5-Methoxytryptophan

5-Methoxytryptophan (5-MTP), or 5-methoxy-L-tryptophan, also known as 5-methoxy-α-carboxytryptamine or as cytoguardin, is an endogenous metabolite of tryptophan with anti-inflammatory and anti-fibrotic effects.^[1][2][3] It is biosynthesized in two steps by tryptophan hydroxylase (TPH) and then by hydroxyindole O-methyltransferase (HIOMT), with 5-hydroxytryptophan (5-HTP) as a metabolic intermediate.^[1][2][3] 5-MTP is also a metabolic precursor of 5-methoxytryptamine.^[4] The compound promotes sleep in rodents similarly to melatonin.^[5] In contrast to melatonin, 5-MTP did not show affinity for melatonin receptors.^[6] It was first described in the scientific literature by at least 1951.^[7]

Other names5-MTP; 5-Methoxy-L-tryptophan; L-5-Methoxytryptophan; 5-MeO-tryptophan; α-Carboxy-5-methoxytryptamine; 5-Methoxy-α-carboxytryptamine; Cytoguardin

ATC code

• None

CAS Number

• 2504-22-5
  25197-96-0

PubChem CID

• 151018

Quick facts Clinical data, Other names ...

5-Methoxytryptophan

Clinical data
Other names	5-MTP; 5-Methoxy-L-tryptophan; L-5-Methoxytryptophan; 5-MeO-tryptophan; α-Carboxy-5-methoxytryptamine; 5-Methoxy-α-carboxytryptamine; Cytoguardin
ATC code	None
Identifiers
IUPAC name (2S)-2-amino-3-(5-methoxy-1H-indol-3-yl)propanoic acid
CAS Number	2504-22-5 25197-96-0
PubChem CID	151018
ChemSpider	106971
UNII	5B7WK2X4JP
ChEBI	CHEBI:74049
CompTox Dashboard (EPA)	DTXSID50862973
Chemical and physical data
Formula	C12H14N2O3
Molar mass	234.255 g·mol−1
3D model (JSmol)	Interactive image
SMILES COC1=CC2=C(C=C1)NC=C2C[C@@H](C(=O)O)N
InChI InChI=1S/C12H14N2O3/c1-17-8-2-3-11-9(5-8)7(6-14-11)4-10(13)12(15)16/h2-3,5-6,10,14H,4,13H2,1H3,(H,15,16)/t10-/m0/s1 Key:KVNPSKDDJARYKK-JTQLQIEISA-N

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