5-Hydroxytryptophan
Title: 5-Hydroxytryptophan
CAS Registry Number: 56-69-9
Additional Names: 5-HTP
Molecular Formula: C11H12N2O3
Molecular Weight: 220.22
Percent Composition: C 59.99%, H 5.49%, N 12.72%, O 21.80%
Literature References: Precursor of serotonin. Synthesis from 5-benzyloxyindole: Ek, Witkop, J. Am. Chem. Soc. 76, 5579 (1954); Shaw, Morris, Biochem. Prep. 9, 92 (1962); from 5-benzyloxytryptophan: Frangatos, Chubb, Can. J. Chem. 37, 1374 (1959); Frangatos, CA 619472 (1961 to Frank W. Horner); Ash, GB 845034 (1960 to May & Baker); from tryptophan: Renson et al., Biochem. Biophys. Res. Commun. 6, 20 (1961). Prepn of L- and D-forms: A. J. Morris, M. D. Armstrong, J. Org. Chem. 22, 306 (1957). Crystal and molecular structure of DL-form: Wakahara et al., Tetrahedron Lett. 1970, 3003. Use of L-5HTP in treatment of myoclonus: M. H. Van Woert, D. Rosenbaum, Adv. Neurol. 26, 107 (1979). Clinical trial in migraine: F. Titus et al., Eur. Neurol. 25, 327 (1986). Review: M. H. Van Woert, Orphan Drugs, F. E. Karch, Ed. (Marcel Dekker, New York, 1982) pp 13-31. Review of antidepressant efficacy: W. F. Byerley et al., J. Clin. Psychopharmacol. 7, 127-137 (1987); of metabolism and clinical experience: T. C. Birdsall, Altern. Med. Rev. 3, 271-280 (1998).
 
Derivative Type: DL-Form
Properties: Minute rods or needles from ethanol, dec 298-300°. uv max (H2O at pH 6.0): 278 nm. Soly in water at 5°: 1.0 g/100 ml; at 100°: 5.5 g/100 ml. Soly in 50% boiling alc: 2.5 g/100 ml. Aq solns are stable at low pH.
Absorption maximum: uv max (H2O at pH 6.0): 278 nm
 
Derivative Type: L-Form
CAS Registry Number: 4350-09-8
Additional Names: Oxitriptan; L-5HTP
Trademarks: Cincofarm (Lepori); Levothym (Lundbeck); Lévotonine (Pan Medica); Oxyfan (Coli); Telesol (Lasa); Tript-Oh (Sigma-Tau)
Properties: Crystals, [a]D20 -32.5° (H2O); [a]D20 +16.0° (4N HCl).
Optical Rotation: [a]D20 -32.5° (H2O); [a]D20 +16.0° (4N HCl)
 
Derivative Type: D-Form
CAS Registry Number: 4350-07-6
Properties: Crystals, [a]D20 +32.2° (H2O).
Optical Rotation: [a]D20 +32.2° (H2O)
 
Therap-Cat: Antidepressant; in treatment of myoclonus.

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