Pregnenolone
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MedKoo CAT#: 328065

CAS#: 145-13-1

Description: Pregnenolone is a natural steroid hormone that serves as a precursor for a wide range of steroids, including mineralocorticoids, glucocorticoids, androgens, and estrogens.

Chemical Structure

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Pregnenolone
CAS# 145-13-1
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 328065
Name: Pregnenolone
CAS#: 145-13-1
Chemical Formula: C21H32O2
Exact Mass: 316.24
Molecular Weight: 316.490
Elemental Analysis: C, 79.70; H, 10.19; O, 10.11

Price and Availability

Size Price Availability Quantity
2g USD 150 Ready to ship
5g USD 300 2 weeks
10g USD 450 2 weeks
25g USD 750 2 weeks
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Synonym: Pregnenolone; NSC 1616; NSC 18158; Prenolon; Regnosone; Skinostelon; Enelone; Natolone; Pregnetan; Pregneton; Pregnolon.

IUPAC/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

InChi Key: ORNBQBCIOKFOEO-QGVNFLHTSA-N

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

SMILES Code: O[C@H](C1)CC[C@@]2(C)C1=CC[C@]3([H])[C@]2([H])CC[C@@]4(C)[C@@]3([H])CC[C@@H]4C(C)=O

Appearance: Solid powder

Purity: >98% (or refer to the Certificate of Analysis)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Product Data:
Product Data
Certificate of Analysis:
View CoA: current batch, Lot# C8M10C12
Safety Data Sheet (SDS):
View Safety Data Sheet (SDS)
Instruction:
View handling instruction
Biological target: Pregnenolone acts as a signaling-specific inhibitor of cannabinoid CB1 receptor, inhibits the effects of tetrahydrocannabinol (THC) that are mediated by the CB1 receptors.
In vitro activity: As shown in the Figures 5A, B, the early activation of ERK MAPK as determined by the phosphorylation of ERK in response to RANLK was significantly attenuated following treatment with Preg (Pregnenolone). The activation phosphorylation of the other MAPK members, p38, and JNK was not affected by Preg treatment (Figures 5A, C, D). The timely and coordinated activation of NF-κB and MAPK is necessary for the subsequent induction of c-Fos and NFATc1. NFATc1 is a crucial transcription factor required for precursor cell fusion and terminal osteoclast differentiation by transcriptionally regulating the expression of numerous osteoclast genes. The expression of c-Fos and NFATc1 was induced 72 h after RANKL stimulation, but was drastically reduced when cells were cultured in the presence of Preg in a dose-dependent manner (Figures 5G–I). Together biochemical analyses suggest that Preg inhibits osteoclast formation in part by suppressing intracellular ROS production and attenuating RANKL-induced activation of ERK MAPK and NF-κB signaling cascades which subsequent reduced the effective downstream induction of Fos and NFATc1. Reference: Front Pharmacol. 2020; 11: 360. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7135856/
In vivo activity: To assess this, PREG (Pregnenolone) (6 mg/kg s.c. once daily for 9 days, from PND 15 to 23) was administered to VEH or PCE offspring, and acute VTA-containing slices were prepared 1 and 2 days following the last administration (Fig. 6a), when PREG is cleared from the brain. Remarkably, PREG rescued LTD at excitatory synapses on dopamine neurons to CTRL levels (Fig. 6b), without affecting synaptic efficacy in CTRL offspring. Moreover, PREG ameliorated PCE-induced dopamine neuron excitability in PCE slices, measured by resting membrane potential (Fig. 6c), as well as spontaneous (Fig. 6d–f) and evoked firing activity (Fig. 6g,,h).h). PREG also fully restored the alterations in synaptic properties imposed by PCE on excitatory and inhibitory inputs on dopamine cells (Supplementary Fig. 12). Most importantly, PREG selectively prevented larger acute THC-induced enhancement of dopamine levels in NAcS (Fig. 6i,,j),j), and THC-induced disruption of somatosensory gating functions in PCE offspring (Fig. 6k). Finally, PREG mechanism of action was dissociated from its downstream neurosteroid metabolites (Supplementary Fig.13). Collectively, these results indicate that PREG prevents PCE-induced hyperdopaminergic states and confers resilience towards heightened acute effects of THC in PCE animals. Reference: Nat Neurosci. 2019 Dec; 22(12): 1975–1985. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6884689/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 17.3 54.50
Ethanol 22.0 69.51
Acetonitrile 1.0 3.16
Methanol 1.0 3.16

