Cocaine hydrochloride

First the five protons (integral) of the 1H NMR spectrum (SH = 7.50 - 7.94) in the chemical shift range appropriate for aromatics indicate a monosubstituted benzene ring with typical coupling constants (8,0 Hz for ortho protons, 1.5 Hz for met a protons.). The chemical shift values especially for the protons which are positioned ortho to the substituent (SH = 7.94) reflect a -M effect. Using the CH COLOC plot it can be established from the correlation signal 5c/Sh = 166.417.94 that it is a benzoyl group A. 

In the HH COSY plot it is possible to take as starting point the peripheral H signal at 5H = 5.59 in order to trace out the connectivities B of the aliphatic H atoms  

The H and 13C NMR spectra also indicate an NCH group (8C/8H = 39.612.92) and an OCH3 group (5q Sh - 53.4/3.6(5). The CH connectivities D of the NCH3 protons (dH = 2.92) across three bonds to the C atoms at 5c = 65.3 and 64.5, derived from the CH COLOC plot, are especially informative, because the combination of C and D gives the iV-methylpiperidine residue E with four spare bonds  

Thus the ecgonin methyl ester fragment J ean elearly be reeognised only the link to the O atom still remains to be established. The attaehment of the O atom is identified by the large ehemieal shift value (Sfj = 5.59) of the proton on the same earbon atom. The parts A and J then give the skeleton K of eoeaine. 

The fine strueture of the //signal at 3 = 5.59 (3-H) reveals the relative eonfiguration of C-2 and C-3. A doublet (11.5 Hz) of pseudotriplets (7.0 Hz) is observed for an antiperiplanar proton (11.5 Hz) and two synclinal eoupling partners (7.0 Hz). From that the cis eonfiguration of benzoyloxy-and methoxyearbonyl groups is dedueed (strueture L). 

It is then possible to read off from the CH COSY plot those CH links C which belong to B and to see that between Sh = 2.22 and 2.51 the protons of approximately three methylene groups overlap (integral). Two of these form AB systems in the NMR spectrum Sh = 2.24 AB 2.44 at 5c 23.7 Sh = 2.22 AB 2.51 at 5c = 24.9) one pair of the methylene protons approximates the Aj system Sh = 2.44 at 5c = 33.9) even at 400 MHz. 

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Spectral searching and stripping in the analysis of a mixture of mannitol and cocaine hydrochloride, (a) IR spectrum for the mixture (b) Library IR spectrum of mannitol (c) Result of subtracting mannitol s IR spectrum from that of the mixture ... 

Trachelantamine, according to Syrneva, has a weak atropine-like action and also produces local anaesthesia. Its hydrolytic product, trache-lantamidine, which is structurally identical with tsoretronecanol, yields a p-aminobenzoyl derivative of -which the crystalline hydrochloride, m.p. 230-2°, is said to be as potent a local anaesthetic as cocaine hydrochloride. The chloro- -heliotridane (p. 606) formed by the aetion of thionyl ehloride on trachelantamidine reacts with 6-methoxy-8-aminoquinoline to form 6-methoxy-8-(pseMdoheliotridylamino)-quinoline,... 

Crack cocaine A concentrated form of the drug (free base) formed by heating cocaine hydrochloride (the salt) with sodium bicarbonate Cocaine HCl + NaHC03 > Cocaine + NaCl + H20 + C02. 

The dried coca leaf is treated, through a chemical process, with an acid solution such as sulfuric acid, producing raw cocaine or coca paste. The coca paste which contains approximately 70% cocaine, is put through another chemical process with hydrochloric acid creating a hydrochloric salt or cocaine hydrochloride which is soluble in water. This particular process is very time consuming and can take from 1 to 2 weeks to complete. This process is used by both the legitimate and illicit manufacturers of cocaine. 

A chemist from the Federal Bureau of Narcotics and Dangerous Drugs, who was in Bolivia to observe clandestine cocaine operations, related the following step-by-step procedure for manufacturing cocaine. The method can be conveniently divided into three major steps (1) extraction of cocaine from the leaf and chemical conversion to the sulfate (2) treatment of cocaine sulfate with potassium permanganate and conversion to the free base (aka paste) and (3) conversion of the paste or free base to cocaine hydrochloride. In general, steps (1) and (2) are carried out in sulfate labs while step (3) is performed in crystal labs. 

Cocaine base (paste) to cocaine hydrochloride Step 3 ... 

