| Identification | More | [Name]
Pregnenolone | [CAS]
145-13-1 | [Synonyms]
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)-ETHANONE
3BETA-HYDROXY-5-PREGNEN-20-ONE
3BETA-HYDROXYPREGN-5-EN-20-ONE
3b-hydroxy-5-pregnen-20-one
5-PREGNEN-3BETA-OL-20-ONE
5-pregnenolone
DELTA5-PREGNEN-3BETA-OL-20-ONE
DELTA5-PREGNEN-3B-OL-20-ONE
DELTA-5-PREGNENE-3B-OL-20-ONE
DELTA5-PREGNENOLONE
PREGNENOLONE
pregnolon
prenolon
(3-beta)-pregn-5-en-20-on
3-beta-hydroxy-pregn-5-en-20-on
5-pregnen-3B-ol-20-one
Pregnenlolone
Pregnenolone Micron
3Hydroxy-5-Pregnen-20-one
3β-Hydroxypregn-5-en-20-one | [EINECS(EC#)]
205-647-4 | [Molecular Formula]
C21H32O2 | [MDL Number]
MFCD00003628 | [Molecular Weight]
316.48 | [MOL File]
145-13-1.mol |
| Chemical Properties | Back Directory | [Appearance]
white to off-white powder | [Melting point ]
188-190 °C
| [alpha ]
28.5 º (c=1, EtOH) | [Boiling point ]
395.89°C (rough estimate) | [density ]
1.0382 (rough estimate) | [vapor pressure ]
0-0Pa at 20-25℃ | [refractive index ]
1.5344 (estimate) | [Fp ]
9℃ | [storage temp. ]
Refrigerator | [solubility ]
ethanol: soluble10mg/mL, clear, colorless to faintly yellow | [form ]
Powder | [pka]
15.00±0.70(Predicted) | [color ]
White to off-white | [Water Solubility ]
41mg/L(room temperature) | [Merck ]
7733 | [BRN ]
2059026 | [Major Application]
clinical testing
clinical testing | [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 | [InChIKey]
ORNBQBCIOKFOEO-QGVNFLHTSA-N | [SMILES]
O[C@H]1CC[C@@]2([C@@H]3[C@H]([C@H]4[C@@]([C@H](CC4)C(=O)C)(CC3)C)CC=C2C1)C | [LogP]
4.4 at 20℃ | [CAS DataBase Reference]
145-13-1(CAS DataBase Reference) | [NIST Chemistry Reference]
Pregnenolone(145-13-1) |
| Safety Data | Back Directory | [Symbol(GHS) ]
 
GHS02,GHS07 | [Signal word ]
Danger | [Hazard statements ]
H225-H302+H312+H332-H319 | [Precautionary statements ]
P210-P280-P305+P351+P338 | [Safety Statements ]
S22:Do not breathe dust .
S24/25:Avoid contact with skin and eyes . | [RIDADR ]
UN 1648 3 / PGII | [WGK Germany ]
3
| [RTECS ]
TU5560700
| [REACH Registrations]
Active | [HS Code ]
29144000 | [Storage Class]
3 - Flammable liquids | [Hazard Classifications]
Acute Tox. 4 Dermal
Acute Tox. 4 Inhalation
Acute Tox. 4 Oral
Eye Irrit. 2
Flam. Liq. 2 |
| Raw materials And Preparation Products | Back Directory | [Raw materials]
16-Dehydropregnenolone-->Pregna-5,17(20)-diene-3,20-diol,diacetate, (3b)- (9CI)-->Pregn-5-en-20-one,3-hydroxy-, cyclic 1,2-ethanediyl dithioacetal, (3b)- (9CI)-->Difluoromethyldiphenylphosphine Oxide-->Pregnenolone acetate-->20alpha-Hydroxycholesterol-->3-tert-Butyldimethylsilyloxy Pregnenolone-->Bromomethyl methyl ether-->beta-Sitosterol-->16-Dehydropregnenolone acetate | [Preparation Products]
Progesterone-->Finasteride-->GANAXOLONE-->17alpha-Hydroxypregnenolone-->Methyl 3-oxo-4-androstene-17beta-carboxylate-->CORTICOSTERONE-->1-((3R,10S,13S,17S)-3-hydroxy-3-(methoxymethyl)-10,13-dimethylhexadecahydro-1H-cyclopenta[a]phenanthren-17-yl)ethanone |
| Hazard Information | Back Directory | [Description]
Pregnenolone serves as the common precursor in the formation of the adrenocorticoids and other steroid
hormones. This C21 steroid is converted via enzymatic oxidations and isomerization of the double bond to a
number of physiologically active C21 steroids, including the female sex hormone progesterone and the
adrenocorticoids hydrocortisone (cortisol), corticosterone, and aldosterone. Oxidative cleavage of the
two-carbon side chain of pregnenolone and subsequent enzymatic oxidations and isomerization lead to C19
steroids, including the androgens testosterone and dihydrotestosterone. The final group of steroids, the C18
female sex hormones, are derived from oxidative aromatization of the A ring of androgens to produce estrogens. | [Chemical Properties]
white to off-white powder | [Uses]
glucocortcoid, antiinflammatory | [Uses]
