616-68-2

Basic information

• Product Name: Trimecaine
• Synonyms: trimecaine;Mesocaine;2-(Diethylamino)-N-mesitylacetamide;2-(Diethylamino)-N-(2,4,6-trimethylphenyl)acetamide;2-Diethylamino-2',4',6'-trimethylacetanilide;Diethylglycinemesidide;Mesidicaine;Msokain
• CAS NO: 616-68-2
• Molecular Formula: C₁₅H₂₄N₂O
• Molecular Weight: 248.36
• EINECS: 210-487-3
• Mol File: 616-68-2.mol
• Article Data: 0

Chemical Properties

• Melting Point: 44°
• Boiling Point: bp6 187°; bp0.6 154-155°
• Flash Point: 171.702 °C
• Appearance: white crystalline powder
• Density: 1.015 g/cm³
• Vapor Pressure: 2.24E-05mmHg at 25°C
• Refractive Index: 1.544
• PKA: 14.24±0.70(Predicted)
• CAS DataBase Reference: Trimecaine(CAS DataBase Reference)
• NIST Chemistry Reference: Trimecaine(616-68-2)
• EPA Substance Registry System: Trimecaine(616-68-2)

Safety Data

• Hazardous Substances Data: 616-68-2(Hazardous Substances Data)

Usage

General Description

Trimecaine, also known as mesocaine, is a local anesthetic commonly used in medicine. Its main function is to stop or reduce pain in specific areas of the body by blocking nerve signals, hence it is primarily used during surgical procedures or for minor medical issues such as skin irritation or minor burns. It is a tertiary amino compound with anesthetic, antiarrhythmic, and analgesic properties. Trimecaine was first synthesized in the mid-20th century and its usage has been widespread in clinical practice since then. Though its side effects are mostly minor, in rare cases it can cause allergic reactions. Its suitability for use largely depends on the individual's health status and it is not recommended for people with certain medical conditions such as liver disease.

InChI:InChI=1/C15H24N2O/c1-6-17(7-2)10-14(18)16-15-12(4)8-11(3)9-13(15)5/h8-9H,6-7,10H2,1-5H3,(H,16,18)

Synthetic route

N-(chloroacetyl)-2,4,6-trimethylaniline (3910-51-8) + diethylamine (109-89-7) → trimecaine (616-68-2)

Conditions	Yield
With benzene

nitromesitylene (603-71-4) → trimecaine (616-68-2)

Conditions	Yield
Multi-step reaction with 3 steps 1: aq.-ethanolic sulfuric acid / bei der elektrochemischen Reduktion 2: sodium acetate; aqueous acetic acid 3: benzene View Scheme

2,4,6-trimethylaniline (88-05-1) → trimecaine (616-68-2)

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium acetate; aqueous acetic acid 2: benzene View Scheme

trimecaine (616-68-2) + allyl bromide (106-95-6) → Allyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79143-64-9)

Conditions	Yield
In acetone at 70 - 90℃; for 9h;	94%

trimecaine (616-68-2) + methyl iodide (74-88-4) → Diethyl-methyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide (68638-18-6)

Conditions	Yield
In acetone at 70 - 90℃; for 6h;	94%

trimecaine (616-68-2) + benzyl chloride (100-44-7) → Benzyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-66-1)

Conditions	Yield
In acetone at 70 - 90℃; for 14h;	93%

trimecaine (616-68-2) + 2-propynyl chloride (624-65-7) → Diethyl-prop-2-ynyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-65-0)

Conditions	Yield
In acetone at 70 - 90℃; for 10h;	92%

trimecaine (616-68-2) + ethyl iodide (75-03-6) → Triethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide (68638-19-7)

Conditions	Yield
In acetone at 70 - 90℃; for 10h;	90%

trimecaine (616-68-2) + 1-bromomethyl-2-chlorobenzene (611-17-6) → (2-Chloro-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79154-29-3)

Conditions	Yield
In acetone at 70 - 90℃; for 15h;	88%

trimecaine (616-68-2) + para-bromophenacyl bromide (99-73-0) → [2-(4-Bromo-phenyl)-2-oxo-ethyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79143-69-4)

