Chemical substance record

Naxagolide

88058-88-2C₁₅H₂₁NO₂247.338 g/mol

Organic/Inorganic Small MoleculeChEBI source record

An organic heterotricyclic compound that is (4aR,10bR)-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazine substituted by propyl and hydroxy groups at positions 4 and 9, respectively. It is a potent dopamine D2-receptor agonist and its hydrochloride salt was under clinical development by Merck & Co as a potential antiparkinsonian agent (now discontinued). — ChEBI

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Identity & molecular properties

Source-linked values

CAS number	88058-88-2	ChEBI ↗
Molecular formula	C₁₅H₂₁NO₂	ChEBI ↗
Molar mass	247.338 g/mol	ChEBI ↗
Monoisotopic mass	247.15723 Da	ChEBI ↗
Formal charge	0	ChEBI ↗
ChEBI identifier	CHEBI:177372	ChEBI ↗

Cross-source molecular data

PubChem

Molar mass	247.33 g/mol	PubChem ↗
Exact mass	247.157228913 Da	PubChem ↗
Computed XLogP	2.4	PubChem ↗
Topological polar surface area (Å²)	32.7	PubChem ↗
H-bond donors	1	PubChem ↗
H-bond acceptors	3	PubChem ↗
Rotatable bonds	2	PubChem ↗

PubChem computed values are shown separately from the ChEBI record. An exact InChIKey match was used to connect the records. Molecular descriptors do not describe a supplied product’s purity, particle size or performance.

Names & structural identifiers

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Source preferred name

naxagolide

IUPAC name

(4aR,10bR)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-ol

InChIKey

JCSREICEMHWFAY-HUUCEWRRSA-N

SMILES

[H][C@@]12CCc3ccc(O)cc3[C@@]1([H])OCCN2CCC

InChI

InChI=1S/C15H21NO2/c1-2-7-16-8-9-18-15-13-10-12(17)5-3-11(13)4-6-14(15)16/h3,5,10,14-15,17H,2,4,6-9H2,1H3/t14-,15-/m1/s1

Names & synonyms

(4aR,10bR)-4-propyl-3,4,4a,5,6,10b-hexahydro-2H-naphtho[1,2-b][1,4]oxazin-9-olnaxagolidanaxagolidum

Names are supplied by ChEBI. Trade names and related synonyms may describe a broader product context.

Classification & relationships

ChEBI ontology

organic heterotricyclic compoundChEBI parent class · 26979 ↗phenolsChEBI parent class · 33853 ↗tertiary amino compoundChEBI parent class · 50996 ↗

phenols organic heterocyclic compound organic molecular entity

Roles recorded in ChEBI

anticonvulsantantiparkinson drugdopamine agonist

Database role annotations describe reported biological or chemical roles; they are not product approvals or recommendations for use.

Mass ↔ amount of substance

Calculated from sourced mass

Amount

Input unit

Equivalent amount

0.00404305 mol

Uses 247.338 g/mol from ChEBI. Assumes the substance described by this record; no purity or concentration correction is applied.

Elemental composition

Theoretical mass fractions

C

Carbon · 15 atoms

72.84%

O

Oxygen · 2 atoms

12.94%

H

Hydrogen · 21 atoms

8.56%

N

Nitrogen · 1 atom

5.66%

Calculated theoretical mass fractions from the reported formula and PubChem periodic-table atomic masses. These are not assay or purity results.

Research & patent references

Selected source associations

Synthesis and pharmacological evaluation of thiopyran analogues of the dopamine D3 receptor-selective agonist (4aR,10bR)-(+)-trans-3,4,4a,10b-tetrahydro-4-n-propyl-2H,5H [1]b enzopyrano[4,3-b]-1,4-oxazin-9-ol (PD 128907). ↗Journal of medicinal chemistry · 2000 Jul 27 · PMID 10956195

Pinealectomy blocks stress-induced motor stimulation but not sensitization and tolerance to a dopamine D2 receptor agonist. ↗Psychopharmacology · 2000 Oct · PMID 11105937

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Sources & record history

Checked 27 Sep 2026

Identity, formula, mass, synonyms & ontologyEMBL-EBI ChEBI · CHEBI:177372

Release 255, 9 September 2026. ChEBI three-star (manually annotated) source entry. View original record ↗ · CC BY 4.0

Additional molecular descriptorsNCBI PubChem · CID 57533 · retrieved 2026-09-27

PubCAS formats source data, connects references and computes explicitly labelled conversions. CAS cross-references are supplied by ChEBI; they do not constitute CAS verification or endorsement.

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