Fix.← Previous revisionRevision as of 07:48, 27 October 2026 Line 20: Line 20: * [[Androsterone]]: 5α-androstan-3α-ol-17-one – GABAA receptor positive allosteric modulator{{cite journal | vauthors = Kaminski RM, Marini H, Kim WJ, Rogawski MA | title = Anticonvulsant activity of androsterone and etiocholanolone | journal = Epilepsia | volume = 46 | issue = 6 | pages = 819–27 | year = 2005 | pmid = 15946323 | pmc = 1181535 | doi = 10.1111/j.1528-1167.2005.00705.x }} * [[Androsterone]]: 5α-androstan-3α-ol-17-one – GABAA receptor positive allosteric modulator{{cite journal | vauthors = Kaminski RM, Marini H, Kim WJ, Rogawski MA | title = Anticonvulsant activity of androsterone and etiocholanolone | journal = Epilepsia | volume = 46 | issue = 6 | pages = 819–27 | year = 2005 | pmid = 15946323 | pmc = 1181535 | doi = 10.1111/j.1528-1167.2005.00705.x }} * [[Etiocholanolone]]: 5β-androstan-3α-ol-17-one – GABAA receptor positive allosteric modulator * [[Etiocholanolone]]: 5β-androstan-3α-ol-17-one – GABAA receptor positive allosteric modulator ⚫ * [[Sipasterol]] (YC-9; androtriol; annaosanchun): 5α-androstane-3β,5α,6β-triol – undefined mechanism of action The following are proneurosteroids: The following are proneurosteroids: Line 45: Line 44: ===Synthetic=== ===Synthetic=== ====Cholestanes==== ====Cholestanes==== * [[Acebrochol]] (cholesteryl acetate dibromide): 5α,6β-dibromocholestan-3β-ol 3β-acetate – GABAA receptor positive allosteric modulator * [[Acebrochol]] (cholesteryl acetate dibromide): 5α,6β-dibromocholestan-3β-ol 3β-acetate – GABAA receptor positive allosteric modulator Line 71: Line 69: * [[Progesterone carboxymethyloxime]] (P4-3-CMO) – of progesterone and by extension pregnanediones, pregnanolones, and pregnanediols (see above){{cite journal|last1=Basu|first1=Krishnakali|last2=Mitra|first2=Ashim K.|title=Effects of 3-hydrazone modification on the metabolism and protein binding of progesterone|journal=International Journal of Pharmaceutics|volume=65|issue=1–2|year=1990|pages=109–114|issn=0378-5173|doi=10.1016/0378-5173(90)90015-V}}{{cite journal|last1=Basu|first1=Krishnakali|last2=Kildsig|first2=Dane O.|last3=Mitra|first3=Ashim K.|title=Synthesis and kinetic stability studies of progesterone derivatives|journal=International Journal of Pharmaceutics|volume=47|issue=1–3|year=1988|pages=195–203|issn=0378-5173|doi=10.1016/0378-5173(88)90231-1}} * [[Progesterone carboxymethyloxime]] (P4-3-CMO) – of progesterone and by extension pregnanediones, pregnanolones, and pregnanediols (see above){{cite journal|last1=Basu|first1=Krishnakali|last2=Mitra|first2=Ashim K.|title=Effects of 3-hydrazone modification on the metabolism and protein binding of progesterone|journal=International Journal of Pharmaceutics|volume=65|issue=1–2|year=1990|pages=109–114|issn=0378-5173|doi=10.1016/0378-5173(90)90015-V}}{{cite journal|last1=Basu|first1=Krishnakali|last2=Kildsig|first2=Dane O.|last3=Mitra|first3=Ashim K.