2- (3-indolyl) ethylamine

Structural formula
General
Surname	2- (3-indolyl) ethylamine
other names	Tryptamine; 3- (2-aminoethyl) indole;
Molecular formula	C 10 H 12 N 2
Brief description	Hardly flammable crystalline solid
External identifiers / databases
EC number	200-510-5
ECHA InfoCard	100,000,464
PubChem	1150
DrugBank	DB08653
Wikidata	Q409439
properties
Molar mass	160.22 g mol −1
Physical state	firmly
Melting point	118 ° C
boiling point	136-138 ° C (0.2 hPa)
solubility	very sparingly soluble in water (1 g l −1 at 20 ° C); soluble in DMSO and methanol; practically insoluble in ether, benzene and chloroform;
safety instructions
H and P phrases	H: 302-317-318
	P: 280-302 + 352-305 + 351 + 338-333 + 313
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

2- (3-Indolyl) ethylamine (tryptamine) is a chemical compound from the tryptamine group and namesake of this group of substances.

Occurrence

2- (3-Indolyl) ethylamine is a monoamine compound that is a precursor molecule for many hormones and neurotransmitters. The biosynthesis generally starts from the amino acid tryptophan . The enzyme aromatic- L- amino acid decarboxylase decarboxylates tryptophan, producing tryptamine. Substitutions lead to a group of compounds collectively known as tryptamines . The most popular tryptamines are serotonin , an important neurotransmitter , and melatonin , a hormone that is involved in regulating the sleep-wake cycle.

Extraction and presentation

Tryptamine can be prepared by the Abramovitch-Shapiro synthesis method.

properties

2- (3-Indolyl) ethylamine is a flammable, difficult to ignite, crystalline solid that is very sparingly soluble in water.

use

2- (3-Indolyl) ethylamine is used in the manufacture of biologically active compounds such as neurotransmitters, psychotropic drugs, and ω-mercaptooctyltryptamide.

Individual evidence

↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2- (3-indolyl) ethylamine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .
↑ ^a ^b Datasheet Tryptamine, 98 +% from AlfaAesar, accessed on April 18, 2017 ( PDF )(JavaScript required) .
^ Gerhard Eisenbrand, Peter Schreier: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006 . Georg Thieme Verlag, 2014, ISBN 3-13-179532-8 , p. 1773 ( limited preview in Google Book search).
↑ Entry on tryptamines in the Human Metabolome Database (HMDB) , accessed on April 18, 2017.
↑ Abramovitch RA, Shapiro D.: 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and β-carbolines. In: Journal of the Chemical Society (Resumed). 1956, p. 4589, doi : 10.1039 / JR9560004589 .

[GESTIS-1] ↑ ^a ^b ^c ^d ^e ^f ^g ^h Entry on 2- (3-indolyl) ethylamine in the GESTIS substance database of the IFA , accessed on January 9, 2019(JavaScript required) .

[Alfa-2] Datasheet Tryptamine, 98 +% from AlfaAesar, accessed on April 18, 2017 ( PDF )(JavaScript required) .

[Gerhard_Eisenbrand,_Peter_Schreier-3] Gerhard Eisenbrand, Peter Schreier: RÖMPP Lexikon Lebensmittelchemie, 2nd edition, 2006 . Georg Thieme Verlag, 2014, ISBN 3-13-179532-8 , p. 1773 ( limited preview in Google Book search).

[4] Entry on tryptamines in the Human Metabolome Database (HMDB) , accessed on April 18, 2017.

[DOI10.1039/JR9560004589-5] Abramovitch RA, Shapiro D.: 880. Tryptamines, carbolines, and related compounds. Part II. A convenient synthesis of tryptamines and β-carbolines. In: Journal of the Chemical Society (Resumed). 1956, p. 4589, doi : 10.1039 / JR9560004589 .