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Alanycarb

PubChem CID
9576091
Structure
Alanycarb_small.png
Alanycarb_3D_Structure.png
Molecular Formula
Synonyms
  • Alanycarb
  • 83130-01-2
  • Alanycarb [ISO]
  • 767O73WB8X
  • ethyl 3-[benzyl-[methyl-[(Z)-1-methylsulfanylethylideneamino]oxycarbonylamino]sulfanylamino]propanoate
Molecular Weight
399.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-24
  • Modify:
    2025-01-25
Description
Alanycarb is a carbamate ester and an ethyl ester. It has a role as a carbamate insecticide, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an agrochemical and a nematicide.
Alanycarb is a carbamate pesticide. Carbamate pesticides are derived from carbamic acid and kill insects in a similar fashion as organophosphate insecticides. They are widely used in homes, gardens and agriculture. The first carbamate, carbaryl, was introduced in 1956 and more of it has been used throughout the world than all other carbamates combined. Because of carbaryl's relatively low mammalian oral and dermal toxicity and broad control spectrum, it has had wide use in lawn and garden settings. Most of the carbamates are extremely toxic to Hymenoptera, and precautions must be taken to avoid exposure to foraging bees or parasitic wasps. Some of the carbamates are translocated within plants, making them an effective systemic treatment. (L795)
L795: Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. http://edis.ifas.ufl.edu/PI088

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Alanycarb.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

ethyl 3-[benzyl-[methyl-[(Z)-1-methylsulfanylethylideneamino]oxycarbonylamino]sulfanylamino]propanoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C17H25N3O4S2/c1-5-23-16(21)11-12-20(13-15-9-7-6-8-10-15)26-19(3)17(22)24-18-14(2)25-4/h6-10H,5,11-13H2,1-4H3/b18-14-
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GMAUQNJOSOMMHI-JXAWBTAJSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCOC(=O)CCN(CC1=CC=CC=C1)SN(C)C(=O)O/N=C(/C)\SC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C17H25N3O4S2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 KEGG ID

2.3.6 Metabolomics Workbench ID

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
399.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.4
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
399.12864863 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
399.12864863 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
122 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
26
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
471
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
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
1
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)

3.2 Chemical Classes

3.2.1 Pesticides

Insecticides
Active substance -> EU Pesticides database: Not approved

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.2 Mass Spectrometry

4.2.1 LC-MS

1 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
400.1359
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
Ionization
ESI
Ionization Mode
positive
Collision Energy
60 (nominal)
Retention Time
12.8 min
Top 5 Peaks

91.0542 100

73.0284 26.80

150.0373 26.54

123.0263 22.80

138.0372 21.10

Thumbnail
Thumbnail
License
CC BY
2 of 3
View All
MoNA ID
MS Category
Experimental
MS Type
LC-MS
MS Level
MS2
Precursor Type
[M+H]+
Precursor m/z
400.1359
Instrument
Q Exactive Orbitrap Thermo Scientific
Instrument Type
LC-ESI-QFT
Ionization
ESI
Ionization Mode
positive
Collision Energy
75 (nominal)
Retention Time
12.8 min
Top 5 Peaks

91.0542 100

73.0284 22.43

123.0263 18.54

150.0373 10.25

138.0372 8.28

Thumbnail
Thumbnail
License
CC BY

6 Chemical Vendors

7 Agrochemical Information

7.1 Agrochemical Category

Pesticide active substances -> Insecticides

7.2 EU Pesticides Data

Active Substance
alanycarb
Status
Not approved [Reg. (EC) No 1107/2009]

8 Pharmacology and Biochemistry

8.1 Metabolism / Metabolites

The carbamates are hydrolyzed enzymatically by the liver; degradation products are excreted by the kidneys and the liver. (L793)
L793: IPCS Intox Database (1987). Antimony pentoxide. http://www.intox.org/databank/documents/chemical/antpenta/ukpid36.htm

9 Use and Manufacturing

9.1 Uses

Alanycarb is widely used as an insecticide or pesticide in homes, gardens and agricultural applications. It is a synthetic compound.

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

1 of 2
View All
Pictogram(s)
Acute Toxic
Irritant
Environmental Hazard
Signal
Danger
GHS Hazard Statements

H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]

H330 (100%): Fatal if inhaled [Danger Acute toxicity, inhalation]

H400 (100%): Very toxic to aquatic life [Warning Hazardous to the aquatic environment, acute hazard]

Precautionary Statement Codes

P260, P264, P270, P271, P273, P284, P301+P317, P304+P340, P316, P320, P330, P391, P403+P233, P405, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary

Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

Acute Tox. 2 (100%)

Aquatic Acute 1 (100%)

Acute toxicity (Oral) - Category 4

Specific target organ toxicity - Single exposure - Category 1 (systemic toxicity, nervous system)

Specific target organ toxicity - Repeated exposure - Category 2 (systemic toxicity, nervous system)

Hazardous to the aquatic environment (Acute) - Category 1

Hazardous to the aquatic environment (Long-term) - Category 1

11 Toxicity

11.1 Toxicological Information

11.1.1 Toxicity Summary

Alanycarb is a cholinesterase or acetylcholinesterase (AChE) inhibitor. Carbamates form unstable complexes with chlolinesterases by carbamoylation of the active sites of the enzymes. This inhibition is reversible. A cholinesterase inhibitor suppresses the action of acetylcholine esterase. Because of its essential function, chemicals that interfere with the action of acetylcholine esterase are potent neurotoxins, causing excessive salivation and eye-watering in low doses. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Acetylcholine esterase breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions, in order to allow the muscle or organ to relax. The result of acetylcholine esterase inhibition is that acetylcholine builds up and continues to act so that any nerve impulses are continually transmitted and muscle contractions do not stop.