|title=Synthesis and kinetic stability studies of progesterone derivatives|journal=International Journal of Pharmaceutics|volume=47|issue=1–3|year=1988|pages=195–203|issn=0378-5173|doi=10.1016/0378-5173(88)90231-1}} ==Excitatory== ====Androstanes==== ⚫ * [[Sipasterol]] (YC-9; androtriol; annaosanchun): 5α-androstane-3β,5α,6β-triol – undefined mechanism of action ==Excitatory== ===Natural=== ===Natural=== ====Cholestanes==== ====Cholestanes==== * [[Cerebrosterol]] (24(''S'')-Hydroxycholesterol): cholest-5-en-3β,24''S''-diol – NMDA receptor positive allosteric modulator{{cite journal | vauthors = Paul SM, Doherty JJ, Robichaud AJ, Belfort GM, Chow BY, Hammond RS, Crawford DC, Linsenbardt AJ, Shu HJ, Izumi Y, Mennerick SJ, Zorumski CF | title = The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors | journal = J. Neurosci. | volume = 33 | issue = 44 | pages = 17290–300 | year = 2013 | pmid = 24174662 | pmc = 3812502 | doi = 10.1523/JNEUROSCI.2619-13.2013 }} * [[Cerebrosterol]] (24(''S'')-Hydroxycholesterol): cholest-5-en-3β,24''S''-diol – NMDA receptor positive allosteric modulator{{cite journal | vauthors = Paul SM, Doherty JJ, Robichaud AJ, Belfort GM, Chow BY, Hammond RS, Crawford DC, Linsenbardt AJ, Shu HJ, Izumi Y, Mennerick SJ, Zorumski CF | title = The major brain cholesterol metabolite 24(S)-hydroxycholesterol is a potent allosteric modulator of N-methyl-D-aspartate receptors | journal = J. Neurosci. | volume = 33 | issue = 44 | pages = 17290–300 | year = 2013 | pmid = 24174662 | pmc = 3812502 | doi = 10.1523/JNEUROSCI.2619-13.2013 }} Line 93: Line 92: ===Synthetic=== ===Synthetic=== ====Androstanes==== ====Androstanes==== * [[17-Phenylandrostenol]] (17-PA): 17-phenyl-5α-androst-16-en-3α-ol – GABAA receptor negative allosteric modulator * [[17-Phenylandrostenol]] (17-PA): 17-phenyl-5α-androst-16-en-3α-ol – GABAA receptor negative allosteric modulator Line 104: Line 102: ==Mixed== ==Mixed== ===Natural=== ===Natural=== ====Cholestanes==== ====Cholestanes==== * [[Cholesterol]]: cholest-5-en-3β-ol – NMDA receptor positive allosteric modulator, possible GABAA receptor positive allosteric modulator, many other actions{{cite journal | vauthors = Hénin J, Salari R, Murlidaran S, Brannigan G | title = A predicted binding site for cholesterol on the GABAA receptor | journal = Biophys. J. | volume = 106 | issue = 9 | pages = 1938–49 | year = 2014 | pmid = 24806926 | pmc = 4017285 | doi = 10.1016/j.bpj.2014.03.024 | bibcode = 2014BpJ...106.1938H }}{{cite journal | vauthors = Levitan I, Singh DK, Rosenhouse-Dantsker A | title = Cholesterol binding to ion channels | journal = Front Physiol | volume = 5 | pages = 65 | year = 2014 | pmid = 24616704 | pmc = 3935357 | doi = 10.3389/fphys.2014.00065 | doi-access = free }}{{cite journal | vauthors = Lange Y, Steck TL | title = Active membrane cholesterol as a physiological effector | journal = Chem. Phys. Lipids | volume = 199 | pages = 74–93 | year = 2016 | pmid = 26874289 | doi = 10.1016/j.chemphyslip.2016.02.003 }} * [[Cholesterol]]: cholest-5-en-3β-ol – NMDA receptor positive allosteric modulator, possible GABAA receptor positive