Etiocholanolone

Modify Date: 2024-01-02 15:40:25

Etiocholanolone Structure
Etiocholanolone structure
Common Name Etiocholanolone
CAS Number 53-42-9 Molecular Weight 290.440
Density 1.1±0.1 g/cm3 Boiling Point 413.1±45.0 °C at 760 mmHg
Molecular Formula C19H30O2 Melting Point 148~150°C (lit.)
MSDS Chinese USA Flash Point 176.4±21.3 °C

 Use of Etiocholanolone


Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent neurosteroid positive allosteric modulator (PAM) of the GABAA receptor than its enantiomer form[2].

 Names

Name 3α-hydroxy-5β-androstan-17-one
Synonym More Synonyms

 Etiocholanolone Biological Activity

Description Etiocholanolone (5β-Androsterone) is the excreted metabolite of testosterone and has anticonvulsant activity[1]. Etiocholanolone is a less potent neurosteroid positive allosteric modulator (PAM) of the GABAA receptor than its enantiomer form[2].
Related Catalog
In Vitro Etiocholanolone (10 μM) coapplication with GABA leads to an increase in the relative frequency of long openings (fraction of OT3, site A2 effect), but it is ineffective at increasing the duration of long openings (site B effect) or at decreasing the relative frequency of the activation-related closed time component (site A1 effect)[2].
In Vivo Etiocholanolone (intraperitoneal injection; 0-109.1 mg/kg; single dose) exhibits ED50 values of 57.6 and 109.1 mg/kg in the 6-Hz and PTZ tests, respectively. Protective activity in the 6-Hz test of 5β,3α-A persists for 2 h and is shorter than ent-5β,3α-A treatment (3 hours) in mice[1].
References

[1]. Ping Li,et al. Natural and Enantiomeric Etiocholanolone Interact With Distinct Sites on the Rat alpha1beta2gamma2L GABAA Receptor. Mol Pharmacol. 2007 Jun;71(6):1582-90.

[2]. Dorota Zolkowska, et al. Anticonvulsant Potencies of the Enantiomers of the Neurosteroids Androsterone and Etiocholanolone Exceed Those of the Natural Forms. Psychopharmacology (Berl). 2014 Sep;231(17):3325-32.

 Chemical & Physical Properties

Density 1.1±0.1 g/cm3
Boiling Point 413.1±45.0 °C at 760 mmHg
Melting Point 148~150°C (lit.)
Molecular Formula C19H30O2
Molecular Weight 290.440
Flash Point 176.4±21.3 °C
Exact Mass 290.224579
PSA 37.30000
LogP 3.75
Vapour Pressure 0.0±2.2 mmHg at 25°C
Index of Refraction 1.536
Storage condition 2-8°C

 Safety Information

Personal Protective Equipment Eyeshields;Gloves;type N95 (US);type P1 (EN143) respirator filter
Hazard Codes F,Xn
Risk Phrases 11-20/21/22-36
Safety Phrases 16-36/37
RIDADR NONH for all modes of transport
WGK Germany 3

 Synthetic Route

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 Synonyms

3a-Hydroxy-5b-androstane-17-one
Androsterone, (5β)-
3alpha-hydroxy-5beta-androstan-17-one
5β-Androsterone
(5b)-Androsterone
5-Isoandrosterone
3α-hydroxy-5β-androstane-17-one
5β-Androstan-17-one, 3α-hydroxy-
5BETA-ANDROSTERONE
MFCD00064133
(3α,5β)-3-Hydroxyandrostan-17-one
ETIOCHOLANOLON
3α-Etiocholanolone
Androstan-17-one, 3-hydroxy-, (3α,5β)-
19-noretiocholanolone
ETIOCHOLANONE
3a-Etiocholanolone
3α-hydroxy-5β-androstan-17-one
5b-Androsterone
Etiocholan-3a-ol-17-one
Etiocholan-3α-ol-17-one
Etiocholan-3.α.-ol-17-one
EINECS 200-835-2
Etiocholanolone