Cecil

Base Information

• Chemical Name: Cecil
• CAS No.: 50-36-2
• Molecular Formula: C17H21NO4
• Molecular Weight: 303.358
• European Community (EC) Number: 200-032-7
• Mol file: 50-36-2.mol

Synonyms:50-36-2;Methyl (1R,2R,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate;Cocaine (TN);Cocaine (USP);D00110;methyl (1S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate

 This product is a nationally controlled contraband, and the Lookchem platform doesn't provide relevant sales information.

Chemical Property of Cecil

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 98°
• Refractive Index: 1.568
• Boiling Point: 395.189 °C at 760 mmHg
• PKA: pKa (15°) 8.61; pKb (15°) 5.59
• Flash Point: 192.804 °C
• PSA: 55.84000
• Density: 1.223 g/cm³
• LogP: 1.80560
• Storage Temp.: 2-8°C
• Water Solubility.: 1.664g/L(25 oC)
• XLogP3: 2.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 303.14705815
• Heavy Atom Count: 22
• Complexity: 432

Purity/Quality:

Safty Information:

• Pictogram(s): T
• Hazard Codes: T,Xn,F
• Statements: 23/24/25-43-36-20/21/22-11
• Safety Statements: 26-36/37-45-36/37/39-22-16

MSDS Files:

SDS file from LookChem

Useful:

• Chemical Classes: Biological Agents -> Plant Toxins
• Canonical SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
• Isomeric SMILES: CN1[C@H]2CC[C@@H]1[C@H](C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
• Description: Cocaine is best known as an illegal drug that produces a euphoric “high” in individuals who use it. Cocaine is an alkaloid obtained from the leaves of the coca plant, Erythroxylum coca, which is native to northwestern South America and Central America. Cocaine (Item No. 16186) is an analytical reference material categorized as a tropane. Cocaine has a high potential for abuse and has been found in samples seized by law enforcement. Cocaine is regulated as a Schedule II compound in the United States. This product is intended for research and forensic applications.
• Physical properties: Appearance: pure white crystal, odorless. Solubility: insoluble in water (1:600); soluble in chloroform (1:0.7), ethyl ether (1:3), ethanol (1:7), and other organic solvents; soluble in acetone, benzene, ethyl acetate, two carbonyl sulfide, and petroleum ether; show monoclinic flaky crystal in ethanol. Melting point: 98° (it can be slowly evaporated over 90°), the specific rotation of ?16°.
• Uses: Cocaine is derived from the leaves of the erythroxylum coca plant and was first used as an anaesthetic by Karl Koller in 1884. It is a potent vasoconstrictor, blocking reuptake of noradrenaline, but has significant potential for systemic toxicity. Cocaine has been used in nasal surgery as a paste or 4% solution for its properties of topical anaesthesia and vasoconstriction. Use of cocaine is known since early times.It occurs in the South American coca leaves.Chewing of leaves mixed with lime was acommon practice among natives, who traveledgreat distances without experiencingfatigue (Cordell 1978). Cocaine is obtainedby extraction of coca leaves. It is also preparedby methylation and benzoylation of thealkaloid, ecgonine. The dilute aqueous solutionsof its hydrochloride is used as a topicalanesthetic in ophthalmology. Cocaine and itsderivatives are controlled substances listedin the U.S. Code of Federal Regulations(Title 21, Parts 321.1 and 1308.12, 1987). Anesthetic (topical). It was widely used as a topical anesthetic in dentistry and in ophthalmology; it also found use as an appetite suppressant, a drug used to treat morphine addiction, a stimulant, and a general elixir. Its popularity to treat depression was originally advanced by Sigmund Freud (1856 1939). Cocaine is used medicinally for local anesthesia and vasoconstriction, especially in surgery involving the ear, nose, and throat. It is the only naturally occurring anesthetic. Although it is still used in limited quantities for surgery, many surgeons and anesthesiologists have turned to safer alternatives such as lidocaine and benzocaine. Also, the use of alternatives eliminates the storage of a well-known addictive drug in clinics and hospital pharmacies.
• Indications: It is mainly used for local anesthesia in various operations. It is also suitable for nasal, pharyngeal, ear, urethra, vagina, and other operations (with 5–10% solution). 2% to 3% solution is used for eye surgery.
• Clinical Use: Cocaine has a very interesting history. The coca plant was used by South American Indians for religious and mystical purposes and as a stimulant both to increase endurance and to alleviate hunger. It was introduced into Europe during the 1800s, and at the end of the 19th century, cocaine use was popular and socially acceptable. Various cocaine-containing preparations were available, and it also was used to “fortify” wines (e.g., Vin Coca). For a period of approximately 20 years, until just after the turn of the century, it was a constituent of the soft drink Coca-Cola. Additionally, cocaine was used for therapeutic reasons but was later supplanted by amphetamine.