allosteric modulator, many other actions{{cite journal | vauthors = Hénin J, Salari R, Murlidaran S, Brannigan G | title = A predicted binding site for cholesterol on the GABAA receptor | journal = Biophys. J. | volume = 106 | issue = 9 | pages = 1938–49 | year = 2014 | pmid = 24806926 | pmc = 4017285 | doi = 10.1016/j.bpj.2014.03.024 | bibcode = 2014BpJ...106.1938H }}{{cite journal | vauthors = Levitan I, Singh DK, Rosenhouse-Dantsker A | title = Cholesterol binding to ion channels | journal = Front Physiol | volume = 5 | pages = 65 | year = 2014 | pmid = 24616704 | pmc = 3935357 | doi = 10.3389/fphys.2014.00065 | doi-access = free }}{{cite journal | vauthors = Lange Y, Steck TL | title = Active membrane cholesterol as a physiological effector | journal = Chem. Phys. Lipids | volume = 199 | pages = 74–93 | year = 2016 | pmid = 26874289 | doi = 10.1016/j.chemphyslip.2016.02.003 }} Line 114: Line 110: ==Neurotrophic== ==Neurotrophic== ===Natural=== ===Natural=== ====Androstanes==== ====Androstanes==== * [[Dehydroepiandrosterone]] (DHEA; prasterone): androst-5-en-3β-ol-17-one – [[TrkA]], [[TrkC]], and [[low-affinity nerve growth factor receptor|p75NTR]] agonist, [[TrkB]] [[ligand (biochemistry)|ligand]] * [[Dehydroepiandrosterone]] (DHEA; prasterone): androst-5-en-3β-ol-17-one – [[TrkA]], [[TrkC]], and [[low-affinity nerve growth factor receptor|p75NTR]] agonist, [[TrkB]] [[ligand (biochemistry)|ligand]] Line 125: Line 119: ===Synthetic=== ===Synthetic=== ====Androstanes==== ====Androstanes==== * [[BNN-20]]: 17β-spiro-(androst-5-en-17,2'-oxiran)-3β-ol – TrkA, TrkB, and p75NTR agonist * [[BNN-20]]: 17β-spiro-(androst-5-en-17,2'-oxiran)-3β-ol – TrkA, TrkB, and p75NTR agonist Line 133: Line 126: ==Antineurotrophic== ==Antineurotrophic== ===Natural=== ===Natural=== ====Androstanes==== ====Androstanes==== * [[Testosterone]]: androst-4-en-17β-ol-3-one – TrkA and p75NTR antagonist * [[Testosterone]]: androst-4-en-17β-ol-3-one – TrkA and p75NTR antagonist Line 148: Line 139: ===Natural=== ===Natural=== ====Androstanes==== ====Androstanes==== * [[3α-Androstenol]]: 5α-androst-16-en-3α-ol * [[3α-Androstenol]]: 5α-androst-16-en-3α-ol Line 161: Line 151: ===Synthetic=== ===Synthetic=== ====Androstanes==== ====Androstanes==== * [[Fasedienol]] (Aloradine; PH94B; 4-androstadienol): androsta-4,16-dien-3β-ol * [[Fasedienol]] (Aloradine; PH94B; 4-androstadienol): androsta-4,16-dien-3β-ol Line 175: Line 164: ==Others== ==Others== ===Natural=== ===Natural=== ====Pregnanes==== ====Pregnanes==== * [[Pregnenolone]] (P5): pregn-5-en-3β-ol-20-one – [[microtubule-associated protein 2|MAP2]] ligand * [[Pregnenolone]] (P5): pregn-5-en-3β-ol-20-one – [[microtubule-associated protein 2|MAP2]] ligand Line 190: Line 177: ===Synthetic=== ===Synthetic=== ====Pregnanes==== ====Pregnanes==== * [[3β-Methoxypregnenolone]] (MAP-4343): 3β-methoxypregn-5-en-20-one – MAP2 ligand * [[3β-Methoxypregnenolone]] (MAP-4343): 3β-methoxypregn-5-en-20-one – MAP2 ligand Line 203: Line 189: ==References== ==References== {{Reflist|2}} {{Reflist}}