Cannabis Compound Database: Showing Compound Card for Dimethylpyrazine (CDB000594)

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Record Information

Version

1.0

Created at

2020-03-19 00:45:39 UTC

Updated at

2021-01-13 18:12:57 UTC

CannabisDB ID

CDB000594

Secondary Accession Numbers

Not Available

Cannabis Compound Identification

Common Name

Dimethylpyrazine

Description

2,3-Dimethylpyrazine, also known as fema 3271, 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. Some alkylpyrazines are naturally occurring highly aromatic substances which often have a very low odor threshold and contribute to the taste and aroma of various foods including coffee and wines. 2,3-Dimethylpyrazine is a moderately basic compound (based on its pKa). 2,3-Dimethylpyrazine is an almond, butter, and caramel tasting compound. Outside of the human body, 2,3-Dimethylpyrazine has been detected, but not quantified in, several different foods, such as asparagus, fruits, red bell peppers, orange bell peppers, and green bell peppers. This could make 2,3-dimethylpyrazine a potential biomarker for the consumption of these foods. It occurs naturally in asparagus, black or green tea, crispbread, malt, raw shrimp, soya, squid, Swiss cheeses, and wheat bread. It occurs naturally in baked potato, black or green tea, crispbread, French fries, malt, peated malt, raw asparagus, roasted barley, roasted filberts or pecans, squid, wheat bread, wild rice (Zizania aquatica), and wort. 2,3-Dimethylpyrazine 2,3-Dimethylpyrazine is a component of the aroma of roasted sesame seeds. Alkylpyrazines are also formed during the cooking of some foods via Maillard reactions. Alkylpyrazines are chemical compounds based on pyrazine with different substitution patterns. 2,3-Dimethylpyrazine is also a constituent of cannabis smoke. 2,3-Dimethylpyrazine is volatilized during the combustion of cannabis.

Structure

MOL SDF 3D-SDF PDB SMILES InChI View 3D Structure

Synonyms

Value	Source
2,3-DMP Pyrazine	MeSH
23-Dimethyl-pyrazine	ChEMBL, HMDB
2,3-Dimethyl-1,4-diazine	HMDB
2,3-Dimethyl-pyrazine	HMDB
FEMA 3271	HMDB

Chemical Formula

C₆H₈N₂

Average Molecular Weight

108.14

Monoisotopic Molecular Weight

108.0687

IUPAC Name

2,3-dimethylpyrazine

Traditional Name

pyrazine, 2,3-dimethyl-

CAS Registry Number

5910-89-4

SMILES

CC1=NC=CN=C1C

InChI Identifier

InChI=1S/C6H8N2/c1-5-6(2)8-4-3-7-5/h3-4H,1-2H3

InChI Key

OXQOBQJCDNLAPO-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:

Food

Biological:

Plant:

Poaceae

Animal

Biological location:

Subcellular:

Cytoplasm

Cell and elements:

Extracellular

Role

Biological role:

Nutrient

Physical Properties

State

Solid

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
logP	0.54	Not Available

Predicted Properties

Property	Value	Source
logP	0.63	ALOGPS
logP	-0.2	ChemAxon
logS	0.22	ALOGPS
pKa (Strongest Basic)	1.62	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	30.93 m³·mol⁻¹	ChemAxon
Polarizability	11.75 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)	splash10-066u-9200000000-81c62da205b82b71c5f4	2015-03-01	View Spectrum
GC-MS	Dimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-066u-9300000000-a8e384b21f05e8366901	Spectrum
GC-MS	Dimethylpyrazine, non-derivatized, GC-MS Spectrum	splash10-066u-9300000000-a8e384b21f05e8366901	Spectrum
Predicted GC-MS	Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	splash10-0a4i-9800000000-84b80cbd4522b6d41120	Spectrum
Predicted GC-MS	Dimethylpyrazine, non-derivatized, Predicted GC-MS Spectrum - 70eV, Positive	Not Available	Spectrum

MS/MS

Type	Description	Splash Key	View
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-be85de85cd4c9c268d1f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-1900000000-e32b9221fcb3b6f14e7f	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0ldl-9000000000-c45c1029e88c6f7f1abe	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-8bc06f3195c254237e31	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-0900000000-c7cbca7309a958b109e0	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0pb9-9400000000-bbf99b74f59a4b21d37c	2016-08-03	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0a4i-0900000000-1d4d8b4513a018558199	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-0a4i-1900000000-5e56bb9f78bc0c56fa72	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0006-9000000000-12edac38431654aaa839	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0a4i-0900000000-f6048b98ce921f15f893	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-0a4i-9700000000-36854acac26b155e72da	2021-09-24	View Spectrum
Predicted MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-0udi-9000000000-5dfe58276533b985a7b6	2021-09-24	View Spectrum

NMR

Type	Description	View
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 22.53 MHz, CDCl₃, experimental)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, D₂O, predicted)	Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, D₂O, predicted)	Spectrum
1D NMR	¹H 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

HMDB0032971

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

FDB010958

KNApSAcK ID

C00052588

Chemspider ID

20843

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Alkylpyrazine

METLIN ID

Not Available

PubChem Compound

22201

PDB ID

Not Available

ChEBI ID

Not Available

References

General References

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 ]

Showing Compound Card for Dimethylpyrazine (CDB000594)

Structure for CDB000594 (Dimethylpyrazine)