Norpipanone

{{Short description|Opioid analgesic drug}}

{{Drugbox

| IUPAC_name = 4,4-diphenyl-6-(1-piperidinyl)-3-hexanone

| image = Norpipanone2DCSD.svg

| image_class = skin-invert-image

| CAS_number = 561-48-8

| CAS_supplemental =

| ATC_prefix = None

| ATC_suffix =

| PubChem = 22391

| ChemSpiderID = 21015

| C=23 | H=29 | N=1 | O=1

| smiles = O=C(C(c1ccccc1)(c2ccccc2)CCN3CCCCC3)CC

| synonyms = Herchst 10495, NIH-7557

| StdInChI = 1S/C23H29NO/c1-2-22(25)23(20-12-6-3-7-13-20,21-14-8-4-9-15-21)16-19-24-17-10-5-11-18-24/h3-4,6-9,12-15H,2,5,10-11,16-19H2,1H3

| StdInChIKey = WCDSHELZWCOTMI-UHFFFAOYSA-N

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

| excretion =

| pregnancy_category =

| legal_AU = S9

| legal_BR = A1

| legal_BR_comment = {{Cite web |author=Anvisa |author-link=Brazilian Health Regulatory Agency |date=2023-03-31 |title=RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial |trans-title=Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control|url=https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |url-status=live |archive-url=https://web.archive.org/web/20230803143925/https://www.in.gov.br/en/web/dou/-/resolucao-rdc-n-784-de-31-de-marco-de-2023-474904992 |archive-date=2023-08-03 |access-date=2023-08-16 |publisher=Diário Oficial da União |language=pt-BR |publication-date=2023-04-04}}

| legal_CA = Schedule I

| legal_DE = Anlage I

| legal_US = Schedule I

| routes_of_administration =

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

| UNII = 127X8DJ74M

| KEGG_Ref = {{keggcite|correct|kegg}}

| KEGG = D12701

}}

Norpipanone (INN, BAN; Hexalgon) is an opioid analgesic related to methadone which was developed in Germany and distributed in Hungary, Argentina, and other countries.{{cite book | first = John B | last = Buckingham | name-list-style = vanc | title = Dictionary of Organic Compounds | url = https://books.google.com/books?id=C3Uo1co4Wv0C&pg=PA2883 | access-date = 11 May 2012 | date = December 1995 | publisher = CRC Press | isbn = 978-0-412-54090-5 | page = 2883}}{{cite book | first = David S. | last = Patterson | name-list-style = vanc | title = Foreign Relations of the United States, 1961-1963, Volume XXV: Organization of Foreign Policy; Information Policy; United Nations; Scientific Matters | url = https://books.google.com/books?id=wn4hSwZRaXsC&pg=PA766 | access-date = 11 May 2012 | date = 12 March 2002 | publisher = Government Printing Office | isbn = 978-0-16-050885-1 | pages = 766–767}} It had originally not been under international control but upon observation of case reports of addiction it was reviewed and shortly thereafter became a controlled substance. In the United States, it is a Schedule I controlled substance (ACSCN 9636, zero annual manufacturing quota as of 2014). The salts in use are the hydrobromide (free base conversion ratio 0.806) and hydrochloride (0.902).