Tryptophol
| Tryptophol | |
|---|---|
 |
|
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2-(1H-Indol-3-yl)ethanol |
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Other names
Indole-3-ethanol; 3-Indole ethyl alcohol |
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| Identifiers | |
| CAS number | 526-55-6  |
| PubChem | 10685 |
| ChEMBL | CHEMBL226545 |
| Jmol-3D images | Image 1 |
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| Properties | |
| Molecular formula | C10H11NO |
| Molar mass | 161.20 g mol−1 |
| Melting point |
59 °C |
| Except where noted otherwise, data are given for materials in their standard state (at 25 °C, 100 kPa) | |
| Infobox references | |
Tryptophol is a chemical compound that induces sleep in humans. It is formed in the liver after disulfiram treatment.[1] It is also produced by the trypanosomal parasite in sleeping sickness.[1][2]
It is also found in wine as a secondary product of alcoholic fermentation.[3][4] It has been first described by Felix Ehrlich in 1912. Ehrlich demonstrated that yeast attacks the natural amino acids essentially by splitting off carbon dioxide and re-placing the amino group with hydroxyl. By this reaction, the tryptophan gives rise to tryptophol.[5]
It is used in the synthesis of the drug indoramin.
Precursor [edit]
Tryptophol have been used as precursor in the synthesis of tryptamines like DMT.[6]
See also [edit]
References [edit]
- ^ a b Cornford, E. M.; Bocash, W. D.; Braun, L. D.; Crane, P. D.; Oldendorf, W. H.; MacInnis, A. J. (1979). "Rapid distribution of tryptophol (3-indole ethanol) to the brain and other tissues". Journal of Clinical Investigation 63 (6): 1241–1248. doi:10.1172/JCI109419. PMC 372073. PMID 447842.
- ^ Richard Seed, J.; Seed, T. M.; Sechelski, J. (1978). "The biological effects of tryptophol (indole-3-ethanol): Hemolytic, biochemical and behavior modifying activity". Comparative Biochemistry and Physiology Part C: Comparative Pharmacology 60 (2): 175. doi:10.1016/0306-4492(78)90091-6.
- ^ Ribéreau-Gayon, P.; Sapis, J. C. (1965). "On the presence in wine of tyrosol, tryptophol, phenylethyl alcohol and gamma-butyrolactone, secondary products of alcoholic fermentation". Comptes rendus hebdomadaires des seances de l'Academie des sciences. Serie D: Sciences naturelles 261 (8): 1915–1916. PMID 4954284. (Article in French)
- ^ Gil, C.; Gómez-Cordovés, C. (1986). "Tryptophol content of young wines made from Tempranillo, Garnacha, Viura and Airén grapes". Food Chemistry 22: 59. doi:10.1016/0308-8146(86)90009-9.
- ^ Richard W. Jackson (1930). "A synthesis of tryptophol". Journal of Biological Chemistry 88 (3): 659–662.
- ^ https://www.erowid.org/archive/rhodium/chemistry/tryptophol.html
