7-Hydroxytryptophan
Names
IUPAC name
2-amino-3-(7-hydroxy-1H-indol-3-yl)propanoic acid
Identifiers
ChEBI
ChemSpider
MeSH
5-Hydroxytryptophan
InChI=1S/C11H12N2O3/c12-8(11(15)16)4-6-5-13-10-7(6)2-1-3-9(10)14/h1-3,5,8,13-14H,4,12H2,(H,15,16)
Key: VQSRKJZICBNQJG-UHFFFAOYSA-N
C1=CC2=C(C(=C1)O)NC=C2CC(C(=O)O)N
Properties
C 11 H 12 N 2 O 3
Molar mass
−1
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
7-Hydroxytryptophan (7-HTP ) is a non-proteinogenic amino acid . It is also a 5-hydroxytryptophan (5-HTP) positional isomer , a L-tryptophan derivative , structurally belonging to the hydroxytryptophan family, and a substituted tryptophan with a hydroxyl group at position 7 of the indole ring . It is not a precursor of serotonin . 7-Hydroxytryptophan is a metabolite detected in human urine .
It has been investigated for its role as a precursor in melanin -related oxidative processes .[ 1] [ 2]
7-Hydroxytryptophan is found in human urine , but its formation pathway in the body is unknown.
7-Hydroxytryptophan is present in the mussel adhesive protein Pvfp-1 of Perna viridis as a post-translationally modified tryptophan residue. This modified residue exhibits redox activity, potentially substituting for DOPA .[ 3]
7-Hydroxytryptophan was first identified in fungi and was isolated from the fruiting bodies of the fungus Cortinarius purpurascens , where it can serve as a precursor for the synthesis of azepino-indole alkaloids (so-called purpurascenins A–C) via the Pictet–Spengler reaction .[ 4]
7-Hydroxytryptophan in archaea [ edit ] 7-hydroxytryptophan has been identified as a rare post-translational modification in the active site of the enzyme MCR (methyl-coenzyme M reductase ) in methanotrophic archaea (ANME-MCR group) But the role of ANME is assumed to be that 7-hydroxytryptophan compensates for the lack of arginine methylation .[ 5]
In normal tissues , 7-HTP either remains metabolically inactive or is incorporated into normal amino acid metabolism pathways without the formation of toxic products.
In tumor cells expressing tryptophan hydroxylase , 7-hydroxytryptophan is enzymatically converted in situ into the toxic compound 5,7-dihydroxytryptamine (5,7-DHT ). This metabolite induces apoptosis selectively in serotonin -producing tumor cells . And also interferes with the autocrine ability to synthesize serotonin . The conversion of 7-HTP to 5,7-DHT is completely inhibited by the specific tryptophan hydroxylase inhibitor para-chlorophenylalanine (Fenclonine).[ 6] [ 7]
Oxidase from the gill plates of mussels (Mytilus edulis oxidize 7-Hydroxytryptophan and other related compounds, whereas mammalian ceruloplasmin has almost no effect on the compounds.[ 8]
^ Smaniotto, Anna; Comai, Stefano; Bertazzo, Antonella; Costa, Carlo V. L.; Allegri, Graziella; Seraglia, Roberta; Traldi, Pietro (2006). "A mass spectrometric investigation on the possible role of tryptophan and 7-hydroxytryptophan in melanogenesis". Journal of Mass Spectrometry: JMS . 41 (7): 921– 930. doi :10.1002/jms.1051 . ISSN 1076-5174 . PMID 16810640 . ^ PubChem. "7-Hydroxytryptophan" . pubchem.ncbi.nlm.nih.gov . Retrieved 2026-02-18 . ^ Zhao, Hua; Sagert, Jason; Hwang, Dong Soo; Waite, J. Herbert (2009-08-28). "Glycosylated hydroxytryptophan in a mussel adhesive protein from Perna viridis" . The Journal of Biological Chemistry . 