Chlorophenylbiguanide

Chlorophenylbiguanide
Identifiers
	IUPAC name 2-(3-chlorophenyl)-1-(diaminomethylidene)guanidine;
CAS Number	48144-44-1 ;
PubChem CID	1354;
IUPHAR/BPS	2287;
ChemSpider	27570 ;
UNII	910A4X901V;
ChEMBL	ChEMBL42752 ;
CompTox Dashboard (EPA)	DTXSID70197436 ;
Chemical and physical data
Formula	C8H12ClN5
Molar mass	213.67 g·mol−1
3D model (JSmol)	Interactive image;
	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) ; Key:MKWFJPZMYHPQIA-UHFFFAOYSA-N ;
	(verify)

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 α_2A-adrenergic receptor.^[4] It has anxiogenic, emetic and hypothermic effects in animal studies.^[5]^[6]^[7]^[8]

References

^ 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.
^ 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. S2CID 2883317.
^ 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.
^ 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. S2CID 8322690.
^ 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. S2CID 10407491.
^ 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. S2CID 22484359.
^ 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. S2CID 23055852.
^ 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. S2CID 26082449.

External links

Media related to Chlorophenylbiguanide at Wikimedia Commons

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[pmid25541413-1] 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.

[pmid23810831-2] 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. S2CID 2883317.

[pmid15966738-3] 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.

[pmid7908122-4] 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. S2CID 8322690.

[pmid1523283-5] 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. S2CID 10407491.

[pmid10907673-6] 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. S2CID 22484359.

[pmid12419412-7] 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. S2CID 23055852.

[pmid19735696-8] 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. S2CID 26082449.

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Identifiers

IUPAC name 2-(3-chlorophenyl)-1-(diaminomethylidene)guanidine
CAS Number	48144-44-1^Y
PubChem CID	1354
IUPHAR/BPS	2287
ChemSpider	27570^Y
UNII	910A4X901V
ChEMBL	ChEMBL42752^Y
CompTox Dashboard (EPA)	DTXSID70197436
Chemical and physical data
Formula	C₈H₁₂ClN₅
Molar mass	213.67 g·mol⁻¹
3D model (JSmol)	Interactive image
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)

Chlorophenylbiguanide

See also

References

External links