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1-Cocaine(CAS No. 50-36-2)

1-Cocaine C17H21NO4 (cas 50-36-2) Molecular Structure

50-36-2 Structure

Identification and Related Records

【Name】
1-Cocaine
【Iupac name】
methyl
(3S,4R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate
【CAS Registry number】
50-36-2
【Synonyms】
(1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate
1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate
2-beta-Carbomethoxy-3-beta-benzoxytropane
2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester)
2beta-Carbomethoxy-3beta-benzoxytropane
3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether
3-Tropanylbenzoate-2-carboxylic acid methyl ester
3beta-Hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid methyl ester benzoate
8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-
Benzoylmethylecgonine
【EINECS(EC#)】
200-032-7
【Molecular Formula】
C17H21 N O4 (Products with the same molecular formula)
【Molecular Weight】
303.39
【Inchi】
InChI=1/C17H21NO4/c1-18-12-8-9-13(18)15(17(20)21-2)14(10-12)22-16(19)11-6-4-3-5-7-11/h3-7,12-15H,8-10H2,1-2H3/t12-,13+,14-,15+/m0/s1
【InChIKey】
ZPUCINDJVBIVPJ-PFSRBDOWSA-N
【Canonical SMILES】
CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
【Isomers smiles】
CN1C2CCC1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
【MOL File】
50-36-2.mol

Chemical and Physical Properties

【Appearance】
White powder
【Density】
1.22g/cm3
【Boiling Point】
395.2°Cat760mmHg
【Refractive Index】
1.568
【Flash Point】
192.8°C
【Solubilities】
Soluble 1 in 30 arachis oil
Greater than 10% in benzene
1 g/600 ml water, 270 ml water @ 80 deg C; 1 g/6.5 ml alcohol; 1 g/0.7 ml chloroform; 1 g/3.5 ml ether; 1 g/12 ml oil turpentine; 1 g/12 ml olive oil; 1 g/30-50 ml liquid petrolatum.
Sol in acetone, ethyl acetate, carbon disulfide
1 in 10 of castor oil; /considered soluble/
1 in 80 to 120 of liquid or soft paraffin; /considered sparingly soluble/<
【Color/Form】
Colorless to white crystals or white powder
The cocaine alkaloid (freebase) is a colorless, ... transparent, crystalline substance ... /Freebase/
Monoclinic tablets from alcohol
【Storage temp】
2-8°C
【Spectral properties】
Index of refraction: 1.5022 @ 98 deg C
Specific rotation -16.3 @ 20 deg C (chloroform, concn= 4%)
MASS: 2-654 (Archives of Mass Spectral Data, John Wiley & Sons, New York)
Intense mass spectral peaks: 82 m/z, 182 m/z, 198 m/z, 303 m/z
【Computed Properties】
Molecular Weight:303.35294 [g/mol]
Molecular Formula:C17H21NO4
XLogP3:2.3
H-Bond Donor:0
H-Bond Acceptor:5
Rotatable Bond Count:5
Exact Mass:303.147058
MonoIsotopic Mass:303.147058
Topological Polar Surface Area:55.8
Heavy Atom Count:22
Formal Charge:0
Complexity:432
Isotope Atom Count:0
Defined Atom Stereocenter Count:2
Undefined Atom Stereocenter Count:2
Defined Bond Stereocenter Count:0
Undefined Bond Stereocenter Count:0
Covalently-Bonded Unit Count:1
Feature 3D Acceptor Count:2
Feature 3D Cation Count:1
Feature 3D Ring Count:2
Effective Rotor Count:6.2
Conformer Sampling RMSD:0.8
CID Conformer Count:23

Safety and Handling

【Hazard Codes】
CNS stimulant, a poison. Possession is illegal in U.S.
【Risk Statements】
23/24/25-43
【Safety Statements 】
S26;S36/37;S36/37/39;S45
【HazardClass】
6.1(a)
【Safety】

