Tryptamine

Title: Tryptamine
CAS Registry Number: 61-54-1
CAS Name: 1H-Indole-3-ethanamine
Additional Names: 3-(2-aminoethyl)indole; 2-(3-indolyl)ethylamine
Molecular Formula: C10H12N2
Molecular Weight: 160.22
Percent Composition: C 74.96%, H 7.55%, N 17.48%
Literature References: Occurs in plants. Synthesis starting with nitroethylene and indole: Noland, Hartman, J. Am. Chem. Soc. 76, 3227 (1954). Alternate routes: Thesing, Schulde, Ber. 85, 324 (1952); Jackson, Smith, J. Chem. Soc. 1965, 3498; Tacconi, Farmaco Ed. Sci. 20, 902 (1965); S. Takano et al., Heterocycles 6, 1167 (1977); I. Fleming, M. Woolias, J. Chem. Soc. Perkin Trans. 1 1979, 829. X-ray structure determn: Wakahara et al., Tetrahedron Lett. 1970, 4999. Review of tryptamine syntheses: J. E. Saxton in R. H. F. Manske, The Alkaloids vol. VIII (1965) pp 8-10.
Properties: Needles from petr ether, mp 118°. uv max (ethanol): 222, 282, 290 nm (log e 4.56, 3.78, 3.71). Sol in ethanol, acetone. Practically insol in water, ether, benzene, chloroform.
Melting point: mp 118°
Absorption maximum: uv max (ethanol): 222, 282, 290 nm (log e 4.56, 3.78, 3.71)
Derivative Type: Hydrochloride
Molecular Formula: C10H12N2.HCl
Molecular Weight: 196.68
Percent Composition: C 61.07%, H 6.66%, N 14.24%, Cl 18.03%
Properties: Needles from ethanol + ethyl acetate, mp 248°. uv max (95% ethanol): 221, 275, 281, 290 nm (log e 4.52, 3.73, 3.75, 3.69).
Melting point: mp 248°
Absorption maximum: uv max (95% ethanol): 221, 275, 281, 290 nm (log e 4.52, 3.73, 3.75, 3.69)
Tryptazan Tryptophan Tryptophol TSQ Tsuduranine

Tryptamine
Identifiers
CAS number 61-54-1 YesY
PubChem 1150
ChEMBL CHEMBL6640 N
IUPHAR ligand 125
Jmol-3D images Image 1
Properties
Molecular formula C10H12N2
Molar mass 160.22 g mol−1
Appearance white to orange crystalline powder[1]
Melting point 113-116˚C[1]
Boiling point 137˚C[1]
Solubility in water negligible solubility in water[1]
Hazards
Flash point 185˚C[1]
 N (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

Tryptamine is a monoamine alkaloid found in plants, fungi, and animals. It contains an indole ring structure, and is structurally similar to the amino acid tryptophan, from which it derives its name. Tryptamine is found in trace amounts in the brains of mammals and is believed to play a role as a neuromodulator or neurotransmitter.[2]

The tryptamine chemical structure is the backbone for a group of compounds termed collectively tryptamines. This group includes many biologically active compounds, including neurotransmitters and psychedelic drugs.

The concentration of tryptamine in rat brains is about 3.5 pmol/g.[3]