Once the cocaine has been legally produced from the coca leaf, it is exported to various countries for medicinal use, basically as a topical local anesthetic (applied to the surface, not injected, only treating a particular area). In the United States the crystalline powder is imported to pharmaceutical companies who process and package the cocaine for medical use. Merck Pharmaceutical Company and Mallinckrodt Chemical Works distribute cocaine in crystalline form (Hydrochloride Salt) in dark colored glass bottles to pharmacies and hospitals throughout the United States. Cocaine, in the alkaloid form (base drug containing no additives such as hydrochloride in the crystalline form) is rarely used for medicinal purposes. Cocaine hydrochloride crystals or flakes come in Vs, A and 1 ounce bottles from the manufacturer and has a wholesale price of approximately 20 to 25 per ounce (100% pure). 

Coca leaves and cocaine hydrochloride. Above, an unusual crystalline form below cocaine as it usually appears on the illicit market. 

Hatsukami DK, Fischman MW. (1996). Crack cocaine and cocaine hydrochloride. Are the differences myth or reality JAMA. 276(19) 1580-88. 

Cocaine hydrochloride (1 mg/ml in methanol) (Sigma) Evaporate the methanol and resuspend in incubation buffer at a concentration of 10 mM. 

Cocaine hydrochloride remains useful primarily because of the vasoconstriction it provides with topical use. Toxicity prohibits its use for other than topical anesthesia. 

Cocaine is found in several forms. It can be extracted from the coca leaf to form coca paste (basuco, pitillo), which is not water soluble but can be smoked. The paste can be further treated to form cocaine hydrochloride (cocaine powder), which can be dissolved in water and injected, or can be snorted into the nostril. 

Freebase cocaine and crack cocaine, each containing cocaine base, are prepared from cocaine hydrochloride by adding ammonia and ether or sodium bicarbonate and heat, respectively. Applying heat to evaporate the ether can cause the ether to ignite, which can cause severe burns. In preparing crack cocaine, the... 

Cocaine hydrochloride is a water-soluble salt that can be injected or absorbed by any mucosal membrane (eg, nasal snorting). When heated in an alkaline solution, it is transformed into the free base, "crack cocaine," which can then be smoked. Inhaled crack cocaine is rapidly absorbed in the lungs and penetrates swiftly into the brain, producing an almost instantaneous "rush."... 

For the fourth year in a row, Colombia topped the ranking of the world s largest cocaine seizures. It seized 217 mt of cocaine hydrochloride (HC1) and cocaine base in 2005, equivalent to 29 per cent of the world total and an increase from 19 per cent in 1995. Seizures in Colombia increased by 16 per cent from a year earlier, representing the highest cocaine seizures ever reported by a country. In 2005, the interception rate 2 of cocaine produced in Colombia rose to 29 per cent, up from 25 per cent in 2004 and 13 per cent in 2000, clearly reflecting continued enforcement efforts in the country. 

Coca cultivators do not create the finished drug, however. The processing of cocaine base into cocaine hydrochloride requires a laboratory of some sophistication, so these are generally operated by specialists, not... 

Cocaine is used medically by otorhinolaryngologists and plastic surgeons as an epinephrine cocaine mixture. Solutions for topical application are typically less than 4% cocaine hydrochloride. In the U.S. cocaine is a scheduled drug under the federal Controlled Substances Act of 1970. Refined cocaine, in the form of the base or hydrochloride salt, is self-administered by many routes, including snorting, smoking, genital application, and by injection. 

Perez-Reyes et al.8 estimated that only 32% of a dose of cocaine base placed in a pipe is actually inhaled by the smoker. Cone9 compared the pharmacokinetics and pharmacodynamics of cocaine by the intravenous, intranasal, and smoked routes of administration in the same subjects. Venous plasma cocaine concentrations peaked within 5 min by the intravenous and smoked routes. Estimated peak cocaine concentrations ranged from 98 to 349 ng/ml and 154 to 345 ng/ml after intravenous administration of 25-mg cocaine hydrochloride and 42-mg cocaine base by the smoked route, respectively. After dosing by the intranasal route (32 mg cocaine hydrochloride) estimated peak plasma cocaine concentrations ranged from 40 to 88 ng/ml after 0.39 to 0.85 h.9 In this study, the average bioavailability of cocaine was 70.1% by the smoked route and 93.7% by the intranasal route. Jenkins et al.10 described the correlation between pharmacological effects and plasma cocaine concentrations in seven volunteers after they had smoked 10 to 40 mg cocaine. The mean plasma... 

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