Showing Compound Card for Neurine  (CDB000228)

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Record Information
Version1.0
Created at2020-03-19 00:25:39 UTC
Updated at2020-11-18 16:34:56 UTC
CannabisDB IDCDB000228
Secondary Accession NumbersNot Available
Cannabis Compound Identification
Common NameNeurine 
DescriptionN, N, N-Trimethylethenaminium hydroxide, also known as neurine, is an alkaloid found in egg yolk, brain, bile and in cadavers. It is formed during putrefaction of biological tissues by the dehydration of choline. It is a poisonous, syrupy liquid with a fishy odor. Neurine is a quaternary ammonium salt with three methyl groups and one vinyl group attached to the nitrogen atom. Synthetically, neurine can be prepared by the reaction of acetylene with trimethylamine. Neurine is unstable and decomposes readily to form trimethylamine. Neurine is a quartenary base found in the roots of a Mexican variant of cannabis plants (PMID: 6991645 ).
Structure
Thumb
MOLSDFPDBSMILESInChI
Synonyms
ValueSource
Ammonium, trimethylvinyl-, hydroxideHMDB
Ethenaminium, N,N,N-trimethyl-, hydroxide (9ci)HMDB
N,N,N-Trimethylethenaminium hydroxideHMDB
NeirinHMDB
NeirineHMDB
NeurinHMDB
Trimethyl vinyl ammonium hydroxideHMDB
Trimethyl(vinyl)ammonium hydroxideHMDB
Vinyltrimethylammonium hydroxideHMDB
VitaloidHMDB
Chemical FormulaC5H13NO
Average Molecular Weight103.16
Monoisotopic Molecular Weight103.0997
IUPAC Nameethenyltrimethylazanium hydroxide
Traditional Nameethenyltrimethylazanium hydroxide
CAS Registry Number463-88-7
SMILES
[OH-].C[N+](C)(C)C=C
InChI Identifier
InChI=1S/C5H12N.H2O/c1-5-6(2,3)4;/h5H,1H2,2-4H3;1H2/q+1;/p-1
InChI KeyNIPLIJLVGZCKMP-UHFFFAOYSA-M
Chemical Taxonomy
Description Belongs to the class of organic compounds known as alkaloids and derivatives. These are naturally occurring chemical compounds that contain mostly basic nitrogen atoms. This group also includes some related compounds with neutral and even weakly acidic properties. Also some synthetic compounds of similar structure are attributed to alkaloids. In addition to carbon, hydrogen and nitrogen, alkaloids may also contain oxygen, sulfur and more rarely other elements such as chlorine, bromine, and phosphorus.
KingdomOrganic compounds
Super ClassAlkaloids and derivatives
ClassNot Available
Sub ClassNot Available
Direct ParentAlkaloids and derivatives
Alternative Parents
Substituents
  • Alkaloid or derivatives
  • Quaternary ammonium salt
  • Allylamine
  • Organic nitrogen compound
  • Organic oxygen compound
  • Organopnictogen compound
  • Organic oxide
  • Hydrocarbon derivative
  • Organic salt
  • Organonitrogen compound
  • Organic hydroxide
  • Amine
  • Aliphatic acyclic compound
Molecular FrameworkAliphatic acyclic compounds
External DescriptorsNot Available
Ontology
Not Available
Physical Properties
StateSolid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water SolubilityNot AvailableNot Available
logPNot AvailableNot Available
Predicted Properties
PropertyValueSource
logP-1ALOGPS
logP-3.5ChemAxon
logS-1ALOGPS
Physiological Charge1ChemAxon
Hydrogen Acceptor Count0ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area0 ŲChemAxon
Rotatable Bond Count1ChemAxon
Refractivity39.59 m³·mol⁻¹ChemAxon
Polarizability10.9 ųChemAxon
Number of Rings0ChemAxon
BioavailabilityYesChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Spectra
EI-MS/GC-MS
TypeDescriptionSplash KeyView
Predicted GC-MSNeurine , non-derivatized, Predicted GC-MS Spectrum - 70eV, Positivesplash10-0fb9-9200000000-7bf5dede56152a6232d3Spectrum
MS/MS
TypeDescriptionSplash KeyView
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Positivesplash10-0udi-0900000000-eb55acb76cc56d505ea42017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Positivesplash10-0udi-0900000000-32b1b16dc85b008308d12017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Positivesplash10-0fy9-9200000000-2edc72477b94a4a8eb1f2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 10V, Negativesplash10-0udi-1900000000-85c717011a5d9bd52b6c2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 20V, Negativesplash10-0udi-4900000000-cdafe859a91f1ae1098d2017-09-01View Spectrum
Predicted MS/MSPredicted LC-MS/MS Spectrum - 40V, Negativesplash10-0fg9-9300000000-8766201f9e4156985b902017-09-01View Spectrum
NMRNot Available
Pathways
Pathways
Protein Targets
EnzymesNot Available
TransportersNot Available
Metal BindingsNot Available
ReceptorsNot Available
Transcriptional FactorsNot Available
Concentrations Data
Not Available
HMDB IDHMDB0031259
DrugBank IDNot Available
Phenol Explorer Compound IDNot Available
FoodDB IDFDB003299
KNApSAcK IDNot Available
Chemspider IDNot Available
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkNeurine
METLIN IDNot Available
PubChem Compound10042
PDB IDNot Available
ChEBI IDNot Available
References
General References
  1. Turner CE, Elsohly MA, Boeren EG: Constituents of Cannabis sativa L. XVII. A review of the natural constituents. J Nat Prod. 1980 Mar-Apr;43(2):169-234. doi: 10.1021/np50008a001. [PubMed:6991645 ]