3β-Methoxypregnenolone

3β-Methoxypregnenolone (developmental code name MAP-4343), or pregnenolone 3β-methyl ether, also known as 3β-methoxypregn-5-en-20-one, is a synthetic neuroactive steroid and derivative of pregnenolone.[1][2][3][4] It interacts with microtubule-associated protein 2 (MAP2) in a similar manner to pregnenolone and is under development for potential clinical use for indications such as the treatment of brain and spinal cord injury and depressive disorders.[1][2][3][4]

3β-Methoxypregnenolone
Clinical data
Other namesPregnenolone 3-methyl ether; 3β-Methoxypregn-5-en-20-one
Identifiers
IUPAC name
  • 1-[(3S,8S,9S,10R,13S,14S,17S)-3-Methoxy-10,13-dimethyl-2,3,4,7,8,9,11,12,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-17-yl]ethanone
CAS Number
PubChem CID
ChemSpider
UNII
Chemical and physical data
FormulaC22H34O2
Molar mass330.512 g·mol−1
3D model (JSmol)
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)OC)C)C
InChI
  • InChI=1S/C22H34O2/c1-14(23)18-7-8-19-17-6-5-15-13-16(24-4)9-11-21(15,2)20(17)10-12-22(18,19)3/h5,16-20H,6-13H2,1-4H3/t16-,17-,18+,19-,20-,21-,22+/m0/s1
  • Key:ZVGQOQHAMHMMNE-BIBIXIOVSA-N

See also

References
  1. "Pregnenolone methyl ether - Mapreg - AdisInsight".
  2. Duchossoy Y, David S, Baulieu EE, Robel P (2011). "Treatment of experimental spinal cord injury with 3β-methoxy-pregnenolone". Brain Res. 1403: 57–66. doi:10.1016/j.brainres.2011.05.065. PMID 21704982. S2CID 42657539.
  3. Bianchi M, Baulieu EE (2012). "3β-Methoxy-pregnenolone (MAP4343) as an innovative therapeutic approach for depressive disorders". Proc. Natl. Acad. Sci. U.S.A. 109 (5): 1713–8. Bibcode:2012PNAS..109.1713B. doi:10.1073/pnas.1121485109. PMC 3277154. PMID 22307636.
  4. Baulieu ÉÉ (2015). "From steroid hormones to depressive states and senile dementias: New mechanistic, therapeutical and predictive approaches". Comptes Rendus Biologies. 338 (8–9): 613–6. doi:10.1016/j.crvi.2015.06.003. PMID 26251072.


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