PNU-22394

PNU-22394
Identifiers
	IUPAC name 6-Methyl-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole;
CAS Number	15923-78-1
PubChem (CID)	27559
ChemSpider	25649
ChEMBL	CHEMBL6557
Chemical and physical data
Formula	C13H16N2
Molar mass	200.279 g/mol
3D model (Jmol)	Interactive image
	SMILES C3CNCCc2c3c1ccccc1n2C ;
	InChI InChI=1S/C13H16N2/c1-15-12-5-3-2-4-10(12)11-6-8-14-9-7-13(11)15/h2-5,14H,6-9H2,1H3 ; Key:ZBXDOQWPGBISAR-UHFFFAOYSA-N ;
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PNU-22394 is a drug which acts as an agonist at serotonin 5-HT₂ receptors, with strongest binding affinity for 5-HT_2A and 5-HT_2C and slightly weaker at 5-HT_2B, although it is only a full agonist at 5-HT_2C, but partial agonist at 5-HT_2A and 5-HT_2B. It has anorectic effects in both animal studies and human trials,^[1]^[2] along with "Pro-Cognitive Properties",^[3] although it has never been developed for medical use.

References[edit]

^ McCall, R. B.; Franklin, S. R.; Hyslop, D. K.; Knauer, C. S.; Chio, C. L.; Haber, C. L.; Fitzgerald, L. W. (2001). "PNU-22394, a 5-HT2C receptor agonist, reduced feeding in rodents and produces weight loss in humans" (Online). 27 (309.2). Presentation Number 309.2. Convention Center Exhibit Hall, Poster Board TT-45, San Diego, CA: Society for Neuroscience Abstracts. Retrieved 18 July 2014.
^ Garfield AS, Heisler LK (2009). "Pharmacological targeting of the serotonergic system for the treatment of obesity". The Journal of Physiology. 587 (1): 49–60. doi:10.1113/jphysiol.2008.164152. PMC 2670022. PMID 19029184.
^ Jensen, Anders A.; Plath, Niels; Pedersen, Martin Holst Friborg; Isberg, Vignir; et al. (2013). "Design, Synthesis, and Pharmacological Characterization of N- and O-Substituted 5,6,7,8-Tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol Analogues: Novel 5-HT2A/5-HT2C Receptor Agonists with Pro-Cognitive Properties". Journal of Medicinal Chemistry. 56 (3): 1211–1227. doi:10.1021/jm301656h. ISSN 0022-2623.

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[McCall2001-1] McCall, R. B.; Franklin, S. R.; Hyslop, D. K.; Knauer, C. S.; Chio, C. L.; Haber, C. L.; Fitzgerald, L. W. (2001). "PNU-22394, a 5-HT2C receptor agonist, reduced feeding in rodents and produces weight loss in humans" (Online). 27 (309.2). Presentation Number 309.2. Convention Center Exhibit Hall, Poster Board TT-45, San Diego, CA: Society for Neuroscience Abstracts. Retrieved 18 July 2014.

[pmid19029184-2] Garfield AS, Heisler LK (2009). "Pharmacological targeting of the serotonergic system for the treatment of obesity". The Journal of Physiology. 587 (1): 49–60. doi:10.1113/jphysiol.2008.164152. PMC 2670022. PMID 19029184.

[Jensen2013-3] Jensen, Anders A.; Plath, Niels; Pedersen, Martin Holst Friborg; Isberg, Vignir; et al. (2013). "Design, Synthesis, and Pharmacological Characterization of N- and O-Substituted 5,6,7,8-Tetrahydro-4H-isoxazolo[4,5-d]azepin-3-ol Analogues: Novel 5-HT2A/5-HT2C Receptor Agonists with Pro-Cognitive Properties". Journal of Medicinal Chemistry. 56 (3): 1211–1227. doi:10.1021/jm301656h. ISSN 0022-2623.

[1]

[2]

[3]

PNU-22394

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Identifiers


IUPAC name 6-Methyl-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole
CAS Number	15923-78-1^Y
PubChem (CID)	27559
ChemSpider	25649^N
ChEMBL	CHEMBL6557^N
Chemical and physical data
Formula	C₁₃H₁₆N₂
Molar mass	200.279 g/mol
3D model (Jmol)	Interactive image
SMILES C3CNCCc2c3c1ccccc1n2C
InChI InChI=1S/C13H16N2/c1-15-12-5-3-2-4-10(12)11-6-8-14-9-7-13(11)15/h2-5,14H,6-9H2,1H3^N Key:ZBXDOQWPGBISAR-UHFFFAOYSA-N^N
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