Acetylleucine

Acetylleucine
	; (S)-(−)-N-Acetyl-leucine
Names
	IUPAC name 2-Acetamido-4-methylpentanoic acid
	Other names N-Acetylleucine; N-Acetyl-L-Leucine
Identifiers
CAS Number	Racemic: 99-15-0 ; S (−): 1188-21-2 ; R ( ): 19764-30-8 ;
3D model (JSmol)	Racemic: Interactive image;
Beilstein Reference	1724849 (S)-(−)
ChEBI	Racemic: CHEBI:17786 ;
ChEMBL	Racemic: ChEMBL174357 ; S (−): ChEMBL56021 ;
ChemSpider	Racemic: 1918 ; S (−): 64075 ; R ( ): 1042393 ;
EC Number	Racemic: 202-734-9;
Gmelin Reference	985259 (S)-(−)
KEGG	Racemic: D07350 ;
MeSH	acetylleucine
PubChem CID	Racemic: 1995; S (−): 70912; R ( ): 1241420;
UNII	Racemic: K76S41V71X ; S (−): E915HL7K2O ; R ( ): 91WU82GA22 ;
	InChI InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12) Key: WXNXCEHXYPACJF-UHFFFAOYSA-N ;
	SMILES Racemic: CC(C)CC(NC(C)=O)C(O)=O;
Properties
Chemical formula	C8H15NO3
Molar mass	173.212 g·mol−1
Appearance	White crystals
Melting point	−115 to −113 °C; −175 to −172 °F; 158 to 160 K
log P	−0.265
Acidity (pKa)	3.666
Basicity (pKb)	10.331
Pharmacology
ATC code	N07CA04 (WHO)
Related compounds
Related compounds	ENU
	Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Acetylleucine (N-acetyl-leucine) is a modified leucine amino acid.

Two forms are commercialized: N-acetyl-DL-leucine (sold under the brand Tanganil, among others, and used in the treatment of vertigo^[2]) and N-acetyl-L-leucine (levacetylleucine, sold under the brand name Aqneursa, and used for the treatment of neurological manifestations of Niemann-Pick disease type C).^[3]

References

^ "N-Acetyl-DL-leucine". PubChem Open Chemistry Database. Retrieved 26 March 2017.
^ "N07CA04 (acetylleucine)". WHO Collaborating Centre for Drug Statistics Methodology. Norwegian Institute of Public Health. 19 December 2016. Retrieved 26 March 2017.
^ Oertel WH, Janzen A, Henrich MT, Geibl FF, Sittig E, Meles SK, et al. (2 September 2024). "Acetyl-DL-leucine in two individuals with REM sleep behavior disorder improves symptoms, reverses loss of striatal dopamine-transporter binding and stabilizes pathological metabolic brain pattern—case reports". Nature Communications. 15 (1): 7619. doi:10.1038/s41467-024-51502-7. ISSN 2041-1723. PMC 11369233. PMID 39223119.

[1] "N-Acetyl-DL-leucine". PubChem Open Chemistry Database. Retrieved 26 March 2017.

[2] "N07CA04 (acetylleucine)". WHO Collaborating Centre for Drug Statistics Methodology. Norwegian Institute of Public Health. 19 December 2016. Retrieved 26 March 2017.

[3] Oertel WH, Janzen A, Henrich MT, Geibl FF, Sittig E, Meles SK, et al. (2 September 2024). "Acetyl-DL-leucine in two individuals with REM sleep behavior disorder improves symptoms, reverses loss of striatal dopamine-transporter binding and stabilizes pathological metabolic brain pattern—case reports". Nature Communications. 15 (1): 7619. doi:10.1038/s41467-024-51502-7. ISSN 2041-1723. PMC 11369233. PMID 39223119.

[1]

[2]

[3]

Names
(S)-(−)-N-Acetyl-leucine
IUPAC name 2-Acetamido-4-methylpentanoic acid^[1]
Other names N-Acetylleucine; N-Acetyl-L-Leucine
Identifiers
CAS Number	Racemic: 99-15-0^Y S (−): 1188-21-2^Y R ( ): 19764-30-8^Y
3D model (JSmol)	Racemic: Interactive image
Beilstein Reference	1724849 (S)-(−)
ChEBI	Racemic: CHEBI:17786^Y
ChEMBL	Racemic: ChEMBL174357^Y S (−): ChEMBL56021^Y
ChemSpider	Racemic: 1918^Y S (−): 64075^Y R ( ): 1042393^Y
EC Number	Racemic: 202-734-9
Gmelin Reference	985259 (S)-(−)
KEGG	Racemic: D07350^Y
MeSH	acetylleucine
PubChem CID	Racemic: 1995 S (−): 70912 R ( ): 1241420
UNII	Racemic: K76S41V71X^Y S (−): E915HL7K2O^Y R ( ): 91WU82GA22^Y
InChI InChI=1S/C8H15NO3/c1-5(2)4-7(8(11)12)9-6(3)10/h5,7H,4H2,1-3H3,(H,9,10)(H,11,12)^Y Key: WXNXCEHXYPACJF-UHFFFAOYSA-N^Y
SMILES Racemic: CC(C)CC(NC(C)=O)C(O)=O
Properties
Chemical formula	C₈H₁₅NO₃
Molar mass	173.212 g·mol⁻¹
Appearance	White crystals
Melting point	−115 to −113 °C; −175 to −172 °F; 158 to 160 K
log P	−0.265
Acidity (pK_a)	3.666
Basicity (pK_b)	10.331
Pharmacology
ATC code	N07CA04 (WHO)
Related compounds
Related compounds	ENU
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references