Last updated
  • 1-(5-fluoro-1H-indol-3-yl)propan-2-amine
CAS Number
PubChem CID
CompTox Dashboard (EPA)
Chemical and physical data
Formula C11H13FN2
Molar mass 192.237 g·mol−1
3D model (JSmol)
  • Fc1cc2c(cc1)[nH]cc2CC(N)C
  • InChI=1S/C11H13FN2/c1-7(13)4-8-6-14-11-3-2-9(12)5-10(8)11/h2-3,5-7,14H,4,13H2,1H3 Yes check.svgY
 X mark.svgNYes check.svgY  (what is this?)    (verify)

5-Fluoro-α-methyltryptamine (5-Fluoro-αMT, 5F-AMT), also known as PAL-544, [1] is a putative stimulant, entactogen, and psychedelic tryptamine derivative related to α-methyltryptamine (αMT). It has been found to act as a well-balanced serotonin-norepinephrine-dopamine releasing agent, [1] a 5-HT2A receptor agonist, [2] and a potent and specific MAO-A inhibitor. [3] [4] [5] [6] which suggests that 5-fluoro-αMT could be an active psychedelic in humans, although it is not known to have been tested in humans and could be dangerous due to its strong inhibition of MAO-A.


See also

Related Research Articles

<i>alpha</i>-Methyltryptamine Chemical compound

α-Methyltryptamine is a psychedelic, stimulant, and entactogen drug of the tryptamine class. It was originally developed as an antidepressant by workers at Upjohn in the 1960s, and was used briefly as an antidepressant in Russia under the trade name Indopan before being discontinued.

5-Methoxy-<i>N</i>,<i>N</i>-diisopropyltryptamine Psychedelic tryptamine

5-Methoxy-N,N-diisopropyltryptamine is a psychedelic tryptamine and the methoxy derivative of diisopropyltryptamine (DiPT).

<span class="mw-page-title-main">5-MeO-aMT</span> Chemical compound

5-MeO-aMT or 5-methoxy-α-methyltryptamine, α,O-Dimethylserotonin (Alpha-O) is a potent psychedelic tryptamine. It is soluble in ethanol.

<i>alpha</i>-Ethyltryptamine Chemical compound

α-Ethyltryptamine, also known as etryptamine, is a psychedelic, stimulant, and entactogenic drug of the tryptamine class. It was originally developed and marketed as an antidepressant under the brand name Monase by Upjohn in the 1960s.

<span class="mw-page-title-main">5-MeO-AET</span> Chemical compound

5-Methoxy-alpha-ethyltryptamine (5-MeO-α-ET) is a psychoactive drug and member of the tryptamine chemical class. It produces psychedelic and stimulant effects.

<span class="mw-page-title-main">4-Hydroxyamphetamine</span> Group of stereoisomers

4-Hydroxyamphetamine (4HA), also known as hydroxyamfetamine, hydroxyamphetamine, oxamphetamine, norpholedrine, para-hydroxyamphetamine, and α-methyltyramine, is a drug that stimulates the sympathetic nervous system.

<span class="mw-page-title-main">Monoamine oxidase B</span> Protein-coding gene in the species Homo sapiens

Monoamine oxidase B, also known as MAOB, is an enzyme that in humans is encoded by the MAOB gene.

<i>alpha</i>-Methylserotonin Chemical compound

α-Methylserotonin (αMS), also known as α-methyl-5-hydroxytryptamine (α-methyl-5-HT) or 5-hydroxy-α-methyltryptamine (5-HO-αMT), is a tryptamine derivative closely related to the neurotransmitter serotonin (5-HT). It acts as a non-selective serotonin receptor agonist and has been used extensively in scientific research to study the function of the serotonin system.

<span class="mw-page-title-main">4-Benzylpiperidine</span> Chemical compound

4-Benzylpiperidine is a drug and research chemical used in scientific studies. It acts as a monoamine releasing agent with 20- to 48-fold selectivity for releasing dopamine versus serotonin. It is most efficacious as a releaser of norepinephrine, with an ec50 of 109/41.4/5246nM for DA/NE/5HT, respectively. It has a fast onset of action and a short duration. It also functions as a monoamine oxidase inhibitor (MAOI) with preference for MAO-A.

