Physostigmine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Physostigmine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Physostigmine?

The molecule Physostigmine presents a molecular formula of C15H21N3O2 and its IUPAC name is [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate.

Physostigmine is a molecule that has been used for centuries as a medicinal remedy. It comes from from the plant physostigma venenosum and has a long history of use in treating a variety of conditions, including seizures, Alzheimer's disease, and glaucoma. Physostigmine considered to work by increasing the level of acetylcholine in the brain, which is a neurotransmitter that is essential for memory and learning. There is some evidence to suggest that physostigmine may also be effective in treating depression and anxiety..

3D structure

Cartesian coordinates

Geometry of Physostigmine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Physostigmine PIJVFDBKTWXHHD-HIFRSBDPSA-N chemical compound 2D structure molecule svg
Physostigmine

 

Molecule descriptors

 
IUPAC name[(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
InChI codeInChI=1S/C15H21N3O2/c1-15-7-8-17(3)13(15)18(4)12-6-5-10(9-11(12)15)20-14(19)16-2/h5-6,9,13H,7-8H2,1-4H3,(H,16,19)/t13-,15+/m1/s1
InChI KeyPIJVFDBKTWXHHD-HIFRSBDPSA-N
SMILESCNC(=O)Oc1ccc2c(c1)[C@]1(C)CCN(C)[C@@H]1N2C

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-) physostigmine
  • (-)-physostigmine
  • (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
  • (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
  • (3aS,8aR)-1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate; 2-hydroxybenzoic acid
  • (3aS-cis)-1,2,3,3a,8,8a-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)indol-5-ol methylcarbamate (ester)
  • 1,2,3,3A.BETA.,8A.BETA.-HEXAHYDRO-1,3A,8-TRIMETHYLPYRROLO(2,3-B)-INDOL-5-YL METHYLCARBAMATE
  • 1,2,3,3abeta,8abeta-Hexahydro-1,3a,8-trimethylpyrrolo(2,3-b)-indol-5-yl methylcarbamate
  • 57-47-6
  • 9U1VM840SP
  • AC-15983
  • ACon1_000097
  • Antilirium
  • BCP19735
  • BDBM11023
  • BDBM50004000
  • BDBM50222010
  • BPBio1_000388
  • BSPBio_000352
  • BSPBio_002189
  • C06535
  • CCG-38605
  • CCRIS 3422
  • CS 58525
  • CS-0034353
  • Calabarine
  • Carbamic acid, ester with eseroline
  • Carbamic acid, methyl-, ester with eseroline
  • D00196
  • DB00981
  • DSSTox_CID_3471
  • DSSTox_GSID_23471
  • DSSTox_RID_77040
  • DivK1c_006477
  • E 8375
  • EU-0100483
  • Erserine
  • Eserine
  • Eserine sulfate
  • Eserine; Antilirium; Physostol; Esromiotin; Ezerin
  • Eserinum
  • Eserolein, methylcarbamate
  • Eserolein, methylcarbamate (ester)
  • Esromiotin
  • Ezerin
  • Fysostigmin
  • GTPL6598
  • HMS1921G06
  • HMS2089M11
  • HMS2236L08
  • HMS3261B07
  • HSDB 3161
  • HY-N6608
  • KBio1_001421
  • KBio2_001396
  • KBio2_002278
  • KBio2_003964
  • KBio2_004846
  • KBio2_006532
  • KBio2_007414
  • KBio3_001689
  • KBio3_001842
  • KBioGR_001433
  • KBioGR_002061
  • KBioGR_002533
  • KBioSS_001396
  • KBioSS_002279
  • LP00483
  • Lopac0_000483
  • MCV 4484
  • MCV-4484
  • MEGxp0_001872
  • MFCD00151090
  • MLS001304022
  • Methyl-carbamic acid, ester with eseroline
  • NCGC00093889-01
  • NCGC00093889-02
  • NCGC00093889-03
  • NCGC00093889-04
  • NCGC00093889-05
  • NCGC00093889-06
  • NCGC00093889-07
  • NCGC00093889-08
  • NCGC00093889-09
  • NCGC00093889-10
  • NCGC00093889-12
  • NCGC00093889-13
  • NCGC00093889-20
  • NCGC00255345-01
  • NCGC00261168-01
  • NIH 10421
  • NSC 30782
  • NSC-30782
  • NSC30782
  • P0406
  • Physostigmine
  • Physostol
  • Prestwick0_000566
  • Prestwick1_000566
  • Prestwick2_000566
  • Prestwick3_000566
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, 5-(N-methylcarbamate), (3aS,8aR)-
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS,8aR)-
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)
  • Pyrrolo(2,3-b)indol-5-ol, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
  • Pyrrolo[2, 1,2,3,3a,8,8a-hexahydro-1,3a,8-trimethyl-, methylcarbamate (ester), (3aS-cis)-
  • Q410595
  • SBI-0050467.P004
  • SDCCGMLS-0066585.P001
  • SDCCGSBI-0050467.P005
  • SMR000718753
  • SPECTRUM1500753
  • SR-01000075341-1
  • SpecPlus_000381
  • WLN: T B556 EN GNTT&J B1 E1 G1 KOVM1
  • [(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
  • cid_657348
  • cogmine
  • eserin
  • physostigmin
  • physostigmine
  • physostigmine.salicylic acid

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC91689892
  • CAS-57-47-6
  • UNII-9U1VM840SP
  • AKOS016843649
  • BRD-K25650355-001-02-5
  • BRD-K25650355-059-02-3
  • BRD-K25650355-059-12-2
  • DTXSID3023471
  • CHEMBL94
  • CHEMBL537674
  • CHEBI:27953
  • Tox21_111228
  • Tox21_301591
  • Tox21_500483
  • Tox21_111228_1
  • EINECS 200-332-8
  • SPBio_000339
  • SPBio_000774
  • SPBio_001285
  • SPBio_002571
  • SCHEMBL24044
  • Spectrum_000916
  • Spectrum_001789
  • Spectrum2_000330
  • Spectrum2_000757
  • Spectrum2_001283
  • Spectrum3_000545
  • Spectrum3_000901
  • Spectrum4_000997
  • Spectrum4_001631
  • Spectrum4_001913
  • Spectrum5_000441
  • Spectrum5_000626
  • Spectrum5_001672

Physico-Chemical properties

IUPAC name[(3aR,8bS)-3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl] N-methylcarbamate
Molecular formulaC15H21N3O2
Molecular weight275.346
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity84.93
LogP2.2
Topological polar surface area44.8

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.