Lidocaine is the monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline.
Definition
Lidocaine is the monocarboxylic acid amide resulting from the formal condensation of N,N-diethylglycine with 2,6-dimethylaniline. It has a role as a xenobiotic, a local anaesthetic, an anti-arrhythmia drug, an environmental contaminant and a drug allergen. It is a member of benzenes, a monocarboxylic acid amide and a tertiary amino compound. It is functionally related to a glycinamide.
Source: PubChem
US FDA substance register · UNII 98PI200987 · registered name Lidocaine · single chemical substance
Cosmetic roles
Safety & regulatory references
- Banned
- Argentina · ASEAN · Brazil · Canada · China · European Union · South Korea · Taiwan · United Kingdom
Source: ASEAN Cosmetic Directive · EU Cosmetics Regulation · Health Canada Cosmetic Ingredient Hotlist · MFDS (Korea) cosmetic regulatory information · Taiwan FDA cosmetic ingredients · UK cosmetics regulations (OPSS)
EU Cosmetics Regulation, Annex II (prohibited substances), entry 399
Health Canada Cosmetic Ingredient Hotlist · prohibited in cosmetics
Restriction II/399
Source: EU CosIng ingredient list
More data — names, identifiers, properties, test records, literature
Names & identifiers
- CAS No.chemical registry number
- 137-58-6
- EC No.EU chemical inventory number
- 205-302-8
- DTXSIDUS EPA chemical ID
- DTXSID1045166
- DTXCIDUS EPA compound ID
- DTXCID9025166
- IUPAC
- N-(2,6-Dimethylphenyl)-N~2~,N~2~-diethylglycinamide
- Molecular formula
- C14H22N2O
- Molecular weight
- 234.343 g/mol
Measured properties
- Appearance
- Solid · Needles from benzene or alcohol
- Odour
- Characteristic odor · odourless
- Boiling point
- 159-160 °C at 2.00E+00 mm Hg · BP: 180-182 °C at 4 mm Hg, 159-160 °C at 2 mm Hg
- Melting point
- 68.5 °C · 68 °C
- Solubility
- 4100 mg/L (at 30 °C) · VERY SOL IN ALC, SOL IN CHLOROFORM, INSOL IN ETHER, WHITE CRYSTALLINE POWDER /LIDOCAINE HYDROCHLORIDE/
- Stability
- Commercially available solutions of lidocaine hydrochloride in 5% dextrose usually are stable for 18 months after the date of manufacture. Commercially available solutions of lidocaine hydrochloride in 5% dextrose may be provided in plastic containers. · Stable under recommended storage conditions.
- Dissociation constant
- 7.928 · 7.95
- Melting/freezing point
- 68.5 ℃
- Initial boiling point and range
- 180~182 ℃
- Water solubility
- 4100 ㎎/ℓ (exp)
- n-Octanol/water partition coefficient (Kow)
- 2.26
- Molecular weight
- 234.3373
Values measured on the substance itself. The KOSHA data are a reference for writing and reviewing safety data sheets, not a specification for a commercial raw material.
Source: PubChem · KOSHA safety data sheets (Korea)
What products actually use it for
What the 2 products reported to the US EPA with this ingredient use it for. Products outside cosmetics are included, so the top few rows are its main uses.
- Pharmaceutical (EPA)1
- No specific technical function1
Source: US EPA CompTox dashboard
Irritation and sensitisation studies
5 skin studies and 2 eye studies are on record.
The study conclusions largely agree (100%). These tests are on the raw material itself; irritation at the amount in a finished product is a different question.
See all 7 studies
- Category 6.3A (Category 2)
Skin Irritation · Read Across - Classification not possible
Skin Irritation · Screening - Category 6.5B (Category 1)
Skin Sensitization · Read Across - Category 1
Skin Sensitization · Screening - SkinIrr2
Skin Irritation · QSAR Predicted - Category 6.4A (Category 2A)
Eye Irritation · Read Across - Classification not possible
Eye Irritation · Screening
Source: US EPA CompTox dashboard
Related literature
- Lidocaine anaphylaxis and lidocaine-specific immunoglobulin E measurement · 2013
- Effect of Laurocapram on Percutaneous Absorption of Lidocaine in Lidocaine Spray in Vitro · 2010
- Pharmacokinetics of lidocaine following the application of 5% lidocaine patches to cats. · 2008
- Lidocaine for airway topicalisation · 2008
- Lidocaine for airway topicalisation · 2008
Linked databases 21
- ASEAN Cosmetic Directive
- ChEBI
- ChEMBL
- EU CosIng ingredient list 2
- EU Cosmetics Regulation
- EU prohibited substances (Annex II)
- Health Canada Cosmetic Ingredient Hotlist
- KOSHA safety data sheets (Korea)
- MFDS (Korea) cosmetic regulatory information 2 3
- NIST Chemistry WebBook
- PubChem 2
- Taiwan FDA cosmetic ingredients
- Tlooto literature search 2 3 4 5
- UK cosmetics regulations (OPSS)
- UniChem cross-reference IDs
- US EPA CompTox dashboard 2
- US EPA DSSTox chemical database
- US FDA substance registration (GSRS)
- US FDA Unique Ingredient Identifier (UNII)
- Wikidata
- Wikipedia · Korean · English · Japanese · Chinese