284 (35): 23344– 23352. doi :10.1074/jbc.M109.022517 ISSN 0021-9258 . PMC 2749108 PMID 19584055 . ^ Lam, Yen T. H.; Hoppe, Jana; Dang, Quang N.; Porzel, Andrea; Soboleva, Alena; Brandt, Wolfgang; Rennert, Robert; Hussain, Hidayat; Davari, Mehdi D.; Wessjohann, Ludger; Arnold, Norbert (2023-06-23). "Purpurascenines A-C, Azepino-Indole Alkaloids from Cortinarius purpurascens: Isolation, Biosynthesis, and Activity Studies on the 5-HT2A Receptor". Journal of Natural Products . 86 (6): 1373– 1384. doi :10.1021/acs.jnatprod.2c00716 . ISSN 1520-6025 . PMID 37306303 . ^ "Hydroxytryptophan - an overview | ScienceDirect Topics" . www.sciencedirect.com . Retrieved 2026-02-23 .^ Walther, Diego J.; Peter, Jens-Uwe; Bader, Michael (2002-06-15). "7-Hydroxytryptophan, a novel, specific, cytotoxic agent for carcinoids and other serotonin-producing tumors". Cancer . 94 (12): 3135– 3140. doi :10.1002/cncr.10592 . ISSN 0008-543X . PMID 12115345 . ^ Walther, Diego J.; Peter, Jens-Uwe; Bader, Michael (2002-06-15). "7-hydroxytryptophan, a novel, specific, cytotoxic agent for carcinoids and other serotonin-producing tumors" Cancer . 94 (12): 3135– 3140. doi :10.1002/cncr.10592 . ISSN 0008-543X . PMID 12115345 . ^ Blaschko, H.; Levine, W. G. (1960). "A comparative study of hydroxyindole oxidases" . British Journal of Pharmacology and Chemotherapy . 15 (4): 625– 633. doi :10.1111/j.1476-5381.1960.tb00290.x . ISSN 0366-0826 . PMC 1482277 PMID 19108143 .
Tryptamines
1-Methyl-DMT (1,N ,N -TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N ,N -TMT (2-methyl-DMT) 3-IAAR 4-Fluoro-DMT 4-Fluoro-T 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-Nitro-T (Nitro-I) 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T 7-Hydroxytryptophan Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) DALT DAT DBT Desformylflustrabromine DET (T-9) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N -Benzyltryptamine (T-NB, NB-T)N -DEAOP-NETN -DEAOP-NMTNAT NBoc-DMT (NB-DMT) NET/NETP NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan 4-Hydroxytryptamines esters /ethers 5-Hydroxy- and5-methoxytryptamines
2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan )5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N ,N -TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N ,N ,O -TMS; O -methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MBT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O ,N -DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O -methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N ,N ,N -TMS) Bufotenin (5-HO-DMT; N ,N -DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N -CA-5-MT) L-741604 MS-245 N -DEAOP-5-MeO-NETN -DEAOP-5-MeO-NMTN -Feruloylserotonin (moschamine)NB-5-MeO-DALT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O -Acetylbufotenine (5-AcO-DMT)O -Pivalylbufotenine (5-t -BuCO-DMT)Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT) N -Acetyltryptaminesα-Alkyltryptamines
5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O -DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N ,O -TMS (5-MeO-α,N -DMT) α,N ,N ,O -TeMS (5-MeO-α,N ,N -TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 α-Ketotryptamines Cyclized tryptamines
