Cannabis Compound Database: Showing Compound Card for 2,3,5-Trimethylpyrazine (CDB005932)

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Record Information

Version

1.0

Created at

2020-04-27 17:10:59 UTC

Updated at

2021-01-06 19:06:59 UTC

CannabisDB ID

CDB005932

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

2,3,5-Trimethylpyrazine

Description

2,3,4-Trimethylpyrazine, also known as fema 3244, belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms. Trimethylpyrazine is a moderately basic compound (based on its pKa). Trimethylpyrazine is a cocoa, earthy, and hazelnut tasting compound. Outside of the human body, trimethylpyrazine is found, on average, in the highest concentration in kohlrabis. trimethylpyrazine has also been detected, but not quantified in, several different foods, such as green vegetables, pepper (c. annuum), orange bell peppers, potato, and red bell peppers. This could make trimethylpyrazine a potential biomarker for the consumption of these foods. Found in many foodstuffs e.g. asparagus, baked potato, wheat bread, Swiss cheese, coffee, black tea, roasted filbert and peanut, soybean etc. Trimethylpyrazine is formed during the combustion of cannabis and is therefore a constituent of cannabis smoke ( Ref:DOI ).

Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
235-Trimethyl-pyrazine	ChEMBL, HMDB
2,3,5-TRIMETHYL pyrazine	HMDB, MeSH
2,3,5-Trimethyl-pyrazine	HMDB
2,3,6-Trimethylpyrazine	HMDB
FEMA 3244	HMDB
Pyrazine, 2,3,5-trimethyl	HMDB
Trimethyl-pyrazine	HMDB

Chemical Formula

C₇H₁₀N₂

Average Molecular Weight

122.17

Monoisotopic Molecular Weight

122.0844

IUPAC Name

2,3,5-trimethylpyrazine

Traditional Name

pyrazine, trimethyl-

CAS Registry Number

14667-55-1

SMILES

CC1=CN=C(C)C(C)=N1

InChI Identifier

InChI=1S/C7H10N2/c1-5-4-8-6(2)7(3)9-5/h4H,1-3H3

InChI Key

IAEGWXHKWJGQAZ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as pyrazines. Pyrazines are compounds containing a pyrazine ring, which is a six-member aromatic heterocycle, that consists of two nitrogen atoms (at positions 1 and 4) and four carbon atoms.

Kingdom

Organic compounds

Super Class

Organoheterocyclic compounds

Class

Diazines

Sub Class

Pyrazines

Direct Parent

Pyrazines

Alternative Parents

Substituents

Pyrazine
Heteroaromatic compound
Azacycle
Organic nitrogen compound
Organopnictogen compound
Hydrocarbon derivative
Organonitrogen compound
Aromatic heteromonocyclic compound

Molecular Framework

Aromatic heteromonocyclic compounds

External Descriptors

Not Available

Ontology

Disposition

Route of exposure:

Enteral:

Ingestion

Source:

Biological:

Animal

Plant:

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Industrial application:

Food and nutrition:

Flavoring agent

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	0.95	Not Available

Predicted Properties

Property	Value	Source
logP	1.11	ALOGPS
logP	-0.068	ChemAxon
logS	-0.37	ALOGPS
pKa (Strongest Basic)	2.08	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	2	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	25.78 Å²	ChemAxon
Rotatable Bond Count	0	ChemAxon
Refractivity	35.52 m³·mol⁻¹	ChemAxon
Polarizability	13.94 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

EI-MS/GC-MS

Type	Description	Splash Key	View
EI-MS	Mass Spectrum (Electron Ionization)	splash10-006x-9300000000-0bf83855966f2520d689	2015-03-01	View Spectrum
GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-006x-9200000000-9f6faed991931d5ad1ee	Spectrum
GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-40504210dd3941e2c04a	Spectrum
GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-006x-9200000000-9f6faed991931d5ad1ee	Spectrum
GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-0006-9200000000-40504210dd3941e2c04a	Spectrum
Predicted GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-00di-8900000000-a14528e7d6edd51f8dc6	Spectrum
Predicted GC-MS	2,3,5-Trimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
MS/MS	LC-MS/MS Spectrum - Orbitrap 4V, positive	splash10-00di-2900000000-76363ef0f48afd63a91a	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 5V, positive	splash10-00di-7900000000-e98f2f5a6e323c824048	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 6V, positive	splash10-0ab9-9400000000-35d807ba9ebeef9ae55c	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 7V, positive	splash10-0pb9-9100000000-fff3de03d74c83ae57e0	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - Orbitrap 9V, positive	splash10-0zfr-9000000000-715231eb0f6256a14836	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 8V, positive	splash10-001i-9000000000-9b38357d8213dfc04a21	2020-07-22	View Spectrum
MS/MS	LC-MS/MS Spectrum - n/a 8V, positive	splash10-0a4i-9000000000-5c4795e954d5c3e9b74e	2020-07-22	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-9fd5c695f7b8a4cfe63d	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-2900000000-bb37b6ad64235815e0f4	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0zgl-9000000000-8acc5bf685bbdae5968f	2015-04-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-0900000000-434c116a57f2e3b72058	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-00di-0900000000-65f5a51dc79dd6ae5de8	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pi0-9800000000-dfd2d2cc903cdbd80f8e	2015-04-25	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-00di-0900000000-1fbfd2b4b0ef1b9b6fee	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-00di-9400000000-a6ecdcbe708aeefa02c5	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-100u-9000000000-7d5a8bbe136aa07e5c95	2021-09-23	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-00di-1900000000-7b36c336b1384f9bab4b	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-006x-9300000000-49f0534d4a86e681b444	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-b33164d500a1075f7e25	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 90 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 25.16 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum

Pathways

Not Available

Protein Targets

Enzymes

Not Available

Transporters

Not Available

Metal Bindings

Not Available

Receptors

Not Available

Transcriptional Factors

Not Available

Concentrations Data

Not Available

External Links

HMDB ID

HMDB0031844

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB008527

KNApSAcK ID

C00053868

Chemspider ID

24972

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

26808

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

Not Available

Showing Compound Card for 2,3,5-Trimethylpyrazine (CDB005932)

Structure for CDB005932 (2,3,5-Trimethylpyrazine)