An intermediate in serotonin biosynthesis
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5-hydroxy-L-Tryptophan

Item No. 20539

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
5-hydroxy-L-tryptophan
CAS Number
4350-09-8
Synonyms
  • 5-HTP
  • L-5-Hydroxytryptophan
  • Oxitriptan
Molecular Formula
C11H12N2O3
Formula Weight
220.2
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
Acetic Acid (2%): 1 mg/mlMethanol: 0.1 mg/ml
λmax
209, 275 nm
SMILES
OC1=CC=C2C(C(C[C@H](N)C(O)=O)=CN2)=C1
InChi Code
InChI=1S/C11H12N2O3/c12-9(11(15)16)3-6-5-13-10-2-1-7(14)4-8(6)10/h1-2,4-5,9,13-14H,3,12H2,(H,15,16)/t9-/m0/s1
InChi Key
LDCYZAJDBXYCGN-VIFPVBQESA-N
Shipping & Storage Information
Storage
Room temperature
Shipping
Room temperature in continental US; may vary elsewhere
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    1 g

    $36

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    5 g

    $120

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    10 g

    $219

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    25 g

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    Product Description

    5-hydroxy-L-Tryptophan (5-HTP) is an intermediate in the biosynthesis of serotonin from tryptophan.1 When injected systemically in animals, 5-HTP is converted to serotonin and has both peripheral and central nervous system effects.2,3,4 In ex vivo studies, 5-HTP can be metabolized to melatonin with circadian rhythmicity, using serotonin as an intermediate.5 5-HTP can also be synthesized by gut microbiota and acts as an activator of the aryl hydrocarbon receptor.6

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Martinez, A., Knappskog, P.M., and Haavik, J. A structural approach into human tryptophan hydroxylase and its implications for the regulation of serotonin biosyntheis. Curr. Med. Chem. 8(9), 1077-1091 (2001).

    2. Haberzettl, R., Fink, H., and Bert, B. The murine serotonin syndrome - evaluation of responses to 5-HT-enhancing drugs in NMRI mice. Behav. Brain Res. 277, 204-210 (2015).

    3. Laporta, J., Moore, S.A.E., Weaver, S.R., et al. Increasing serotonin concentrations alter calcium and energy metabolism in dairy cows. J. Endocrinol. 226(1), 43-55 (2015).

    4. Schmid, C.L., and Bohn, L.M. Serotonin, but not N-methyltryptamines, activates the serotonin 2A receptor via a β-arrestin2/Src/Akt signaling complex in vivo. J. Neurosci. 30(40), 13513-13524 (2010).

    5. Cahill, G.M., and Besharse, J.C. Circadian regulation of melatonin in the retina of Xenopus laevis: imitation by serotonin availability. J. Neurochem. 54(2), 716-719 (1990).

    6. Sridharan, G.V., Choi, K., Klemashevich, C., et al. Prediction and quantification of bioactive microbiota metabolites in the mouse gut. Nat. Commun. 5, 5492 (2014).