Compound: cocaine
SMILES: O=C(O[C@@H]1[C@H](C(=O)OC)[C@@H]2N(C)[C@H](C1)CC2)c3ccccc3
InChIKey: ZPUCINDJVBIVPJ-LJISPDSOSA-N
Synonyms: cocaine, Benzoylmethylecgonine, Neurocaine, L-Cocaine, Kokain, Cocain, (-)-Cocaine, Cocaina, beta-Cocain, Methyl Benzoylecgonine, cocainum, Eritroxilina, Erytroxylin, Bernies, Kokayeen, Burese, Corine, Kokan, Dama blanca, l-Cocain, 50-36-2, Pimp's drug, White girl or lady, Snow, Nose candy, Girl [Street Name], Rock [Street Name], Toot [Street Name], Flake [Street Name], (r)-(-)-cocaine, Ecgonine, methyl ester, benzoate (ester), Gold dust [Street Name], 2-beta-Carbomethoxy-3-beta-benzoxytropane, Happy dust [Street Name], I5Y540LHVR, 2beta-Carbomethoxy-3beta-benzoxytropane, IDS-NC-004, 3-Tropanylbenzoate-2-carboxylic acid methyl ester, CHEBI:27958, (1R,2R,3S,5S)-2-Methoxycarbonyltropan-3-yl benzoate, RX0041, Star dust [Street Name], Green gold [Street Name], RX-0041, Happy trails [Street Name], methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, DTXSID2038443, 3beta-Hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid methyl ester benzoate, 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate, 3-(Benzoyloxy)-8-methyl-8-azabicyclo-(3.2.1)octane-2-carboxylic acid methyl ether, Methyl 3-beta-hydroxy-1-alpha-H,5-alpha-H-tropane-2-beta-carboxylate benzoate (ester), Girl (Street Name), Rock (Street Name), Toot (Street Name), Flake (Street Name), Gold dust (Street Name), Star dust (Street Name), Green gold (Street Name), Happy dust (Street Name), Happy trails (Street Name), 2-Methyl-3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester), 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R-(exo,exo))-, methyl [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, [1R-(exo,exo)]-3-(benzoyloxy)-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, methyl ester, methyl (1R,2R,3S,5S)-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate, methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate, methyl (1R,2R,3S,5S)-3-benzoyloxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylate, methyl (1R-(exo,exo))-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylate, (1R-(exo,exo))-3-(benzoyloxy)-8-methyl-8-azabicyclo(3.2.1)octane-2-carboxylic acid, methyl ester, RefChem:6631, DTXCID501030562, methyl (1S,3S,4R,5R)-3-benzoyloxy-8-methyl-8-azabicyclo(3.2.1)octane-4-carboxylate, 200-032-7, Leaf, Cocaine free base, 1-Cocaine, Star-spangled powder, Coke, Cocaine, l-, Bernice, Cholly, Cecil, Girl, Happy dust, Gold dust, Star dust, HSDB 6469, 2-beta-Tropanecarboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester), Methyl 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylate benzoate (ester), COC, Jam, Crack, Flake, Blow, Crack cocaine, Lady, Toot, Happy trails, Green gold, 3beta-Hydroxy-2beta-tropanecarboxylic acid methyl ester benzoate (ester), C" Carrie, Blow [Street Name], Lady [Street Name], Cecil [Street Name], Sleighride, Badrock, Bazooka, Bernice [Street Name], Blizzard, Cabello, Charlie, Cocktail, Goofball, Moonrocks, Blast, Candy, Caviar, Freeze, Heaven, Snort, Trails, Coca, Cola, Hell, Toke, Yeyo, Bouncing Powder, Chicken Scratch, Happy powder, Florida Snow, Sweet Stuff, L-Cocaine (1.0 mg/ml in Methanol), Prime Time, C Carrie, Foo Foo, Kibbles n' Bits, Snow (birds), G-Rock, methyl (1R,2R,3S,5S)-8-methyl-3-[(phenylcarbonyl)oxy]-8-azabicyclo[3.2.1]octane-2-carboxylate, Cholly [Street Name], Cocaine [USP:BAN], UNII-I5Y540LHVR, Line, Cocaine base, EINECS 200-032-7, Cocaine (-), 1i7z, COCAINE [VANDF], COCAINUM [HPUS], COCAINE [HSDB], COCAINE [MI], COCAINE [MART.], COCAINE [WHO-DD], Epitope ID:158626, SCHEMBL21930, CHEMBL370805, GTPL2286, COCAINE [USP MONOGRAPH], DEA No. 9041, BDBM22418, Cocaine, 1mg/ml in Acetonitrile, (1R,2R,3S,5S)-2-(methoxycarbonyl)tropan-3-yl benzoate, 1q72, Cocaine 0.1 mg/ml in Acetonitrile, Cocaine 1.0 mg/ml in Acetonitrile, AKOS015965554, DB00907, FC111889, NS00000403, C01416, Q41576, METHYL 3B-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLATE BENZOATE (ESTER), 1-alpha-H,5-alpha-H-Tropane-2-beta-carboxylic acid, 3-beta-hydroxy-, methyl ester, benzoate (ester) (8CI), 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-(benzoyloxy)-8-methyl-, methyl ester, (1R,2R,3S,5S)- (9CI), METHYL (1R,2R,3S,5S)-3-(BENZOYLOXY)-8-METHYL-8-AZABICYCLO(3.2.1) OCTANE-2-CARBOXYLATE