A human poison by ingestion and possibly other routes. Poison experimentally by ingestion, intraperitoneal, intravenous, subcutaneous, and parenteral routes. Human central nervous system effects by ingestion and possibly other routes: general anesthesia, hallucinations or distorted perceptions, and convulsions. An eye irritant. A widely abused, controlled substance. Abuse leads to habituation or addiction. In medicine, it is used as a local narcotic anesthetic applied topically to mucous membranes. The free base is soluble in fats and thus is used for ointments and oily solutions. For water-soluble applications, the sulfate or hydrochloride is used. When heated to decomposition it emits highly toxic fumes.
Hazard Codes: ToxicT
Risk Statements: 23/24/25-43
 R23/24/25:Toxic by inhalation, in contact with skin and if swallowed. 
R43:May cause sensitization by skin contact.
Safety Statements: 26-36/37-45-36/37/39-22 
S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. 
S36/37:Wear suitable protective clothing and gloves. 
S45:In case of accident or if you feel unwell, seek medical advice immediately (show the label whenever possible.) 
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection. 
S22:Do not breathe dust.
RIDADR: UN 1648 3/PG 2
WGK Germany: 3
RTECS: YM2800000
HazardClass: 6.1(a)
PackingGroup: II

【PackingGroup 】
II
【Skin, Eye, and Respiratory Irritations】
An eye irritant.
【Transport】
UN 1648 3/PG 2
【Formulations/Preparations】
... Cocaine hydrochloride /is/ the usual cocaine preparation available on the street ... /Cocaine hydrochloride/
Cocaine Hydrochloride Tablets for Topical Solution (USP). Solution tablets containing cocaine hydrochloride.
Brompton's mixture ... is usually prepared as a combination of morphine & cocaine in an alcohol & syrup base ...
Grade: technical, NF.
The cocaine alkaloid (freebase) ... makes a popping or cracking sound when heated (hence the term crack). ... A solution of cocaine hydrochloride can also be heated ... with baking soda added until a solid "rock" is formed ...
... Speedball (heroin and cocaine) ... /From table/
... Liquid lady (alcohol and cocaine) ...
... Combination of phencyclidine (PCP) and cocaine /is/ called "space base".
A paste form of cocaine ... is called "bazooka", "buscuso," or "pasta." It is produced by combining dried coca leaves, alkaline bases, water, kerosene, and sulfuric acid. This paste then is dried and smoked in mixture with tobacco or marijuana.
C; Bernice; Blow; Cadillac or champagne of drugs; Dama blanca; Flake; Gold dust; Green gold; Happy trails; Jam; Lady; Nose candy; Pimp's drug; Rock; Snow; Star-spangled powder; Toot; White girl or lady
Bernies; Burese; "C" Carrie; Cecil; Coke; Corine; Happy dust; Star dust;
Girl; Leaf
【Exposure Standards and Regulations】
Schedules of controlled substances are established by section 202 of the Controlled Substances Act (21 U.S.C. 812). Schedule II includes cocaine, DEA Code #9041; Drug class: Substances, vegetable origin or chemical synthesis.
【Other Preventative Measures】
SRP: The scientific literature for the use of contact lenses in industry is conflicting. The benefit or detrimental effects of wearing contact lenses depend not only upon the substance, but also on factors including the form of the substance, characteristics and duration of the exposure, the uses of other eye protection equipment, and the hygiene of the lenses. However, there may be individual substances whose irritating or corrosive properties are such that the wearing of contact lenses would be harmful to the eye. In those specific cases, contact lenses should not be worn. In any event, the usual eye protection equipment should be worn even when contact lenses are in place.
【Protective Equipment and Clothing】
An eye irritant.
【Specification】

  Cocaine (CAS NO.50-36-2), its Synonyms are "C" Carrie ; (1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate ; 1-Cocaine ; 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate ; 2-beta-Carbomethoxy-3-beta-benzoxytropane ; 2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester) ; 2beta-Carbomethoxy-3beta-benzoxytropane ; 3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether ; 3-Tropanylbenzoate-2-carboxylic acid methyl ester ; 3beta-Hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid methyl ester benzoate ; 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))- ; Benzoylmethylecgonine ; Bernice [Street Name] . It is a crystalline tropane alkaloid that is obtained from the leaves of the coca plant.