Pregnenolone is a steroid hormone involved in the steroidogenesis of progesterone, mineralocorticoids, glucocorticoids, androgens, and estrogens. As such it is a prohormone. Pregnenolone is a GABAA an
tagonist and increases neurogenesis in the hippocampus. It is a modulator of cytochrome P 450-3A | [Definition]
ChEBI: 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. | [benefits]
Promotes Memory and Learning: Some research suggests that pregnenolone can promote memory and learning while providing other brain-based health benefits related to cognitive function. It works by protecting against inflammation in the nervous system, with neuroinflammatory diseases often coinciding with decreased pregnenolone levels.
Reduces Depression Symptoms: Pregnenolone directly affects other substances in the human body, such as MT-associated proteins (MAPs). MAP defects have been linked with major depressive disorder (MDD), and taking pregnenolone may positively affect MAP levels, potentially helping to ease depressive symptoms.
Improves Schizophrenia Symptoms: Taking a pregnenolone supplement may also help improve symptoms for people with schizophrenia. Research published in 2018 adds that taking pregnenolone for one month appears to provide benefits for individuals experiencing their first schizophrenic episode who have not yet started antipsychotic treatment.
Fewer Drug and Alcohol Cravings: When people with alcohol use disorder (AUD) try to quit drinking, the cravings they experience can make this process much harder. In a 2023 study involving 43 people with AUD, those taking 300 milligrams (mg) of pregnenolone daily had fewer alcohol cravings after being exposed to stress or typical drinking cues. A 2022 study found similar results for people with cocaine use disorder. In this case, participants took either 300 mg or 500 mg of pregnenolone daily. After two weeks, they had reduced stress and cue-induced cravings for this drug. The group taking 500 mg daily also had reductions in their stress and cue-induced anxiety levels.
| [General Description]
Pregnenolone is an endogenous steroid hormone involved in the biological synthesis of other hormones. Pregnenolone is monitored as an ancillary test for congenital adrenal hyperplasia (CAH), particularly in situations where diagnosis of 21-hydroxylase and 11-hydroxylase deficiency has been ruled out. This Certified Spiking Solution? is suitable for use in LC-MS/MS testing methods as a starting material in the preparation of calibrators, controls and linearity standards. | [Side effects]
When taken by mouth: Pregnenolone is possibly safe when used for up to 12 weeks. It is usually well-tolerated. Side effects might include acne, agitation, diarrhea, drowsiness, excitement, hair loss, skin rashes, sweating, and tremor. There isn't enough reliable information to know if pregnenolone is safe when used for longer than 12 weeks.
| [in vitro]
pregnenolone is the precursor from which almost all of the other steroid hormones are made, including dhea, testosterone, progesterone, the estrogens and cortisol. pregnenolone also operates as a powerful neurosteroid in the brain, which modulates the transmission of messages from neuron to neuron and strongly influencing learning and memory processes [1]. | [in vivo]
the ability of pregnenolone sulfate derivatives (pregs) to modulate the age-induced learning impairment was tested in 16- month-old mice using the step-down type of passive avoidance. decreased step-down latency was observed in the passive avoidance task in 16-month-old mice compared to 3-month-old mice, revealing retention deficits in old mice. pretraining injections of pregs dose-dependently improved the 24 h delay retention performances in this task in old mice [1]. | [storage]
Store at 4°C | [References]
[1] 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. |
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