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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 | Hazard Symbols | T | |
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 |
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.
DOT Classification: Forbidden
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 %.
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 %.
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. |