Compound: physostigmine
SMILES: O=C(Oc1cc2c(N(C)[C@@H]3[C@]2(CCN3C)C)cc1)NC
InChIKey: PIJVFDBKTWXHHD-HIFRSBDPSA-N
Synonyms: physostigmine, Eserine, 57-47-6, Physostol, Esromiotin, (-)-physostigmine, Ezerin, Calabarine, Fysostigmin, Erserine, cogmine, eserin, Eserinum, Eserolein, methylcarbamate (ester), DTXSID3023471, MCV 4484, MCV-4484, NIH 10421, NSC-30782, 9U1VM840SP, Methyl-carbamic acid, ester with eseroline, Carbamic acid, methyl-, ester with eseroline, DTXCID603471, Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-, CHEBI:27953, (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol methylcarbamate (ester), (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate, [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate, ((3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo(2,3-b)indol-7-yl) N-methylcarbamate, (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo(2,3-b)indol-5-yl N-methylcarbamate, RefChem:56714, 200-332-8, Antilirium, (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate, NSC30782, CHEMBL94, NCGC00093889-03, Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis), Fysostigmin [Czech], CHEMBL537674, CAS-57-47-6, CCRIS 3422, HSDB 3161, EINECS 200-332-8, Eserolein, methylcarbamate, NSC 30782, Physostigmine [USP:BAN], RCRA waste no. P204, physostigmin, UNII-9U1VM840SP, CS 58525, (-) physostigmine, Eserine (TN), Physostigmine (USP), Spectrum_000916, Spectrum_001789, ESERINUM [HPUS], SpecPlus_000381, Prestwick0_000566, Prestwick1_000566, Prestwick2_000566, Prestwick3_000566, Spectrum2_000330, Spectrum2_000757, Spectrum2_001283, Spectrum3_000545, Spectrum3_000901, Spectrum4_000997, Spectrum4_001631, Spectrum4_001913, Spectrum5_000441, Spectrum5_000626, Spectrum5_001672, PHYSOSTIGMINE [MI], physostigmine.salicylic acid, 1,2,3,3abeta,8abeta-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)-indol-5-yl methylcarbamate, PHYSOSTIGMINE [HSDB], Lopac0_000483, SCHEMBL24044, BSPBio_000352, BSPBio_002189, KBioGR_001433, KBioGR_002061, KBioGR_002533, KBioSS_001396, KBioSS_002279, PHYSOSTIGMINE [VANDF], MLS001304022, orb104785, DivK1c_006477, PHYSOSTIGMINE [MART.], SPECTRUM1500753, SPBio_000339, SPBio_000774, SPBio_001285, SPBio_002571, PHYSOSTIGMINE [WHO-DD], BPBio1_000388, cid_657348, GTPL6598, MEGxp0_001872, SCHEMBL29482277, ACon1_000097, BDBM11023, KBio1_001421, KBio2_001396, KBio2_002278, KBio2_003964, KBio2_004846, KBio2_006532, KBio2_007414, KBio3_001689, KBio3_001842, Eserolein,methylcarbamate (ester), HMS1921G06, HMS2089M11, HMS2236L08, HMS3261B07, Carbamic acid, ester with eseroline, HY-N6608, MSK40315, PHYSOSTIGMINE [USP IMPURITY], Tox21_111228, Tox21_301591, Tox21_500483, BDBM50004000, BDBM50222010, CCG-38605, EBC-26402, AKOS016843649, Tox21_111228_1, DB00981, FE59473, LP00483, SDCCGMLS-0066585.P001, SDCCGSBI-0050467.P005, NCGC00093889-01, NCGC00093889-02, NCGC00093889-04, NCGC00093889-05, NCGC00093889-06, NCGC00093889-07, NCGC00093889-08, NCGC00093889-09, NCGC00093889-10, NCGC00093889-12, NCGC00093889-13, NCGC00093889-20, NCGC00255345-01, NCGC00261168-01, AC-15983, AC-37456, DA-56831, Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-, SMR000718753, SBI-0050467.P004, CS-0034353, EU-0100483, NS00004015, P0406, Physostigmine 100 microg/mL in Acetonitrile, C06535, D00196, E 8375, G60920, EN300-23839407, Q410595, SR-01000075341-1, WLN: T B556 EN GNTT&J B1 E1 G1 KOVM1, BRD-K25650355-001-02-5, BRD-K25650355-059-02-3, BRD-K25650355-059-12-2, BRD-K25650355-059-18-9, BRD-K25650355-065-02-0, (3aS,8aR)-1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl hydrogen methylcarbonimidate, (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate hydrochloride, (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; 2-hydroxybenzoic acid, 1,2,3,3A.BETA.,8A.BETA.-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)-INDOL-5-YL METHYLCARBAMATE, Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-methylcarbamate), (3aS,8aR)-, Pyrrolo[2, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
Theoretical properties:
molecular_formula: C15H21N3O2
molecular_weight: 275.35 g/mol
exact_mass: 275.16337692 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 4
rotatable_bond_count: 2
heavy_atom_count: 20
topological_polar_surface_area: 44.8 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
physical_state: ORTHORHOMBIC SPHENOIDAL PRISMS OR CLUSTERS OF LEAFLETS FROM ETHER OR BENZENE
color: ORTHORHOMBIC SPHENOIDAL PRISMS OR CLUSTERS OF LEAFLETS FROM ETHER OR BENZENE
odor: ODORLESS
melting_point: 221 to 223 °F (EPA, 1998)
Descriptions:
pubchem: Physostigmine is a carbamate ester and an indole alkaloid. It has a role as an EC 3.1.1.8 (cholinesterase) inhibitor, a miotic and an antidote to curare poisoning.
chembl: PHYSOSTIGMINE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 3.0.
wikipedia: Physostigmine (also known as eserine from éséré, the West African name for the Calabar bean) is a highly toxic parasympathomimetic alkaloid, specifically, a reversible cholinesterase inhibitor. It occurs naturally in the Calabar bean and the fruit of the Manchineel tree.
The chemical was synthesized for the first time in 1935 by Percy Lavon Julian and Josef Pikl. It is available in the U.S. under the trade names Antilirium and Isopto Eserine, and as eserine salicylate and eserine sulfate. Today, physostigmine is most commonly used for its medicinal value. However, before its discovery by Sir Robert Christison in 1846, it was much more prevalent as an ordeal poison. The positive medical applications of the drug were first suggested in the gold medal-winning final thesis of Thomas Richard Fraser at the University of Edinburgh in 1862.