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Purity: ≥98%
Pregnenolone (NSC-1616; NSC-18158; Prenolon; Regnosone; Skinostelon; Enelone; Natolone; Pregnetan; Pregneton; Pregnolon) is an endogenous/naturally occurring steroidal hormone that has been used in the treatment of fatigue, Alzheimer's disease, trauma and injuries. It is neurosteroid and a key precursor for the biosynthesis of many steroids including progesterone, glucocorticoids, mineralocorticoids, androgens, and estrogens, making it a prohormone. It has been observed to inhibit GABA-gated chloride currents by enhancing receptor desensitization.
| ln Vitro |
The stimulation of CB1 receptors raises levels of pregnenolone in the brain, which counteracts most of the known behavioral and physical effects of THC by acting as a negative feedback loop on CB1 receptor activity. Pregnenolone most likely binds to a different location than orthosteric ligands, acting as a signaling-specific negative allosteric modulator. Pregnenolone solely affects agonist effectiveness; it has no effect on agonist binding[1]. Applying 100 nM of pregnenolone to slices before to THC treatment considerably reduces its impact (15.11±1.8% of inhibition). Pregnenolone's pre-synaptic activity is most likely the cause of these effects. Pregnenolone thus prevents the paired-pulse ratio (PPR) from increasing as a result of THC, but it has no effect on the amplitude or decay time of the miniature EPSC (mEPSC)[1].
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| ln Vivo |
Administering pregnenolone (2–6 mg/kg) blunts the memory impairment caused by THC in mice and prevents THC-induced food intake in Wistar rats and C57BL/6N mice, but it does not change these behaviors in and of themselves. Pregnenolone injections (2 and 4 mg/kg) prior to each self-administration session lower WIN 55,212-2 intake and lower the progressive ratio schedule's break-point[1].
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| ADME/Pharmacokinetics |
Metabolism / Metabolites
Pregnenolone has known human metabolites that include 1-(3,16-Dihydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, 2-Hydroxy-1-(3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone, and Pregn-5-en-20-on-3b-yl sulfurate. |
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| Additional Infomation |
Pregnenolone is a 20-oxo steroid that is pregn-5-ene substituted by a beta-hydroxy group at position 3 and an oxo group at position 20. It has a role as a human metabolite and a mouse metabolite. It is a 20-oxo steroid, a C21-steroid and a 3beta-hydroxy-Delta(5)-steroid. It derives from a hydride of a pregnane.
A 21-carbon steroid, derived from cholesterol and found in steroid hormone-producing tissues. Pregnenolone is the precursor to gonadal steroid hormones and the adrenal corticosteroids. Pregnenolone has been reported in Abedus herberti, Locusta migratoria, and other organisms with data available. Pregnenolone is an endogenous steroid hormone synthesized from cholesterol, which can act either as a neuroactive steroid or as a prohormone for progestogens, mineralocorticoids, glucocorticoids, androgens, estrogens, and the neuroactive steroids. A 21-carbon steroid, derived from CHOLESTEROL and found in steroid hormone-producing tissues. Pregnenolone is the precursor to GONADAL STEROID HORMONES and the adrenal CORTICOSTEROIDS. |
| Molecular Formula |
C21H32O2
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| Molecular Weight |
316.48
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| Exact Mass |
316.24
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| CAS # |
145-13-1
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| Related CAS # |
Pregnenolone monosulfate sodium;1852-38-6;Pregnenolone-d4-1;61574-54-7;Pregnenolone monosulfate;1247-64-9;Pregnenolone-d4;Pregnenolone-13C2,d2;2483824-26-4
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| PubChem CID |
8955
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| Appearance |
White to off-white solid powder
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| Density |
1.1±0.1 g/cm3
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| Boiling Point |
443.3±45.0 °C at 760 mmHg
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| Melting Point |
188-190 °C
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| Flash Point |