Theoretical properties:
molecular_formula: C17H21NO4
molecular_weight: 303.35 g/mol
exact_mass: 303.14705815 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 0
hydrogen_bond_acceptor_count: 5
rotatable_bond_count: 5
heavy_atom_count: 22
topological_polar_surface_area: 55.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: Colorless to white crystals or white powder
color: Colorless to white crystals or white powder
boiling_point: BP: 187 °C at 0.1 mm Hg
vapor_pressure: 0.00000019 [mmHg]
Descriptions:
{"pubchem": "Cocaine can cause developmental toxicity and female reproductive toxicity according to an independent committee of scientific and health experts.", "chebi": "A tropane alkaloid obtained from leaves of the South American shrub <em>Erythroxylon coca</em>.", "chembl": "COCAINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.", "wikipedia": "Cocaine is a stimulant of the central nervous system and tropane alkaloid, derived primarily from the leaves of two coca species native to South America: Erythroxylum coca and E. novogranatense. The leaves are processed into cocaine paste, a crude mixture of coca alkaloids, from which cocaine base is isolated and then converted to cocaine hydrochloride. Although total synthesis is possible, it is complex and not used for production. Historically, cocaine was a standard topical medication used as a local anesthetic with intrinsic vasoconstrictor properties. However, its high abuse potential, adverse effects, and cost have limited its medical use and led to its replacement by alternative medicines.\nStreet cocaine is commonly snorted, injected, or smoked as crack cocaine; its effects last up to 90 minutes depending on the route of administration. Pharmacologically, cocaine acts as a serotonin\u2013norepinephrine\u2013dopamine reuptake inhibitor (SNDRI), producing reinforcing effects such as euphoria, increased alertness, concentration, libido, and reduced fatigue and appetite.\nCocaine has numerous adverse effects. Acute use can cause vasoconstriction, tachycardia, hypertension, hyperthermia, or seizures, while overdose may lead to stroke, heart attack, or sudden cardiac death. It also produces a spectrum of psychiatric symptoms, including agitation, paranoia, anxiety, irritability, psychosis, hallucinations, delusions, violence, and suicidal or homicidal thinking. Prenatal exposure poses risks to fetal development. Chronic use may result in cocaine dependence, withdrawal symptoms, neurotoxicity, and nasal damage, including cocaine-induced midline destructive lesions.\nCoca cultivation and initial processing occur primarily in Latin America, especially in the Andes regions of Bolivia, Peru, and Colombia. Cultivation is expanding into Central America, including Honduras, Guatemala, and Belize. Violence linked to the cocaine trade continues to affect Latin America and the Caribbean and is expanding into Western Europe, Asia, and Africa as transnational organized crime groups compete globally. Cocaine remains the world's fastest-growing illicit drug market.\nCoca chewing dates back at least 8,000 years in South America. Large-scale cultivation occurred in Taiwan and Java prior to World War II. The cocaine boom\u2014a sharp rise in illegal production and trade\u2014began in the late 1970s and peaked in the 1980s. Cocaine is regulated under international drug control conventions, though its legal status varies nationally: several countries have decriminalized possession of small quantities."}