Tetrahydrocortisol

{{chembox

| Verifiedfields = changed

| verifiedrevid = 470604176

| ImageFile=tetrahydrocortisol.png

| ImageClass = skin-invert-image

| ImageSize=200px

| IUPACName=3α,11β,17,21-Tetrahydroxy-5β-pregnan-20-one

| SystematicName=2-Hydroxy-1-(1R,3aS,3bS,5aR,7R,9aS,9bS,10S,11aS)-1,7,10-trihydroxy-9a,11a-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-1-yl]ethan-1-one

| OtherNames=Urocortisol; 3α,5β-Tetrahydrocortisol; 3α,5β-Cortisol

|Section1={{Chembox Identifiers

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

| ChemSpiderID = 5655

| InChI = 1/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1

| InChIKey = AODPIQQILQLWGS-GXBDJPPSBG

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

| StdInChI = 1S/C21H34O5/c1-19-7-5-13(23)9-12(19)3-4-14-15-6-8-21(26,17(25)11-22)20(15,2)10-16(24)18(14)19/h12-16,18,22-24,26H,3-11H2,1-2H3/t12-,13-,14+,15+,16+,18-,19+,20+,21+/m1/s1

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

| StdInChIKey = AODPIQQILQLWGS-GXBDJPPSSA-N

| CASNo_Ref = {{cascite|correct|CAS}}

| CASNo=53-02-1

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

| UNII = 7P2O6MFN8O

| PubChem=5864

| ChEBI_Ref = {{ebicite|correct|EBI}}

| ChEBI = 28320

| SMILES = O=C(CO)[C@@]4(O)CC[C@H]3[C@H]2[C@@H]([C@@]1([C@@H](C[C@H](O)CC1)CC2)C)[C@@H](O)C[C@@]34C

}}

|Section2={{Chembox Properties

| Formula=C₂₁H₃₄O₅

| MolarMass=366.49 g/mol

| Appearance=

| Density=

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|Section3={{Chembox Hazards

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Tetrahydrocortisol, or urocortisol, also known as 3α,11β,17α,21-tetrahydroxy-5β-pregnan-20-one, is a steroid and an inactive metabolite of cortisol.{{cite book|author1=Thomas L. Lemke|author2=David A. Williams|title=Foye's Principles of Medicinal Chemistry|url=https://books.google.com/books?id=Sd6ot9ul-bUC&pg=PA915|date=24 January 2012|publisher=Lippincott Williams & Wilkins|isbn=978-1-60913-345-0|pages=915–}}

Tetrahydrocortisol is a neurosteroid and has been found to act as a negative allosteric modulator of the GABA_A receptor, similarly to pregnenolone sulfate.{{cite journal | vauthors = Nikolaou N, Hodson L, Tomlinson JW | title = The role of 5-reduction in physiology and metabolic disease: evidence from cellular, pre-clinical and human studies | journal = J Steroid Biochem Mol Biol | volume = 207 | issue = | pages = 105808 | date = March 2021 | pmid = 33418075 | doi = 10.1016/j.jsbmb.2021.105808 | s2cid = 230716310 | url = }}{{cite journal | vauthors = Chen M, Penning TM | title = 5β-Reduced steroids and human Δ(4)-3-ketosteroid 5β-reductase (AKR1D1) | journal = Steroids | volume = 83 | issue = | pages = 17–26 | date = May 2014 | pmid = 24513054 | pmc = 3971473 | doi = 10.1016/j.steroids.2014.01.013 | url = }}{{cite journal | vauthors = Penland SN, Morrow AL | title = 3alpha,5beta-Reduced cortisol exhibits antagonist properties on cerebral cortical GABA(A) receptors | journal = Eur J Pharmacol | volume = 506 | issue = 2 | pages = 129–32 | date = December 2004 | pmid = 15588732 | doi = 10.1016/j.ejphar.2004.11.007 | url = }}