188.9±21.3 °C
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| Vapour Pressure |
0.0±2.4 mmHg at 25°C
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| Index of Refraction |
1.550
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| LogP |
4.52
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| Hydrogen Bond Donor Count |
1
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| Hydrogen Bond Acceptor Count |
2
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| Rotatable Bond Count |
1
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| Heavy Atom Count |
23
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| Complexity |
550
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| Defined Atom Stereocenter Count |
7
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| SMILES |
CC(=O)[C@H]1CC[C@@H]2[C@@]1(CC[C@H]3[C@H]2CC=C4[C@@]3(CC[C@@H](C4)O)C)C
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| InChi Key |
ORNBQBCIOKFOEO-QGVNFLHTSA-N
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| InChi Code |
InChI=1S/C21H32O2/c1-13(22)17-6-7-18-16-5-4-14-12-15(23)8-10-20(14,2)19(16)9-11-21(17,18)3/h4,15-19,23H,5-12H2,1-3H3/t15-,16-,17+,18-,19-,20-,21+/m0/s1
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| Chemical Name |
1-((3S,8S,9S,10R,13S,14S,17S)-3-hydroxy-10,13-dimethyl-2,3,4,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethan-1-one
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| Synonyms |
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| HS Tariff Code |
2934.99.9001
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| Storage |
Powder -20°C 3 years 4°C 2 years In solvent -80°C 6 months -20°C 1 month |
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| Shipping Condition |
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
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| Solubility (In Vitro) |
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| Solubility (In Vivo) |
Solubility in Formulation 1: ≥ 2.5 mg/mL (7.90 mM) (saturation unknown) in 10% DMSO + 90% (20% SBE-β-CD in Saline) (add these co-solvents sequentially from left to right, and one by one), clear solution.
For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of 20% SBE-β-CD physiological saline solution and mix evenly. Preparation of 20% SBE-β-CD in Saline (4°C，1 week): Dissolve 2 g SBE-β-CD in 10 mL saline to obtain a clear solution. Solubility in Formulation 2: ≥ 2.5 mg/mL (7.90 mM) (saturation unknown) in 10% DMSO + 90% Corn Oil (add these co-solvents sequentially from left to right, and one by one), clear solution. For example, if 1 mL of working solution is to be prepared, you can add 100 μL of 25.0 mg/mL clear DMSO stock solution to 900 μL of corn oil and mix evenly. View More
Solubility in Formulation 3: 1.25 mg/mL (3.95 mM) in 10% DMSO + 40% PEG300 + 5% Tween80 + 45% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Solubility in Formulation 4: 10 mg/mL (31.60 mM) in 50% PEG300 50% Saline (add these co-solvents sequentially from left to right, and one by one), suspension solution; with ultrasonication. Preparation of saline: Dissolve 0.9 g of sodium chloride in 100 mL ddH₂ O to obtain a clear solution. |
| Preparing Stock Solutions | 1 mg | 5 mg | 10 mg | |
| 1 mM | 3.1598 mL | 15.7988 mL | 31.5976 mL | |
| 5 mM | 0.6320 mL | 3.1598 mL | 6.3195 mL | |
| 10 mM | 0.3160 mL | 1.5799 mL | 3.1598 mL |
*Note: Please select an appropriate solvent for the preparation of stock solution based on your experiment needs. For most products, DMSO can be used for preparing stock solutions (e.g. 5 mM, 10 mM, or 20 mM concentration); some products with high aqueous solubility may be dissolved in water directly. Solubility information is available at the above Solubility Data section. Once the stock solution is prepared, aliquot it to routine usage volumes and store at -20°C or -80°C. Avoid repeated freeze and thaw cycles.
Calculation results
Working concentration： mg/mL；
Method for preparing DMSO stock solution： mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.
Method for preparing in vivo formulation:：Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O，mix and clarify.
(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
(2) Be sure to add the solvent(s) in order.
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