5-HTP (5-Hydroxytryptophan)
Sleep & Stress Support
Overview
- 5‑Hydroxytryptophan (5‑HTP) is a naturally occurring amino acid precursor to the neurotransmitter serotonin.
- It is derived from the essential amino acid L‑tryptophan.
- It is commonly taken as a dietary supplement to support mood, sleep, and appetite regulation by increasing central serotonin synthesis.
Chemistry
- 5‑HTP’s chemical formula is C₁₁H₁₂N₂O₃, with a molecular weight of 220.23 g mol⁻¹.
- Its IUPAC name is 3-(2‑amino‑ethyl)-5-hydroxyindole.
- The molecule consists of an indole ring (a fused benzene‑pyrrole) bearing a hydroxyl group at the 5‑position and an attached side chain (−CH₂‑CH₂‑NH₂) at the 3‑position, which is the same side chain as in tryptophan but lacks the carboxyl group; instead, it has a terminal amino group.
- The compound is a white crystalline powder, soluble in water and slightly soluble in ethanol.
- Its pKa values (≈9.5 for the amine, ≈2.4 for the phenolic hydroxyl) influence its ionization at physiological pH, allowing efficient transport across the intestinal epithelium and the blood‑brain barrier via the large‑neutral‑amino‑acid transporter.
- The molecule is chiral; the natural L‑enantiomer is the biologically active form.
Sources & Quality
- Commercial 5‑HTP is primarily extracted from the seed coats of the African plant Griffonia simplicifolia, which contains up to 20 % 5‑HTP in dry weight.
- The seeds are milled, and 5‑HTP is isolated through aqueous extraction followed by purification steps such as ion-exchange chromatography and crystallization.
- Synthetic routes exist, typically via oxidation of L‑tryptophan with a hydroxylation step, but these are less common due to cost.
- Quality‑grade supplements should be standardized to ≥ 95 % pure L‑5‑HTP, be free of heavy metals, and comply with GMP (Good Manufacturing Practice) standards.
- Third‑party testing (e.g., USP, NSF) confirms potency and lack of contaminants.
- Because the seed also contains other indole compounds, reputable manufacturers use purification to avoid co‑extraction of untested alkaloids.
- For maximal bioavailability, capsules with enteric coating can protect 5‑HTP from gastric degradation.
Where to Buy 5-HTP (5-Hydroxytryptophan)
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