5-Hydroxytryptophan

5-Hydroxytryptophan

Names
IUPAC name 2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoic acid
Identifiers
CAS Number	4350-09-8 N
3D model (Jmol)	Interactive image
ChEBI	CHEBI:17780 Y
ChEMBL	ChEMBL350221 Y
ChemSpider	388413 Y
ECHA InfoCard	100.022.193
IUPHAR/BPS	4671
KEGG	D07339 Y
MeSH	5-Hydroxytryptophan
PubChem	144
UNII	C1LJO185Q9 Y
InChI 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 Y Key: LDCYZAJDBXYCGN-VIFPVBQESA-N Y InChI=1/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 Key: LDCYZAJDBXYCGN-VIFPVBQEBZ
SMILES O=C(O)[C@@H](N)Cc2c1cc(O)ccc1nc2
Properties
Chemical formula	C11H12N2O3
Molar mass	220.23 g·mol−1
Density	1.484 g/mL
Melting point	298 to 300 °C (568 to 572 °F; 571 to 573 K)
Boiling point	520.6 °C (969.1 °F; 793.8 K)
Pharmacology
ATC code	N06AX01 (WHO)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
N  (what is YN ?)
Infobox references

5-Hydroxytryptophan (5-HTP), also known as oxitriptan (INN), is a naturally occurring amino acid and chemical precursor as well as a metabolic intermediate in the biosynthesis of the neurotransmitters serotonin and melatonin from tryptophan.

5-HTP is sold over the counter in the United States, Canada, and the United Kingdom as a dietary supplement for use as an antidepressant, appetite suppressant, and sleep aid. It is also marketed in many European countries for the indication of major depression under the trade names Cincofarm, Levothym, Levotonine, Oxyfan, Telesol, Tript-OH, and Triptum.

A 2002 review by the Cochrane Collaboration concluded that although the data evaluated suggests that 5-HTP is more effective than placebo in the treatment of depression, the evidence was insufficient to be conclusive due to a severe lack of high quality research. More and larger studies are needed to determine if 5-HTP is truly effective in treating depression.

5-HTP is sometimes taken by people coming down from MDMA to relieve post-MDMA dysphoria. As 5-HTP is a necessary precursor for the brain to produce more serotonin, and MDMA use depletes a person's natural serotonin levels, it is believed that taking 5-HTP after consuming MDMA will speed up serotonin production. DanceSafe claims that the anecdotal evidence is widespread and that the theory is physiologically reasonable. A research conducted by Wang et al. in 2007 suggested a recovery, when MDMA-induced depletions of 5-HT were restored in rats after administering 5-HTP.