5-Bromotryptamine

5-Bromotryptamine (5-Br-T; developmental code name PAL-518) is a serotonin receptor modulator and monoamine releasing agent of the tryptamine family.^[1] It is the 5-bromo derivative of tryptamine.^[1]

Other names5-Bromo-T; 5-Br-T; PAL-518; PAL518

Drug classSerotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonin–dopamine releasing agent

ATC code

None

CAS Number

3610-42-2

Quick facts Clinical data, Other names ...

5-Bromotryptamine
Clinical data

Other names	5-Bromo-T; 5-Br-T; PAL-518; PAL518
Drug class	Serotonin receptor modulator; Serotonin 5-HT_2A receptor agonist; Serotonin–dopamine releasing agent
ATC code	None
Identifiers
IUPAC name 2-(5-bromo-1H-indol-3-yl)ethanamine
CAS Number	3610-42-2
PubChem CID	77158
ChemSpider	69595
ChEMBL	ChEMBL1288717
CompTox Dashboard (EPA)	DTXSID40957504
Chemical and physical data
Formula	C₁₀H₁₁BrN₂
Molar mass	239.116 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C1=CC2=C(C=C1Br)C(=CN2)CCN
InChI InChI=1S/C10H11BrN2/c11-8-1-2-10-9(5-8)7(3-4-12)6-13-10/h1-2,5-6,13H,3-4,12H2 Key:CGHUQJRRADEHTQ-UHFFFAOYSA-N

The drug acts as a potent full agonist of the serotonin 5-HT_2A receptor, with an EC₅₀Tooltip half-maximal effective concentration of 5.14 nM and an E_maxTooltip maximal efficacy of 108%.^[1] It is also a potent full agonist of the serotonin 5-HT_2B receptor.^[2]^[3]^[4] In addition to its serotonin receptor agonism, 5-bromotryptamine is a serotonin–dopamine releasing agent (SDRA), with EC₅₀ values for induction of monoamine release of 75 nM for serotonin, 478 nM for dopamine, and >10,000 nM for norepinephrine in rat brain synaptosomes.^[1]

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.^[5]^[6]^[7]^[8]^[9]^[2]^[10] However, given intravenously at sufficiently high doses, tryptamine is still known to be able to produce weak and short-lived psychoactive effects in humans.^[11]^[6]^[1]^[10]

The chemical synthesis of 5-bromotryptamine has been described.^[1]^[12]

5-Bromotryptamine was first described in the scientific literature by 1965.^[13]

References

[1]
Blough BE, Landavazo A, Partilla JS, Decker AM, Page KM, Baumann MH, et al. (October 2014). "Alpha-ethyltryptamines as dual dopamine-serotonin releasers". Bioorganic & Medicinal Chemistry Letters. 24 (19): 4754–4758. doi:10.1016/j.bmcl.2014.07.062. PMC 4211607. PMID 25193229.
[2]
Boess FG, Martin IL (1994). "Molecular biology of 5-HT receptors". Neuropharmacology. 33 (3–4): 275–317. doi:10.1016/0028-3908(94)90059-0. PMID 7984267.
[3]
Wainscott DB, Cohen ML, Schenck KW, Audia JE, Nissen JS, Baez M, et al. (March 1993). "Pharmacological characteristics of the newly cloned rat 5-hydroxytryptamine2F receptor". Molecular Pharmacology. 43 (3): 419–426. doi:10.1016/S0026-895X(25)13628-6. PMID 8450835.
[4]
Wainscott DB, Lucaites VL, Kursar JD, Baez M, Nelson DL (February 1996). "Pharmacologic characterization of the human 5-hydroxytryptamine2B receptor: evidence for species differences". The Journal of Pharmacology and Experimental Therapeutics. 276 (2): 720–727. doi:10.1016/S0022-3565(25)12346-X. PMID 8632342.
[5]
Jones RS (1982). "Tryptamine: a neuromodulator or neurotransmitter in mammalian brain?". Progress in Neurobiology. 19 (1–2): 117–139. doi:10.1016/0301-0082(82)90023-5. PMID 6131482.
[6]
Shulgin A (1997). Tihkal: The Continuation. Transform Press. #53. T. ISBN 978-0-9630096-9-2. Retrieved 17 August 2024. (with 250 mg, intravenously) "Tryptamine was infused intravenously over a period of up to 7.5 minutes. Physical changes included an increases in blood pressure, in the amplitude of the patellar reflex, and in pupillary diameter. The subjective changes are not unlike those seen with small doses of LSD. A point-by-point comparison between the tryptamine and LSD syndromes reveals a close similarity which is consistent with the hypothesis that tryptamine and LSD have a common mode of action."
[7]
Nichols DE (2012). "Structure–activity relationships of serotonin 5-HT2A agonists". Wiley Interdisciplinary Reviews: Membrane Transport and Signaling. 1 (5): 559–579. doi:10.1002/wmts.42. ISSN 2190-460X.
[8]
Nichols DE (2018). Chemistry and Structure-Activity Relationships of Psychedelics. Current Topics in Behavioral Neurosciences. Vol. 36. pp. 1–43. doi:10.1007/7854_2017_475. ISBN 978-3-662-55878-2. PMID 28401524.
[9]
Prozialeck WC, Vogel WH (February 1979). "MAO inhibition and the effects of centrally administered LSD, serotonin, and 5-methoxytryptamine on the conditioned avoidance response in rats". Psychopharmacology. 60 (3): 309–310. doi:10.1007/BF00426673. PMID 108709. In contrast, MAO inhibition greatly increased brain levels of 5-HT and 5-MT (Prozialeck and Vogel, 1978). For instance, clorgyline and deprenyl increased brain levels of 5-HT 8.5-fold and 4.4-fold and of 5-MT 20-fold and 5-fold, respectively.
[10]
Martin WR, Sloan JW (1970). "Effects of infused tryptamine in man". Psychopharmacologia. 18 (3): 231–237. doi:10.1007/BF00412669. PMID 4922520.
[11]
Martin WR, Sloan JW (1977). "Pharmacology and Classification of LSD-like Hallucinogens". Drug Addiction II. Berlin, Heidelberg: Springer Berlin Heidelberg. pp. 305–368. doi:10.1007/978-3-642-66709-1_3. ISBN 978-3-642-66711-4. MARTIN and SLOAN (1970) found that intravenously infused tryptamine increased blood pressure, dilated pupils, enhanced the patellar reflex, and produced perceptual distortions. [...] Tryptamine, but not DMT, increases locomotor activity in the mouse, while both antagonize reserpine depression (V ANE et al., 1961). [...] In the rat, tryptamine causes backward locomotion, Straub tail, bradypnea and dyspnea, and clonic convulsions (TEDESCHI et al., 1959). [...] Tryptamine produces a variety of changes in the cat causing signs of sympathetic activation including mydriasis, retraction of nictitating membrane, piloerection, motor signs such as extension of limbs and convulsions and affective changes such as hissing and snarling (LAIDLAW, 1912). [...]
[12]
Matzdorf T (2010). 5-Carboxamidotryptamin-Derivate als Liganden für 5-HT7- und 5-HT2A-Rezeptoren: Synthese und In-vitro-Pharmakologie (PhD thesis). Universität Regensburg. doi:10.5283/EPUB.13400.
[13]
Buznikov GA, Zherebchenko PG, Chudakova IV (1965). "Effect of various indolylalkylamines on the motor cells of mollusk embryos and the blood vessels of the rabbit ear". Bulletin of Experimental Biology and Medicine. 59 (5): 527–531. doi:10.1007/BF00783076. ISSN 0007-4888.

5-Bromotryptamine

See also

References

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