【Octanol/Water Partition Coefficient】
log Kow= 2.30
【Disposal Methods】
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

Use and Manufacturing

【Use and Manufacturing】
Methods of Manufacturing

Derivation: By extraction of the leaves of Erythroxylon coca with sodium carbonate solution, treatment of the latter with dilute acid and extraction with ether, evaporation of the solvent, re-solution of the alkaloid and subsequent crystallization. Also synthetically from the alkaloid ecgonine.
From the leaves of Erythroxylon coca Lam. and other species of Erythroxylon, Erythroxylaceae or by synthesis. Extraction procedure: Squibb, Pharm J. (3) 15, 775, 796; 16, 67 (1885); Emde in Ullmann's Enzyklopadie der Technischen Chemie; Schwyzer, Die Fabrikation pharmazeutischer und chemisch-technischer Produkte (Berlin, 1931).
U.S. Imports

(1986) 1.50X10+3 lb /Coca leaves/
Consumption Patterns

... The National Household Survey in 1992 indicated that approximately 22.6 million people have tried cocaine, five million within the last year before the survey (down from 12 million in 1985 and 8 million in 1988), and 1.3 million used it at least once within the month before the survey. ... The number of people who have used cocaine in the last 30 days /was/ 5.8 million in 1985 and 1.6 million in 1990 to 1.3 million in 1992. ... The number of people using cocaine on a daily or weekly basis is rising. Of the current three million regular users, about 500,000 use crack (freebase cocaine).
... Most addicts are male, under the age of 40, and use multiple drugs (75%). ... Eighty-four percent of persons diagnosed with cocaine dependence also met the criteria for alcohol dependence. A history of marijuana use was reported by 98% of cocaine addicts.
Annual /cocaine/ drug use in young adults age 18-25: 8.1% (1974), 7.0% (1976), 10.2% (1977), 19.6% (1979), 18.8% (1982), 16.3% (1985), 12.1% (1988), and 7.5% (1990) /From table/
Annual /cocaine/ drug use in adults age 26 and over: 0.6% (1976), 0.9% (1977), 2.0% (1979), 3.8% (1982), 4.2% (1985), 2.7% (1988), and 2.4% (1990) /From table/
A survey of cocaine users revealed that 61% were intranasal users, 21% smoked the freebase form, and 18% were IV users.
A profile drawn from interviews with hundreds of serious cocaine abusers indicates that the cocaine abuser tends to be well-educated (14 years of education), employed (77%), and well-paid (37% earn more than $25,000 annually).

