Dihydromuscimol

Dihydromuscimol (DHM), or 4,5-dihydromuscimol, is a synthetic GABA_A receptor agonist and GABA reuptake inhibitor which was derived from the Amanita muscaria constituent muscimol.^[1][2][3] The compound is a dihydroisoxazole derivative.^[4]

Other namesDHM; 4,5-Dihydromuscimol

Drug classGABA_A receptor agonist; GABA reuptake inhibitor

ATC code

• None

CAS Number

• 72241-46-4

Quick facts Clinical data, Other names ...

Dihydromuscimol

Left: (S)-dihydromuscimol Right: (R)-dihydromuscimol
Clinical data
Other names	DHM; 4,5-Dihydromuscimol
Drug class	GABAA receptor agonist; GABA reuptake inhibitor
ATC code	None
Identifiers
IUPAC name 5-(aminomethyl)-1,2-oxazolidin-3-one
CAS Number	72241-46-4
PubChem CID	194439
ChemSpider	168713
ChEMBL	ChEMBL40363
CompTox Dashboard (EPA)	DTXSID50992981
Chemical and physical data
Formula	C4H8N2O2
Molar mass	116.120 g·mol−1
3D model (JSmol)	Interactive image
SMILES C1C(ONC1=O)CN
InChI InChI=1S/C4H8N2O2/c5-2-3-1-4(7)6-8-3/h3H,1-2,5H2,(H,6,7) Key:ZHCZZTNIHDWRNS-UHFFFAOYSA-N

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The compound has two enantiomeric forms. (S)-Dihydromuscimol is a selective and extremely potent GABA_A receptor agonist, while (R)-dihydromuscimol is a GABA reuptake inhibitor and a weak GABA_A receptor agonist.^[5][6][7][8] Dihydromuscimol is equipotent to muscimol as a GABA_A receptor agonist but is more potent as a GABA reuptake inhibitor.^[7][8] However, (S)-dihydromuscimol is slightly more potent than muscimol as a GABA_A receptor agonist.^[6] The enantiomer is the most potent GABA_A receptor agonist that has been discovered as of 2004.^[1][8]

Dihydromuscimol was first described in the scientific literature by Povl Krogsgaard-Larsen and colleagues by 1979.^[4][3] The aminomethyl side chain of dihydromuscimol may be just as susceptible to metabolism as that of muscimol, and hence the drug has not been extensively used in animal studies.^[9]