A serotonin releasing agent (SRA) is a type of drug that induces the release of serotonin into the neuronal synaptic cleft. A selective serotonin releasing agent (SSRA) is an SRA with less significant or no efficacy in producing neurotransmitter efflux at other types of monoamine neurons.

A serotonin–dopamine releasing agent (SDRA) is a type of drug which induces the release of serotonin and dopamine in the body and/or brain.

<span class="mw-page-title-main">Amiflamine</span>

Amiflamine (FLA-336) is a reversible inhibitor of monoamine oxidase A (MAO-A), thereby being a RIMA, and, to a lesser extent, semicarbazide-sensitive amine oxidase (SSAO), as well as a serotonin releasing agent (SRA). It is a derivative of the phenethylamine and amphetamine chemical classes. The (+)-enantiomer is the active stereoisomer.

<span class="mw-page-title-main">4-Methyl-α-ethyltryptamine</span> Chemical compound

4-Methyl-α-ethyltryptamine (4-Me-αET) is a putative stimulant, psychedelic, and entactogen drug of the tryptamine class. It is a designer drug and is sold online as a "research chemical".

<span class="mw-page-title-main">7-Methyl-α-ethyltryptamine</span> Chemical compound

7-Methyl-α-ethyltryptamine (7-Me-αET) is a tryptamine derivative related to α-ethyltryptamine (αET). It was discovered by a team at Upjohn in the early 1960s. It has similar pharmacological effects to αET, but is both 3-4 times more potent as a serotonin releasing agent, and 10 times more potent as a monoamine oxidase inhibitor, making it potentially hazardous as this pharmacological profile is shared with drugs such as PMA and 4-MTA, which are known to be dangerous in humans when used at high doses.

<span class="mw-page-title-main">Substituted tryptamine</span> Class of indoles

Substituted tryptamines, or serotonin analogues, are organic compounds which may be thought of as being derived from tryptamine itself. The molecular structures of all tryptamines contain an indole ring, joined to an amino (NH2) group via an ethyl (−CH2–CH2−) sidechain. In substituted tryptamines, the indole ring, sidechain, and/or amino group are modified by substituting another group for one of the hydrogen (H) atoms.

<span class="mw-page-title-main">Head-twitch response</span>

The head-twitch response (HTR) is a rapid side-to-side head movement that occurs in mice and rats after the serotonin 5-HT2A receptor is activated. The prefrontal cortex may be the neuroanatomical locus mediating the HTR. Many serotonergic hallucinogens, including lysergic acid diethylamide (LSD), induce the head-twitch response, and so the HTR is used as a behavioral model of hallucinogen effects. However while there is generally a good correlation between compounds that induce head twitch in mice and compounds that are hallucinogenic in humans, it is unclear whether the head twitch response is primarily caused by 5-HT2A receptors, 5-HT2C receptors or both, though recent evidence shows that the HTR is mediated by the 5-HT2A receptor and modulated by the 5-HT2C receptor. Also, the effect can be non-specific, with head twitch responses also produced by some drugs that do not act through 5-HT2 receptors, such as phencyclidine, yohimbine, atropine and cannabinoid receptor antagonists. As well, compounds such as 5-HTP, fenfluramine, 1-Methylpsilocin, Ergometrine, and 3,4-di-methoxyphenethylamine (DMPEA) can also produce head twitch and do stimulate serotonin receptors, but are not hallucinogenic in humans. This means that while the head twitch response can be a useful indicator as to whether a compound is likely to display hallucinogenic activity in humans, the induction of a head twitch response does not necessarily mean that a compound will be hallucinogenic, and caution should be exercised when interpreting such results.

<span class="mw-page-title-main">6-Fluoro-AMT</span> Chemical compound

6-Fluoro-α-methyltryptamine is a tryptamine derivative related to compounds such as alpha-methyltryptamine and 5-MeO-AMT, which has been sold as a designer drug. Animal tests showed it to be somewhat less active than AMT or 5-fluoro-AMT, but it was nevertheless allegedly manufactured and sold from the laboratory operated by Leonard Pickard and Gordon Todd Skinner, who described 6-fluoro-AMT as "a beast".

