AC-263093

AC-263093
Identifiers
	IUPAC name 2-[(E)-(3,4-dibromophenyl)methylideneamino]guanidine;
CAS Number	849459-86-5;
PubChem CID	44542176;
ChemSpider	24636697;
ChEMBL	ChEMBL573297;
Chemical and physical data
Formula	C8H8Br2N4
Molar mass	319.988 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1=CC(=C(C=C1/C=N/N=C(N)N)Br)Br;
	InChI InChI=1S/C8H8Br2N4/c9-6-2-1-5(3-7(6)10)4-13-14-8(11)12/h1-4H,(H4,11,12,14)/b13-4+; Key:VMYFCUKMGMFQNH-YIXHJXPBSA-N;

AC-263093 is a drug used in scientific research which acts as an agonist at the neuropeptide FF receptor NPFF2 and an antagonist for the closely related NPFF1 receptor. In animal studies it reduced tolerance to morphine but also produced hyperalgesia and anxiety.^[1]^[2]^[3]^[4] Related compounds such as AC-099 with Cl or CF3 replacing the bromine substituents have similar activity as NPFF2 agonists or partial agonists but with relatively lower potency.^[5]

References

^ Malin DH, Henceroth MM, Izygon JJ, Nghiem DM, Moon WD, Anderson AP, et al. (January 2015). "Reversal of morphine tolerance by a compound with NPFF receptor subtype-selective actions". Neuroscience Letters. 584: 141–145. doi:10.1016/j.neulet.2014.10.018. PMID 25459291.
^ Lin YT, Kao SC, Day YJ, Chang CC, Chen JC (July 2016). "Altered nociception and morphine tolerance in neuropeptide FF receptor type 2 over-expressing mice". European Journal of Pain. 20 (6): 895–906. doi:10.1002/ejp.814. PMID 26648516.
^ Lin YT, Liu HL, Day YJ, Chang CC, Hsu PH, Chen JC (May 2017). "Activation of NPFFR2 leads to hyperalgesia through the spinal inflammatory mediator CGRP in mice". Experimental Neurology. 291: 62–73. doi:10.1016/j.expneurol.2017.02.003. PMID 28179153.
^ Lin YT, Yu YL, Hong WC, Yeh TS, Chen TC, Chen JC (August 2017). "NPFFR2 Activates the HPA Axis and Induces Anxiogenic Effects in Rodents". International Journal of Molecular Sciences. 18 (8): 1810. doi:10.3390/ijms18081810. PMC 5578197. PMID 28825666.
^ Journigan VB, Mésangeau C, Vyas N, Eans SO, Cutler SJ, McLaughlin JP, et al. (November 2014). "Nonpeptide small molecule agonist and antagonist original leads for neuropeptide FF1 and FF2 receptors". Journal of Medicinal Chemistry. 57 (21): 8903–8927. doi:10.1021/jm500989n. PMC 4234442. PMID 25268943.

[1] Malin DH, Henceroth MM, Izygon JJ, Nghiem DM, Moon WD, Anderson AP, et al. (January 2015). "Reversal of morphine tolerance by a compound with NPFF receptor subtype-selective actions". Neuroscience Letters. 584: 141–145. doi:10.1016/j.neulet.2014.10.018. PMID 25459291.

[2] Lin YT, Kao SC, Day YJ, Chang CC, Chen JC (July 2016). "Altered nociception and morphine tolerance in neuropeptide FF receptor type 2 over-expressing mice". European Journal of Pain. 20 (6): 895–906. doi:10.1002/ejp.814. PMID 26648516.

[3] Lin YT, Liu HL, Day YJ, Chang CC, Hsu PH, Chen JC (May 2017). "Activation of NPFFR2 leads to hyperalgesia through the spinal inflammatory mediator CGRP in mice". Experimental Neurology. 291: 62–73. doi:10.1016/j.expneurol.2017.02.003. PMID 28179153.

[4] Lin YT, Yu YL, Hong WC, Yeh TS, Chen TC, Chen JC (August 2017). "NPFFR2 Activates the HPA Axis and Induces Anxiogenic Effects in Rodents". International Journal of Molecular Sciences. 18 (8): 1810. doi:10.3390/ijms18081810. PMC 5578197. PMID 28825666.

[5] Journigan VB, Mésangeau C, Vyas N, Eans SO, Cutler SJ, McLaughlin JP, et al. (November 2014). "Nonpeptide small molecule agonist and antagonist original leads for neuropeptide FF1 and FF2 receptors". Journal of Medicinal Chemistry. 57 (21): 8903–8927. doi:10.1021/jm500989n. PMC 4234442. PMID 25268943.

[1]

[2]

[3]

[4]

[5]