5-Fluorotryptamine

5-Fluorotryptamine (5-fluoro-T, 5-FT, or 5-F-T; code name PAL-284) is a serotonin receptor agonist and monoamine releasing agent of the tryptamine family.^[1][2]

5-Fluorotryptamine

Clinical data
Other names	5-Fluoro-T; 5-FT; 5-F-T; PAL-284; PAL284
Drug class	Serotonin receptor agonist; Monoamine releasing agent
Identifiers
IUPAC name 2-(5-fluoro-1H-indol-3-yl)ethanamine
CAS Number	576-16-9 2711-58-2 (hydrochloride)
PubChem CID	164682
IUPHAR/BPS	146
ChemSpider	144367
UNII	AY99XA22FG
ChEMBL	ChEMBL275628
CompTox Dashboard (EPA)	DTXSID20206229
Chemical and physical data
Formula	C10H11FN2
Molar mass	178.210 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1=CC2=C(C=C1F)C(=CN2)CCN
InChI InChI=1S/C10H11FN2/c11-8-1-2-10-9(5-8)7(3-4-12)6-13-10/h1-2,5-6,13H,3-4,12H2 Key:ZKIORVIXEWIOGB-UHFFFAOYSA-N

Pharmacology

5-FT is known to have affinity for the serotonin 5-HT_1A and 5-HT_2A receptors, with K_i values of 18 nM and 6.0–3,908 nM, respectively.^[3][4][5] It is a full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 2.64 to 58 nM and an E_maxTooltip half-maximal effective concentration of 110%.^[2][4] The drug is also an agonist of the serotonin 5-HT_1A receptor, with an EC₅₀ of 129 nM.^[4] 5-HT shows high affinity for the serotonin 5-HT_2B and 5-HT_2C receptors as well (K_i = 5.7 nM and 3.72 nM, respectively).^[5] In addition to its serotonin receptor agonism, 5-FT is a serotonin–dopamine releasing agent (SDRA), with EC₅₀ values for induction of monoamine release of 10.1 nM for serotonin, 82.3 nM for dopamine, and 464 nM for norepinephrine.^[2] The drug is also a weak monoamine oxidase inhibitor (MAOI), with IC₅₀Tooltip half-maximal inhibitory concentration values of 13,200 nM for monoamine oxidase A (MAO-A) and 52,500 nM for monoamine oxidase B (MAO-B).^[1][6]

Despite its serotonin 5-HT_2A receptor agonism, 5-FT failed to induce the head-twitch response, a behavioral proxy of psychedelic effects, in rodents, suggesting that it may not have hallucinogenic effects in humans.^[1][6]

Tryptamines without substitutions at the amine or alpha carbon, such as tryptamine, serotonin (5-hydroxytryptamine; 5-HT), and 5-methoxytryptamine (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.^{[7][8][9][10][11][12][13]} However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.^{[14][8][2][13]}

History

5-FT was first described in the scientific literature by 1983.^[15]

See also

• 6-Fluorotryptamine (6-FT)
• 7-Chlorotryptamine (7-CT)
• 5-Fluoro-AMT
• 5-Fluoro-AET
• 5-Fluoro-DMT
• 5-Fluoro-DET
• Bretisilocin (5-fluoro-MET)
• 5-Fluoro-EPT
• 5-Methyltryptamine
• 5-Methoxytryptamine