WAY-163909

WAY-163909
Identifiers
	IUPAC name (11R,15R)-7,10-diazatetracyclo[8.5.1.05,16.011,15]hexadeca-1,3,5(16)-triene;
CAS Number	428868-32-0 ;
PubChem CID	10130594;
ChemSpider	8306109;
UNII	MN9LW8268N;
ChEMBL	ChEMBL1628670;
CompTox Dashboard (EPA)	DTXSID40436021 ;
Chemical and physical data
Formula	C14H18N2
Molar mass	214.312 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES C1C[C@H]2[C@@H](C1)N3CCNCC4=C3C2=CC=C4;
	InChI InChI=1S/C14H18N2/c1-3-10-9-15-7-8-16-13-6-2-4-11(13)12(5-1)14(10)16/h1,3,5,11,13,15H,2,4,6-9H2/t11-,13-/m1/s1; Key:XOSKJKGKWRIMGV-DGCLKSJQSA-N;

WAY-163,909 is a drug which acts as a potent and reasonably selective agonist for the serotonin 5-HT_2C receptor.^[1]^[2] It has antipsychotic-like effects in animal models,^[3]^[4] and has been used to study the role of the 5-HT_2C receptor subtype in the action of addictive drugs such as nicotine and methamphetamine.^[5]^[6]

References

^ Dunlop J, Sabb AL, Mazandarani H, Zhang J, Kalgaonker S, Shukhina E, et al. (May 2005). "WAY-163909 [(7bR, 10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indole], a novel 5-hydroxytryptamine 2C receptor-selective agonist with anorectic activity". The Journal of Pharmacology and Experimental Therapeutics. 313 (2): 862–9. doi:10.1124/jpet.104.075382. PMID 15705738. S2CID 767189.
^ Dunlop J, Marquis KL, Lim HK, Leung L, Kao J, Cheesman C, Rosenzweig-Lipson S (2006). "Pharmacological profile of the 5-HT(2C) receptor agonist WAY-163909; therapeutic potential in multiple indications". CNS Drug Reviews. 12 (3–4): 167–77. doi:10.1111/j.1527-3458.2006.00167.x. PMC 6506193. PMID 17227285.
^ Marquis KL, Sabb AL, Logue SF, Brennan JA, Piesla MJ, Comery TA, et al. (January 2007). "WAY-163909 [(7bR,10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indole]: A novel 5-hydroxytryptamine 2C receptor-selective agonist with preclinical antipsychotic-like activity". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 486–96. doi:10.1124/jpet.106.106989. PMID 17038512. S2CID 40512921.
^ Grauer SM, Graf R, Navarra R, Sung A, Logue SF, Stack G, et al. (May 2009). "WAY-163909, a 5-HT2C agonist, enhances the preclinical potency of current antipsychotics". Psychopharmacology. 204 (1): 37–48. doi:10.1007/s00213-008-1433-z. PMID 19107466. S2CID 27417671.
^ Zaniewska M, McCreary AC, Przegaliński E, Filip M (October 2007). "Effects of the serotonin 5-HT2A and 5-HT2C receptor ligands on the discriminative stimulus effects of nicotine in rats". European Journal of Pharmacology. 571 (2–3): 156–65. doi:10.1016/j.ejphar.2007.05.067. PMID 17617403.
^ Odabas-Geldiay M, Shields H, Berro LF, Rice KC, Howell LL (January 2019). "Effects of acute treatments with the serotonin 2A antagonist M100907 alone or in combination with the serotonin 2C agonist WAY163909 on methamphetamine self-administration in rhesus monkeys". Drug and Alcohol Dependence. 194: 252–256. doi:10.1016/j.drugalcdep.2018.10.018. PMC 6312465. PMID 30469095.

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[1] Dunlop J, Sabb AL, Mazandarani H, Zhang J, Kalgaonker S, Shukhina E, et al. (May 2005). "WAY-163909 [(7bR, 10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indole], a novel 5-hydroxytryptamine 2C receptor-selective agonist with anorectic activity". The Journal of Pharmacology and Experimental Therapeutics. 313 (2): 862–9. doi:10.1124/jpet.104.075382. PMID 15705738. S2CID 767189.

[2] Dunlop J, Marquis KL, Lim HK, Leung L, Kao J, Cheesman C, Rosenzweig-Lipson S (2006). "Pharmacological profile of the 5-HT(2C) receptor agonist WAY-163909; therapeutic potential in multiple indications". CNS Drug Reviews. 12 (3–4): 167–77. doi:10.1111/j.1527-3458.2006.00167.x. PMC 6506193. PMID 17227285.

[3] Marquis KL, Sabb AL, Logue SF, Brennan JA, Piesla MJ, Comery TA, et al. (January 2007). "WAY-163909 [(7bR,10aR)-1,2,3,4,8,9,10,10a-octahydro-7bH-cyclopenta-[b][1,4]diazepino[6,7,1hi]indole]: A novel 5-hydroxytryptamine 2C receptor-selective agonist with preclinical antipsychotic-like activity". The Journal of Pharmacology and Experimental Therapeutics. 320 (1): 486–96. doi:10.1124/jpet.106.106989. PMID 17038512. S2CID 40512921.

[4] Grauer SM, Graf R, Navarra R, Sung A, Logue SF, Stack G, et al. (May 2009). "WAY-163909, a 5-HT2C agonist, enhances the preclinical potency of current antipsychotics". Psychopharmacology. 204 (1): 37–48. doi:10.1007/s00213-008-1433-z. PMID 19107466. S2CID 27417671.

[5] Zaniewska M, McCreary AC, Przegaliński E, Filip M (October 2007). "Effects of the serotonin 5-HT2A and 5-HT2C receptor ligands on the discriminative stimulus effects of nicotine in rats". European Journal of Pharmacology. 571 (2–3): 156–65. doi:10.1016/j.ejphar.2007.05.067. PMID 17617403.

[6] Odabas-Geldiay M, Shields H, Berro LF, Rice KC, Howell LL (January 2019). "Effects of acute treatments with the serotonin 2A antagonist M100907 alone or in combination with the serotonin 2C agonist WAY163909 on methamphetamine self-administration in rhesus monkeys". Drug and Alcohol Dependence. 194: 252–256. doi:10.1016/j.drugalcdep.2018.10.018. PMC 6312465. PMID 30469095.

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See also

References