CAS 516-54-1

3α-Hydroxy-5α-pregnan-20-one

Description:

3α-Hydroxy-5α-pregnan-20-one, commonly known as allopregnanolone, is a neuroactive steroid and a metabolite of progesterone. It is characterized by its structure, which includes a steroid backbone with a hydroxyl group at the 3α position and a double bond at the 5α position. This compound is known for its role in the central nervous system, where it acts as a positive modulator of the GABA_A receptor, influencing neuronal excitability and contributing to anxiolytic and sedative effects. Allopregnanolone is also involved in various physiological processes, including the regulation of mood, stress response, and neuroprotection. Its synthesis occurs primarily in the adrenal glands and the brain, and it can be derived from progesterone through enzymatic conversion. The substance has garnered interest in research related to mental health, particularly in the context of anxiety and depression, as well as potential therapeutic applications in neurodegenerative diseases. Its CAS number, 516-54-1, is used for identification in chemical databases and regulatory contexts.

Formula: C₂₁H₃₄O₂

InChI: InChI=1S/C21H34O2/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/h14-19,23H,4-12H2,1-3H3/t14-,15+,16-,17+,18-,19-,20-,21+/m0/s1

InChI key: InChIKey=AURFZBICLPNKBZ-SYBPFIFISA-N

SMILES: C[C@@]12[C@@]3([C@]([C@]4([C@](C)(CC3)[C@@H](C(C)=O)CC4)[H])(CC[C@]1(C[C@H](O)CC2)[H])[H])[H]

Synonyms:

• (+)-3α-Hydroxy-5α-pregnan-20-one
• (3α)-Allopregnanolone
• (3α,5α)-3-Hydroxypregnan-20-one
• 3α,5α-Pregnanolone
• 3α,5α-THP
• 3α,5α-Tetrahydroprogesterone
• 3α-Hydroxy-5α-dihydroprogesterone
• 3α-Hydroxy-5α-pregnane-20-one
• 5α-Pregnan-20-one, 3α-hydroxy-
• 5α-Pregnan-3α-ol-20-one
• 5α-Pregnane-3α-ol-20-one
• Allopregnan-3α-ol-20-one
• Allopregnanolone
• Allopregnanolone (SAGE-547)
• Allotetrahydroprogesterone
• Brexanolone
• Pregnan-20-one, 3-hydroxy-, (3α,5α)-
• Sage 547

Allopregnanolone

CAS: 516-54-1

Formula: C₂₁H₃₄O₂

Color and Shape: White To Off-White Solid

Molecular weight: 318.50

Ref: 4Z-P-325

Allopregnanolone-d5

CAS: 516-54-1

Formula: C₂₁H₂₉D₅O₂

Molecular weight: 323.53

Ref: 4Z-P-3299

5a-Pregnan-3a-ol-20-one

CAS: 516-54-1

Formula: C₂₁H₃₄O₂

Purity: ≥ 97.0%

Color and Shape: White powder

Molecular weight: 318.49

Ref: 7W-GL7373

5alpha-Pregnan-3alpha-ol-20-one-17alpha,21,21,21-d4

CAS: 203805-85-0, 516-54-1

Purity: 98 atom % D

Color and Shape: White Solid

Molecular weight: 322.52

Ref: 3U-D6894

3-Hydroxy-5-Methyl-N-Phenyl-2-1H-Pyridone

CAS: 516-54-1

Formula: C₁₂H₁₁NO₂

Color and Shape: White To Off-White Solid

Molecular weight: 201.23

Ref: 4Z-P-325008

(3alpha)-Allopregnanolone-d5

Controlled Product

CAS: 516-54-1

Applications Labelled (3α)-Allopregnanolone. (3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain.
References Puja, G. et al.: Neuron, 4, 759 (1990); Belelli, D. et ael. Neurosteroid, 6, 565 (2006); Viapiano, M. et al.: Neurochem. Res., 23, 155 (1998);

Formula: C₂₁H₂₉D₅O₂

Color and Shape: Neat

Molecular weight: 323.52

Ref: TR-A547102

(3a)-Allopregnanolone

Controlled Product

CAS: 516-54-1

Applications (3α)-Allopregnanolone acts as a GABAA receptor positive allosteric modulator. (3α)-Allopregnanolone is a metabolite of Progesterone (P755900). (3α)-Allopregnanolone is a neuroactive steroid present in the blood and also the brain. In 2019, the US Food and Drug Administration approved (3α)-Allopregnanolone as an intravenous infusion for treating postpartum depression.
References Puja, G. et al.: Neuron, 4, 759 (1990); Belelli, D. et ael. Neurosteroid, 6, 565 (2006); Viapiano, M. et al.: Neurochem. Res., 23, 155 (1998);

Formula: C₂₁H₃₄O₂

Color and Shape: White To Off-White

Molecular weight: 318.49

Ref: TR-A547100

Allopregnanolone

CAS: 516-54-1

Formula: C₂₁H₃₄O₂

Molecular weight: 318.5

Ref: ST-EA-CP-P133070

5alpha-Pregnan-3a-ol-20-one

Controlled Product

CAS: 516-54-1

5alpha-Pregnan-3a-ol-20-one is a low potency endogenous steroid that has been shown to have physiological effects in the brain. It is synthesized from progesterone by 3β-hydroxysteroid dehydrogenase and 5α-reductase type I and metabolized through pregnane X receptor (PXR) and constitutive androstane receptor (CAR). 5alpha-Pregnan-3a-ol-20-one may be involved in the regulation of neuronal death and is found to have a protective effect on experimental models against glutamate induced neuronal death. 5alpha-Pregnan-3a-ol-20-one has also been found to be present at physiological levels in maternal blood, which may be associated with its role in fetal development.

Formula: C₂₁H₃₄O₂

Purity: Min. 98 Area-%

Color and Shape: White Off-White Powder

Molecular weight: 318.49 g/mol

Ref: 3D-FA158661