Norboletone

{{Short description|Chemical compound}}

{{Drugbox

| verifiedrevid = 444029421

| IUPAC_name = (8R,9S,10R,13S,14S,17S)-13,17-diethyl-17-hydroxy-1,2,6,7,8,9,10,11,12,14,15,16-dodecahydrocyclopenta[a]phenanthren-3-one

| image = Norboletone.svg

| width = 225px

| tradename =

| pregnancy_AU =

| pregnancy_US =

| pregnancy_category =

| legal_AU =

| legal_CA = Schedule IV

| legal_UK =

| legal_US =

| legal_status =

| routes_of_administration = By mouth

| class = Androgen; Anabolic steroid

| bioavailability =

| protein_bound =

| metabolism =

| elimination_half-life =

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

| CAS_number = 1235-15-0

| ATC_prefix = None

| ATC_suffix =

| PubChem = 66255

| DrugBank_Ref = {{drugbankcite|correct|drugbank}}

| DrugBank =

| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}

| ChemSpiderID = 59638

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

| UNII = U3BZU2241A

| synonyms = Norbolethone; 17α-Ethyl-18-methyl-19-nortestosterone; 17α-Ethyl-18-methylestr-4-en-17β-ol-3-one; 13β-Ethyl-17α-hydroxy-18,19-dinorpregn-4-en-3-one

| C=21 | H=32 | O=2

| SMILES = O=C4\C=C3/[C@@H]([C@H]2CC[C@]1([C@@H](CC[C@@]1(O)CC)[C@@H]2CC3)CC)CC4

| StdInChI_Ref = {{stdinchicite|correct|chemspider}}

| StdInChI = 1S/C21H32O2/c1-3-20-11-9-17-16-8-6-15(22)13-14(16)5-7-18(17)19(20)10-12-21(20,23)4-2/h13,16-19,23H,3-12H2,1-2H3/t16-,17+,18+,19-,20-,21-/m0/s1

| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}

| StdInChIKey = FTBJKONNNSKOLX-XUDSTZEESA-N

}}

Norboletone ({{abbrlink|INN|International Nonproprietary Name}}) (former proposed brand name Genabol), or norbolethone, is a synthetic and orally active anabolic–androgenic steroid (AAS) which was never marketed.{{cite book| vauthors = Fainaru-Wada M, Williams L |title=Game of Shadows: Barry Bonds, BALCO, and the Steroids Scandal that Rocked Professional Sports|url=https://books.google.com/books?id=AtXm74CbIJoC&pg=PT75|date=23 March 2006|publisher=Penguin Publishing Group|isbn=978-1-101-21676-7|pages=75–}} It was first developed in 1966 by Wyeth Laboratories and was investigated for use as an agent to encourage weight gain and for the treatment of short stature, but was never marketed commercially because of fears that it might be toxic.{{cite news| title = Inventor of 'clear' steroid gets 3 months in prison | url=http://www.sfgate.com/cgi-bin/article.cgi?file=/c/a/2006/08/04/MNG3LKBCR712.DTL&type=printable | work=The San Francisco Chronicle | vauthors = Lee HK | date=2006-08-04}} It subsequently showed up in urine tests on athletes in competition in the early 2000s.{{cite journal | vauthors = Catlin DH, Ahrens BD, Kucherova Y | title = Detection of norbolethone, an anabolic steroid never marketed, in athletes' urine | journal = Rapid Communications in Mass Spectrometry | volume = 16 | issue = 13 | pages = 1273–1275 | year = 2002 | pmid = 12112254 | doi = 10.1002/rcm.722 | bibcode = 2002RCMS...16.1273C }}

Norboletone was found to have been brought to the market by the chemist Patrick Arnold, of the Bay Area Laboratory Co-operative (BALCO), an American nutritional supplement company. It is reputed to have been the active ingredient in the original formulation of the "undetectable" steroid formulation known as "The Clear" before being replaced by the more potent drug tetrahydrogestrinone.{{cite press release |url=http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%20press.htm |title=Chemist Who Created "The Clear" Sentenced |publisher=United States Attorney for the Northern District of California |date=2006-08-04 |access-date=2007-10-08 |url-status=dead |archive-url=https://web.archive.org/web/20061014084938/http://www.usdoj.gov/usao/can/press/2006/2006_08_04_arnold_sentencing%20press.htm |archive-date=2006-10-14 }}{{cite journal | vauthors = Knight J | title = Drugs bust reveals athletes' secret steroid | journal = Nature | volume = 425 | issue = 6960 | pages = 752 | date = October 2003 | pmid = 14574369 | doi = 10.1038/425752a | s2cid = 4380612 | doi-access = free | bibcode = 2003Natur.425..752K }}

In 2002, Don Catlin, the founder and then-director of the UCLA Olympic Analytical Lab, identified norboletone for the first time in an athlete's urine sample. In the same year, U.S. bicycle racer Tammy Thomas was caught using it and was banned from her sport. The following year, Catlin identified and developed a test for tetrahydrogestrinone (THG), the second reported designer anabolic sample—a key development in the BALCO Affair.{{cite news | title = Catlin has made a career out of busting juicers | url = https://www.usatoday.com/sports/olympics/2007-02-28-catlin-drug-lab_N.htm | newspaper = USA Today | date = 2007-02-28}}

Norboletone is on the World Anti-Doping Agency's list of prohibited substances,{{cite web | url=http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | title=The World Anti-Doping Code: The 2012 Prohibited List | publisher=World Anti-Doping Agency | access-date=2012-07-17 | url-status=dead | archive-url=https://web.archive.org/web/20120513020202/http://www.wada-ama.org/Documents/World_Anti-Doping_Program/WADP-Prohibited-list/2012/WADA_Prohibited_List_2012_EN.pdf | archive-date=2012-05-13 }} and is therefore banned from use in most major sports.