Showing Compound Card for Promecarb (CDB000530)

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IdentificationTaxonomyOntologyPhysical propertiesSpectraProtein targetPathwaysConcentrationsLinksReferencesenzymes (1) Show 2 proteinsXML
Record Information
Version1.0
Created at2020-03-19 00:42:05 UTC
Updated at2020-12-07 19:07:30 UTC
CannabisDB IDCDB000530
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NamePromecarb
Description3-methyl-5-(1-methylethyl)-Phenol methylcarbamate or Promecarb belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group. Promecarb is a very weakly acidic compound (based on its pKa). It is an odorless, colorless, crystalline solid and it was used as a non-systemic contact insecticide. Promecarb 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 ( Ref:DOI ). Promecarb is no longer approved for sale or use in the USA. Promecarb’s mechanism of action is through the inhibition of the enzyme acetylcholine esterase. Acetylcholine esterase (ACE) is an enzyme that breaks down the neurotransmitter acetylcholine, which is released at nerve and muscle junctions; its breakdown allows the muscle or organ to relax. The inhibition of ACE results in the accumulation of acetyl choline at motor nerves synapses, causing overstimulation of the nicotinic and muscarinic receptors at the neuromuscular junction. Promecarb has also been detected as a volatile component of cannabis samples obtained in police seizures (PMID: 26657499 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
3-Methyl-5-isopropylphenyl N-methylcarbamateMeSH
CarbamultMeSH
m-Cym-5-yl methylcarbamateMeSH
3-Cym-5-yl methylcarbamateMeSH
Chemical FormulaC12H17NO2
Average Molecular Weight207.27
Monoisotopic Molecular Weight207.1259
IUPAC Name3-methyl-5-(propan-2-yl)phenyl N-methylcarbamate
Traditional Name3-isopropyl-5-methylphenyl N-methylcarbamate
CAS Registry Number2631-37-0
SMILES
CN=C(O)OC1=CC(C)=CC(=C1)C(C)C
InChI Identifier
InChI=1S/C12H17NO2/c1-8(2)10-5-9(3)6-11(7-10)15-12(14)13-4/h5-8H,1-4H3,(H,13,14)
InChI KeyDTAPQAJKAFRNJB-UHFFFAOYSA-N
Chemical Taxonomy
Description Belongs to the class of organic compounds known as phenyl methylcarbamates. These are aromatic compounds containing a methylcarbamic acid esterified with a phenyl group.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenyl methylcarbamates
Direct ParentPhenyl methylcarbamates
Alternative Parents
Substituents
  • Phenyl methylcarbamate
  • Cumene
  • Phenylpropane
  • Phenoxy compound
  • Toluene
  • Carbamic acid ester
  • Carbonic acid derivative
  • Carbonyl group
  • Hydrocarbon derivative
  • Organic oxide
  • Organopnictogen compound
  • Organooxygen compound
  • Organonitrogen compound
  • Organic oxygen compound
  • Organic nitrogen compound
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
Role

Industrial application:

Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP2.82ALOGPS
logP3.23ChemAxon
logS-3.2ALOGPS
pKa (Strongest Acidic)14.77ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count1ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area38.33 ŲChemAxon
Rotatable Bond Count3ChemAxon
Refractivity60 m³·mol⁻¹ChemAxon
Polarizability23.66 ųChemAxon
Number of Rings1ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
EI-MSMass Spectrum (Electron Ionization)splash10-0f79-2900000000-9cc92fd2f0dee29c15c52014-09-20View Spectrum
Predicted GC-MSPromecarb, 1 TMS, Predicted GC-MS Spectrum - 70eV, PositiveNot AvailableSpectrum
MS/MS
TypeDescriptionSplash KeyView
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0190000000-a5f52733f725ac7b6dfc2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 0V, positivesplash10-0a4i-0390000000-4370363aad7442d45a6b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 1V, positivesplash10-0zfr-0950000000-229b13ceb54fc3e8b98b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 2V, positivesplash10-0udi-0910000000-c838b07cfdc8d3aa17f92020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 3V, positivesplash10-0udi-0900000000-d5187dbbac16ba3824752020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0zfr-0900000000-eae14c41f9c257e91abe2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 4V, positivesplash10-0pb9-0900000000-0a4ef7339145dce345052020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 5V, positivesplash10-0a4i-0900000000-84a2a3a3784b05f517322020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 6V, positivesplash10-0a4i-0900000000-9d0c21869311a4ba9ae62020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 7V, positivesplash10-0a4i-0900000000-106cf9d7802462a4d09b2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 8V, positivesplash10-0a4i-0900000000-afa154b2c7eb691938cf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 9V, positivesplash10-0a4i-0900000000-c26b56b2b12b5c4d1edf2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 12V, positivesplash10-0a4i-2900000000-5df5b168211a25443e852020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 15V, positivesplash10-0a4l-6900000000-abb7cf37b117ecebe5aa2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 18V, positivesplash10-052f-9300000000-67381698dfd1e84fff0f2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 22V, positivesplash10-0006-9100000000-b55283e4527d88867c6d2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - Orbitrap 27V, positivesplash10-00kf-9000000000-eb3624ddd6d6a3b0282e2020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0udi-0900000000-e9f12672e941d9e39c542020-07-22View Spectrum
MS/MSLC-MS/MS Spectrum - n/a 14V, positivesplash10-0006-9000000000-032721f0001349351fef2020-07-22View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0pb9-5950000000-0921d07bd7a21397e6562016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0zgi-3900000000-d4ffe818f995514ae19c2016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0a59-8900000000-1737f242b2dd2ac0a5822016-08-03View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0a4i-9550000000-0bc8f7c6c634cd5586d62016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0a4j-7910000000-2612d028c6df8658bc242016-08-04View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0a5a-8900000000-19b6a0e25b404861f2092016-08-04View Spectrum
NMR
TypeDescriptionView
Pathways
Pathways
Protein Targets
Enzymes
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
TransportersNot Available
Metal BindingsNot Available
Receptors
Protein NameGene NameLocusUniprot IDDetails
AcetylcholinesteraseACHE7q22P22303 details
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDNot Available
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDC18956
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkPromecarb
METLIN IDNot Available
PubChem Compound17516
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Rice S, Koziel JA: Characterizing the Smell of Marijuana by Odor Impact of Volatile Compounds: An Application of Simultaneous Chemical and Sensory Analysis. PLoS One. 2015 Dec 10;10(12):e0144160. doi: 10.1371/journal.pone.0144160. eCollection 2015. [PubMed:26657499 ]

Enzymes

Enzyme Details
1. Acetylcholinesterase
General function:
Involved in carboxylesterase activity
Specific function:
Terminates signal transduction at the neuromuscular junction by rapid hydrolysis of the acetylcholine released into the synaptic cleft. Role in neuronal apoptosis.
Gene Name:
ACHE
Uniprot ID:
P22303
Molecular weight:
67795.525