Biomedical Effects and Toxicity

【Pharmacological Action】
- Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate.
- Drugs that block the transport of DOPAMINE into axon terminals or into storage vesicles within terminals. Most of the ADRENERGIC UPTAKE INHIBITORS also inhibit dopamine uptake.
- Drugs used to cause constriction of the blood vessels.
【Therapeutic Uses】
Anesthetics, Local; Dopamine Uptake Inhibitors; Vasoconstrictor Agents
In modern medicine, cocaine is used primarily by otolaryngologists, plastic surgeons, and emergency physicians. Cocaine is /a/ ... local anesthetic and vasoconstrictor of mucous membranes and as such enjoys wide use in nasal surgery, rhinoplasty, and emergency nasotracheal intubation.
/ Former Use/: It is usually reserved for hospital patients with acute sinusitis. As a topical decongestant, cocaine is used in 2% solution ...
/Has been found to be/ useful during emergency nasotracheal intubation.
/Cocaine/ is no longer used in ophthalmic surgery.
MEDICATION (VET): In a 5% solution, it has been used for many years for instillation into the eye of the horse preparatory to surgery or examination. Concn of 3-5% have been employed in the dog for this purpose. Good local anesthesia of the conjunctiva & many parts of the eyeball results. ... Cocaine solutions in concn of 5-10% are used to anesthetize mucous membranes of the nose, larynx, & buccal cavity in large animals. In smaller species, concn of 5% are adequate.
Previously, cocaine was added to analgesic mixtures for terminally ill patients (eg, Brompton's cocktail) to elevate mood and counteract narcotic induced resp and CNS depression. ... Randomized controlled trials failed to justify the addition of cocaine and suggested that the presence of cocaine may lead to restlessness, agitation, confusion, or hallucinations.
Use /as surface anesthetic/ is now almost entirely restricted to surgery of nose and throat, and occasionally to ophthalmic surgery.
Cocaine hydrochloride is indicated to provide local anesthesia and vasoconstriction of accessible mucous membranes, especially in the oral, laryngeal, and nasal cavities, prior to instrumentation (eg, bronchoscopy) or surgical procedures. Cocaine's toxicity must be considered prior to its use, especially when it is being applied to the tracheobronchial tree. /Cocaine hydrochloride; Included in US product labeling/
Although cocaine is an acceptable topical anesthetic for dental procedures, it is no longer extensively used in dentistry because of its toxicity. /Cocaine hydrochloride; Included in US product labeling/
THERAP CAT: Anesthetic (local)
THERAP CAT (VET): Topical anesthetic (ophthalmic)
The most serious physical effect of cocaine use is the overdose, a somewhat elusive phenomenon since several users tended to equate overdose with death, and moderate or even severe overdose symptoms sometimes were not recognized as such by users. Many users said that they did not know it was possible to overdose. For example, while 10% of the respondents reported that they had overdosed on cocaine, 12% had experienced convulsions, 155 reported loss of consciousness, and 17% had experienced at least one of the latter two overdose symptoms.
【Biomedical Effects and Toxicity】
Applied topically /to patients/, cocaine is rapidly absorbed from the nasal mucosa with detectable serum levels at 15 minutes and peak levels of its major metabolite 4 to 5 hr after application.
Cocaine is rapidly and well absorbed from the nasal, oral, and pulmonary routes.
Plasma cocaine concentration rapidly incr for the first 20-30 min after insufflation, reaching a peak between 15 and 60 minutes. Peak plasma concn range between 120 and 474 ng/ml after a 1.5 mg/kg cocaine dose, but max euphoric effects occur before peak levels, about 15-20 min postinsufflation. Absorption by the nasal route at therapeutic doses is 98% complete after 4 hr.
At 2 mg/kg, orally admin cocaine produces mean peak plasma levels statistically similar to those produced by the intranasal route. Oral admin produce detectable plasma cocaine at 30 minutes, with peak levels reached between 50 & 90 minutes. ... /In one study/, the peak subjective "high" after oral dosing was more intense than that induced by insufflation but was delayed (45-90 minutes compared with 15-60 minutes by insufflation). One possible explanation is that cocaine is better absorbed in alkaline medium of the small intestine than in the acid medium of the stomach. Similar relative bioavailability (ie, about 60%) exists in intranasal & oral routes at doses of 2 mg/kg.
When smoked, absorption of the free base from the lung is rapid & efficient, producing concn in plasma of more than 900 ng/ml; peak values of 150 to 200 ng/ml are reached 30 to 40 minutes after the inhalation of 96 mg of crystalline cocaine hydrochloride. /Cocaine hydrochloride/
The volume of distribution of cocaine is 1.2 to 1.9 l/kg. At autopsy, the highest cocaine concentrations are found in the urine and kidney, followed by the brain, blood, liver, and bile. ... Cocaine plasma levels remain detectable for 4 to 6 hr. ... Cocaine easily diffuses across the blood-brain barrier. At peak plasma cocaine levels after acute exposures, the brain/blood cocaine ratio is approximately 4. Since plasma cocaine levels fall more rapidly than brain concn, this ratio incr to 20 within 1-2 hr postexposure. A brain/blood ratio over 10 is the most common ratio seen in cocaine overdose cases. Cocaine is not detectable in animal brain tissue more than 6 to 8 hr postexposure.
A ratio /of benzoylecgonine to cocaine/ less than 100 in urine suggests that cocaine was ingested less than 10 hours before the sample was collected.
Similar oral and nasal cocaine doses produce similar peak blood levels and times to peak blood level (about 60 min), yet the onset and magnitude of both subjective effects and cardiovascular changes such as heart rate and blood pressure increase are much more rapidly after intranasal administration. Effects begin within a minute or so after spraying the dose in the nasopharynx with a 10% cocaine solution and within a few minutes of administration of cocaine as a crystalline material. No one has done enough early plasma sampling after administration to properly define the earliest phase of uptake, but initial uptake appears to be faster when cocaine is taken nasally than when taken orally. For example, after 2 mg/kg dose, plasma levels at 15 minutes were 5.7 ng/ml with the oral route and 17.5 ng/ml after nasal administration, yet the peak plasma levels at 1 hr were similar. It is likely that plasma concentrations do not adequately reflect brain levels of the drug, and that brain levels are important determinants of the sought after effects.
Cocaine is excreted almost exclusively in the urine. Only 4%-6% is excreted in the feces. Both THC and cocaine, as well as most other drugs, are extensively metabolized. The urinary as well as fecally excreted compounds are primarily metabolites with only a minor fraction of unchanged drugs.
A significant amount of the maternal dose of cocaine and benzylecgonine is retained by the placenta, which later leaches out into both fetal and maternal circulation.
In a /human/ heart weighing 350 g, 2.5% of the injected dose was in the heart 2-3 min after iv administration. The uptake and clearance of carbon-11 from the heart were faster than in the brain. In the heart, the time for clearance to 50% of maximum uptake was 10 min, whereas in the brain it was 25 min.

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