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Substance Name: Cocaine [USP:BAN]
RN: 50-36-2
UNII: I5Y540LHVR
InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-N
Note
- An alkaloid ester extracted from the leaves of plants including coca. It is a local anesthetic and vasoconstrictor and is clinically used for that purpose, particularly in the eye, ear, nose, and throat. It also has powerful central nervous system effects similar to the amphetamines and is a drug of abuse. Cocaine, like amphetamines, acts by multiple mechanisms on brain catecholaminergic neurons; the mechanism of its reinforcing effects is thought to involve inhibition of dopamine uptake.
Molecular Formula
- C17-H21-N-O4
Molecular Weight
- 303.3559
- All
- Classifications
- Links to Resources
- Names & Synonyms
- Registry Numbers
- Structure Descriptors
- Toxicity
- Physical Properties
Classification Codes
Classification Codes
- Anesthetic (Topical)
- Anesthetics
- Anesthetics, Local
- Cardiovascular Agents
- Central Nervous System Agents
- Central Nervous System Depressants
- Dopamine Agents
- Dopamine Uptake Inhibitors
- Drug / Therapeutic Agent
- Human Data
- Membrane Transport Modulators
- Neurotransmitter Agents
- Neurotransmitter Uptake Inhibitors
- Peripheral Nervous System Agents
- Reproductive Effect
- Sensory System Agents
- Skin / Eye Irritant
- Vasoconstrictor Agents
Superlist Classification Code
- DEA Schedule II
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Links to Resources
NLM Resources (File Locators)
Regulatory Agencies (Superlist Locators)
Other Resources (Internet Locators)
Search for this InChIKey on the Web
Names and Synonyms
Name of Substance
- Cocaine
- Cocaine [USP:BAN]
MeSH Heading
- Cocaine
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
- 1-Cocaine
- 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]
- Bernies
- Blow [Street Name]
- Burese
- C Carrie
- Cecil [Street Name]
- Cholly [Street Name]
- Cocaina
- Cocaine
- Cocaine, l-
- Coke
- Corine
- Crack
- Crack cocaine
- Dama blanca
- Ecgonine, methyl ester, benzoate (ester)
- EINECS 200-032-7
- Eritroxilina
- Erytroxylin
- Flake [Street Name]
- Girl [Street Name]
- Gold dust [Street Name]
- Green gold [Street Name]
- Happy dust [Street Name]
- Happy trails [Street Name]
- HER
- HSDB 6469
- Jam
- Kokain
- Kokan
- Kokayeen
- L-Cocaine
- Lady [Street Name]
- Leaf
- Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylate benzoate (ester)
- Methyl 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester)
- Methyl Benzoylecgonine
- Neurocaine
- Nose candy
- Pimp's drug
- Rock [Street Name]
- Snow
- Star dust [Street Name]
- Star-spangled powder
- Toot [Street Name]
- UNII-I5Y540LHVR
- White girl or lady
Systematic Names
- 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate
- 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-
- Cocaine
Superlist Names
- Cocaine
- DEA No. 9041
Registry Numbers
CAS Registry Number
- 50-36-2
FDA UNII
- I5Y540LHVR
Related Registry Number
- 53-21-4 (hydrochloride)
System Generated Number
- 0000050362
Structure Descriptors
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/s1InChIKey
ZPUCINDJVBIVPJ-LJISPDSOSA-NSmiles
CN1[C@H]2CC[C@@H]1[C@H]([C@H](C2)Toxicity
| 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) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD AUTONOMIC NERVOUS SYSTEM: SYMPATHOMIMETIC | 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: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) | 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) | LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: EXCITEMENT BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) | Journal of Toxicology, Clinical Toxicology. Vol. 25, Pg. 419, 1987. |
| infant | TDLo | oral | 25800ng/kg (0.0258mg/kg) | CARDIAC: PULSE RATE INCREASE WITHOUT FALL IN BP BEHAVIORAL: MUSCLE CONTRACTION OR SPASTICITY) 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 LUNGS, THORAX, OR RESPIRATION: RESPIRATORY STIMULATION BEHAVIORAL: EXCITEMENT | Arzneimittel-Forschung. Drug Research. Vol. 16, Pg. 1275, 1966. |
| mouse | LD50 | oral | 99mg/kg (99mg/kg) | BEHAVIORAL: CONVULSIONS OR EFFECT ON SEIZURE THRESHOLD BEHAVIORAL: EXCITEMENT | 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) | CARDIAC: CARDIOMYOPATHY INCLUDING INFARCTION BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY) 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. |
Physical Properties
| Physical Property | Value | Units | Temp (deg C) | Source |
|---|---|---|---|---|
| Melting Point | 98 | deg C | EXP | |
| pKa Dissociation Constant | 8.61 | (none) | 15 | EXP |
| log P (octanol-water) | 2.3 | (none) | EXP | |
| Water Solubility | 1800 | mg/L | 22 | EXP |
| Vapor Pressure | 1.91E-07 | mm Hg | 25 | EXP |
| Henry's Law Constant | 4.24E-11 | atm-m3/mole | 25 | EST |
| Atmospheric OH Rate Constant | 5.30E-11 | cm3/molecule-sec | 25 | EST |
Physical property data is provided to ChemIDplus by SRC, Inc.