Compound: Ecgonine
SMILES: O=C(O)[C@H]1[C@@H](O)C[C@H]2N([C@@H]1CC2)C
InChIKey: PHMBVCPLDPDESM-FKSUSPILSA-N
Synonyms: Ecgonine, (-)-Ecgonine, 1-Ecgonine, 481-37-8, 3beta-Hydroxy-2beta-tropanecarboxylic acid, DX2E9E17AV, (1R,2R,3S,5S)-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, CHEBI:4743, IDS-NE-001, DTXSID701019899, 3beta-hydroxy-1alphaH,5alphaH-tropane-2beta-carboxylic acid, (1R,2R,3S,5S)-3-HYDROXY-8-METHYL-8-AZABICYCLO(3.2.1)OCTANE-2-CARBOXYLIC ACID, RefChem:590540, 3 beta-hydroxy-2 beta-tropanecarboxylic acid, DTXCID601022522, 207-565-4, DL-Ecgonine, (+/-)-Ecgonine, Ecgonine, (+/-)-, Ecgonine (+/-)-form [MI], Ekgonin, 342I22959I, 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-hydroxy-8-methyl-, (1R-(exo,exo))-, 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-hydroxy-8-methyl-, monohydrate, (exo,exo)-, 54808-87-6, L-ecgonine, [1R-(exo,exo)]-3-Hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, 8-Azabicyclo(3.2.1)octane-2-carboxylic acid, 3-hydroxy-8-methyl-, (1R,2R,3S,5S)-, EINECS 207-565-4, UNII-DX2E9E17AV, ecgonin, Cocaine precusor in Coca leaves, 8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3-hydroxy-8-methyl-, (1R,2R,3S,5S)-, 8-Azabicyclo[3.2.1]octane-2-carboxylic acid, 3-hydroxy-8-methyl-, [1R-(exo,exo)]-, UNII-342I22959I, ECGONINE [MI], ECGONINE [WHO-DD], SCHEMBL24495, 1alphaH,5alphaH-Tropane-2beta-carboxylic acid, 3-beta-hydroxy-, DB01525, NS00007456, Q420028, 3.BETA.-HYDROXY-2.BETA.-TROPANECARBOXYLIC ACID, 3beta-hydroxy-1alphaH,-5alphaH-tropane-2beta-carboxylic acid, [1R*-(Exo,exo)]-3-hydroxy-8-methyl-8-azabicyclo[3.2.1]octane-2-carboxylic acid, 3.BETA.-HYDROXY-1.ALPHA.H,5.ALPHA.H-TROPANE-2.BETA.-CARBOXYLIC ACID, 876657-17-9
Theoretical properties:
molecular_formula: C9H15NO3
molecular_weight: 185.22 g/mol
exact_mass: 185.10519334 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 2
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 1
heavy_atom_count: 13
topological_polar_surface_area: 60.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
Descriptions:
pubchem: Ecgonine is a tropane alkaloid that consists of tropane bearing carboxy and hydroxy substituents at positions 2 and 3 respectively and having (1R,2R,3S,5S)-configuration. It is both a metabolite of and a precursor to cocaine. It has a role as a metabolite and a mouse metabolite. It is a tropane alkaloid and a 2-hydroxy monocarboxylic acid.
chebi: A tropane alkaloid that consists of tropane bearing carboxy and hydroxy substituents at positions 2 and 3 respectively and having (1<i>R</i>,2<i>R</i>,3<i>S</i>,5<i>S</i>)-configuration. It is both a metabolite of and a precursor to cocaine.
wikipedia: Ecgonine is a tropane alkaloid (alkaloid derivative of tropane) found naturally in coca leaves. It has a close structural relation to cocaine: it is both a metabolite and a precursor, and as such, it is a controlled substance in many jurisdictions, as are some 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 198–199 °C. 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 280 °C with hydrochloric acid, eliminates carbon dioxide and yields tropidine, C8H13N.
An alkaloid that contains methylecgonine is called isococamine. It is worth pointing out that the structure on the pubchem website is different from the one quoted in John Glasby's book of alkaloids.