Preparing Stock Solutions

The following data is based on the product molecular weight 316.49 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol: 1. Sun X, Zhang C, Guo H, Chen J, Tao Y, Wang F, Lin X, Liu Q, Su L, Qin A. Pregnenolone Inhibits Osteoclast Differentiation and Protects Against Lipopolysaccharide-Induced Inflammatory Bone Destruction and Ovariectomy-Induced Bone Loss. Front Pharmacol. 2020 Mar 27;11:360. doi: 10.3389/fphar.2020.00360. PMID: 32292342; PMCID: PMC7135856. 2. Murugan S, Jakka P, Namani S, Mujumdar V, Radhakrishnan G. The neurosteroid pregnenolone promotes degradation of key proteins in the innate immune signaling to suppress inflammation. J Biol Chem. 2019 Mar 22;294(12):4596-4607. doi: 10.1074/jbc.RA118.005543. Epub 2019 Jan 15. PMID: 30647133; PMCID: PMC6433066. 3. Frau R, Miczán V, Traccis F, Aroni S, Pongor CI, Saba P, Serra V, Sagheddu C, Fanni S, Congiu M, Devoto P, Cheer JF, Katona I, Melis M. Prenatal THC exposure produces a hyperdopaminergic phenotype rescued by pregnenolone. Nat Neurosci. 2019 Dec;22(12):1975-1985. doi: 10.1038/s41593-019-0512-2. Epub 2019 Oct 14. PMID: 31611707; PMCID: PMC6884689. 4. Busquets-Garcia A, Soria-Gómez E, Redon B, Mackenbach Y, Vallée M, Chaouloff F, Varilh M, Ferreira G, Piazza PV, Marsicano G. Pregnenolone blocks cannabinoid-induced acute psychotic-like states in mice. Mol Psychiatry. 2017 Nov;22(11):1594-1603. doi: 10.1038/mp.2017.4. Epub 2017 Feb 21. PMID: 28220044; PMCID: PMC5447368.
In vitro protocol: 1. Sun X, Zhang C, Guo H, Chen J, Tao Y, Wang F, Lin X, Liu Q, Su L, Qin A. Pregnenolone Inhibits Osteoclast Differentiation and Protects Against Lipopolysaccharide-Induced Inflammatory Bone Destruction and Ovariectomy-Induced Bone Loss. Front Pharmacol. 2020 Mar 27;11:360. doi: 10.3389/fphar.2020.00360. PMID: 32292342; PMCID: PMC7135856. 2. Murugan S, Jakka P, Namani S, Mujumdar V, Radhakrishnan G. The neurosteroid pregnenolone promotes degradation of key proteins in the innate immune signaling to suppress inflammation. J Biol Chem. 2019 Mar 22;294(12):4596-4607. doi: 10.1074/jbc.RA118.005543. Epub 2019 Jan 15. PMID: 30647133; PMCID: PMC6433066.
In vivo protocol: 1. Frau R, Miczán V, Traccis F, Aroni S, Pongor CI, Saba P, Serra V, Sagheddu C, Fanni S, Congiu M, Devoto P, Cheer JF, Katona I, Melis M. Prenatal THC exposure produces a hyperdopaminergic phenotype rescued by pregnenolone. Nat Neurosci. 2019 Dec;22(12):1975-1985. doi: 10.1038/s41593-019-0512-2. Epub 2019 Oct 14. PMID: 31611707; PMCID: PMC6884689. 2. Busquets-Garcia A, Soria-Gómez E, Redon B, Mackenbach Y, Vallée M, Chaouloff F, Varilh M, Ferreira G, Piazza PV, Marsicano G. Pregnenolone blocks cannabinoid-induced acute psychotic-like states in mice. Mol Psychiatry. 2017 Nov;22(11):1594-1603. doi: 10.1038/mp.2017.4. Epub 2017 Feb 21. PMID: 28220044; PMCID: PMC5447368.

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1: Weng JH, Chung BC. Nongenomic actions of neurosteroid pregnenolone and its metabolites. Steroids. 2016 Jul;111:54-9. doi: 10.1016/j.steroids.2016.01.017. Review. PubMed PMID: 26844377.

2: Vallée M. Neurosteroids and potential therapeutics: Focus on pregnenolone. J Steroid Biochem Mol Biol. 2016 Jun;160:78-87. doi: 10.1016/j.jsbmb.2015.09.030. Review. PubMed PMID: 26433186.

