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1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate

PubChem CID
4811
Structure
1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate_small.png
1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate_3D_Structure.png
Molecular Formula
Synonyms
  • 1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
  • CHEMBL11773
  • (3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl) N-methylcarbamate
  • (+)-Physostigmine
  • 7128-53-2
Molecular Weight
275.35 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-25
Description
1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate is a pyrroloindole.
See also: Physostigmine (annotation moved to).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(3,4,8b-trimethyl-2,3a-dihydro-1H-pyrrolo[2,3-b]indol-7-yl) N-methylcarbamate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=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)
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

PIJVFDBKTWXHHD-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC12CCN(C1N(C3=C2C=C(C=C3)OC(=O)NC)C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H21N3O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

7128-53-2

2.3.2 ChEBI ID

2.3.3 ChEMBL ID

2.3.4 DSSTox Substance ID

2.3.5 Metabolomics Workbench ID

2.3.6 Nikkaji Number

2.3.7 Wikidata

2.4 Synonyms

2.4.1 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
275.35 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
0.7
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
275.16337692 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
275.16337692 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
44.8 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
20
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
403
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Copyright
Copyright © 2022-2024 Chemical Block, Russia, Leninsky Prospect 47 - Database Compilation Copyright © 2022-2024 John Wiley & Sons, Inc. All Rights Reserved.
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4.1.2 13C NMR Spectra

1 of 2
Instrument Name
Varian CFT-20
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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2 of 2
Instrument Name
Jeol FX-100
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 9
View All
Authors
Ara T, Morishita Y, Shibata D, Kazusa DNA Research Institute
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
MS Level
MS
Ionization Mode
POSITIVE
Column Name
DB-17MS
Retention Time
959.963 sec
Top 5 Peaks

246 999

290 819

233 767

232 755

218 317

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License
CC BY-SA
2 of 9
View All
Authors
Kusano M, Fukushima A, Plant Science Center, RIKEN.
Instrument
Pegasus III TOF-MS system, Leco; GC 6890, Agilent Technologies
Instrument Type
GC-EI-TOF
MS Level
MS
Ionization Mode
POSITIVE
Retention Time
490.231 sec
Top 5 Peaks

73 999

246 557

290 421

233 386

232 374

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License
CC BY-SA

4.2.2 MS-MS

1 of 2
NIST Number
1183241
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
276.1707
Total Peaks
5
m/z Top Peak
219.1
m/z 2nd Highest
245.1
m/z 3rd Highest
233.1
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2 of 2
NIST Number
1006335
Instrument Type
IT/ion trap
Collision Energy
0
Spectrum Type
MS2
Precursor Type
[M+H]+
Precursor m/z
276.1707
Total Peaks
6
m/z Top Peak
219
m/z 2nd Highest
162
m/z 3rd Highest
233
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4.2.3 LC-MS

1 of 39
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
10 V
Precursor m/z
276
Precursor Adduct
[M+H]+
Top 5 Peaks

276.6 999

219.3 746

233.4 25

101.9 18

259.4 15

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License
CC BY-NC-SA
2 of 39
View All
Authors
Kakazu Y, Horai H, Institute for Advanced Biosciences, Keio Univ.
Instrument
API3000, Applied Biosystems
Instrument Type
LC-ESI-QQ
MS Level
MS2
Ionization Mode
POSITIVE
Collision Energy
20 V
Precursor m/z
276
Precursor Adduct
[M+H]+
Top 5 Peaks

219.3 999

162.2 441

233.2 83

176.3 71

245.5 21

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License
CC BY-NC-SA

4.2.4 Other MS

1 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
276.164
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

162.086853 100

219.107895 72.35

176.100327 26.58

233.124207 14.17

163.088913 7.42

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2 of 2
MS Category
Experimental
MS Type
Other
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
219.108
Instrument
qTof
Ionization Mode
positive
Top 5 Peaks

162.084854 100

219.107986 6.30

163.089050 6.14

147.060715 2.72

158.990845 0.73

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6 Chemical Vendors

7 Literature

7.1 Consolidated References

7.2 Springer Nature References

7.3 Thieme References

7.4 Chemical Co-Occurrences in Literature

7.5 Chemical-Gene Co-Occurrences in Literature

7.6 Chemical-Disease Co-Occurrences in Literature

8 Patents

8.1 Depositor-Supplied Patent Identifiers

8.2 WIPO PATENTSCOPE

9 Interactions and Pathways

9.1 Chemical-Target Interactions

10 Biological Test Results

10.1 BioAssay Results

11 Taxonomy

12 Classification

12.1 ChEBI Ontology

12.2 ChEMBL Target Tree

12.3 EPA DSSTox Classification

12.4 EPA Substance Registry Services Tree

12.5 MolGenie Organic Chemistry Ontology

13 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
    1,3a,8-trimethyl-1H,2H,3H,3aH,8H,8aH-pyrrolo[2,3-b]indol-5-yl N-methylcarbamate
    https://www.bindingdb.org/rwd/bind/chemsearch/marvin/MolStructure.jsp?monomerid=10709
  2. ChEBI
    1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
    https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:182905
  3. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  4. EPA DSSTox
    1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
    https://comptox.epa.gov/dashboard/DTXSID00859010
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. Japan Chemical Substance Dictionary (Nikkaji)
  6. MassBank Europe
  7. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  8. SpectraBase
    (3aS,8aR)-1,3a,8-trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
    https://spectrabase.com/spectrum/FN0CkQlKOsE
  9. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  10. Metabolomics Workbench
    (3,4,8B-Trimethyl-2,3A-Dihydro-1H-Pyrrolo[2,3-B]Indol-7-Yl) N-Methylcarbamate
    https://www.metabolomicsworkbench.org/data/StructureData.php?RegNo=122688
  11. Natural Product Activity and Species Source (NPASS)
    (3,4,8B-Trimethyl-2,3A-Dihydro-1H-Pyrrolo[2,3-B]Indol-7-Yl) N-Methylcarbamate
    https://bidd.group/NPASS/compound.php?compoundID=NPC315498
  12. Springer Nature
  13. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  14. Wikidata
    1,3a,8-Trimethyl-1,2,3,3a,8,8a-hexahydropyrrolo[2,3-b]indol-5-yl methylcarbamate
    https://www.wikidata.org/wiki/Q104194838
  15. PubChem
  16. EPA Substance Registry Services
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
  19. NCBI
CONTENTS