Chlorophenylbiguanide

meta-Chlorophenylbiguanide (1-(3-Chlorophenylbiguanide, m-CPBG) is an allosteric agonist and modulator of the 5-HT3 receptor[1][2][3] and an antagonist of the α2A-adrenergic receptor.[4] It has anxiogenic, emetic and hypothermic effects in animal studies.[5][6][7][8]

Chlorophenylbiguanide
Identifiers
IUPAC name
  • 2-(3-chlorophenyl)-1-(diaminomethylidene)guanidine
CAS Number
PubChem CID
IUPHAR/BPS
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC8H12ClN5
Molar mass213.67 g·mol−1
3D model (JSmol)
SMILES
  • c1ccc(Cl)cc1NC(=N)NC(=N)N
InChI
  • InChI=1S/C8H10ClN5/c9-5-3-1-2-4-6(5)13-8(12)14-7(10)11/h1-4H,(H6,10,11,12,13,14) Y
  • Key:MKWFJPZMYHPQIA-UHFFFAOYSA-N Y
  (verify)

See also
  • mCPP
  • Bufotenidine (5-HTQ)

References
  1. Miles TF, Lester HA, Dougherty DA (2015). "Allosteric activation of the 5-HT3AB receptor by mCPBG". Neuropharmacology. 91: 103–8. doi:10.1016/j.neuropharm.2014.12.018. PMC 4312754. PMID 25541413.
  2. Michaelson SD, Paulsen IM, Kozuska JL, Martin IL, Dunn SM (2013). "Importance of recognition loops B and D in the activation of human 5-HT3 receptors by 5-HT and meta-chlorophenylbiguanide". Neuropharmacology. 73: 398–403. doi:10.1016/j.neuropharm.2013.06.017. PMID 23810831.
  3. Suryanarayanan A, Joshi PR, Bikádi Z, Mani M, Kulkarni TR, Gaines C, Schulte MK (2005). "The loop C region of the murine 5-HT3A receptor contributes to the differential actions of 5-hydroxytryptamine and m-chlorophenylbiguanide". Biochemistry. 44 (25): 9140–9. doi:10.1021/bi050661e. PMID 15966738.
  4. Schlicker E, Kathmann M, Exner HJ, Detzner M, Göthert M (1994). "the 5-HT3 receptor agonist 1-(m-chlorophenyl)-biguanide facilitates noradrenaline release by blockade of alpha 2-adrenoceptors in the mouse brain cortex". Naunyn-Schmiedeberg's Archives of Pharmacology. 349 (1): 20–24. doi:10.1007/bf00178201. PMID 7908122.
  5. Andrews N, File SE (1992). "Are there changes in sensitivity to 5-HT3 receptor ligands following chronic diazepam treatment?". Psychopharmacology. 108 (3): 333–7. doi:10.1007/BF02245120. PMID 1523283.
  6. Dukat M, Young R, Darmani NN, Ahmed B, Glennon RA (June 2000). "The 5-HT3 agent N-(3-chlorophenyl)guanidine (MD-354) serves as a discriminative stimulus in rats and displays partial agonist character in a shrew emesis assay". Psychopharmacology. 150 (2): 200–7. doi:10.1007/s002130000410. PMID 10907673.
  7. Castro L, Varjão B, Maldonado I, Campos I, Duque B, Fregoneze J, Reis de Oliveira I, De Castro-e-Silva E (November 2002). "Central 5-HT(3) receptors and water intake in rats". Physiology & Behavior. 77 (2–3): 349–59. doi:10.1016/S0031-9384(02)00872-7. PMID 12419412.
  8. Naumenko VS, Kondaurova EM, Popova NK (November 2009). "Central 5-HT3 receptor-induced hypothermia in mice: interstrain differences and comparison with hypothermia mediated via 5-HT1A receptor". Neuroscience Letters. 465 (1): 50–4. doi:10.1016/j.neulet.2009.09.005. PMID 19735696.


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