3: Smith CC, Gibbs TT, Farb DH. Pregnenolone sulfate as a modulator of synaptic plasticity. Psychopharmacology (Berl). 2014 Sep;231(17):3537-56. doi: 10.1007/s00213-014-3643-x. Review. PubMed PMID: 24997854; PubMed Central PMCID: PMC4625978.

4: Harteneck C. Pregnenolone sulfate: from steroid metabolite to TRP channel ligand. Molecules. 2013 Sep 27;18(10):12012-28. doi: 10.3390/molecules181012012. Review. PubMed PMID: 24084011.

5: Katsumata N. Genetic defects in pregnenolone synthesis. Pediatr Endocrinol Rev. 2012 Oct;10 Suppl 1:98-109. Review. PubMed PMID: 23330251.

6: Marx CE, Bradford DW, Hamer RM, Naylor JC, Allen TB, Lieberman JA, Strauss JL, Kilts JD. Pregnenolone as a novel therapeutic candidate in schizophrenia: emerging preclinical and clinical evidence. Neuroscience. 2011 Sep 15;191:78-90. doi: 10.1016/j.neuroscience.2011.06.076. Review. PubMed PMID: 21756978.

7: Ritsner MS. The clinical and therapeutic potentials of dehydroepiandrosterone and pregnenolone in schizophrenia. Neuroscience. 2011 Sep 15;191:91-100. doi: 10.1016/j.neuroscience.2011.04.017. Review. PubMed PMID: 21549182.

8: Ritsner MS. Pregnenolone, dehydroepiandrosterone, and schizophrenia: alterations and clinical trials. CNS Neurosci Ther. 2010 Spring;16(1):32-44. doi: 10.1111/j.1755-5949.2009.00118.x. Review. PubMed PMID: 20070787.

9: Schumacher M, Liere P, Akwa Y, Rajkowski K, Griffiths W, Bodin K, Sjövall J, Baulieu EE. Pregnenolone sulfate in the brain: a controversial neurosteroid. Neurochem Int. 2008 Mar-Apr;52(4-5):522-40. Review. PubMed PMID: 18068870.

10: Shimizu Y. [Pregnenolone, pregnenolone sulfate]. Nihon Rinsho. 2005 Aug;63 Suppl 8:336-9. Review. Japanese. PubMed PMID: 16149523.

11: Mayo W, George O, Darbra S, Bouyer JJ, Vallée M, Darnaudéry M, Pallarès M, Lemaire-Mayo V, Le Moal M, Piazza PV, Abrous N. Individual differences in cognitive aging: implication of pregnenolone sulfate. Prog Neurobiol. 2003 Sep;71(1):43-8. Review. PubMed PMID: 14611866.

12: Vallée M, Mayo W, Le Moal M. Role of pregnenolone, dehydroepiandrosterone and their sulfate esters on learning and memory in cognitive aging. Brain Res Brain Res Rev. 2001 Nov;37(1-3):301-12. Review. PubMed PMID: 11744095.

13: Shimizu Y, Yanaihara T. [Pregnenolone, pregnenolone sulfate]. Nihon Rinsho. 1999 Dec;57 Suppl:162-5. Review. Japanese. PubMed PMID: 10778089.

14: Nakamura S, Mikami S, Futoeda T. [Pregnenolone]. Nihon Rinsho. 1995 Mar;53 Su Pt 2:464-6. Review. Japanese. PubMed PMID: 8753281.

15: Roberts E. Pregneolone--from Selye to Alzheimer and a model of the pregnenolone sulfate binding site on the GABAA receptor. Biochem Pharmacol. 1995 Jan 6;49(1):1-16. Review. PubMed PMID: 7840775.

16: Akwa Y, Young J, Kabbadj K, Sancho MJ, Zucman D, Vourc'h C, Jung-Testas I, Hu ZY, Le Goascogne C, Jo DH, et al. Neurosteroids: biosynthesis, metabolism and function of pregnenolone and dehydroepiandrosterone in the brain. J Steroid Biochem Mol Biol. 1991;40(1-3):71-81. Review. PubMed PMID: 1835645.

17: Burstein S, Gut M. Biosynthesis of pregnenolone. Recent Prog Horm Res. 1971;27:303-49. Review. PubMed PMID: 4946132.