PNU-22394

{{short description|Chemical compound}}

{{Drugbox

| Verifiedfields = changed

| verifiedrevid = 455158813

| IUPAC_name = 6-Methyl-1,2,3,4,5,6-hexahydro-azepino[4,5-b]indole

| image = PNU-22394.svg

| image_class = skin-invert-image

| width = 220

| image2 = PNU-22394-3D-balls.png

| image_class2 = bg-transparent

| tradename =

| CAS_number_Ref = {{cascite|correct|??}}

| CAS_number = 15923-78-1

| PubChem = 27559

| UNII_Ref = {{fdacite|correct|FDA}}

| UNII = J7HPJ854EA

| ChEMBL_Ref = {{ebicite|changed|EBI}}

| ChEMBL = 6557

| ChemSpiderID_Ref = {{chemspidercite|changed|chemspider}}

| ChemSpiderID = 25649

| C=13 | H=16 | N=2

| smiles = C3CNCCc2c3c1ccccc1n2C

| StdInChI_Ref = {{stdinchicite|changed|chemspider}}

| StdInChI = 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

| StdInChIKey_Ref = {{stdinchicite|changed|chemspider}}

| StdInChIKey = ZBXDOQWPGBISAR-UHFFFAOYSA-N

}}

PNU-22394 is a drug of the ibogalog group 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,{{cite journal | vauthors = McCall RB, Franklin SR, Hyslop DK, Knauer CS, Chio CL, Haber CL, Fitzgerald LW |title= PNU-22394, a 5-HT2C receptor agonist, reduced feeding in rodents and produces weight loss in humans |date= 2001 |others= Presentation Number 309.2 | volume = 27 | issue = 309.2 |publisher=Society for Neuroscience Abstracts |url=http://www.sfn.org/Annual-Meeting/Past-and-Future-Annual-Meetings/Abstract-Archive/Abstract-Archive-Detail?AbsYear=2001&AbsID=4715 |location= Convention Center Exhibit Hall, Poster Board TT-45, San Diego, CA |format= Online |access-date= 18 July 2014}}{{cite journal | vauthors = Garfield AS, Heisler LK | title = Pharmacological targeting of the serotonergic system for the treatment of obesity | journal = The Journal of Physiology | volume = 587 | issue = 1 | pages = 49–60 | date = January 2009 | pmid = 19029184 | pmc = 2670022 | doi = 10.1113/jphysiol.2008.164152 }} along with "Pro-Cognitive Properties",{{cite journal | vauthors = Jensen AA, Plath N, Pedersen MH, Isberg V, Krall J, Wellendorph P, Stensbøl TB, Gloriam DE, Krogsgaard-Larsen P, Frølund B | display-authors = 6 | title = 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-HT(2A)/5-HT(2C) receptor agonists with pro-cognitive properties | journal = Journal of Medicinal Chemistry | volume = 56 | issue = 3 | pages = 1211–27 | date = February 2013 | pmid = 23301527 | doi = 10.1021/jm301656h | citeseerx = 10.1.1.691.154 }} although it has never been developed for medical use.