α-Methyl-5-hydroxytryptophan

α-Methyl-5-hydroxytryptophan (α-Me-5-HTP) is a synthetic tryptamine derivative, an artificial amino acid, and a prodrug of α-methylserotonin.^[1][2] It is the α-methylated derivative of 5-hydroxytryptophan (5-HTP), while αMS is the α-methylated analogue of serotonin.^[1][2] Along with α-methyltryptophan (α-MTP), α-Me-5-HTP has been suggested for potential therapeutic use in the treatment of conditions thought by some authors to be related to serotonin deficiency, such as depression.^[2]

Other namesalpha-Methyl-5-hydroxytryptophan; alpha-Methyl-L-5-hydroxytryptophan; α-Me-5-HTP; α-Methyl-5-HTP; αM-5-HTP; alpha-Me-5-HTP; alpha-Methyl-5-HTP

Drug classTyrosine hydroxylase inhibitor; Serotonin receptor agonist

CAS Number

• 150852-19-0

PubChem CID

• 6453138

Quick facts Clinical data, Other names ...

α-Methyl-5-HTP

Clinical data
Other names	alpha-Methyl-5-hydroxytryptophan; alpha-Methyl-L-5-hydroxytryptophan; α-Me-5-HTP; α-Methyl-5-HTP; αM-5-HTP; alpha-Me-5-HTP; alpha-Methyl-5-HTP
Drug class	Tyrosine hydroxylase inhibitor; Serotonin receptor agonist
Identifiers
IUPAC name (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)-2-methylpropanoic acid
CAS Number	150852-19-0
PubChem CID	6453138
ChemSpider	4955531
CompTox Dashboard (EPA)	DTXSID70970468
Chemical and physical data
Formula	C12H14N2O3
Molar mass	234.255 g·mol−1
3D model (JSmol)	Interactive image
SMILES C[C@](CC1=CNC2=C1C=C(C=C2)O)(C(=O)O)N
InChI InChI=1S/C12H14N2O3/c1-12(13,11(16)17)5-7-6-14-10-3-2-8(15)4-9(7)10/h2-4,6,14-15H,5,13H2,1H3,(H,16,17)/t12-/m0/s1 Key:QNQKTYDMWUGLPA-LBPRGKRZSA-N

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αMS is a non-selective serotonin receptor agonist, including of the serotonin 5-HT₂ receptors, and has been described as a "substitute neurotransmitter" of serotonin.^[2][3][4][5] However, whereas αMS itself is too hydrophilic to efficiently cross the blood–brain barrier, thus being peripherally selective, α-MTP and α-Me-5-HTP are able to cross the blood–brain barrier and, following transformation, deliver αMS into the brain.^[2][6] Besides αMS, α-methylmelatonin can be formed in small amounts from α-Me-5-HTP.^[7]

In addition to their serotonergic activity, α-Me-5-HTP and αMS have been found to act as norepinephrine releasing agents similarly to α-methylphenylalanine and to other α-alkylated tryptamines.^[8][9][10] Moreover, α-Me-5-HTP is also a tyrosine hydroxylase inhibitor similarly to α-methyltyrosine, as well as an aromatic L-amino acid decarboxylase (AAAD) inhibitor, and has been found to deplete levels of brain norepinephrine in animals, although not levels of brain dopamine.^{[2][11][8][12][13]} Because of these actions, α-Me-5-HTP shows antihypertensive effects and reduces locomotor activity in animals.^[12]