5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD )Harmala alkaloidsβ-carbolines (e.g., 5-methoxyharmalan , 6-MeO-THH , 6-methoxyharmalan , 9-Me-BC , β-carboline (norharman) , fenharmane , harmaline , harmalol , harmane , harmine , LY-266,097 , pinoline , tetrahydroharmine , tryptoline )Iboga alkaloidsibogaine , ibogamine , noribogaine , tabernanthine )Ibogalogs (e.g., catharanthalog , fluorogainalog , ibogainalog , ibogaminalog (DM-506) , LS-22925 , noribogainalog , noribogaminalog , PHA-57378 , PNU-22394 , tabernanthalog )Imidazolylindoles (e.g., AGH-107 , AGH-192 , AH-494 )Metralindole Morpholinylethylindoles (e.g., mor-T , 5-MeO-mor-T )Partial ergolines and lysergamides (e.g., NDTDI , RU-27849 , RU-28251 , RU-28306 , FHATHBIN , LY-178210 , Bay R 1531 (LY-197206) , LY-293284 , 10,11-seco-LSD , 10,11-secoergoline (α,N -Pip-T) , CT-5252 )Pertines (e.g., alpertine , milipertine , oxypertine , solypertine )Piperidinylethylindoles (e.g., pip-T , 5-MeO-pip-T , indoramin , indolylethylfentanyl )Pyrrolidinylethylindoles (e.g., pyr-T , 4-HO-pyr-T , 5-MeO-pyr-T , 4-F-5-MeO-pyr-T , L-760790 )Pyrrolidinylmethylindoles (e.g., MPMI , 4-HO-MPMI (lucigenol) , 5F-MPMI , 5-MeO-MPMI , CP-122288 , CP-135807 , eletriptan , MSP-2020 )Tetrahydrocarbazolamines (e.g., ciclindole , flucindole , frovatriptan , LY-344864 , ramatroban )Tetrahydropyridinylindoles (e.g., RS134-49 , RU-28253 , NEtPhOH-THPI )Tetrahydropyrroloquinolines (e.g., bufothionine , O -methylnordehydrobufoteninedehydrobufotenine )Yohimbans (e.g., yohimbine , rauwolscine , spegatrine , corynanthine , ajmalicine , reserpine , deserpidine , rescinnamine ) Isotryptamines Related compounds
2-Azapsilocin 2,3-Dihydro-L-tryptophan 2,3-Dihydrotryptamine 2,3-Dihydro-DMT 2,3-Dihydro-NMT 2,3-Dihydro-DET 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline , alosetron , gevotroline , latrepirdine , lurosetron , mebhydrolin , tiflucarbine )Amedalin Benzindopyrine Benzofurans (e.g., 3-APB (1-oxa-AMT) , 5-MeO-DiBF (1-oxa-5-MeO-DiPT) , BPAP , 3-F-BPAP , dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT) , mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT) , MiPBF (1-oxa-MiPT) , oxa-noribogaine )Benzothiophenes (e.g., S-DMT (1-thia-DMT) , 3-APBT (1-thia-AMT) )Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT , DMHT )I-32 IAL IN-399 Indalpine Indazolethylamines (e.g., AL-34662 , AL-38022A , O -methyl-AL-34662VU6067416 , YM-348 )Indenylethylamines (e.g., C-DMT (1-carba-DMT) )Indolizinylethylamines (e.g., TACT908 (2ZEDMA) , 1ZP2MA , 1Z2MAP1O )Indolylaminopropanes (e.g., 1-API , 2-API , 4-API , 5-API (5-IT; PAL-571) , 6-API (6-IT) , 7-API )Iprindole Masupirdine Medmain Molindone Non-tryptamine triptans (e.g., avitriptan , LY-334370 , naratriptan )
Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134 )Phenethylamines (e.g., phenethylamine , amphetamine )Piperidinylbenzimidazolines (e.g., benperidol , timiperone )Piperazinylbenzisothiazoles (e.g., lurasidone , perospirone , tiospirone , ziprasidone )Piperidinylbenzisoxazoles (e.g., iloperidone , milsaperidone , ocaperidone , paliperidone , risperidone )Piperidinylindoles (e.g., BRL-54443 , LY-334370 , naratriptan , sertindole , SN-22 )Pirlindole Pyridinylbenzimidazoles (e.g., droperidol )Pyridinylindoles (e.g., tepirindole )Pyridopyrroloquinoxalines (e.g., IHCH-7113 , IHCH-7079 , IHCH-7086 , lumateperone , deulumateperone , ITI-1549 )Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA) , 3-pyrrolylethylamine (3-NEA) , 3-pyrrolylpropylamine )Pyrrolopyridinylethylamines (e.g., WAY-208466 )Quinolinylethylamines (e.g., mefloquine )Ro60-0213 Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088 , LY-367265 , RU-24,969 )Tetrahydropyridinylpyrrolopyridines (e.g., (R )-69 (3IQ) , (R )-70 , CP-93129 , CP-94253 )Tetrindole Tipindole Zilpaterol (RU-42173)
