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Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Dihydromuscimol (DHM), or 4,5-dihydromuscimol, is a synthetic GABAA 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]

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

CAS No.
72241-46-4
Chemical Name:
dihydromuscimol
Synonyms
dihydromuscimol;5-(Aminomethyl)isoxazolidine-3-one;3-Isoxazolidinone, 5-(aminomethyl)-;5-(Aminomethyl)-4,5-dihydro-3(2H)-isoxazolone
CBNumber:
CB51354404
Molecular Formula:
C4H8N2O2
Molecular Weight:
116.12
MDL Number:
MOL File:
72241-46-4.mol
Last updated:2023-07-12 16:43:50
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5-(Aminomethyl)isoxazolidin-3-one

GABA-A receptor pharmacologyEnantioselectivityRadioligand binding

⚠ Attention: For research use only. Not for human or veterinary use.
Molecular FormulaC4H8N2O2
Molecular Weight116.12 g/mol
CAS No.72241-46-4

Technical Parameters

Basic Identity
Product Name 5-(Aminomethyl)isoxazolidin-3-one
CAS 72241-46-4
Synonyms
(RS)-4,5-dihydromuscimol, dihydromuscimol
Molecular Formula C4H8N2O2
Molecular Weight 116.12 g/mol
Structural Identifiers
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)
InChIKey ZHCZZTNIHDWRNS-UHFFFAOYSA-N
Commercial & Availability
Standard Pack Sizes 10 mg / 50 mg / 100 mg / Bulk Custom
Availability In Stock
Custom Synthesis Available on request

5-(Aminomethyl)isoxazolidin-3-one (CAS 72241-46-4): A Bifunctional GABA-A Agonist and Reuptake Inhibitor for Neuroscience Research Procurement

5-(Aminomethyl)isoxazolidin-3-one (CAS 72241-46-4), universally referred to as dihydromuscimol (DHM) or (RS)-4,5-dihydromuscimol, is a synthetic, partially saturated heterocyclic analogue of the Amanita muscaria alkaloid muscimol [1]. It belongs to the isoxazolidin-3-one class and functions as both a gamma-aminobutyric acid type A (GABA-A) receptor orthosteric agonist and a GABA reuptake inhibitor, making it a bifunctional pharmacological probe [2]. The compound exists as a racemic mixture of (S)-(+) and (R)-(-) enantiomers, which exhibit strikingly divergent pharmacological profiles: the (S)-enantiomer is among the most potent GABA-A agonists ever characterized, while the (R)-enantiomer preferentially inhibits GABA transport [3]. DHM has been employed as a rigid conformational probe in GABA receptor structure–activity studies since its first description in 1979 [2].

1

Bifunctional probe: GABA-A orthosteric agonism and GABA reuptake inhibition in a single scaffold

2

Enantiomer-paired control for independent receptor activation and transporter modulation studies

3

Conformationally constrained muscimol analog for GABA-A orthosteric pharmacophore mapping

Why Muscimol, THIP, or Isoguvacine Cannot Replace 5-(Aminomethyl)isoxazolidin-3-one in Experimental Pharmacology

Substituting dihydromuscimol with muscimol, THIP (gaboxadol), or isoguvacine in a neuroscience research protocol introduces critical confounds. Unlike these single-mechanism GABA-A agonists, DHM possesses a bifunctional profile where the (S)-enantiomer acts as an ultra-potent GABA-A agonist (IC50 ~4 nM) while the (R)-enantiomer selectively inhibits GABA reuptake, a property entirely absent in muscimol [1]. This enantiomer-specific divergence—quantified as approximately a 62.5-fold difference in GABA-A binding affinity between (S)- and (R)-DHM—enables dissection of GABA-A receptor activation from GABA transport modulation using a single chemical scaffold, a capability that no other commercially available GABA analogue provides [2]. Furthermore, the 3-hydroxyisoxazoline ring of DHM imposes a distinct conformational constraint compared to the fully aromatic isoxazole of muscimol, directly affecting the geometry of hydrogen-bonding interactions at the GABA-A orthosteric site and yielding a unique efficacy profile across receptor subunit combinations [3].

Mechanism mismatch

Muscimol, THIP, and isoguvacine are GABA-A agonists only; they lack GABA transport inhibition and cannot enable dual-mechanism dissection.

Enantiomer control gap

Achiral GABA analogs cannot provide matched enantiomer pairs; enantioselective receptor binding and uptake separation are lost.

Pharmacophore geometry

The saturated isoxazolidinone ring of DHM yields distinct subunit efficacy fingerprints that aromatic muscimol or THIP may not reproduce.

dihydromuscimol Properties

Density 1.196±0.06 g/cm3(Predicted)
pka 14.69±0.40(Predicted)

dihydromuscimol Preparation Products And Raw materials

Raw materials

Preparation Products

dihydromuscimol 5-(Aminomethyl)-4,5-dihydro-3(2H)-isoxazolone 5-(Aminomethyl)isoxazolidine-3-one 3-Isoxazolidinone, 5-(aminomethyl)- 72241-46-4

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Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

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Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

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Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

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Buy Dihydromuscimol (4-5-dihydromuscimol) Cas 72241-46-4

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See also

  1. dihydromuscimol | 72241-46-4 – ChemicalBook

    Jul 12, 2023 · dihydromuscimol (CAS 72241-46-4) information, including chemical properties, structure, melting point, boiling point, …

  2. CAS No.72241-46-4,dihydromuscimol Suppliers – LookChem

    Find quality suppliers and manufacturers of 72241-46-4 (dihydromuscimol) for price inquiry. where to buy 72241-46-4 …

  3. Dihydromuscimol (CAS 72241-46-4) | Physicochemical properties, …

    Detailed information about Dihydromuscimol (CAS 72241-46-4), including physicochemical properties, SDS, safety data, …

  4. dihydromuscimol CAS # 72241-46-4 – tradingchem.com

    dihydromuscimol (72241-46-4) CAS Registry Number: 72241-46-4 Synonyms: (RS)-4,5-Dihydromuscimol;4,5-Dihydromuscimol; …

  5. dihydromuscimol | CAS#:72241-46-4 | Chemsrc – 化源网

    Nov 30, 2025 · Chemsrc provides dihydromuscimol (CAS#:72241-46-4) MSDS, density, melting point, boiling point, structure, …

  6. Buy dihydromuscimol Industrial Grade from CHEMLYTE SOLUTIONS …

    CHEMLYTE SOLUTIONS CO.,LTD, with approximately 752539 visits to its shop, is a reputable Manufactory that has been providing …

  7. Buy dihydromuscimol from Dayang Chem (Hangzhou) Co.,Ltd – ECHEMI

    Dayang Chem (Hangzhou) Co.,Ltd, with approximately 939434 visits to its shop, is a reputable Manufactory that has been providing …

  8. 5- (Aminomethyl)isoxazolidin-3-one For Research

    5- (Aminomethyl)isoxazolidin-3-one (CAS 72241-46-4), universally referred to as dihydromuscimol (DHM) or (RS)-4,5 …

  9. 72241-46-4 – ChemBK

    72241-46-4 dihydromuscimol CAS: 72241-46-4 Molecular Formula: Home Product Category 72241-46-4 Home CAS CAS 722 CAS …

  10. Dihydromuscimol | C4H8N2O2 | CID 194439 – PubChem

    Dihydromuscimol | C4H8N2O2 | CID 194439 – structure, chemical names, physical and chemical properties, classification, patents, …

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