Conditions	Yield
In acetone at 70 - 90℃; for 10h;	87%

trimecaine (616-68-2) + 2,4-dimethyl-benzyl chloride (824-55-5) → (2,4-Dimethyl-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-67-2)

Conditions	Yield
In acetone at 70 - 90℃; for 9h;	87%

trimecaine (616-68-2) + 1-Bromo-2-bromomethyl-benzene (3433-80-5) → (2-Bromo-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79154-28-2)

Conditions	Yield
In acetone at 70 - 90℃; for 9h;	85%

trimecaine (616-68-2) + ethyl bromoacetate (105-36-2) → Ethoxycarbonylmethyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79143-70-7)

Conditions	Yield
In acetone at 70 - 90℃; for 20h;	76%

trimecaine (616-68-2) + 2-Chloro-N,N-diethylacetamide (2315-36-8) → Diethylcarbamoylmethyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-73-0)

Conditions	Yield
In acetone at 70 - 90℃; for 8h;	75%

trimecaine (616-68-2) + Chloroacetamide (79-07-2) → Carbamoylmethyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-72-9)

Conditions	Yield
In acetone at 70 - 90℃; for 20h;	74.5%

trimecaine (616-68-2) + 2-bromoethanol (540-51-2) → Diethyl-(2-hydroxy-ethyl)-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79143-68-3)

Conditions	Yield
In acetone at 70 - 90℃; for 12h;	74%

2-iodo-propane (75-30-9) + trimecaine (616-68-2) → Diethyl-isopropyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide (68638-21-1)

Conditions	Yield
In acetone at 70 - 90℃; for 14h;	72%

trimecaine (616-68-2) + Ethyl 2-bromopropionate (535-11-5, 41978-69-2) → (1-Ethoxycarbonyl-ethyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide (79143-71-8)

Conditions	Yield
In acetone at 70 - 90℃; for 20h;	71%

2-chloro-N-(2-methoxyphenyl)acetamide (55860-22-5) + trimecaine (616-68-2) → Diethyl-[(2-methoxy-phenylcarbamoyl)-methyl]-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-75-2)

Conditions	Yield
In acetone at 70 - 90℃; for 16h;	70%

trimecaine (616-68-2) + 1-iodo-propane (107-08-4) → Diethyl-propyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide (68638-20-0)

Conditions	Yield
In acetone at 70 - 90℃; for 13h;	68%

N-(chloroacetyl)-2,4,6-trimethylaniline (3910-51-8) + trimecaine (616-68-2) → Diethyl-bis-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-74-1)

Conditions	Yield
In acetone at 70 - 90℃; for 15h;	62%

N-benzyl-N-phenylchloroacetamide (2653-14-7) + trimecaine (616-68-2) → [(Benzyl-phenyl-carbamoyl)-methyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride (79143-76-3)

Conditions	Yield
In acetone at 70 - 90℃; for 14h;	53%

trimecaine (616-68-2) → N,N-diethyl-thioglycine-(2,4,6-trimethyl-anilide) (101261-52-3)

Conditions	Yield
With tetraphosphorus decasulfide

Upstream product

• 88-05-1 2,4,6-trimethylaniline 
• 603-71-4 nitromesitylene 
• 3910-51-8 N-(chloroacetyl)-2,4,6-trimethylaniline 
• 109-89-7 diethylamine 

Downstream Products

• 79154-29-3 (2-Chloro-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 68638-19-7 Triethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide 
• 79143-65-0 Diethyl-prop-2-ynyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 79154-28-2 (2-Bromo-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 79143-72-9 Carbamoylmethyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 79143-68-3 Diethyl-(2-hydroxy-ethyl)-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 79143-71-8 (1-Ethoxycarbonyl-ethyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 79143-67-2 (2,4-Dimethyl-benzyl)-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 79143-69-4 [2-(4-Bromo-phenyl)-2-oxo-ethyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 79143-73-0 Diethylcarbamoylmethyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 79143-64-9 Allyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; bromide 
• 68638-20-0 Diethyl-propyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; iodide 
• 79143-66-1 Benzyl-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride 
• 79143-76-3 [(Benzyl-phenyl-carbamoyl)-methyl]-diethyl-[(2,4,6-trimethyl-phenylcarbamoyl)-methyl]-ammonium; chloride