1.0 2011-09-21 00:37:44 UTC 2018-05-29 01:53:10 UTC FDB023968 Ecgonine Ecgonine is an organic chemical and tropane alkaloid found naturally in coca leaves. It is has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance, as are all known substances which can be used as precursors to ecgonine itself. Structurally, ecgonine is a cycloheptane derivative with a nitrogen bridge. It is obtained by hydrolysis of cocaine with acids or alkalis, and crystallizes with one molecule of water, the crystals melting at 198-199oC. It is levorotary, and on warming with alkalis gives iso-ecgonine, which is dextrorotary. It is a tertiary base, and has the properties of an acid and an alcohol. It is the carboxylic acid corresponding to tropine, for it yields the same products on oxidation, and by treatment with phosphorus pentachloride is converted into anhydroecgonine, C9H13NO2, which, when heated to 280oC with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N. [HMDB] (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid 3-b-Hydroxy-2-b-tropanecarboxylic acid 3-beta-Hydroxy-2-beta-tropanecarboxylic acid Ekgonin L-ecgonine C9H15NO3 185.2203 185.105193351 (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid ecgonine 481-37-8 CN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8+/m0/s1 PHMBVCPLDPDESM-RLXKETGRSA-N belongs to the class of organic compounds known as tropane alkaloids. These are organic compounds containing the nitrogenous bicyclic alkaloid parent N-Methyl-8-azabicyclo[3.2.1]octane. Tropane alkaloids Organic compounds Alkaloids and derivatives Tropane alkaloids Aliphatic heteropolycyclic compounds Amino acids Azacyclic compounds Beta hydroxy acids and derivatives Carbonyl compounds Carboxylic acids Cyclic alcohols and derivatives Hydrocarbon derivatives Monocarboxylic acids and derivatives N-alkylpyrrolidines Organic oxides Organopnictogen compounds Piperidinecarboxylic acids Secondary alcohols Trialkylamines Alcohol Aliphatic heteropolycyclic compound Amine Amino acid Amino acid or derivatives Azacycle Beta-hydroxy acid Carbonyl group Carboxylic acid Carboxylic acid derivative Cyclic alcohol Hydrocarbon derivative Hydroxy acid Monocarboxylic acid or derivatives N-alkylpyrrolidine Organic nitrogen compound Organic oxide Organic oxygen compound Organoheterocyclic compound Organonitrogen compound Organooxygen compound Organopnictogen compound Piperidine Piperidinecarboxylic acid Pyrrolidine Secondary alcohol Tertiary aliphatic amine Tertiary amine Tropane alkaloid Tropane alkaloids Solid logp -0.69 ALOGPS logs 0.75 ALOGPS solubility 1.05e+03 g/l ALOGPS logp -3.1 ChemAxon pka_strongest_acidic 3.48 ChemAxon pka_strongest_basic 9.69 ChemAxon iupac (2R,3S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid ChemAxon average_mass 185.2203 ChemAxon mono_mass 185.105193351 ChemAxon smiles CN1C2CCC1[C@H]([C@@H](O)C2)C(O)=O ChemAxon formula C9H15NO3 ChemAxon inchi InChI=1S/C9H15NO3/c1-10-5-2-3-6(10)8(9(12)13)7(11)4-5/h5-8,11H,2-4H2,1H3,(H,12,13)/t5?,6?,7-,8+/m0/s1 ChemAxon inchikey PHMBVCPLDPDESM-RLXKETGRSA-N ChemAxon polar_surface_area 60.77 ChemAxon refractivity 46.57 ChemAxon polarizability 18.83 ChemAxon rotatable_bond_count 1 ChemAxon acceptor_count 4 ChemAxon donor_count 2 ChemAxon physiological_charge 0 ChemAxon formal_charge 0 ChemAxon Specdb::MsMs 297001 Specdb::MsMs 297002 Specdb::MsMs 297003 Specdb::MsMs 338404 Specdb::MsMs 338405 Specdb::MsMs 338406 Specdb::MsMs 2371717 Specdb::MsMs 2371718 Specdb::MsMs 2371719 Specdb::MsMs 2564469 Specdb::MsMs 2564470 Specdb::MsMs 2564471 Specdb::CMs 14039 Specdb::CMs 39037 Specdb::CMs 133550 Specdb::CMs 141284 Specdb::NmrOneD 74752 Specdb::NmrOneD 74753 Specdb::NmrOneD 74754 Specdb::NmrOneD 74755 Specdb::NmrOneD 74756 Specdb::NmrOneD 74757 Specdb::NmrOneD 74758 Specdb::NmrOneD 74759 Specdb::NmrOneD 74760 Specdb::NmrOneD 74761 Specdb::NmrOneD 74762 Specdb::NmrOneD 74763 Specdb::NmrOneD 74764 Specdb::NmrOneD 74765 Specdb::NmrOneD 74766 Specdb::NmrOneD 74767 Specdb::NmrOneD 74768 Specdb::NmrOneD 74769 Specdb::NmrOneD 74770 Specdb::NmrOneD 74771 HMDB06548 #<Reference:0x000055ce304db710> #<Reference:0x000055ce304db558> #<Reference:0x000055ce304db3a0> #<Reference:0x000055ce304db1e8> #<Reference:0x000055ce304db030> #<Reference:0x000055ce304dae78> #<Reference:0x000055ce304dacc0> #<Reference:0x000055ce304dab08> Anatidae Type 1 specific Anatidae 8830 Beefalo Type 1 specific Bos taurus X Bison bison 297284 Bison Type 1 specific Bison bison 9901 Buffalo Type 1 specific Bubalus bubalis 89462 Cattle (Beef, Veal) Type 1 specific Bos taurus 9913 Chicken Type 1 specific Gallus gallus 9031 Columbidae (Dove, Pigeon) Type 1 specific Columbidae 8930 Deer Type 1 specific Cervidae 9850 Domestic goat Type 1 specific Capra aegagrus hircus 9925 Domestic pig Type 1 specific Sus scrofa domestica 9825 Elk Type 1 specific Cervus canadensis 1574408 Emu Type 1 specific Dromaius novaehollandiae 8790 European rabbit Type 1 specific Oryctolagus 9984 Greylag goose Type 1 specific Anser anser 8843 Guinea hen Type 1 specific Numida meleagris 8996 Horse Type 1 specific Equus caballus 9796 Mallard duck Type 1 specific Anas platyrhynchos 8839 Mountain hare Type 1 specific Lepus timidus 62621 Mule deer Type 1 specific Odocoileus 9871 Ostrich Type 1 specific Struthio camelus 8801 Pheasant Type 1 specific Phasianus colchicus 9054 Quail Type 1 specific Phasianidae 9005 Rabbit Type 1 specific Leporidae 9979 Rock ptarmigan Type 1 specific Lagopus muta 64668 Sheep (Mutton, Lamb) Type 1 specific Ovis aries 9940 Squab Type 1 specific Columba 8931 Turkey Type 1 specific Meleagris gallopavo 9103 Velvet duck Type 1 specific Melanitta fusca 371864 Wild boar Type 1 specific Sus scrofa 9823 Arylacetamide deacetylase P22760 AADAC