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Cocaine

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Name

Cocaine

EINECS 200-032-7
CAS No. 50-36-2 Density 1.223 g/cm3
PSA 55.84000 LogP 1.80560
Solubility 1.664g/L(25 oC) Melting Point 98°
Formula C17H21NO4 Boiling Point 395.189 °C at 760 mmHg
Molecular Weight 303.358 Flash Point 192.804 °C
Transport Information UN 1648 3/PG 2 Appearance White powder
Safety 26-36/37-45-36/37/39-22 Risk Codes 23/24/25-43
Molecular Structure Molecular Structure of 50-36-2 (COCAINE) Hazard Symbols ToxicT
Synonyms

(1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate;2-beta-Carbomethoxy-3-beta-benzoxytropane;2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester);3-Tropanylbenzoate-2-carboxylic acid methyl ester;Benzoylmethylecgonine;UNII-I5Y540LHVR;Neurocaine;

Article Data 31

Cocaine History

For over a thousand years South American indigenous peoples have chewed the coca leaf (Erythroxylon coca), a plant that contains vital nutrients as well as numerous alkaloids, including cocaine. 
  Cocaine (CAS NO.50-36-2) alkaloid was first isolated by the German chemist Friedrich Gaedcke in 1855.
The first synthesis and elucidation of the structure of the cocaine molecule was by Richard Willstatter in 1898. The synthesis started from tropinone, a related natural product and took five steps.
Carl Koller experimented with cocaine for ophthalmic usage. In an infamous experiment in 1884, he experimented upon himself by applying a cocaine solution to his own eye and then pricking it with pins. His findings were presented to the Heidelberg Ophthalmological Society. Also in 1884, Jellinek demonstrated the effects of cocaine as a respiratory system anesthetic. In 1885, William Halsted demonstrated nerve-block anesthesia, and James Corning demonstrated peridural anesthesia. 1898 saw Heinrich Quincke use cocaine for spinal anaesthesia.
In 1879 cocaine began to be used to treat morphine addiction. Cocaine was introduced into clinical use as a local anaesthetic in Germany in 1884.
In 1885 the U.S. manufacturer Parke-Davis sold cocaine in various forms, including cigarettes, powder, and even a cocaine mixture that could be injected directly into the user's veins with the included needle.
In early 20th-century Memphis, Tennessee, cocaine was sold in neighborhood drugstores on Beale Street, costing five or ten cents for a small boxful.
In 1909, Ernest Shackleton took “Forced March” brand cocaine tablets to Antarctica, as did Captain Scott a year later on his ill-fated journey to the South Pole.

Cocaine Standards and Recommendations

DOT Classification:  Forbidden

Cocaine Specification

The Cocaine with CAS registry number of 50-36-2 is also known as 8-Azabicyclo[3.2.1]octane-2-carboxylicacid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R,2R,3S,5S)-. The IUPAC name is Methyl (3S,4R)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-4-carboxylate. Its EINECS registry number is 200-032-7. In addition, the formula is C17H21NO4 and the molecular weight is 303.35. Its purest form is a white powder that at low levels causes damage to health. What's more, this chemical is a powerful nervous system stimulant. However, cocaine is a popular recreational drug in many countries that the production, distribution and sale of cocaine products is restricted in most countries.

Physical properties about Cocaine are: (1)ACD/LogP: 2.28; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 7.4): 1; (4)ACD/BCF (pH 5.5): 1; (5)ACD/BCF (pH 7.4): 1; (6)ACD/KOC (pH 5.5): 1; (7)ACD/KOC (pH 7.4): 11; (8)#H bond acceptors: 5; (9)#Freely Rotating Bonds: 5; (10)Index of Refraction: 1.568; (11)Molar Refractivity: 81.109 cm3; (12)Molar Volume: 248.072 cm3; (13)Surface Tension: 48.483 dyne/cm; (14)Density: 1.223 g/cm3; (15)Flash Point: 192.804 °C; (16)Enthalpy of Vaporization: 64.532 kJ/mol; (17)Boiling Point: 395.189 °C at 760 mmHg; (18)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Cocaine: it is prepared by reaction of (1R)-3exo-benzoyloxy-tropane-2exo-carboxylic acid with diazomethane. The reaction needs solvent CH2Cl2 and the yield is about 95 %.

Cocaine is prepared by reaction of (1R)-3exo-benzoyloxy-tropane-2exo-carboxylic acid with diazomethane.

Uses of Cocaine: it is used to produce (1R)-3exo-benzoyloxy-nortropane-2exo-carboxylic acid methyl ester. The reaction occurs with reagent 1-chloroethyl chloroformate and solvent 1,2-dichloro-ethane with other condition of heating for 28 hours. The yield is about 71 %.

Cocaine is used to produce (1R)-3exo-benzoyloxy-nortropane-2exo-carboxylic acid methyl ester.

When you are using this chemical, please be cautious about it. As a chemical, it may cause sensitisation by skin contact and it is toxic by inhalation, in contact with skin and if swallowed. During using it, wear suitable protective clothing, gloves and eye/face protection. Do not breathe dust. In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. If accident happens or you feel unwell seek medical advice immediately.

