|Formula C11H12N2O3||Molar mass 220.2246 g/mol|
IUPAC ID 2-amino-3- (5-hydroxy-1H-indol-3-yl) propanoic acid
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.
Potential side effects of 5-HTP include heartburn, stomach pain, nausea, vomiting, diarrhea, drowsiness, sexual problems, vivid dreams or nightmares, and muscle problems. Because 5-HTP has not been thoroughly studied in a clinical setting, possible side effects and interactions with other drugs are not well known.
When combined with antidepressants of the MAOI or SSRI class, high dose 5-HTP can cause acute serotonin syndrome in rats. In humans 5-HTP has never been clinically associated with serotonin syndrome, although 5-HTP can precipitate mania when added to a MAOI. Due to the rate-limiting nature of the decarboxylase enzyme which converts 5-HTP into serotonin, the risk of serotonin syndrome with monoamine oxidase inhibitors is thought to be quite low unless both MAOIs and 5-HTP are taken in large quantities.
When combined with carbidopa (as a treatment for symptoms of Parkinson's disease), 5-HTP causes nausea and vomiting; however this can be alleviated via administration of granisetron. As mentioned above under pharmacology, cases of scleroderma-like illness have been reported in patients using carbidopa and 5-HTP.
Oral 5-HTP results in an increase in urinary 5-HIAA, a serotonin metabolite, indicating that 5-HTP is peripherally metabolized to serotonin, which is then metabolized. This might cause a false positive test in tests looking for carcinoid syndrome. Due to the conversion of 5-HTP into serotonin by the liver, there may be a significant risk of heart valve disease from serotonin's effect on the heart.
It has been suggested that 5-HTP may cause eosinophilia-myalgia syndrome (EMS), a serious condition which results in extreme muscle tenderness, myalgia, and blood abnormalities. However, there is evidence to show that EMS was likely caused by a contaminant in certain 5-HTP supplements.
5-HTP is decarboxylated to serotonin (5-hydroxytryptamine or 5-HT) by the enzyme aromatic-L-amino-acid decarboxylase with the help of vitamin B6. This reaction occurs both in nervous tissue and in the liver. 5-HTP crosses the blood–brain barrier, while 5-HT does not. Excess 5-HTP, especially when administered with vitamin B6, is thought to be metabolized and excreted.
The psychoactive action of 5-HTP is derived from its increase in production of serotonin in central nervous system tissue.
Research shows that co-administration with carbidopa greatly increases plasma 5-HTP levels. However, several studies have reported that 5-HTP is effective even without a peripheral decarboxylase inhibitor (e.g. carbidopa). Other studies have indicated the risk of a scleroderma-like condition resulting from the combination of 5-HTP and carbidopa.