5-Iodo-A-85380

5-Iodo-A-85380
Identifiers
  • 3-[(2S)-2-azetidinylmethoxy]-5-iodopyridine
CAS Number
PubChem CID
ChemSpider
UNII
ChEBI
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC9H11IN2O
Molar mass290.104 g·mol−1
3D model (JSmol)
  • C1CN[C@@H]1COC2=CC(=CN=C2)I
  • InChI=1S/C9H11IN2O/c10-7-3-9(5-11-4-7)13-6-8-1-2-12-8/h3-5,8,12H,1-2,6H2/t8-/m0/s1
  • Key:RKVRGRXOYDTUEY-QMMMGPOBSA-N

5-Iodo-A-85380 (5IA) is a drug which acts as an agonist at neural nicotinic acetylcholine receptors with high affinity and full agonist activity at the α4β2 subtype, and with slightly lower affinity and partial agonist activity at the α6β2 subtype. It has analgesic effects, and triggers release of dopamine in the brain, with weaker release of acetylcholine and noradrenaline. Like nicotine, but unlike related compounds such as epibatidine, 5-iodo-A-85380 has reinforcing effects and supports self-administration in animal models. It is used for research into nicotine addiction, and also in its 123I radiolabelled form for brain imaging studies.[1][2][3][4][5][6][7][8][9][10][11][12][13]

See also

References

  1. ↑ Koren AO, Horti AG, Mukhin AG, Gündisch D, Kimes AS, Dannals RF, et al. (10 September 1998). "2-, 5-, and 6-Halo-3-(2(S)-azetidinylmethoxy)pyridines: synthesis, affinity for nicotinic acetylcholine receptors, and molecular modeling". Journal of Medicinal Chemistry. 41 (19): 3690–3698. doi:10.1021/jm980170a. PMID 9733494.
  2. ↑ Rasmussen T, Swedberg MD (June 1998). "Reinforcing effects of nicotinic compounds: intravenous self-administration in drug-naive mice". Pharmacology, Biochemistry, and Behavior. 60 (2): 567–573. doi:10.1016/s0091-3057(98)00003-3. PMID 9632242.
  3. ↑ Mukhin AG, Gündisch D, Horti AG, Koren AO, Tamagnan G, Kimes AS, et al. (March 2000). "5-Iodo-A-85380, an alpha4beta2 subtype-selective ligand for nicotinic acetylcholine receptors". Molecular Pharmacology. 57 (3): 642–649. doi:10.1124/mol.57.3.642. PMID 10692507.
  4. ↑ Liu X, Koren AO, Yee SK, Pechnick RN, Poland RE, London ED (6 August 2003). "Self-administration of 5-iodo-A-85380, a beta2-selective nicotinic receptor ligand, by operantly trained rats". NeuroReport. 14 (11): 1503–1505. doi:10.1097/00001756-200308060-00020. PMID 12960773.
  5. ↑ Mogg AJ, Jones FA, Pullar IA, Sharples CG, Wonnacott S (November 2004). "Functional responses and subunit composition of presynaptic nicotinic receptor subtypes explored using the novel agonist 5-iodo-A-85380". Neuropharmacology. 47 (6): 848–859. doi:10.1016/j.neuropharm.2004.06.013. PMID 15527819.
  6. ↑ Ueda M, Iida Y, Mukai T, Mamede M, Ishizu K, Ogawa M, et al. (June 2004). "5-[123I]Iodo-A-85380: assessment of pharmacological safety, radiation dosimetry and SPECT imaging of brain nicotinic receptors in healthy human subjects". Annals of Nuclear Medicine. 18 (4): 337–344. doi:10.1007/BF02984473. PMID 15359928.
  7. ↑ Ueda M, Iida Y, Kitamura Y, Kawashima H, Ogawa M, Magata Y, et al. (14 March 2008). "5-Iodo-A-85380, a specific ligand for alpha 4 beta 2 nicotinic acetylcholine receptors, prevents glutamate neurotoxicity in rat cortical cultured neurons". Brain Research. 1199: 46–52. doi:10.1016/j.brainres.2007.10.107. PMID 18269932.
  8. ↑ Livingstone PD, Srinivasan J, Kew JN, Dawson LA, Gotti C, Moretti M, et al. (February 2009). "alpha7 and non-alpha7 nicotinic acetylcholine receptors modulate dopamine release in vitro and in vivo in the rat prefrontal cortex". The European Journal of Neuroscience. 29 (3): 539–550. doi:10.1111/j.1460-9568.2009.06613.x. PMID 19187266.
  9. ↑ Liu X (November 2013). "Positive allosteric modulation of α4β2 nicotinic acetylcholine receptors as a new approach to smoking reduction: evidence from a rat model of nicotine self-administration". Psychopharmacology. 230 (2). Berl: 203–213. doi:10.1007/s00213-013-3145-2. PMC 3797181. PMID 23712602.
  10. ↑ Freitas K, Carroll FI, Negus SS (February 2016). "Comparison of effects produced by nicotine and the α4β2-selective agonist 5-I-A-85380 on intracranial self-stimulation in rats". Experimental and Clinical Psychopharmacology. 24 (1): 65–75. doi:10.1037/pha0000055. PMC 4821675. PMID 26461167.
  11. ↑ Colloby SJ, Field RH, Wyper DJ, O'Brien JT, Taylor JP (November 2016). "A spatial covariance 123I-5IA-85380 SPECT study of α4β2 nicotinic receptors in Alzheimer's disease". Neurobiology of Aging. 47: 83–90. doi:10.1016/j.neurobiolaging.2016.07.017. PMC 5082764. PMID 27565302.
  12. ↑ Akinola LS, Bagdas D, Alkhlaif Y, Jackson A, Gurdap CO, Rahimpour E, et al. (November 2022). "Pharmacological characterization of 5-iodo-A-85380, a β2-selective nicotinic receptor agonist, in mice". Journal of Psychopharmacology. 36 (11). Oxford, England: 1280–1293. doi:10.1177/02698811221132214. PMC 9817006. PMID 36321267.
  13. ↑ Harrison JR, Colloby SJ, O'Brien JT, Taylor JP (29 September 2025). "A spatial covariance 123I-5IA-85380 SPECT study of α4β2 nicotinic receptors in dementia with Lewy bodies". Journal of Neurology. 272 (10) 660. doi:10.1007/s00415-025-13332-5. PMC 12479619. PMID 41021047.
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