Levobupivacaine hydrochloride - ≥98% , Sodium channel protein type IV alpha subunit blocker, CAS No.27262-48-2, Sodium channel protein type IV alpha subunit blocker

CAS: 27262-48-2 Cat. No.: L276455 Molecular Weight: 324.89 EC Number: 690-037-4

GRADE & PURITY ≥98%

Synonyms

27262-48-2 (HCl) | LEVOBUPIVACAINE HCL [VANDF] | Q27114682 | 2-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, monohydrochloride, (2S)- | (+/-)-.BETA.-PINENE | LEVOBUPIVACAINE HYDROCHLORIDE [ORANGE BOOK] | LEVOBUPIVACAINE HYDROCHLORIDE [WHO-DD] |

Storage

Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Store at -20°C. Store under desiccating conditions. The product can be stored for up to 12 months.

Specifications

Synonyms

27262-48-2 (HCl) | LEVOBUPIVACAINE HCL [VANDF] | Q27114682 | 2-Piperidinecarboxamide, 1-butyl-N-(2, 6-dimethylphenyl)-, monohydrochloride, (2S)- | (+/-)-.BETA.-PINENE | LEVOBUPIVACAINE HYDROCHLORIDE [ORANGE BOOK] | LEVOBUPIVACAINE HYDROCHLORIDE [WHO-DD] |

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

(S)-enantiomer of bupivacaine . Reversible sodium channel inhibitor. Acts via blockade of voltage-sensitive ion channels in neuronal membranes, preventing transmission of nerve impulses. Efficacy is similar to that of bupivacaine with a reduce

Storage

Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Action Type

BLOCKER

Mechanism of action

Sodium channel protein type IV alpha subunit blocker

Note

Wherever possible, you should prepare and use solutions on the same day. However, if you need to make up stock solutions in advance, we recommend that you store the solution as aliquots in tightly sealed vials at -20°C. Generally, these will be useable for up to one month. Before use, and prior to opening the vial we recommend that you allow your product to equilibrate to room temperature for at least 1 hour. Toxic, refer to SDS for further information. Need more advice on solubility, usage and handling? Please visit our frequently asked questions (FAQ) page for more details.

Purity

≥98%

Names and Identifiers

• Pubchem Sid: 504756774
• Pubchem Sid Url: https://pubchem.ncbi.nlm.nih.gov/substance/504756774
• Canonical Smiles: CCCCN1CCCCC1C(=O)NC2=C(C=CC=C2C)C.Cl
• IUPAC Name: (2S)-1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide;hydrochloride
• InChIKey: SIEYLFHKZGLBNX-NTISSMGPSA-N
• INCHI: 1S/C18H28N2O.ClH/c1-4-5-12-20-13-7-6-11-16(20)18(21)19-17-14(2)9-8-10-15(17)3;/h8-10,16H,4-7,11-13H2,1-3H3,(H,19,21);1H/t16-;/m0./s1
• Isomeric SMILES: CCCCN1CCCC[C@H]1C(=O)NC2=C(C=CC=C2C)C.Cl
• Alternate CAS: 27262-48-2
• MeSH Entry Terms: Chirocaine;levobupivacaine;levobupivacaine hydrochloride
• Molecular Weight: 324.89
• Reaxy-Rn: 4048737
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=4048737&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Organoheterocyclic compounds
    • Class Piperidines
      • Subclass Piperidinecarboxylic acids and derivatives

• Kingdom: Organic compounds
• Superclass: Organoheterocyclic compounds
• Class: Piperidines
• Subclass: Piperidinecarboxylic acids and derivatives
• Intermediate Tree Nodes: Not available
• Direct Parent: Piperidinecarboxamides
• Alternative Parents: m-Xylenes Trialkylamines Propargyl-type 1,3-dipolar organic compounds Carboximidic acids Azacyclic compounds Organopnictogen compounds Organooxygen compounds Hydrochlorides Hydrocarbon derivatives
• Molecular Framework: Aromatic heteromonocyclic compounds
• Substituents: 2-piperidinecarboxamide - Piperidinecarboxamide - M-xylene - Xylene - Monocyclic benzene moiety - Benzenoid - Tertiary aliphatic amine - Tertiary amine - Carboximidic acid - Carboximidic acid derivative - Azacycle - Organic 1,3-dipolar compound - Propargyl-type 1,3-dipolar organic compound - Amine - Hydrochloride - Hydrocarbon derivative - Organooxygen compound - Organonitrogen compound - Organopnictogen compound - Organic oxygen compound - Organic nitrogen compound - Aromatic heteromonocyclic compound
• Description: This compound belongs to the class of organic compounds known as piperidinecarboxamides. These are compounds containing a piperidine ring substituted with a carboxamide functional group.
• External Descriptors: 1-butyl-N-(2,6-dimethylphenyl)piperidine-2-carboxamide hydrochloride

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Associated Targets(Human)

KCNH2 Tclin HERG (29587 Activities)

Discover Target: KCNH2

Activity Type	Relation	Activity value	Units	Action Type	Journal	PubMed Id	doi	Assay Aladdin ID

Mechanisms of Action

Chemical and Physical Properties

• Solubility: DMSO (Slightly), Methanol (Slightly)
• Molecular Weight: 324.900 g/mol
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 5
• Exact Mass: 324.197 Da
• Monoisotopic Mass: 324.197 Da
• Topological Polar Surface Area: 32.299 Ų
• Heavy Atom Count: 22
• Formal Charge: 0
• Complexity: 321.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 1
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 0
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 0
• Covalently-Bonded Unit Count: 2

XLogP3

References

1. Qiao Bin, Song Xinye, Zhang Weiyi, Xu Ming, Zhuang Bowen, Li Wei, Guo Huanling, Wu Wenxin, Huang Guangliang, Zhang Minru, Xie Xiaoyan, Zhang Nan, Luan Yong, Zhang Chunyang.  (2022)  Intensity-adjustable pain management with prolonged duration based on phase-transitional nanoparticles-assisted ultrasound imaging-guided nerve blockade.  JOURNAL OF NANOBIOTECHNOLOGY,  20  (1): (1-17).  [PMID:36424657] [10.1186/s12951-022-01707-z]

2. Xinye Song, Miao Feng, Hao Chen, Yong Luan.  (2025)  Ultrasound-responsive phase-transitional nanomedicine enables intensity-tunable postoperative analgesia.  Frontiers in Bioengineering and Biotechnology,      [PMID:41220802] [10.3389/fbioe.2025.1704679]

3. Xinye Song, Miao Feng, Jiaju Zhao, Guokai Wu, Mengmeng Bai, Yuanli Luo, Bin Qiao, Yong Luan.  (2026)  Complement-inflammation inhibition via stealth nanomedicine for mild thermo-responsive postoperative on-demand pain management.  Materials Today Bio,      [PMID:] [10.1016/j.mtbio.2026.103037]