| Tryptophan | |
|---|---|
| Systematic name | (S)-2-Amino-3-(1H-indol-3-yl)-propanoic acid |
| Abbreviations | Trp W |
| Chemical formula | C11H12N2O2 |
| Molecular mass | 204.23 g mol−1 |
| Melting point | 289 °C |
| Density | ? g cm-3 |
| Isoelectric point | 5.89 |
| pKa | 2.38 9.34 |
| CAS number | [73-22-3] |
| EINECS number | 200-795-6 |
| SMILES | N/A |
| [image] | |
| Disclaimer and references | |
Tryptophan is an Amino acid and essential in Human nutrition. It is one of the 20 amino acids in the Genetic code (codon UGG). Only the L-stereoisomer appears in mammalian protein.
Tryptophan has been implicated as a possible cause of Schizophrenia in people who cannot metabolize it properly. When improperly metabolized it creates a waste product in the brain which is toxic and causes hallucinations and delusions. Trp has also been indicated as an aid for schizophrenic patients.
In 1989, a large outbreak of a mysterious, disabling, and in some cases deadly autoimmune illness called Eosinophilia-myalgia syndrome was traced to an improperly-prepared Batch of Trp. The bacterial culture used to synthesize Trp by a major Japanese manufacturer, Showa Denko KK, had recently been genetically engineered to increase Trp production: With the higher Trp concentration in the culture medium, the purification process had also been streamlined to reduce costs, and a purification step that used Charcoal absorption to remove impurities had been omitted. This allowed another bacterial metabolite through the purification, resulting in the presence of an end-product contaminant responsible for the toxic effects. Regardless of the origin of the toxicity, Trp was banned from sale in the US, and other countries followed suit. Such bureaucratic action neglecting the most important fact established regarding the biochemistry of Trp: that it is an Essential amino acid that humans cannot live without eating, led to renewed questioning as to whether the FDA was a science based or political agency.
Though Trp supplements are still banned in the US from over-the-counter sale, properly-produced pharmaceutical-grade tryptophan continues to be used legally as an essential Nutrient in infant formulas and intravenous feeding, and, in recent years, compounding pharmacies and some mail-order supplement retailers have begun selling Trp to the general public - sometimes as a supplement for "pets." Trp has also remained on the market as a prescription drug (Tryptan) which some psychiatrists continue to prescribe, particularly as an augmenting agent for people who are unresponsive to antidepressant drugs. Indeed, Trp has continued to be used in clinical and experimental studies employing human patients and subjects. Several of these studies suggest Trp can effectively treat the fall/winter depression variant of Seasonal affective disorder (SAD).
| Tryptamines |
|---|
| 4-Acetoxy-DET | 4-Acetoxy-DIPT | 5-MeO-AMT | 5-MeO-DALT | 5-MeO-DET | 5-MeO-DIPT | 5-MeO-DMT | 5-MeO-MIPT | AET | AMT | Baeocystin | Bufotenin | DET | DIPT | DMT | DPT | Ethocin | Ibogaine | Iprocin | Miprocin | Melatonin | Norbaeocystin | Psilocin | Psilocybin | Rizatriptan | Serotonin | Sumatriptan | Tryptamine | Tryptophan |
| Amino acids |
| Alanine | Arginine | Asparagine | Aspartic acid | Cysteine | Glutamic acid | Glutamine | Glycine | Histidine | Isoleucine | Leucine | Lysine | Methionine | Phenylalanine | Proline | Serine | Threonine | Tryptophan | Tyrosine | Valine |
| Essential amino acid | Protein | Peptide | Genetic code |