HA-966

HA-966 or (±)-3-amino-1-hydroxy-pyrrolidin-2-one is a molecule used in scientific research as a glycine receptor and NMDA receptor antagonist / low efficacy partial agonist. It has neuroprotective and anticonvulsant,^[1] anxiolytic,^[2] antinociceptive^[3] and sedative / hypnotic^[4] effects in animal models. Pilot human clinical trials in the early 1960s showed that HA-966 appeared to benefit patients with tremors of extrapyramidal origin.^[4]

CAS Number

• 1003-51-6

PubChem CID

• 1232

ChemSpider

• 1195

UNII

• F2JLV9220T

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HA-966

Identifiers
IUPAC name 3-Amino-1-hydroxy-pyrrolidin-2-one
CAS Number	1003-51-6
PubChem CID	1232
ChemSpider	1195
UNII	F2JLV9220T
CompTox Dashboard (EPA)	DTXSID90905333
ECHA InfoCard	100.162.446
Chemical and physical data
Formula	C4H8N2O2
Molar mass	116.120 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C1C(CCN1O)N
InChI InChI=1S/C4H8N2O2/c5-3-1-2-6(8)4(3)7/h3,8H,1-2,5H2 Key:HCKUBNLZMKAEIN-UHFFFAOYSA-N

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The two enantiomers of HA-966 have differing pharmacological activity. The glycine/N-methyl-D-aspartate receptor antagonist activity is specific to the (R)-(+)-enantiomer, whereas the sedative and ataxic effects are specific to the (S)-(-)-enantiomer.^[5]

(R)-(+)-HA-966 did not induce drug-appropriate responding in animals trained to discriminate phencyclidine (PCP) from saline, suggesting that the glycine receptor ligand (R)-(+)-HA-966 has a significantly different behavioral profile than drugs affecting the ion channel of the NMDA receptor complex.^[6]

(S)-(-)-HA-966 has been described as a "γ-hydroxybutyric acid (GHB)-like agent"^[7] and a "potent y-butyrolactone-like sedative",^[5] but it shows no affinity for the GABA_B receptor (GABA_BR).^[7]

HA-966 is structurally a cyclized derivative of norvaline hydroxamate.