Technology Process of Cecil

There total 76 articles about Cecil which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 99.0%

CH4O3S*C10H17NO3 (1374753-31-7) + benzoyl chloride (98-88-4) → Cocaine (50-36-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 - 20 ℃; for 17h;

DOI:10.1002/adsc.201100917

Reference yield: 95.0%

diazomethane (186581-53-3,908094-01-9,334-88-3) + benzylecgonine (519-09-5) → Cocaine (50-36-2)

Guidance literature:

In dichloromethane;

DOI:10.1021/jo980153t

Reference yield: 85.0%

formaldehyd (50-00-0,30525-89-4,61233-19-0) + (1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester (1283098-14-5) → Cocaine (50-36-2)

Guidance literature:

(1R,2R,3S,5S)-3-benzoyloxy-8-azabicyclo[3.2.1]octane-2,8-dicarboxylic acid 8-tert-butyl ester 2-methyl ester; With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 1h;

formaldehyd; With sodium cyanoborohydride; In water; acetonitrile; at 20 ℃; for 1h;

DOI:10.1021/jo200069m

upstream raw materials:

benzoic acid anhydride

ecgonine

methyl iodide

methanol

Downstream raw materials:

(1R,8Ξ)-8-allyl-3exo-benzoyloxy-2exo-methoxycarbonyl-8-methyl-nortropanium; bromide

ecgonidine

(+)-pseudoecgonine

ecgonine

Refernces

The biosynthesis of hydroxycinnamoyl quinate esters and their role in the storage of cocaine in Erythroxylum coca

10.1016/j.phytochem.2012.09.009

The research aimed to determine if Erythroxylum coca, the plant from which cocaine is derived, uses hydroxycinnamoyl quinate esters to store tropane alkaloids like cocaine and cinnamoyl cocaine. The study established a correlation between the levels of these alkaloids and two hydroxycinnamoyl esters of quinic acid, chlorogenic acid, and 4-coumaroyl quinate. The researchers isolated and characterized the BAHD acyltransferase enzyme responsible for the final step in hydroxycinnamoyl quinate biosynthesis and found its gene expression to correlate with tropane alkaloid accumulation. They also observed and quantified the physical interaction between chlorogenic acid and cocaine in vitro using UV and NMR spectroscopic methods. The study concluded that hydroxycinnamoyl quinate esters likely serve as complexation partners for the storage of cocaine and other coca alkaloids in E. coca.

LOCAL ANESTHETIC ACTIVITY OF TROPINE ESTERS OF 5-ARYLFURAN-2-CARBOXYLIC ACIDS

10.1007/BF01156482

The study focuses on the synthesis and pharmacological activity of tropine esters of 5-arylfuran-2-carboxylic acids. These compounds were synthesized by reacting 5-arylfuran-2-carbonyl chlorides with a twofold excess of tropine in an inert organic solvent. The synthesized esters were investigated for their local anesthetic properties, local irritant effects, and acute toxicity, and were compared to known local anesthetics such as cocaine, dicaine, and novocaine. The study found that these esters exhibited pronounced local anesthetic properties, with some compounds showing higher activity than cocaine and comparable to dicaine. However, their practical use was limited by their irritant effects observed in animal models. The study also detailed the chemical synthesis process and the properties of the synthesized compounds, including their hydrochlorides and other derivatives.