5-Methyltryptamine

Not to be confused with 5-Methoxytryptamine.

5-Methyltryptamine (5-MeT, 5-Me-T) is a non-selective serotonin receptor agonist and serotonin releasing agent of the tryptamine family that has been used in scientific research.^[1][2] It is related to other 5-substituted tryptamines such as serotonin (5-hydroxytryptamine; 5-HT) and 5-methoxytryptamine (5-MeO-T).^[1][2] The compound is also a positional isomer of N-methyltryptamine (NMT).^[1]

5-Methyltryptamine

Clinical data
Other names	5-MeT; 5-Me-T; 5-Methyl-T; 5-MT; PAL-22; PAL22; NSC-90805; NSC90805
Drug class	Serotonin receptor agonist; Serotonin releasing agent
Identifiers
IUPAC name 2-(5-methyl-1H-indol-3-yl)ethanamine
CAS Number	1821-47-2 1010-95-3 (hydrochloride)
PubChem CID	15760
ChemSpider	14987
ChEBI	CHEBI:125675
ChEMBL	ChEMBL331241
CompTox Dashboard (EPA)	DTXSID10171250
Chemical and physical data
Formula	C11H14N2
Molar mass	174.247 g·mol−1
3D model (JSmol)	Interactive image
SMILES CC1=CC2=C(C=C1)NC=C2CCN
InChI InChI=1S/C11H14N2/c1-8-2-3-11-10(6-8)9(4-5-12)7-13-11/h2-3,6-7,13H,4-5,12H2,1H3 Key:PYOUAIQXJALPKW-UHFFFAOYSA-N

Pharmacology

5-MeT is known to act as a potent serotonin 5-HT_2A receptor full agonist, with an EC₅₀Tooltip half-maximal effective concentration of 6.00 nM and an E_maxTooltip maximal efficacy of 100%.^[1] In addition, it is known to be a ligand of the serotonin 5-HT_1A^[3] and 5-HT_2B receptors^[2] and an agonist of the serotonin 5-HT_1D^[4][5] and 5-HT_2C receptors.^[6][7][8] Similarly to tryptamine and 5-MeO-T, but in contrast to serotonin, 5-MeT shows very low potency as an agonist of the serotonin 5-HT₃ receptor (EC₅₀ = 60,000 nM).^[9]

In addition to acting as an agonist of various serotonin receptors, 5-MeT is a monoamine releasing agent (MRA), with high selectivity for induction of serotonin release over induction of dopamine and norepinephrine release (EC₅₀ = 139 nM, >10,000 nM, and >10,000 nM, respectively, in rat brain synaptosomes).^[1] However, its potency for induction of serotonin release in this system is 23-fold lower than its potency as a serotonin 5-HT_2A receptor agonist.^[1]

Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin, and 5-MeO-T, are known to be very rapidly metabolized and thereby inactivated by monoamine oxidase A (MAO-A) in vivo and to have very short elimination half-lives.^{[10][11][12][13][14][2][15]} However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived serotonergic psychedelic effects in humans.^{[16][11][1][15]}

Chemistry

The predicted log P of 5-MeT is 1.84 to 1.9.^[17][18]

See also

• 1-Methyltryptamine
• 2-Methyltryptamine
• 5-Acetyltryptamine (acetryptine)
• 5-Benzyloxytryptamine
• 5-Carboxamidotryptamine
• 5-(Nonyloxy)tryptamine