Etrabamine

Last updated
Etrabamine
Clinical data
Other namesJL-14839; JL14839; 14.839JL; 6-Methylamino-4,5,6,7-tetrahydrobenzothiazole
Routes of
administration 		Oral [1]
Drug class Dopamine receptor agonist; Dopamine D2 and D3 receptor agonist
ATC code
  • None
Identifiers
  • N-methyl-4,5,6,7-tetrahydro-1,3-benzothiazol-6-amine
CAS Number
PubChem CID
UNII
ChEMBL
Chemical and physical data
Formula C8H12N2S
Molar mass 168.26 g·mol−1
3D model (JSmol)
  • CNC1CCC2=C(C1)SC=N2
  • InChI=1S/C8H12N2S/c1-9-6-2-3-7-8(4-6)11-5-10-7/h5-6,9H,2-4H2,1H3
  • Key:YDSVAKPJAOSZJA-UHFFFAOYSA-N

Etrabamine (INN Tooltip International Nonproprietary Name; developmental code name JL-14839 or 14.839JL), also known as 6-methylamino-4,5,6,7-tetrahydrobenzothiazole, is a dopamine receptor agonist which was under development for the treatment of Parkinson's disease but was never marketed. [1] [2] [3] [4] [5] It is taken orally. [1]

The drug shows affinity for the dopamine D2 and D3 receptors (Ki = 2,620 nM and 300 nM, both for L-etrabamine). [6] [7] [5] It acts as a dopamine D2 and D3 receptor agonist and does not appear to act as an agonist of the dopamine D1 receptor. [5] [6] [7] Etrabamine produces stereotypy in rodents and to a greater extent than apomorphine. [5] [7] This can be blocked by the dopamine D2 and D3 receptor antagonists sulpiride, haloperidol, and pimozide. [5] It reverses the hypolocomotion induced by the dopamine depleting agent reserpine in rodents. [5] The drug reduces levels of dopamine metabolites in the striatum in rodents. [5] It strongly suppresses prolactin levels in rodents. [5]

The chemical synthesis of etrabamine has been described. [7] The chemical structure of etrabamine was unlike that of other dopamine receptor agonists when it was first developed in the 1980s. [3] [5] Subsequently, pramipexole, a closely related derivative of etrabamine, was developed and introduced for the treatment of Parkinson's disease. [4] [3] [6] [8] Pramipexole shows 2.7- and 29-fold higher affinity for the dopamine D2 and D3 receptors than etrabamine, respectively. [6] [7] Various other analogues and derivatives of etrabamine besides pramipexole have also been developed. [3] [6] [9]

Etrabamine was first described in the scientific literature in 1987. [3] [5] It was under development by Logeais. [1] [2] The drug reached phase 2 clinical trials prior to the discontinuation of its development in 1997. [1] [2] [4] Its close derivative pramipexole was first approved for medical use in 1997. [8]

See also

References

  1. 1 2 3 4 5 "Etrabamine". AdisInsight. 14 October 1997. Retrieved 31 January 2026.
  2. 1 2 3 "Delving into the Latest Updates on Etrabamine hydrochloride with Synapse". Synapse. 24 January 2026. Retrieved 31 January 2026.
  3. 1 2 3 4 5 Sasse, B. C. (2007). Development of novel ligands influencing neurotransmission in the central nervous system (Doctoral dissertation, Frankfurt (Main), Univ., Diss., 2007). https://web.archive.org/web/20190315212214/https://core.ac.uk/download/pdf/14504116.pdf "Etrabamine has been developed as a new long-lasting dopamine agonist for Parkinson’s disease in the 1980’s. It has been demonstrated to be more effective than the dopamine agonist apomorphine, has decreased the prolactine secretion and did not modify adenylyl cyclase activity.229"
  4. 1 2 3 Li H, Qiao Z, Xiao X, Cao X, Li Z, Liu M, Jiao Q, Chen X, Du X, Jiang H (March 2025). "G protein-coupled receptors: A golden key to the treasure-trove of neurodegenerative diseases". Clin Nutr. 46: 155–168. doi:10.1016/j.clnu.2025.01.032. PMID   39933302.
  5. 1 2 3 4 5 6 7 8 9 10 Ponzio F, Algeri S, Garattini S, Cioce V, Rusconi L, Sacchetti G, Manuel C, Notelle C, Duvert L, Legeai J (August 1987). "Behavioural and biochemical studies on 6-methylamino-4,5,6,7-tetrahydrobenzothiazole (14.839JL), a new potent dopaminergic agonist". Pharmacol Res Commun. 19 (8): 555–565. doi:10.1016/0031-6989(87)90093-2. PMID   3432322.
  6. 1 2 3 4 5 Stank, Lars (2018). "Talipexol als Leitstruktur zur Darstellung neuer Liganden an D2- und D3-Dopaminrezeptoren" (PDF). Düsseldorfer Dokumenten- und Publikationsservice (in German). Archived from the original on 31 January 2026.
  7. 1 2 3 4 5 "Pharmaceutical compositions containing l-etrabamine, uses thereof, and methods for preparing same". Google Patents. 12 March 1996. Retrieved 31 January 2026.
  8. 1 2 Wilson SM, Wurst MG, Whatley MF, Daniels RN (September 2020). "Classics in Chemical Neuroscience: Pramipexole". ACS Chem Neurosci. 11 (17): 2506–2512. doi:10.1021/acschemneuro.0c00332. PMID   32786316.
  9. ↑ Stark, Holger (2013). P3.6 Bioisosteric Replacements for Optimized Dopamine Receptor Agonists (PDF). Interdisciplinary Chemical Approaches for Neuropathology CM1103, "4th Neuroscience Day, University of Malta". pp. 112–112. doi:10.7423/XJENZA.2013.2.12. Based on the early discovery of Etrabamine and established on the non-ergot dopamine agonist Pramipexole we have developed a series of tetrahydrobenzothiazole derivatives with high receptor affinity, improved receptor subtype selectivity and different efficacy profiles from agonist to antagonist properties.
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