You can still convert the following datas into molecular structure:
1. Canonical SMILES: CN1C2CCC1C(C(C2)OC(=O)C3=CC=CC=C3)C(=O)OC
2. Isomeric SMILES: CN1C2CCC1[C@H]([C@H](C2)OC(=O)C3=CC=CC=C3)C(=O)OC
3. InChI: InChI=1S/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
4. InChIKey: ZPUCINDJVBIVPJ-PFSRBDOWSA-N

The toxicity data is as follows:

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
cat LDLo intravenous 7500ug/kg (7.5mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
cat LDLo subcutaneous 16mg/kg (16mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
cattle LDLo subcutaneous 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1332, 1935.
chicken LDLo subcutaneous 120mg/kg (120mg/kg)   "Ueber die Wirkung Verschiedener Gifte Auf Vogel, Dissertation," Forchheimer, L., Pharmakologischen Institut der Universitat Wurzburg, Fed. Rep. Ger., 1931Vol. -, Pg. -, 1931.
dog LD50 intravenous 13mg/kg (13mg/kg) AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Archives Internationales de Pharmacodynamie et de Therapie. Vol. 235, Pg. 328, 1978.
dog LDLo subcutaneous 3500ug/kg (3.5mg/kg) BEHAVIORAL: GENERAL ANESTHETIC "Nachprufung der Toxicitat von Novocain und Tutocain bei Chloralisierten Tieren, Dissertation," Barke, A., Pharmakologischen Institut der Tierarztlichen Hochschule zu Hannover, Fed. Rep. Ger., 1936Vol. -, Pg. -, 1936.
domestic animals - goat/sheep LDLo subcutaneous 180mg/kg (180mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1332, 1935.
frog LDLo intraspinal 175mg/kg (175mg/kg)   Journal of Pharmacology and Experimental Therapeutics. Vol. 45, Pg. 291, 1932.
frog LDLo subcutaneous 300mg/kg (300mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: EXCITEMENT

CARDIAC: PULSE RATE
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 144, Pg. 197, 1929.
guinea pig LD50 subcutaneous 31mg/kg (31mg/kg) BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX)

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 240, Pg. 523, 1961.
guinea pig LDLo intravenous 20mg/kg (20mg/kg)   Physiological Reviews. Vol. 12, Pg. 190, 1932.
human TCLo inhalation 3571ug/kg (3.571mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annals of Emergency Medicine. Vol. 21, Pg. 772, 1992.
human TDLo intravenous 1786ug/kg (1.786mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD Annals of Emergency Medicine. Vol. 21, Pg. 772, 1992.
human TDLo oral 714mg/kg (714mg/kg) BEHAVIORAL: GENERAL ANESTHETIC

BEHAVIORAL: "HALLUCINATIONS, DISTORTED PERCEPTIONS"

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
JAMA, Journal of the American Medical Association. Vol. 238, Pg. 1391, 1977.
infant TDLo intrapleural 2308ug/kg (2.308mg/kg) BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)
Journal of Toxicology, Clinical Toxicology. Vol. 25, Pg. 419, 1987.
infant TDLo oral 25800ng/kg (0.0258mg/kg) BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY)

CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP

BEHAVIORAL: IRRITABILITY
Pediatric Emergency Care. Vol. 8, Pg. 82, 1992.
man LDLo oral 7353ug/kg (7.353mg/kg)   "Poisoning; Toxicology, Symptoms, Treatments," 2nd ed., Arena, J.M., Springfield, IL, C.C. Thomas, 1970Vol. 2, Pg. 73, 1970.
man TCLo inhalation 7143ug/kg (7.143mg/kg) BEHAVIORAL: IRRITABILITY

GASTROINTESTINAL: NAUSEA OR VOMITING

KIDNEY, URETER, AND BLADDER: OTHER CHANGES IN URINE COMPOSITION
Lancet. Vol. 2, Pg. 1150, 1987.
man TDLo intravenous 14mg/kg/4D-I (14mg/kg) CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION American Journal of Medicine. Vol. 81, Pg. 699, 1986.
mouse LD50 intraperitoneal 59mg/kg (59mg/kg)   Klinische Wochenscrift. Vol. 31, Pg. 97, 1953.
mouse LD50 intravenous 16mg/kg (16mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

BEHAVIORAL: EXCITEMENT

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 oral 99mg/kg (99mg/kg) BEHAVIORAL: EXCITEMENT

BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966.
mouse LD50 subcutaneous 81mg/kg (81mg/kg) BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD

LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION

BEHAVIORAL: EXCITEMENT
Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1025, 1966.
mouse LD50 unreported 108mg/kg (108mg/kg)   Nippon Yakurigaku Zasshi. Japanese Journal of Pharmacology. Vol. 53, Pg. 2S, 1957.
pigeon LDLo subcutaneous 60mg/kg (60mg/kg)   "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." Vol. 4, Pg. 1333, 1935.
rabbit LD50 intravenous 17mg/kg (17mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rabbit LD50 unreported 20mg/kg (20mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 24, Pg. 1957, 1974.
rabbit LDLo oral 126mg/kg (126mg/kg)   "Drug Dosages in Laboratory Animals - A Handbook," Rev. ed., Barnes, C.D., and L.G. Eltherington, Berkeley, Univ. of California Press, 1973Vol. -, Pg. 78, 1973.
rabbit LDLo subcutaneous 50mg/kg (50mg/kg)   Naunyn-Schmiedeberg's Archiv fuer Experimentelle Pathologie und Pharmakologie. Vol. 160, Pg. 53, 1931.
rat LD50 intraperitoneal 70mg/kg (70mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rat LD50 intravenous 17500ug/kg (17.5mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
rat LD50 subcutaneous 250mg/kg (250mg/kg)   Journal of Laboratory and Clinical Medicine. Vol. 15, Pg. 731, 1930.
women TCLo inhalation 14600mg/kg/2Y (14600mg/kg) BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION

LUNGS, THORAX, OR RESPIRATION: DYSPNEA
American Journal of Medicine. Vol. 81, Pg. 699, 1986.
women TDLo intravenous 10mg/kg (10mg/kg) BEHAVIORAL: MUSCLE WEAKNESS

MUSCULOSKELETAL: OTHER CHANGES
American Journal of Medicine. Vol. 85, Pg. 579, 1988.