891
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:
Molecular Weight:
160.22
Beilstein:
125513
EC Number:
MDL number:
UNSPSC Code:
12352100
Recommended Products
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.
Signal Word
Danger
Hazard Statements
Precautionary Statements
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
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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)
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.
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
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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