11.1.2 Carcinogen Classification

Carcinogen Classification
No indication of carcinogenicity to humans (not listed by IARC).

11.1.3 Health Effects

Acute exposure to cholinesterase inhibitors can cause a cholinergic crisis characterized by severe nausea/vomiting, salivation, sweating, bradycardia, hypotension, collapse, and convulsions. Increasing muscle weakness is a possibility and may result in death if respiratory muscles are involved. Accumulation of ACh at motor nerves causes overstimulation of nicotinic expression at the neuromuscular junction. When this occurs symptoms such as muscle weakness, fatigue, muscle cramps, fasciculation, and paralysis can be seen. When there is an accumulation of ACh at autonomic ganglia this causes overstimulation of nicotinic expression in the sympathetic system. Symptoms associated with this are hypertension, and hypoglycemia. Overstimulation of nicotinic acetylcholine receptors in the central nervous system, due to accumulation of ACh, results in anxiety, headache, convulsions, ataxia, depression of respiration and circulation, tremor, general weakness, and potentially coma. When there is expression of muscarinic overstimulation due to excess acetylcholine at muscarinic acetylcholine receptors symptoms of visual disturbances, tightness in chest, wheezing due to bronchoconstriction, increased bronchial secretions, increased salivation, lacrimation, sweating, peristalsis, and urination can occur. Chronically high (>10 years) exposure leads to neuropsychological consequences including disturbances in perception and visuo-motor processing (A15321).
A15321: Roldan-Tapia L, Nieto-Escamez FA, del Aguila EM, Laynez F, Parron T, Sanchez-Santed F: Neuropsychological sequelae from acute poisoning and long-term exposure to carbamate and organophosphate pesticides. Neurotoxicol Teratol. 2006 Nov-Dec;28(6):694-703. Epub 2006 Aug 30. PMID:17029710

11.1.4 Exposure Routes

Inhalation (L793) ; oral (L793); dermal (L793)
L793: IPCS Intox Database (1987). Antimony pentoxide. http://www.intox.org/databank/documents/chemical/antpenta/ukpid36.htm

11.1.5 Symptoms

As with organophosphates, the signs and symptoms are based on excessive cholinergic stimulation. Unlike organophosphate poisoning, carbamate poisonings tend to be of shorter duration because the inhibition of nervous tissue acetylcholinesterase is reversible, and carbamates are more rapidly metabolized. Muscle weakness, dizziness, sweating and slight body discomfort are commonly reported early symptoms. Headache, salivation, nausea, vomiting, abdominal pain and diarrhea are often prominent at higher levels of exposure. Contraction of the pupils with blurred vision, incoordination, muscle twitching and slurred speech have been reported. (L795)
L795: Fishel F (2009). Pesticide Toxicity Profile: Carbamate Pesticides. University of Florida, IFAS Extension. http://edis.ifas.ufl.edu/PI088

11.1.6 Acute Effects

11.1.7 Treatment

If the compound has been ingested, rapid gastric lavage should be performed using 5% sodium bicarbonate. For skin contact, the skin should be washed with soap and water. If the compound has entered the eyes, they should be washed with large quantities of isotonic saline or water. In serious cases, atropine and/or pralidoxime should be administered. Anti-cholinergic drugs work to counteract the effects of excess acetylcholine and reactivate AChE. Atropine can be used as an antidote in conjunction with pralidoxime or other pyridinium oximes (such as trimedoxime or obidoxime), though the use of '-oximes' has been found to be of no benefit, or possibly harmful, in at least two meta-analyses. Atropine is a muscarinic antagonist, and thus blocks the action of acetylcholine peripherally.

12 Literature

12.1 Consolidated References

12.2 Springer Nature References

12.3 Chemical Co-Occurrences in Literature

12.4 Chemical-Gene Co-Occurrences in Literature

12.5 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

15 Classification

15.1 ChEBI Ontology

15.2 KEGG: Pesticides

15.3 ChemIDplus

15.4 UN GHS Classification

15.5 MolGenie Organic Chemistry Ontology

16 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    ethyl 3-[benzyl({[(3Z)-3-methyl-6-oxo-5-oxa-2-thia-4,7-diazaoct-3-en-7-yl]sulfanyl})amino]propanoate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.109.272
    ethyl 3-[benzyl({[(3Z)-3-methyl-6-oxo-5-oxa-2-thia-4,7-diazaoct-3-en-7-yl]sulfanyl})amino]propanoate (EC: 617-442-0)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/15071
  4. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  5. ChEBI
  6. Toxin and Toxin Target Database (T3DB)
    LICENSE
    T3DB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (T3DB) and the original publication.
    http://www.t3db.ca/downloads
  7. EU Pesticides Database
  8. NITE-CMC
    alanycarb - FY2006 (New/original classication)
    https://www.chem-info.nite.go.jp/chem/english/ghs/06-imcg-1127e.html
  9. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
  10. 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
  11. Metabolomics Workbench
  12. NMRShiftDB
  13. Springer Nature
  14. Wikidata
  15. PubChem
  16. GHS Classification (UNECE)
  17. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  18. PATENTSCOPE (WIPO)
CONTENTS