<span class="mw-page-title-main">5-Chloro-αMT</span> Chemical compound

5-Chloro-α-methyltryptamine (5-Chloro-αMT), also known as PAL-542, is a tryptamine derivative related to α-methyltryptamine (αMT) and one of only a few known specific serotonin-dopamine releasing agents (SDRAs). It has been investigated in animals as a potential treatment for cocaine dependence. The EC50 values of 5-chloro-αMT in evoking the in vitro release of serotonin (5-HT), dopamine (DA), and norepinephrine (NE) in rat synaptosomes were reported as 16 nM, 54 nM, and 3434 nM, with an NE/DA ratio of 63.6 and a DA/5-HT ratio of 3.38, indicating that it is a highly specific and well-balanced SDRA. However, 5-chloro-αMT has also been found to act as a potent full agonist of the 5-HT2A receptor, with an EC50 value of 6.27 nM and an efficacy of 105%, and almost assuredly acts as a potent agonist of other serotonin receptors as well.

<span class="mw-page-title-main">7-Chloro-AMT</span>

7-Chloro-α-methyltryptamine (7-Cl-AMT) is a tryptamine derivative with stimulant effects, invented in the 1960s. It is a weak monoamine oxidase inhibitor but its pharmacology has not otherwise been studied by modern techniques, though several closely related compounds are known to act as serotonin–dopamine releasing agents and agonists of the 5-HT2A receptor.

<span class="mw-page-title-main">5-Fluoro-AET</span> Chemical compound

5-Fluoro-α-ethyltryptamine (5-F-AET) is a tryptamine derivative which acts as a serotonin–dopamine releasing agent and agonist of the 5-HT2A receptor.


  1. 1 2 Banks ML, Bauer CT, Blough BE, Rothman RB, Partilla JS, Baumann MH, Negus SS (June 2014). "Abuse-related effects of dual dopamine/serotonin releasers with varying potency to release norepinephrine in male rats and rhesus monkeys". Experimental and Clinical Psychopharmacology. 22 (3): 274–284. doi:10.1037/a0036595. PMC   4067459 . PMID   24796848.
  2. Chairungsrilerd N, Furukawa K, Tadano T, Kisara K, Ohizumi Y (March 1998). "Effect of gamma-mangostin through the inhibition of 5-hydroxy-tryptamine2A receptors in 5-fluoro-alpha-methyltryptamine-induced head-twitch responses of mice". British Journal of Pharmacology. 123 (5): 855–62. doi:10.1038/sj.bjp.0701695. PMC   1565246 . PMID   9535013.
  3. Kinemuchi H, Arai Y (October 1986). "Selective inhibition of monoamine oxidase A and B by two substrate-analogues, 5-fluoro-alpha-methyltryptamine and p-chloro-beta-methylphenethylamine". Research Communications in Chemical Pathology and Pharmacology. 54 (1): 125–8. doi:10.1016/0028-3908(91)90057-i. PMID   3797802. S2CID   34761939.
  4. Kim SK, Toyoshima Y, Arai Y, Kinemuchi H, Tadano T, Oyama K, et al. (April 1991). "Inhibition of monoamine oxidase by two substrate-analogues, with different preferences for 5-hydroxytryptamine neurons". Neuropharmacology. 30 (4): 329–35. doi:10.1016/0028-3908(91)90057-i. PMID   1852266. S2CID   34761939.
  5. Corne SJ, Pickering RW (1967). "A possible correlation between drug-induced hallucinations in man and a behavioural response in mice". Psychopharmacologia. 11 (1): 65–78. doi:10.1007/bf00401509. PMID   5302272. S2CID   3148623.
  6. Yamamoto T, Ueki S (January 1981). "The role of central serotonergic mechanisms on head-twitch and backward locomotion induced by hallucinogenic drugs". Pharmacology, Biochemistry, and Behavior. 14 (1): 89–95. doi:10.1016/0091-3057(81)90108-8. PMID   6258178. S2CID   45561708.

Further reading